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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002268

Secondary Accession Numbers

HMDB02268

Metabolite Identification

Common Name

Alpha-Cryptoxanthin

Description

Alpha-cryptoxanthin is a naturally occurring carotenoid pigment with provitamin A activity whose structure is very similar to that of beta-carotene (HMDB00561). These dietary hydroxycarotenoids have been identified in human serum, milk, and ocular tissues. Industrial production of optically active (3R,6′R)-alpha-cryptoxanthin has not yet been achieved. Little is known about the potential physiological role of alpha-cryptoxanthin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05071312232D          

 41 42  0  0  0  0            999 V2000
    4.9500   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500  -10.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5334   -7.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -7.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789  -10.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5223   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5236   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -9.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3815   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -9.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5249   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -7.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -8.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6683   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6683   -7.5428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5249   -7.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3828   -7.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5414   -9.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5372   -9.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 34 32  1  0  0  0  0
 32 35  1  0  0  0  0
 33 34  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  6  0  0  0
 35 40  1  0  0  0  0
 35 41  1  0  0  0  0
M  END

HMDB0002268
     RDKit          3D
Alpha-Cryptoxanthin
 97 98  0  0  0  0  0  0  0  0999 V2000
  -10.8676    2.3877    0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.0799   -0.6996    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9132   -0.1111    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2799    0.3394    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8908   -2.1144   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
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 41 97  1  0
M  END


  Mrv0541 05071312232D          

 41 42  0  0  0  0            999 V2000
    4.9500   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500  -10.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -9.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3789  -10.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5223   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5236   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381   -9.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3815   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960   -9.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5249   -8.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -7.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2394   -7.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9539   -8.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6683   -8.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6683   -7.5428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5249   -7.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3828   -7.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5414   -9.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5372   -9.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 34 32  1  0  0  0  0
 32 35  1  0  0  0  0
 33 34  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  6  0  0  0
 35 40  1  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002268

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,28,36,38,41H,15,22,27,29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,38?/m0/s1

> <INCHI_KEY>
ORAKUVXRZWMARG-DWADUKLPSA-N

> <FORMULA>
C40H56O

> <MOLECULAR_WEIGHT>
552.872

> <EXACT_MASS>
552.433116414

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
72.46441552790716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-ol

> <ALOGPS_LOGP>
9.10

> <JCHEM_LOGP>
9.936927857666667

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.21727233987641

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3915650785380587

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
193.39390000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-cryptoxanthin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002268
     RDKit          3D
Alpha-Cryptoxanthin
 97 98  0  0  0  0  0  0  0  0999 V2000
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  -11.7381    1.2147    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0781    1.4770    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9779    0.3170    0.5963 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.0412   -0.1703    1.8820 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.2781   -0.7298   -0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1469    0.1562   -2.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8220   -2.1137   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4371   -0.1912    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0799   -0.6996    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0346    0.0951    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1935    2.7276   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -0.7735    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
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 41 96  1  0
 41 97  1  0
M  END

HEADER    PROTEIN                                 07-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAY-13         0                                  
HETATM    1  C   UNK     0       9.240 -15.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.906 -16.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.906 -17.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.240 -18.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.574 -17.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.574 -16.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.329 -14.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.906 -14.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.907 -18.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.907 -15.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.241 -16.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.575 -15.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.575 -14.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.908 -16.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.242 -15.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.576 -16.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.909 -15.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.909 -14.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.243 -16.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.577 -15.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.911 -16.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.244 -15.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.578 -16.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.578 -17.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.912 -15.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.245 -16.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.579 -15.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      31.913 -16.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      31.913 -17.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.246 -15.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      34.580 -16.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      35.914 -15.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.247 -13.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.914 -14.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      37.247 -16.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      38.581 -15.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      38.581 -14.080   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      34.580 -13.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      39.915 -13.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      36.477 -17.724   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      38.336 -17.479   0.000  0.00  0.00           C+0
CONECT    1    2    6    7    8                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1   10                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    5                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   34   35                                                  
CONECT   33   34   37                                                       
CONECT   34   32   33   38                                                  
CONECT   35   32   36   40   41                                             
CONECT   36   35   37                                                       
CONECT   37   36   33   39                                                  
CONECT   38   34                                                            
CONECT   39   37                                                            
CONECT   40   35                                                            
CONECT   41   35                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

COMPND    HMDB0002268
HETATM    1  C1  UNL     1     -10.868   2.388   0.246  1.00  0.00           C  
HETATM    2  C2  UNL     1     -11.738   1.215   0.325  1.00  0.00           C  
HETATM    3  C3  UNL     1     -13.078   1.477   0.516  1.00  0.00           C  
HETATM    4  C4  UNL     1     -13.978   0.317   0.596  1.00  0.00           C  
HETATM    5  O1  UNL     1     -14.041  -0.170   1.882  1.00  0.00           O  
HETATM    6  C5  UNL     1     -13.712  -0.737  -0.452  1.00  0.00           C  
HETATM    7  C6  UNL     1     -12.278  -0.730  -0.950  1.00  0.00           C  
HETATM    8  C7  UNL     1     -12.147   0.156  -2.147  1.00  0.00           C  
HETATM    9  C8  UNL     1     -11.822  -2.114  -1.304  1.00  0.00           C  
HETATM   10  C9  UNL     1     -11.437  -0.191   0.230  1.00  0.00           C  
HETATM   11  C10 UNL     1     -10.080  -0.700   0.177  1.00  0.00           C  
HETATM   12  C11 UNL     1      -8.913  -0.111   0.215  1.00  0.00           C  
HETATM   13  C12 UNL     1      -7.618  -0.833   0.146  1.00  0.00           C  
HETATM   14  C13 UNL     1      -7.468  -2.280   0.034  1.00  0.00           C  
HETATM   15  C14 UNL     1      -6.533  -0.087   0.194  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.181  -0.660   0.135  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.112   0.095   0.185  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.772  -0.462   0.127  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.441  -1.896   0.001  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.704   0.359   0.184  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.344  -0.155   0.131  1.00  0.00           C  
HETATM   22  C21 UNL     1       0.701   0.651   0.185  1.00  0.00           C  
HETATM   23  C22 UNL     1       2.035   0.095   0.129  1.00  0.00           C  
HETATM   24  C23 UNL     1       3.110   0.905   0.182  1.00  0.00           C  
HETATM   25  C24 UNL     1       2.832   2.334   0.296  1.00  0.00           C  
HETATM   26  C25 UNL     1       4.425   0.299   0.125  1.00  0.00           C  
HETATM   27  C26 UNL     1       5.552   0.984   0.168  1.00  0.00           C  
HETATM   28  C27 UNL     1       6.842   0.315   0.107  1.00  0.00           C  
HETATM   29  C28 UNL     1       7.974   0.983   0.148  1.00  0.00           C  
HETATM   30  C29 UNL     1       7.876   2.451   0.259  1.00  0.00           C  
HETATM   31  C30 UNL     1       9.280   0.339   0.092  1.00  0.00           C  
HETATM   32  C31 UNL     1      10.437   0.906   0.127  1.00  0.00           C  
HETATM   33  C32 UNL     1      11.747   0.212   0.066  1.00  0.00           C  
HETATM   34  C33 UNL     1      12.853   0.934   0.118  1.00  0.00           C  
HETATM   35  C34 UNL     1      12.717   2.408   0.233  1.00  0.00           C  
HETATM   36  C35 UNL     1      14.234   0.408   0.085  1.00  0.00           C  
HETATM   37  C36 UNL     1      14.144  -0.992   0.714  1.00  0.00           C  
HETATM   38  C37 UNL     1      13.226  -1.763  -0.188  1.00  0.00           C  
HETATM   39  C38 UNL     1      11.802  -1.270  -0.058  1.00  0.00           C  
HETATM   40  C39 UNL     1      11.099  -1.674  -1.345  1.00  0.00           C  
HETATM   41  C40 UNL     1      11.164  -1.926   1.165  1.00  0.00           C  
HETATM   42  H1  UNL     1     -10.235   2.450  -0.674  1.00  0.00           H  
HETATM   43  H2  UNL     1     -11.505   3.348   0.121  1.00  0.00           H  
HETATM   44  H3  UNL     1     -10.232   2.580   1.118  1.00  0.00           H  
HETATM   45  H4  UNL     1     -13.376   2.502   0.594  1.00  0.00           H  
HETATM   46  H5  UNL     1     -15.012   0.720   0.377  1.00  0.00           H  
HETATM   47  H6  UNL     1     -13.607   0.445   2.543  1.00  0.00           H  
HETATM   48  H7  UNL     1     -13.873  -1.727   0.027  1.00  0.00           H  
HETATM   49  H8  UNL     1     -14.373  -0.605  -1.332  1.00  0.00           H  
HETATM   50  H9  UNL     1     -11.403  -0.226  -2.859  1.00  0.00           H  
HETATM   51  H10 UNL     1     -11.868   1.195  -1.904  1.00  0.00           H  
HETATM   52  H11 UNL     1     -13.135   0.216  -2.665  1.00  0.00           H  
HETATM   53  H12 UNL     1     -12.547  -2.517  -2.049  1.00  0.00           H  
HETATM   54  H13 UNL     1     -10.822  -2.036  -1.795  1.00  0.00           H  
HETATM   55  H14 UNL     1     -11.758  -2.776  -0.406  1.00  0.00           H  
HETATM   56  H15 UNL     1     -11.922  -0.717   1.140  1.00  0.00           H  
HETATM   57  H16 UNL     1      -9.955  -1.831   0.082  1.00  0.00           H  
HETATM   58  H17 UNL     1      -8.899   0.956   0.312  1.00  0.00           H  
HETATM   59  H18 UNL     1      -6.716  -2.664   0.786  1.00  0.00           H  
HETATM   60  H19 UNL     1      -6.964  -2.496  -0.954  1.00  0.00           H  
HETATM   61  H20 UNL     1      -8.346  -2.898   0.157  1.00  0.00           H  
HETATM   62  H21 UNL     1      -6.616   0.976   0.280  1.00  0.00           H  
HETATM   63  H22 UNL     1      -5.091  -1.725   0.049  1.00  0.00           H  
HETATM   64  H23 UNL     1      -4.235   1.191   0.274  1.00  0.00           H  
HETATM   65  H24 UNL     1      -3.317  -2.486  -0.263  1.00  0.00           H  
HETATM   66  H25 UNL     1      -1.749  -1.993  -0.889  1.00  0.00           H  
HETATM   67  H26 UNL     1      -1.944  -2.294   0.913  1.00  0.00           H  
HETATM   68  H27 UNL     1      -1.926   1.410   0.271  1.00  0.00           H  
HETATM   69  H28 UNL     1      -0.147  -1.212   0.048  1.00  0.00           H  
HETATM   70  H29 UNL     1       0.576   1.713   0.269  1.00  0.00           H  
HETATM   71  H30 UNL     1       2.163  -0.969   0.045  1.00  0.00           H  
HETATM   72  H31 UNL     1       2.208   2.468   1.229  1.00  0.00           H  
HETATM   73  H32 UNL     1       3.676   3.003   0.405  1.00  0.00           H  
HETATM   74  H33 UNL     1       2.194   2.728  -0.525  1.00  0.00           H  
HETATM   75  H34 UNL     1       4.535  -0.774   0.043  1.00  0.00           H  
HETATM   76  H35 UNL     1       5.452   2.057   0.253  1.00  0.00           H  
HETATM   77  H36 UNL     1       6.864  -0.756   0.027  1.00  0.00           H  
HETATM   78  H37 UNL     1       7.150   2.830  -0.519  1.00  0.00           H  
HETATM   79  H38 UNL     1       8.791   3.012   0.110  1.00  0.00           H  
HETATM   80  H39 UNL     1       7.367   2.718   1.230  1.00  0.00           H  
HETATM   81  H40 UNL     1       9.245  -0.759   0.016  1.00  0.00           H  
HETATM   82  H41 UNL     1      10.453   1.990   0.209  1.00  0.00           H  
HETATM   83  H42 UNL     1      12.131   2.606   1.165  1.00  0.00           H  
HETATM   84  H43 UNL     1      12.103   2.843  -0.602  1.00  0.00           H  
HETATM   85  H44 UNL     1      13.694   2.936   0.263  1.00  0.00           H  
HETATM   86  H45 UNL     1      14.667   0.374  -0.920  1.00  0.00           H  
HETATM   87  H46 UNL     1      14.861   1.007   0.803  1.00  0.00           H  
HETATM   88  H47 UNL     1      15.135  -1.440   0.821  1.00  0.00           H  
HETATM   89  H48 UNL     1      13.644  -0.845   1.685  1.00  0.00           H  
HETATM   90  H49 UNL     1      13.310  -2.849  -0.037  1.00  0.00           H  
HETATM   91  H50 UNL     1      13.539  -1.509  -1.243  1.00  0.00           H  
HETATM   92  H51 UNL     1      11.891  -2.114  -2.021  1.00  0.00           H  
HETATM   93  H52 UNL     1      10.376  -2.478  -1.119  1.00  0.00           H  
HETATM   94  H53 UNL     1      10.651  -0.795  -1.855  1.00  0.00           H  
HETATM   95  H54 UNL     1      10.751  -1.130   1.797  1.00  0.00           H  
HETATM   96  H55 UNL     1      11.960  -2.496   1.724  1.00  0.00           H  
HETATM   97  H56 UNL     1      10.404  -2.637   0.855  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3    3   10
CONECT    3    4   45
CONECT    4    5    6   46
CONECT    5   47
CONECT    6    7   48   49
CONECT    7    8    9   10
CONECT    8   50   51   52
CONECT    9   53   54   55
CONECT   10   11   56
CONECT   11   12   12   57
CONECT   12   13   58
CONECT   13   14   15   15
CONECT   14   59   60   61
CONECT   15   16   62
CONECT   16   17   17   63
CONECT   17   18   64
CONECT   18   19   20   20
CONECT   19   65   66   67
CONECT   20   21   68
CONECT   21   22   22   69
CONECT   22   23   70
CONECT   23   24   24   71
CONECT   24   25   26
CONECT   25   72   73   74
CONECT   26   27   27   75
CONECT   27   28   76
CONECT   28   29   29   77
CONECT   29   30   31
CONECT   30   78   79   80
CONECT   31   32   32   81
CONECT   32   33   82
CONECT   33   34   34   39
CONECT   34   35   36
CONECT   35   83   84   85
CONECT   36   37   86   87
CONECT   37   38   88   89
CONECT   38   39   90   91
CONECT   39   40   41
CONECT   40   92   93   94
CONECT   41   95   96   97
END

HMDB0002268
     RDKit          3D
Alpha-Cryptoxanthin
 97 98  0  0  0  0  0  0  0  0999 V2000
  -10.8676    2.3877    0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7381    1.2147    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0781    1.4770    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9779    0.3170    0.5963 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.0412   -0.1703    1.8820 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7115   -0.7372   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2781   -0.7298   -0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1469    0.1562   -2.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8220   -2.1137   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4371   -0.1912    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0799   -0.6996    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9132   -0.1111    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6182   -0.8329    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4685   -2.2801    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5330   -0.0871    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1808   -0.6604    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121    0.0945    0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7724   -0.4621    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4406   -1.8956    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7040    0.3592    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440   -0.1546    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7007    0.6506    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346    0.0951    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095    0.9050    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    2.3335    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4254    0.2991    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5522    0.9838    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8421    0.3153    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9736    0.9830    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8764    2.4508    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2799    0.3394    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4368    0.9059    0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7475    0.2116    0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8530    0.9343    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7172    2.4082    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2339    0.4077    0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1437   -0.9915    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2264   -1.7626   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8025   -1.2700   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0989   -1.6745   -1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1641   -1.9265    1.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2355    2.4496   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5045    3.3481    0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2324    2.5802    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3759    2.5021    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0124    0.7199    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6068    0.4447    2.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8727   -1.7267    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3734   -0.6052   -1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4028   -0.2260   -2.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8681    1.1954   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1348    0.2164   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5471   -2.5168   -2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8224   -2.0364   -1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7575   -2.7755   -0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9223   -0.7167    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9548   -1.8309    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8989    0.9559    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7157   -2.6636    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9641   -2.4964   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3459   -2.8981    0.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6160    0.9765    0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0912   -1.7252    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2349    1.1910    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3174   -2.4856   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -1.9931   -0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.2940    0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9256    1.4097    0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475   -1.2119    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    1.7132    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -0.9689    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077    2.4675    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759    3.0033    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935    2.7276   -0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349   -0.7735    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4518    2.0572    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8641   -0.7565    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504    2.8295   -0.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7912    3.0122    0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3668    2.7181    1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2448   -0.7592    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4532    1.9899    0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1315    2.6060    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033    2.8430   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6938    2.9356    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6669    0.3744   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8607    1.0074    0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1346   -1.4396    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6439   -0.8448    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3096   -2.8487   -0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5387   -1.5093   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8908   -2.1144   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3764   -2.4783   -1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6506   -0.7952   -1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7507   -1.1300    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9597   -2.4963    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4037   -2.6367    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 10  2  1  0
 39 33  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  3 45  1  0
  4 46  1  6
  5 47  1  0
  6 48  1  0
  6 49  1  0
  8 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
  9 55  1  0
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 19 65  1  0
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 19 67  1  0
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 22 70  1  0
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 35 83  1  0
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 35 85  1  0
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 36 87  1  0
 37 88  1  0
 37 89  1  0
 38 90  1  0
 38 91  1  0
 40 92  1  0
 40 93  1  0
 40 94  1  0
 41 95  1  0
 41 96  1  0
 41 97  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3'r,6'r)-beta,epsilon-Caroten-3'-ol	Kegg
(3'r,6'r)-b,epsilon-Caroten-3'-ol	Generator
(3'r,6'r)-Β,epsilon-caroten-3'-ol	Generator
a-Cryptoxanthin	Generator
Α-cryptoxanthin	Generator
(3'r,6'r)-Β,ε-caroten-3'-ol	HMDB
(3R)-beta,beta-Carotene-3-ol	HMDB
beta-Caroten-3-ol	HMDB
C15981	HMDB
Caricaxanthin	HMDB
Cryptoxanthin	HMDB
Cryptoxanthine	HMDB

Chemical Formula

C₄₀H₅₆O

Average Molecular Weight

552.872

Monoisotopic Molecular Weight

552.433116414

IUPAC Name

(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-ol

Traditional Name

α-cryptoxanthin

CAS Registry Number

24480-38-4

SMILES

C\C(\C=C\C=C(/C)\C=C\C1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,28,36,38,41H,15,22,27,29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,38?/m0/s1

InChI Key

ORAKUVXRZWMARG-DWADUKLPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (C15981 )
Carotenoids (C15981 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00051 g/L	ALOGPS
logP	9.1	ALOGPS
logP	9.94	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.39 m³·mol⁻¹	ChemAxon
Polarizability	72.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	246.211	31661259
DarkChem	[M-H]-	249.957	31661259
DeepCCS	[M+H]+	260.222	30932474
DeepCCS	[M-H]-	258.397	30932474
DeepCCS	[M-2H]-	291.641	30932474
DeepCCS	[M+Na]+	265.828	30932474
AllCCS	[M+H]+	255.4	32859911
AllCCS	[M+H-H2O]+	253.6	32859911
AllCCS	[M+NH4]+	257.0	32859911
AllCCS	[M+Na]+	257.5	32859911
AllCCS	[M-H]-	227.8	32859911
AllCCS	[M+Na-2H]-	231.2	32859911
AllCCS	[M+HCOO]-	235.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.28 minutes	32390414
Predicted by Siyang on May 30, 2022	44.9652 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5788.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1289.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	483.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	777.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	605.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1791.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1236.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3859.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1295.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2378.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1578.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	909.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	597.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	1144.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.1 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alpha-Cryptoxanthin,1TMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4622.5	Semi standard non polar	33892256
Alpha-Cryptoxanthin,1TMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4596.3	Standard non polar	33892256
Alpha-Cryptoxanthin,1TMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4348.9	Standard polar	33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4804.8	Semi standard non polar	33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4829.9	Standard non polar	33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1	CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C	4446.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-Cryptoxanthin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2100190000-9d58bb486a79a7b0d65b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-Cryptoxanthin GC-MS (1 TMS) - 70eV, Positive	splash10-0bt9-7010029000-faf43dffc0b286002b4a	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Positive-QTOF	splash10-0f79-0513190000-a823a0279255ebaaeef1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Positive-QTOF	splash10-000t-0937200000-73617d89dc5cfe4b8150	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Positive-QTOF	splash10-002k-1649210000-d61b6ac72098bbabce1f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Negative-QTOF	splash10-0udi-0000090000-9648cd92e47a06887473	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Negative-QTOF	splash10-0udi-0000090000-741c92b14aa8e655218b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Negative-QTOF	splash10-000i-0523390000-30cf545a0a3c2e6d481a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Negative-QTOF	splash10-0udi-0201090000-89b12c6670e6ff645b95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Negative-QTOF	splash10-0udr-0655190000-34b4cc9611aa9015ae39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Negative-QTOF	splash10-0avs-0619000000-d6873bb91373d82692a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Positive-QTOF	splash10-0m02-0439550000-2f94eab30c482944b04f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Positive-QTOF	splash10-0079-0539610000-771f480490febb3af835	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Positive-QTOF	splash10-01q1-0329100000-12b336b001d210523254	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Breast Milk

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.140 (0.078-0.240) uM	Adult (>18 years old)	Both	Normal	16046287	details
Blood	Detected and Quantified	0.30 +/- 0.20 uM	Adult (>18 years old)	Both	Normal	15705230	details
Blood	Detected and Quantified	0.29 +/- 0.20 uM	Adult (>18 years old)	Both	Normal	15705230	details
Blood	Detected and Quantified	0.14 +/- 0.018 uM	Adult (>18 years old)	Both	Normal	15930488	details
Blood	Detected and Quantified	0.0832 +/- 0.0307 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	0.465 +/- 0.351 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	9164160	details
Breast Milk	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	9164160	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724629

PDB ID

Not Available

ChEBI ID

10223

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000388

Good Scents ID

Not Available

References

Synthesis Reference

Khachik, Frederick; Liu, Yufa; Showalter, Holly. Process for the preparation of alpha- and beta-cryptoxanthin from lutein and/or lutein esters by catalytic hydrogenation. U.S. Pat. Appl. Publ. (2006), 17 pp. Khachik F, Chang AN, Gana A, Mazzola E. Partial synthesis of (3R,6'R)-alpha-cryptoxanthin and (3R)-beta-cryptoxanthin from (3R,3'R,6'R)-lutein. J Nat Prod. 2007 Feb;70(2):220-6. Epub 2007 Feb 1.

Material Safety Data Sheet (MSDS)

Not Available

General References

Khachik F, Chang AN, Gana A, Mazzola E: Partial synthesis of (3R,6'R)-alpha-cryptoxanthin and (3R)-beta-cryptoxanthin from (3R,3'R,6'R)-lutein. J Nat Prod. 2007 Feb;70(2):220-6. Epub 2007 Feb 1. [PubMed:17266370 ]
Song BJ, Jouni ZE, Ferruzzi MG: Assessment of phytochemical content in human milk during different stages of lactation. Nutrition. 2013 Jan;29(1):195-202. doi: 10.1016/j.nut.2012.07.015. [PubMed:23237648 ]
Ollberding NJ, Maskarinec G, Conroy SM, Morimoto Y, Franke AA, Cooney RV, Wilkens LR, Le Marchand L, Goodman MT, Hernandez BY, Henderson BE, Kolonel LN: Prediagnostic circulating carotenoid levels and the risk of non-Hodgkin lymphoma: the Multiethnic Cohort. Blood. 2012 Jun 14;119(24):5817-23. doi: 10.1182/blood-2012-02-413609. Epub 2012 May 1. [PubMed:22550343 ]
de Azevedo-Meleiro CH, Rodriguez-Amaya DB: Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS. J Sep Sci. 2009 Nov;32(21):3652-8. doi: 10.1002/jssc.200900311. [PubMed:19813226 ]
Breithaupt DE, Yahia EM, Velazquez FJ: Comparison of the absorption efficiency of alpha- and beta-cryptoxanthin in female Wistar rats. Br J Nutr. 2007 Feb;97(2):329-36. [PubMed:17298702 ]

Showing metabocard for Alpha-Cryptoxanthin (HMDB0002268)

MOL for HMDB0002268 (Alpha-Cryptoxanthin)

3D MOL for HMDB0002268 (Alpha-Cryptoxanthin)

3D SDF for HMDB0002268 (Alpha-Cryptoxanthin)

3D-SDF for HMDB0002268 (Alpha-Cryptoxanthin)

PDB for HMDB0002268 (Alpha-Cryptoxanthin)

3D PDB for HMDB0002268 (Alpha-Cryptoxanthin)

SMILES for HMDB0002268 (Alpha-Cryptoxanthin)

INCHI for HMDB0002268 (Alpha-Cryptoxanthin)

Structure for HMDB0002268 (Alpha-Cryptoxanthin)

3D Structure for HMDB0002268 (Alpha-Cryptoxanthin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra