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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:10 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030650

Secondary Accession Numbers

HMDB30650

Metabolite Identification

Common Name

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one

Description

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one, also known as 6-butyryl-8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-4-propylfuro[2,3-H]coumarin or mammea b/ac cyclo F, belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Based on a literature review very few articles have been published on 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one.

Structure

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


  Mrv0541 05061305252D          

 27 29  0  0  0  0            999 V2000
    3.7759    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4309    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3001    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1717    2.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429    3.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309   -1.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 14  1  0  0  0  0
 22 13  2  0  0  0  0
 23 15  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 27 19  1  0  0  0  0
M  END

HMDB0030650
     RDKit          3D
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-...
 53 55  0  0  0  0  0  0  0  0999 V2000
   -2.4759    5.0914   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    4.5820   -0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0932    3.0797   -0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2738    2.5186    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110    3.3237    0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    1.0872    0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2756    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -1.0762    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696   -1.6495    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -2.9605    0.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715   -3.5522    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823   -4.8133    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -2.8322    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -1.4486    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -0.6217    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -1.5148    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -2.2547   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9004   -0.8754    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    0.5276    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878    1.2638    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284   -1.6839    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611   -0.5894   -0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464   -0.6622   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5784   -0.7128    0.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826   -1.9330   -1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    0.4337   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    0.5723   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391    4.3289   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    5.9584    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    5.4817   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    5.0150    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    4.9607   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7232   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532    2.7726    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -3.2794    0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.0154    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5082   -0.0215   -0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -2.1370    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763   -0.7755    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856   -2.2987   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128   -3.2886   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888   -1.7406   -1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0263    2.2157    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -2.6411   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.8058    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -0.5972   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2629   -1.6004    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7007   -0.7882    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    0.2404    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214   -1.8511   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507   -2.1292   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515   -2.7585   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733    0.4562   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 19  6  1  0
 27  7  1  0
 18  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
M  END


  Mrv0541 05061305252D          

 27 29  0  0  0  0            999 V2000
    3.7759    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4309    3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3001    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    3.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1717    2.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3471    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429    3.2175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309   -1.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 14  1  0  0  0  0
 22 13  2  0  0  0  0
 23 15  2  0  0  0  0
 24 18  1  0  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 27 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030650

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O6/c1-5-7-11-9-15(23)27-19-12-10-14(21(3,4)25)26-20(12)17(13(22)8-6-2)18(24)16(11)19/h9,14,24-25H,5-8,10H2,1-4H3

> <INCHI_KEY>
AHRWRZGWPYCGMI-UHFFFAOYSA-N

> <FORMULA>
C21H26O6

> <MOLECULAR_WEIGHT>
374.4275

> <EXACT_MASS>
374.172938564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.57530477838087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-2H,8H,9H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.9701122509999998

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.296109337394064

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.559922239735995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064568269859967

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
101.43649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-8H,9H-furo[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030650
     RDKit          3D
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-...
 53 55  0  0  0  0  0  0  0  0999 V2000
   -2.4759    5.0914   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    4.5820   -0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0932    3.0797   -0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2738    2.5186    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110    3.3237    0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    1.0872    0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2756    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -1.0762    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696   -1.6495    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -2.9605    0.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715   -3.5522    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823   -4.8133    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -2.8322    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -1.4486    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -0.6217    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -1.5148    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -2.2547   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9004   -0.8754    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    0.5276    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878    1.2638    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284   -1.6839    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611   -0.5894   -0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464   -0.6622   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5784   -0.7128    0.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826   -1.9330   -1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    0.4337   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    0.5723   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391    4.3289   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    5.9584    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    5.4817   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    5.0150    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    4.9607   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7232   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532    2.7726    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -3.2794    0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.0154    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5082   -0.0215   -0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -2.1370    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763   -0.7755    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856   -2.2987   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128   -3.2886   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888   -1.7406   -1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0263    2.2157    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -2.6411   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.8058    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -0.5972   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2629   -1.6004    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7007   -0.7882    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    0.2404    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214   -1.8511   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507   -2.1292   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515   -2.7585   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733    0.4562   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 19  6  1  0
 27  7  1  0
 18  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.048   4.889   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.538   5.862   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.791  -1.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.294   0.578   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.320   3.532   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.998   5.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.781   3.484   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.187   4.601   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.864   0.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.748  -0.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.053   2.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.247   0.674   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.648   4.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.173   0.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.136  -0.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.514   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.163   3.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.703   3.388   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.786   0.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.565   1.983   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.482  -0.731   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.080   6.006   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.948  -1.848   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.431   4.745   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.671  -2.040   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.060   1.616   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.597  -0.587   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   21                                                            
CONECT    4   21                                                            
CONECT    5    1    7                                                       
CONECT    6    2    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6   13                                                       
CONECT    9   11   15                                                       
CONECT   10   12   14                                                       
CONECT   11    7    9   16                                                  
CONECT   12   10   19   20                                                  
CONECT   13    8   17   22                                                  
CONECT   14   10   21   26                                                  
CONECT   15    9   23   27                                                  
CONECT   16   11   18   19                                                  
CONECT   17   13   18   20                                                  
CONECT   18   16   17   24                                                  
CONECT   19   12   16   27                                                  
CONECT   20   12   17   26                                                  
CONECT   21    3    4   14   25                                             
CONECT   22   13                                                            
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26   14   20                                                       
CONECT   27   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0030650
HETATM    1  C1  UNL     1      -2.476   5.091  -0.323  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.074   4.582  -0.139  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.093   3.080  -0.075  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.274   2.519   0.108  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.211   3.324   0.183  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.511   1.087   0.198  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.635   0.276   0.101  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.460  -1.076   0.183  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.770  -1.650   0.351  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.921  -2.960   0.431  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.072  -3.552   0.593  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.182  -4.813   0.667  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.240  -2.832   0.695  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.164  -1.449   0.619  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.372  -0.622   0.706  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.624  -1.515   0.647  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.727  -2.255  -0.658  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.900  -0.875   0.446  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.768   0.528   0.369  1.00  0.00           C  
HETATM   20  O4  UNL     1       2.888   1.264   0.468  1.00  0.00           O  
HETATM   21  C17 UNL     1      -1.828  -1.684   0.054  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.561  -0.589  -0.653  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.046  -0.662  -0.556  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.578  -0.713   0.832  1.00  0.00           C  
HETATM   25  C21 UNL     1      -4.483  -1.933  -1.279  1.00  0.00           C  
HETATM   26  O5  UNL     1      -4.601   0.434  -1.207  1.00  0.00           O  
HETATM   27  O6  UNL     1      -2.000   0.572  -0.071  1.00  0.00           O  
HETATM   28  H1  UNL     1      -3.239   4.329  -0.072  1.00  0.00           H  
HETATM   29  H2  UNL     1      -2.659   5.958   0.365  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.657   5.482  -1.341  1.00  0.00           H  
HETATM   31  H4  UNL     1      -0.656   5.015   0.786  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.476   4.961  -0.993  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.482   2.723  -1.070  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.753   2.773   0.749  1.00  0.00           H  
HETATM   35  H8  UNL     1       4.197  -3.279   0.846  1.00  0.00           H  
HETATM   36  H9  UNL     1       4.479  -0.015   1.603  1.00  0.00           H  
HETATM   37  H10 UNL     1       4.508  -0.022  -0.261  1.00  0.00           H  
HETATM   38  H11 UNL     1       5.728  -2.137   1.539  1.00  0.00           H  
HETATM   39  H12 UNL     1       6.476  -0.775   0.703  1.00  0.00           H  
HETATM   40  H13 UNL     1       4.786  -2.299  -1.238  1.00  0.00           H  
HETATM   41  H14 UNL     1       6.113  -3.289  -0.567  1.00  0.00           H  
HETATM   42  H15 UNL     1       6.489  -1.741  -1.320  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.026   2.216   0.444  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.796  -2.641  -0.480  1.00  0.00           H  
HETATM   45  H18 UNL     1      -2.182  -1.806   1.115  1.00  0.00           H  
HETATM   46  H19 UNL     1      -2.229  -0.597  -1.711  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.263  -1.600   1.407  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.701  -0.788   0.748  1.00  0.00           H  
HETATM   49  H22 UNL     1      -4.402   0.240   1.376  1.00  0.00           H  
HETATM   50  H23 UNL     1      -4.121  -1.851  -2.338  1.00  0.00           H  
HETATM   51  H24 UNL     1      -5.551  -2.129  -1.192  1.00  0.00           H  
HETATM   52  H25 UNL     1      -3.851  -2.759  -0.839  1.00  0.00           H  
HETATM   53  H26 UNL     1      -5.573   0.456  -0.952  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5    5    6
CONECT    6    7    7   19
CONECT    7    8   27
CONECT    8    9    9   21
CONECT    9   10   18
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   35
CONECT   14   15   18
CONECT   15   16   36   37
CONECT   16   17   38   39
CONECT   17   40   41   42
CONECT   18   19   19
CONECT   19   20
CONECT   20   43
CONECT   21   22   44   45
CONECT   22   23   27   46
CONECT   23   24   25   26
CONECT   24   47   48   49
CONECT   25   50   51   52
CONECT   26   53
END

HMDB0030650
     RDKit          3D
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-...
 53 55  0  0  0  0  0  0  0  0999 V2000
   -2.4759    5.0914   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    4.5820   -0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0932    3.0797   -0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2738    2.5186    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110    3.3237    0.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    1.0872    0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2756    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -1.0762    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696   -1.6495    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -2.9605    0.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715   -3.5522    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823   -4.8133    0.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -2.8322    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -1.4486    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722   -0.6217    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -1.5148    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -2.2547   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9004   -0.8754    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    0.5276    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878    1.2638    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8284   -1.6839    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611   -0.5894   -0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464   -0.6622   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5784   -0.7128    0.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826   -1.9330   -1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    0.4337   -1.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    0.5723   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391    4.3289   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    5.9584    0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    5.4817   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    5.0150    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    4.9607   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7232   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532    2.7726    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -3.2794    0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.0154    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5082   -0.0215   -0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -2.1370    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763   -0.7755    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856   -2.2987   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128   -3.2886   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4888   -1.7406   -1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0263    2.2157    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962   -2.6411   -0.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.8058    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -0.5972   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2629   -1.6004    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7007   -0.7882    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    0.2404    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214   -1.8511   -2.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507   -2.1292   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8515   -2.7585   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733    0.4562   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 22 27  1  0
 19  6  1  0
 27  7  1  0
 18  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Butyryl-8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-4-propylfuro[2,3-H]coumarin	HMDB
Mammea b/ac cyclo F	HMDB

Chemical Formula

C₂₁H₂₆O₆

Average Molecular Weight

374.4275

Monoisotopic Molecular Weight

374.172938564

IUPAC Name

6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-2H,8H,9H-furo[2,3-h]chromen-2-one

Traditional Name

6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-8H,9H-furo[2,3-h]chromen-2-one

CAS Registry Number

38537-82-5

SMILES

CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O

InChI Identifier

InChI=1S/C21H26O6/c1-5-7-11-9-15(23)27-19-12-10-14(21(3,4)25)26-20(12)17(13(22)8-6-2)18(24)16(11)19/h9,14,24-25H,5-8,10H2,1-4H3

InChI Key

AHRWRZGWPYCGMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Butyrophenone
Benzopyran
1-benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Ketone
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030650)
Cell membrane (HMDB: HMDB0030650)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030650)

Source

Endogenous

Endogenous (HMDB: HMDB0030650)

Plant

Plant (HMDB: HMDB0030650)

Exogenous

Food

Food (HMDB: HMDB0030650)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030650)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	75 - 81 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.61 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.97	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.44 m³·mol⁻¹	ChemAxon
Polarizability	40.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	189.076	31661259
DarkChem	[M-H]-	190.219	31661259
DeepCCS	[M+H]+	191.204	30932474
DeepCCS	[M-H]-	188.594	30932474
DeepCCS	[M-2H]-	223.138	30932474
DeepCCS	[M+Na]+	198.366	30932474
AllCCS	[M+H]+	188.8	32859911
AllCCS	[M+H-H2O]+	186.1	32859911
AllCCS	[M+NH4]+	191.3	32859911
AllCCS	[M+Na]+	192.0	32859911
AllCCS	[M-H]-	195.0	32859911
AllCCS	[M+Na-2H]-	195.5	32859911
AllCCS	[M+HCOO]-	196.1	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.	8.57 minutes	32390414
Predicted by Siyang on May 30, 2022	17.4741 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2856.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	422.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	217.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	826.4 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	921.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1373.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	555.1 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	1819.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	506.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	306.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	448.8 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	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one	CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O	3514.5	Standard polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one	CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O	2952.8	Standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one	CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O	3056.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TMS,isomer #1	CCCC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C	2866.1	Semi standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TMS,isomer #2	CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O	2882.5	Semi standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,2TMS,isomer #1	CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C	2897.3	Semi standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TBDMS,isomer #1	CCCC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C(C)(C)C	3097.3	Semi standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TBDMS,isomer #2	CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O	3115.3	Semi standard non polar	33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,2TBDMS,isomer #1	CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C(C)(C)C	3349.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8129000000-158a31cf9cb6156bf3c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one GC-MS (2 TMS) - 70eV, Positive	splash10-0fhi-9520440000-a833c314fa7befb3aa68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Positive-QTOF	splash10-056r-0009000000-c5fecb41eb0bbf48c45b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Positive-QTOF	splash10-08j0-2019000000-9194746b460d77b08b27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Positive-QTOF	splash10-0a5c-2090000000-f6ea5249f7ad49b4908e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Negative-QTOF	splash10-00di-0009000000-b4cc5aa0b35ae4c7e1cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Negative-QTOF	splash10-0l6r-2039000000-4261801f1cb0a2abdc01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Negative-QTOF	splash10-0600-4193000000-5d9c7ce1a9eab8248bee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Negative-QTOF	splash10-00di-0009000000-4c8686ce268f4e78c86b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Negative-QTOF	splash10-00di-0019000000-d7d8208b2cd92108b577	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Negative-QTOF	splash10-000g-7191000000-0eb2fa6e1a61b2568755	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Positive-QTOF	splash10-004i-0009000000-4c15654bc7c3dc74190a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Positive-QTOF	splash10-004i-0019000000-fa11b42da471006430c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Positive-QTOF	splash10-03kl-2093000000-3275356c6f610a8b7cc9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002556

KNApSAcK ID

C00046116

Chemspider ID

23333299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44546135

PDB ID

Not Available

ChEBI ID

554198

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1821771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one → 6-{[6-butanoyl-8-(2-hydroxypropan-2-yl)-2-oxo-4-propyl-2H,8H,9H-furo[2,3-h]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one (HMDB0030650)

MOL for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

3D MOL for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

3D SDF for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

3D-SDF for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

PDB for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

3D PDB for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

SMILES for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

INCHI for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

Structure for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

3D Structure for HMDB0030650 (8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions