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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 00:15:11 UTC

Update Date

2022-09-22 18:34:58 UTC

HMDB ID

HMDB0038905

Secondary Accession Numbers

HMDB38905

Metabolite Identification

Common Name

Isoangustone A

Description

Isoangustone A belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, isoangustone a is considered to be a flavonoid. Isoangustone A has been detected, but not quantified in, herbs and spices. This could make isoangustone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoangustone A.

Structure

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


  Mrv0541 05061310432D          

 31 33  0  0  0  0            999 V2000
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 21  2  0  0  0  0
 23 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 25 22  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
M  END

HMDB0038905
     RDKit          3D
Isoangustone A
 57 59  0  0  0  0  0  0  0  0999 V2000
    7.3676    2.0993   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6311    1.9670   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    2.1800    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538    1.6770   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    1.5027    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    0.1458    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.0375    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541   -1.2914    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781   -1.4597   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -2.4885   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -2.6154   -1.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.7521   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2323   -1.8985   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2231   -1.0168   -1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5251   -1.1846   -1.7550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003    0.0377   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502    1.0100   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9926    0.5064    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3033    0.4426    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9090    0.9158   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1779   -0.0941    1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859    0.2042    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723    1.2470    0.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -0.6917   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -0.5622    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.3504    0.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.3375    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378   -2.1587    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7981   -3.2379    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6113   -0.9019    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.6457    1.5672 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    1.3651   -2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4457    1.8615   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1998    3.1346   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2819    2.8551    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    2.5366    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8832    1.1903    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793    1.5426   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586    1.6136    1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6820    2.3011    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789    0.8305   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -3.1785   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4168   -2.7316   -2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241   -1.9725   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5794    1.9786    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6007    1.3009   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    0.1509    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0006    1.1060   -0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8231    0.2116   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5121    1.9362   -0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1217   -0.4201    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4109    0.7253    2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6938   -0.9589    2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    1.5615    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -3.3219    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3637   -4.1489    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098   -1.3810    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
  8 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 25  9  1  0
 24 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 27 55  1  0
 29 56  1  0
 31 57  1  0
M  END


  Mrv0541 05061310432D          

 31 33  0  0  0  0            999 V2000
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17  8  1  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 21  2  0  0  0  0
 23 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 18  1  0  0  0  0
 25 22  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31 12  1  0  0  0  0
 31 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038905

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3

> <INCHI_KEY>
QNLGNISMYMFVHP-UHFFFAOYSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.4703

> <EXACT_MASS>
422.172938564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.804669753505465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
6.230441066666666

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.449360709096

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.418737207380767

> <JCHEM_PKA_STRONGEST_BASIC>
-5.231601724739655

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
122.14939999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoangustone A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038905
     RDKit          3D
Isoangustone A
 57 59  0  0  0  0  0  0  0  0999 V2000
    7.3676    2.0993   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6311    1.9670   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    2.1800    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538    1.6770   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    1.5027    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    0.1458    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.0375    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541   -1.2914    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781   -1.4597   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -2.4885   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -2.6154   -1.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.7521   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2323   -1.8985   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2231   -1.0168   -1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5251   -1.1846   -1.7550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003    0.0377   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502    1.0100   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9926    0.5064    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3033    0.4426    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9090    0.9158   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1779   -0.0941    1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859    0.2042    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723    1.2470    0.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -0.6917   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -0.5622    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.3504    0.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.3375    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378   -2.1587    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7981   -3.2379    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6113   -0.9019    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.6457    1.5672 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    1.3651   -2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4457    1.8615   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1998    3.1346   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2819    2.8551    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    2.5366    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8832    1.1903    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793    1.5426   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586    1.6136    1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6820    2.3011    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789    0.8305   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -3.1785   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4168   -2.7316   -2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241   -1.9725   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5794    1.9786    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6007    1.3009   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    0.1509    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0006    1.1060   -0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8231    0.2116   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5121    1.9362   -0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1217   -0.4201    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4109    0.7253    2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6938   -0.9589    2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    1.5615    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -3.3219    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3637   -4.1489    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098   -1.3810    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
  8 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 25  9  1  0
 24 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 27 55  1  0
 29 56  1  0
 31 57  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      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    7   13                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   17                                                       
CONECT    9   15   16                                                       
CONECT   10   16   20                                                       
CONECT   11   19   21                                                       
CONECT   12   18   31                                                       
CONECT   13    1    2    5                                                  
CONECT   14    3    4    6                                                  
CONECT   15    7    9   23                                                  
CONECT   16    9   10   18                                                  
CONECT   17    8   19   24                                                  
CONECT   18   12   16   25                                                  
CONECT   19   11   17   26                                                  
CONECT   20   10   23   27                                                  
CONECT   21   11   22   31                                                  
CONECT   22   21   24   25                                                  
CONECT   23   15   20   28                                                  
CONECT   24   17   22   29                                                  
CONECT   25   18   22   30                                                  
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31   12   21                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0038905
HETATM    1  C1  UNL     1       7.368   2.099  -1.755  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.631   1.967  -0.461  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.426   2.180   0.775  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.354   1.677  -0.475  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.451   1.503   0.666  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.845   0.146   0.686  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.542  -0.038   0.245  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.954  -1.291   0.243  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.578  -1.460  -0.243  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.220  -2.488  -1.098  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.010  -2.615  -1.535  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.934  -1.752  -1.159  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.232  -1.899  -1.632  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.223  -1.017  -1.264  1.00  0.00           C  
HETATM   15  O2  UNL     1      -5.525  -1.185  -1.755  1.00  0.00           O  
HETATM   16  C14 UNL     1      -4.000   0.038  -0.427  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.050   1.010  -0.019  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.993   0.506   0.973  1.00  0.00           C  
HETATM   19  C17 UNL     1      -7.303   0.443   0.821  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.909   0.916  -0.456  1.00  0.00           C  
HETATM   21  C19 UNL     1      -8.178  -0.094   1.917  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.686   0.204   0.067  1.00  0.00           C  
HETATM   23  O3  UNL     1      -2.472   1.247   0.893  1.00  0.00           O  
HETATM   24  C21 UNL     1      -1.691  -0.692  -0.311  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.394  -0.562   0.147  1.00  0.00           C  
HETATM   26  O4  UNL     1      -0.050   0.350   0.915  1.00  0.00           O  
HETATM   27  C23 UNL     1       2.727  -2.338   0.700  1.00  0.00           C  
HETATM   28  C24 UNL     1       4.038  -2.159   1.146  1.00  0.00           C  
HETATM   29  O5  UNL     1       4.798  -3.238   1.604  1.00  0.00           O  
HETATM   30  C25 UNL     1       4.611  -0.902   1.141  1.00  0.00           C  
HETATM   31  O6  UNL     1       5.904  -0.646   1.567  1.00  0.00           O  
HETATM   32  H1  UNL     1       6.936   1.365  -2.479  1.00  0.00           H  
HETATM   33  H2  UNL     1       8.446   1.862  -1.660  1.00  0.00           H  
HETATM   34  H3  UNL     1       7.200   3.135  -2.131  1.00  0.00           H  
HETATM   35  H4  UNL     1       8.282   2.855   0.562  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.854   2.537   1.636  1.00  0.00           H  
HETATM   37  H6  UNL     1       7.883   1.190   1.074  1.00  0.00           H  
HETATM   38  H7  UNL     1       4.879   1.543  -1.469  1.00  0.00           H  
HETATM   39  H8  UNL     1       5.059   1.614   1.602  1.00  0.00           H  
HETATM   40  H9  UNL     1       3.682   2.301   0.724  1.00  0.00           H  
HETATM   41  H10 UNL     1       1.979   0.830  -0.109  1.00  0.00           H  
HETATM   42  H11 UNL     1       1.001  -3.179  -1.387  1.00  0.00           H  
HETATM   43  H12 UNL     1      -3.417  -2.732  -2.296  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.724  -1.972  -2.390  1.00  0.00           H  
HETATM   45  H14 UNL     1      -4.579   1.979   0.315  1.00  0.00           H  
HETATM   46  H15 UNL     1      -5.601   1.301  -0.955  1.00  0.00           H  
HETATM   47  H16 UNL     1      -5.577   0.151   1.921  1.00  0.00           H  
HETATM   48  H17 UNL     1      -9.001   1.106  -0.239  1.00  0.00           H  
HETATM   49  H18 UNL     1      -7.823   0.212  -1.283  1.00  0.00           H  
HETATM   50  H19 UNL     1      -7.512   1.936  -0.738  1.00  0.00           H  
HETATM   51  H20 UNL     1      -9.122  -0.420   1.486  1.00  0.00           H  
HETATM   52  H21 UNL     1      -8.411   0.725   2.656  1.00  0.00           H  
HETATM   53  H22 UNL     1      -7.694  -0.959   2.429  1.00  0.00           H  
HETATM   54  H23 UNL     1      -1.700   1.561   1.342  1.00  0.00           H  
HETATM   55  H24 UNL     1       2.289  -3.322   0.707  1.00  0.00           H  
HETATM   56  H25 UNL     1       4.364  -4.149   1.600  1.00  0.00           H  
HETATM   57  H26 UNL     1       6.510  -1.381   1.912  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    4
CONECT    3   35   36   37
CONECT    4    5   38
CONECT    5    6   39   40
CONECT    6    7    7   30
CONECT    7    8   41
CONECT    8    9   27   27
CONECT    9   10   10   25
CONECT   10   11   42
CONECT   11   12
CONECT   12   13   13   24
CONECT   13   14   43
CONECT   14   15   16   16
CONECT   15   44
CONECT   16   17   22
CONECT   17   18   45   46
CONECT   18   19   19   47
CONECT   19   20   21
CONECT   20   48   49   50
CONECT   21   51   52   53
CONECT   22   23   24   24
CONECT   23   54
CONECT   24   25
CONECT   25   26   26
CONECT   27   28   55
CONECT   28   29   30   30
CONECT   29   56
CONECT   30   31
CONECT   31   57
END

HMDB0038905
     RDKit          3D
Isoangustone A
 57 59  0  0  0  0  0  0  0  0999 V2000
    7.3676    2.0993   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6311    1.9670   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    2.1800    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538    1.6770   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    1.5027    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8454    0.1458    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.0375    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541   -1.2914    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781   -1.4597   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -2.4885   -1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -2.6154   -1.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.7521   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2323   -1.8985   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2231   -1.0168   -1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5251   -1.1846   -1.7550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003    0.0377   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502    1.0100   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9926    0.5064    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3033    0.4426    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9090    0.9158   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1779   -0.0941    1.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859    0.2042    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723    1.2470    0.8930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -0.6917   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -0.5622    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.3504    0.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.3375    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378   -2.1587    1.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7981   -3.2379    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6113   -0.9019    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043   -0.6457    1.5672 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    1.3651   -2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4457    1.8615   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1998    3.1346   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2819    2.8551    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542    2.5366    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8832    1.1903    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793    1.5426   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586    1.6136    1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6820    2.3011    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789    0.8305   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -3.1785   -1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4168   -2.7316   -2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241   -1.9725   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5794    1.9786    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6007    1.3009   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5768    0.1509    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0006    1.1060   -0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8231    0.2116   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5121    1.9362   -0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1217   -0.4201    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4109    0.7253    2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6938   -0.9589    2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    1.5615    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -3.3219    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3637   -4.1489    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098   -1.3810    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
  8 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  6  1  0
 25  9  1  0
 24 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 27 55  1  0
 29 56  1  0
 31 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
5,7,3',4'-Tetrahydroxy-6,5'-diprenylisoflavone	HMDB

Chemical Formula

C₂₅H₂₆O₆

Average Molecular Weight

422.4703

Monoisotopic Molecular Weight

422.172938564

IUPAC Name

3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

isoangustone A

CAS Registry Number

129280-34-8

SMILES

CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O

InChI Identifier

InChI=1S/C25H26O6/c1-13(2)5-7-15-9-16(10-20(27)23(15)28)18-12-31-21-11-19(26)17(8-6-14(3)4)24(29)22(21)25(18)30/h5-6,9-12,26-29H,7-8H2,1-4H3

InChI Key

QNLGNISMYMFVHP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050243 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038905)
Cell membrane (HMDB: HMDB0038905)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038905)

Source

Exogenous

Exogenous (HMDB: HMDB0038905)

Food

Food (HMDB: HMDB0038905)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0038905)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038905)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 - 193 °C	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	0.0058 g/L	ALOGPS
logP	4.6	ALOGPS
logP	6.23	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.42	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.15 m³·mol⁻¹	ChemAxon
Polarizability	46.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	197.67	30932474
DeepCCS	[M-H]-	195.275	30932474
DeepCCS	[M-2H]-	228.349	30932474
DeepCCS	[M+Na]+	203.617	30932474
AllCCS	[M+H]+	205.5	32859911
AllCCS	[M+H-H2O]+	202.9	32859911
AllCCS	[M+NH4]+	208.0	32859911
AllCCS	[M+Na]+	208.7	32859911
AllCCS	[M-H]-	197.2	32859911
AllCCS	[M+Na-2H]-	197.3	32859911
AllCCS	[M+HCOO]-	197.5	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.	9.06 minutes	32390414
Predicted by Siyang on May 30, 2022	17.1385 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3564.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	361.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	815.3 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	902.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1493.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	765.8 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	1658.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	511.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	575.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	262.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	194.3 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoangustone A	CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O	5603.4	Standard polar	33892256
Isoangustone A	CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O	3568.7	Standard non polar	33892256
Isoangustone A	CC(C)=CCC1=CC(=CC(O)=C1O)C1=COC2=C(C(O)=C(CC=C(C)C)C(O)=C2)C1=O	3818.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoangustone A,1TMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O	3802.6	Semi standard non polar	33892256
Isoangustone A,1TMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C	3785.7	Semi standard non polar	33892256
Isoangustone A,1TMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O	3766.2	Semi standard non polar	33892256
Isoangustone A,1TMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O	3807.3	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O	3647.7	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O	3613.2	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3679.2	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C	3641.9	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #5	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C	3609.4	Semi standard non polar	33892256
Isoangustone A,2TMS,isomer #6	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O	3626.8	Semi standard non polar	33892256
Isoangustone A,3TMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O	3579.4	Semi standard non polar	33892256
Isoangustone A,3TMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3580.7	Semi standard non polar	33892256
Isoangustone A,3TMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3552.9	Semi standard non polar	33892256
Isoangustone A,3TMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C	3573.0	Semi standard non polar	33892256
Isoangustone A,4TMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3567.8	Semi standard non polar	33892256
Isoangustone A,1TBDMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4061.2	Semi standard non polar	33892256
Isoangustone A,1TBDMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4055.0	Semi standard non polar	33892256
Isoangustone A,1TBDMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O	4044.0	Semi standard non polar	33892256
Isoangustone A,1TBDMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O	4079.2	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4157.5	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4125.8	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4214.4	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4169.8	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #5	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4129.7	Semi standard non polar	33892256
Isoangustone A,2TBDMS,isomer #6	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O	4155.9	Semi standard non polar	33892256
Isoangustone A,3TBDMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4250.6	Semi standard non polar	33892256
Isoangustone A,3TBDMS,isomer #2	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4309.3	Semi standard non polar	33892256
Isoangustone A,3TBDMS,isomer #3	CC(C)=CCC1=CC(C2=COC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4244.1	Semi standard non polar	33892256
Isoangustone A,3TBDMS,isomer #4	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4249.7	Semi standard non polar	33892256
Isoangustone A,4TBDMS,isomer #1	CC(C)=CCC1=CC(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4381.7	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 - Isoangustone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-2009400000-fcc396668b12f9ceed4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoangustone A GC-MS (3 TMS) - 70eV, Positive	splash10-00di-1000049000-1330420e504cefb1031d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoangustone A 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoangustone A 6V, Positive-QTOF	splash10-02mi-0119500000-08d34dd8a9db84f2de07	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 10V, Positive-QTOF	splash10-00di-0105900000-09af23c5e1012e3c1440	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 20V, Positive-QTOF	splash10-01di-1209300000-c54ae2bd75de8b82f4ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 40V, Positive-QTOF	splash10-01b9-3914200000-6e5d397729c4460abc6f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 10V, Negative-QTOF	splash10-00di-0000900000-7df5cb1698b4620c8029	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 20V, Negative-QTOF	splash10-00di-0155900000-3db7cc32dcda61519cd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 40V, Negative-QTOF	splash10-0pdi-0943100000-b9dafd57755304a4c4ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 10V, Negative-QTOF	splash10-00di-0000900000-1a0e5664f3fc8624ecf1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 20V, Negative-QTOF	splash10-00di-0005900000-727ef5b91ad52e9f747d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 40V, Negative-QTOF	splash10-003u-7159100000-eed20fb3bc7bfc2475f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 10V, Positive-QTOF	splash10-02mi-0019500000-98eab69e0764a08751ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 20V, Positive-QTOF	splash10-08fs-0039100000-db90cccb2448cd99f0f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoangustone A 40V, Positive-QTOF	splash10-06r2-3249000000-29ef362b74f8ed282c89	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	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

FDB018369

KNApSAcK ID

C00009922

Chemspider ID

10211375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21591148

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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.. .

Showing metabocard for Isoangustone A (HMDB0038905)

MOL for HMDB0038905 (Isoangustone A)

3D MOL for HMDB0038905 (Isoangustone A)

3D SDF for HMDB0038905 (Isoangustone A)

3D-SDF for HMDB0038905 (Isoangustone A)

PDB for HMDB0038905 (Isoangustone A)

3D PDB for HMDB0038905 (Isoangustone A)

SMILES for HMDB0038905 (Isoangustone A)

INCHI for HMDB0038905 (Isoangustone A)

Structure for HMDB0038905 (Isoangustone A)

3D Structure for HMDB0038905 (Isoangustone A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra