Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:02 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030141

Secondary Accession Numbers

HMDB30141

Metabolite Identification

Common Name

Isosojagol

Description

Isosojagol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, isosojagol is considered to be a flavonoid. Isosojagol has been detected, but not quantified in, pulses and scarlet beans (Phaseolus coccineus). This could make isosojagol a potential biomarker for the consumption of these foods. Isosojagol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Isosojagol.

Structure

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

HMDB0030141
     RDKit          3D
Isosojagol
 41 44  0  0  0  0  0  0  0  0999 V2000
    5.0668    1.4620    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.2144   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5785    1.3281   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389    0.9043   -0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603    0.7387    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -0.5598    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.7386    1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717   -1.7914    1.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.9609    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -2.9454    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.7519    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -0.5576    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    0.4348    0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.0339    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    0.5147    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3012    1.8721   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5451    2.4491   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896    1.6781   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9513    2.2153   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5483    0.3074   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.3000   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -1.5973    0.1270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -2.1452    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793   -3.4023    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -1.4151    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086    2.2332   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.5277    0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6394    1.7855    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.3373   -2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2159    0.4120   -2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    2.1839   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.7461   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428    1.5880    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    0.8048    1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.9999    1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -3.8783    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -3.8341    0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    2.4931   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481    3.5260   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9998    3.2215   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4667   -0.2910   -0.3350 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 12  6  1  0
 25 14  2  0
 25 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
M  END


  Mrv0541 05061305022D          

 25 28  0  0  0  0            999 V2000
    0.0506   -0.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -0.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043    0.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6435   -0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
 25 18  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030141

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-17-19(25-18(12)14)13-6-4-11(21)9-16(13)24-20(17)23/h3-4,6-9,21-22H,5H2,1-2H3

> <INCHI_KEY>
MQKLGUOASGICKG-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.80342990592938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
4.125888321666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.443727235600855

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.093798964333929

> <JCHEM_PKA_STRONGEST_BASIC>
-4.374138963317734

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
93.86229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isosojagol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030141
     RDKit          3D
Isosojagol
 41 44  0  0  0  0  0  0  0  0999 V2000
    5.0668    1.4620    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.2144   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5785    1.3281   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389    0.9043   -0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603    0.7387    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -0.5598    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.7386    1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717   -1.7914    1.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.9609    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -2.9454    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.7519    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -0.5576    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    0.4348    0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.0339    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    0.5147    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3012    1.8721   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5451    2.4491   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896    1.6781   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9513    2.2153   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5483    0.3074   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.3000   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -1.5973    0.1270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -2.1452    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793   -3.4023    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -1.4151    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086    2.2332   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.5277    0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6394    1.7855    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.3373   -2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2159    0.4120   -2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    2.1839   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.7461   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428    1.5880    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    0.8048    1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.9999    1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -3.8783    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -3.8341    0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    2.4931   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481    3.5260   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9998    3.2215   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4667   -0.2910   -0.3350 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 12  6  1  0
 25 14  2  0
 25 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  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       0.094  -0.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.570  -0.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.128   1.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.241   2.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.201  -0.097   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9   11   16                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    9   21                                                  
CONECT   12    5   15   18                                                  
CONECT   13    6   16   19                                                  
CONECT   14    7   17   18                                                  
CONECT   15    8   12   22                                                  
CONECT   16    9   13   24                                                  
CONECT   17   14   19   20                                                  
CONECT   18   12   14   25                                                  
CONECT   19   13   17   25                                                  
CONECT   20   17   23   24                                                  
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   20                                                            
CONECT   24   16   20                                                       
CONECT   25   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0030141
HETATM    1  C1  UNL     1       5.067   1.462   0.271  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.090   1.214  -0.811  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.579   1.328  -2.209  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.839   0.904  -0.593  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.160   0.739   0.714  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.462  -0.560   0.791  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.105  -1.739   1.023  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.472  -1.791   1.221  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.413  -2.961   1.076  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.052  -2.945   0.886  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.604  -1.752   0.651  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.084  -0.558   0.601  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.736   0.435   0.367  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.971  -0.034   0.254  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.212   0.515   0.016  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.301   1.872  -0.161  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.545   2.449  -0.403  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.690   1.678  -0.467  1.00  0.00           C  
HETATM   19  O3  UNL     1      -6.951   2.215  -0.706  1.00  0.00           O  
HETATM   20  C17 UNL     1      -5.548   0.307  -0.281  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.345  -0.300  -0.041  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.267  -1.597   0.127  1.00  0.00           O  
HETATM   23  C19 UNL     1      -3.094  -2.145   0.355  1.00  0.00           C  
HETATM   24  O5  UNL     1      -2.979  -3.402   0.524  1.00  0.00           O  
HETATM   25  C20 UNL     1      -1.927  -1.415   0.427  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.809   2.233  -0.102  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.691   0.528   0.360  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.639   1.786   1.224  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.781   1.337  -2.951  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.216   0.412  -2.383  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.278   2.184  -2.282  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.209   0.746  -1.499  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.443   1.588   0.910  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.906   0.805   1.541  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.064  -1.000   1.217  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.920  -3.878   1.257  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.565  -3.834   0.909  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.427   2.493  -0.116  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.648   3.526  -0.548  1.00  0.00           H  
HETATM   40  H15 UNL     1      -7.000   3.221  -0.835  1.00  0.00           H  
HETATM   41  H16 UNL     1      -6.467  -0.291  -0.335  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14
CONECT   14   15   25   25
CONECT   15   16   16   21
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   23
CONECT   23   24   24   25
END

HMDB0030141
     RDKit          3D
Isosojagol
 41 44  0  0  0  0  0  0  0  0999 V2000
    5.0668    1.4620    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.2144   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5785    1.3281   -2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389    0.9043   -0.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603    0.7387    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -0.5598    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.7386    1.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717   -1.7914    1.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -2.9609    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -2.9454    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6038   -1.7519    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -0.5576    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    0.4348    0.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.0339    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    0.5147    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3012    1.8721   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5451    2.4491   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6896    1.6781   -0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9513    2.2153   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5483    0.3074   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -0.3000   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -1.5973    0.1270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0944   -2.1452    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793   -3.4023    0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -1.4151    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086    2.2332   -0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    0.5277    0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6394    1.7855    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7814    1.3373   -2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2159    0.4120   -2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    2.1839   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.7461   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428    1.5880    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    0.8048    1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.9999    1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199   -3.8783    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -3.8341    0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4273    2.4931   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481    3.5260   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9998    3.2215   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4667   -0.2910   -0.3350 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 12  6  1  0
 25 14  2  0
 25 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,9-Dihydroxy-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one	ChEBI
3,9-Dihydroxy-10-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one	ChEBI
3,9-Dihydroxy-10-prenylcoumestan	ChEBI
3,9-Dihydroxy-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Molecular Weight

336.338

Monoisotopic Molecular Weight

336.099773622

IUPAC Name

5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

isosojagol

CAS Registry Number

94390-15-5

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-17-19(25-18(12)14)13-6-4-11(21)9-16(13)24-20(17)23/h3-4,6-9,21-22H,5H2,1-2H3

InChI Key

MQKLGUOASGICKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090009 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030141)
Cell membrane (HMDB: HMDB0030141)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030141)

Source

Endogenous

Endogenous (HMDB: HMDB0030141)

Plant

Plant (HMDB: HMDB0030141)
Fabaceae (HMDB: HMDB0030141)

Exogenous

Food

Food (HMDB: HMDB0030141)

Pulse

Bean

Scarlet bean (FooDB: FOOD00132)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0030141)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.98 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	0.063 g/L	ALOGPS
logP	4.63	ALOGPS
logP	4.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.09	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.86 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	181.02	31661259
DarkChem	[M-H]-	177.306	31661259
DeepCCS	[M+H]+	175.621	30932474
DeepCCS	[M-H]-	173.263	30932474
DeepCCS	[M-2H]-	207.118	30932474
DeepCCS	[M+Na]+	182.346	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	176.7	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.1	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	177.1	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. Predicted by Afia on May 17, 2022.	8.06 minutes	32390414
Predicted by Siyang on May 30, 2022	17.7079 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2790.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	515.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	278.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	704.2 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	699.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1475.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	644.5 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	1580.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	514.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	341.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	326.5 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isosojagol	CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=C1C=CC(O)=C2	4402.7	Standard polar	33892256
Isosojagol	CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=C1C=CC(O)=C2	3204.9	Standard non polar	33892256
Isosojagol	CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=C1C=CC(O)=C2	3404.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isosojagol,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1=C2C(=O)OC2=CC(O)=CC=C21	3351.0	Semi standard non polar	33892256
Isosojagol,1TMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3401.9	Semi standard non polar	33892256
Isosojagol,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3409.4	Semi standard non polar	33892256
Isosojagol,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=C2C(=O)OC2=CC(O)=CC=C21	3554.1	Semi standard non polar	33892256
Isosojagol,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3597.3	Semi standard non polar	33892256
Isosojagol,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3854.8	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 - Isosojagol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btc-4449000000-38f56c1f8b7ad055bbe8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosojagol GC-MS (2 TMS) - 70eV, Positive	splash10-014i-3711900000-1b1cef80febc0a310d8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosojagol 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 - Isosojagol 10V, Positive-QTOF	splash10-000i-0029000000-1acce43c8d76b7527703	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 20V, Positive-QTOF	splash10-00li-4097000000-70205205ac0a0ec11362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 40V, Positive-QTOF	splash10-014i-9281000000-8cb34e891484321ddfb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 10V, Negative-QTOF	splash10-000i-0029000000-70bb2cd1b062cd5e72ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 20V, Negative-QTOF	splash10-000i-0059000000-de5c437a27dd8df50f55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 40V, Negative-QTOF	splash10-006x-4391000000-a1f1562ee55203849e83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 10V, Negative-QTOF	splash10-000i-0009000000-dc81427ba733f47873d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 20V, Negative-QTOF	splash10-000i-0019000000-84b1eddb720ad8776f51	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 40V, Negative-QTOF	splash10-0frl-1091000000-8db29a6542faa34e6373	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 10V, Positive-QTOF	splash10-0019-0049000000-ed20812eeada82c0cb68	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 20V, Positive-QTOF	splash10-001i-0090000000-c377c03c86c8b7b67f09	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosojagol 40V, Positive-QTOF	splash10-0ufr-0190000000-9e69c0a09df1fcb6d41b	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

FDB001947

KNApSAcK ID

C00010050

Chemspider ID

20575877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16744613

PDB ID

Not Available

ChEBI ID

142265

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817371

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 Isosojagol (HMDB0030141)

MOL for HMDB0030141 (Isosojagol)

3D MOL for HMDB0030141 (Isosojagol)

3D SDF for HMDB0030141 (Isosojagol)

3D-SDF for HMDB0030141 (Isosojagol)

PDB for HMDB0030141 (Isosojagol)

3D PDB for HMDB0030141 (Isosojagol)

SMILES for HMDB0030141 (Isosojagol)

INCHI for HMDB0030141 (Isosojagol)

Structure for HMDB0030141 (Isosojagol)

3D Structure for HMDB0030141 (Isosojagol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra