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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:32 UTC

Update Date

2022-03-07 02:53:03 UTC

HMDB ID

HMDB0031633

Secondary Accession Numbers

HMDB31633

Metabolite Identification

Common Name

Orientanol B

Description

Orientanol B belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Orientanol B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, orientanol b has been detected, but not quantified in, green vegetables. This could make orientanol b a potential biomarker for the consumption of these foods.

Structure

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

HMDB0031633
     RDKit          3D
Orientanol B
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.3456   -2.4352    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -1.1811    1.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751   -0.7187    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7839   -1.5202    1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.1308    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    0.1039    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    0.8990    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    0.5154    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.4333    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418    1.0265   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    0.8300   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7359    0.4093   -2.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6707    1.0208    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.5174    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.1782   -1.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657    0.0303   -1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.0922   -1.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.3127   -1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2937    0.3817   -2.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5952    0.4727   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    0.4154    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251    0.1946    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    0.0762    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.3823    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -1.8932    1.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4606   -2.5344    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.2217    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -2.5376    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829   -2.4997    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891    1.8765   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    1.5296    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4339    2.4381   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.8795   -2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1379   -0.1918   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0272    1.3417   -2.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6718   -0.0944   -1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5186    2.1038    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3083    0.4259    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.9209    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6102   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7366   -0.0293   -3.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5159    1.2891   -2.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233    0.6494    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816    0.5422    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0497    0.7346    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.4908    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -2.0338    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 23 14  1  0
 25  5  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
M  END


  Mrv0541 05061306022D          

 25 28  0  0  0  0            999 V2000
    7.8559   -3.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6613   -4.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9506   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5796   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7559   -3.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -3.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  6  1  0  0  0  0
 14  9  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 18 13  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20  9  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
 24 11  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031633

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1CO2

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O4/c1-12(2)4-5-13-8-16-19(10-18(13)23-3)24-11-17-15-7-6-14(22)9-20(15)25-21(16)17/h4,6-10,17,21-22H,5,11H2,1-3H3

> <INCHI_KEY>
FZFGGNNUYSILSL-UHFFFAOYSA-N

> <FORMULA>
C21H22O4

> <MOLECULAR_WEIGHT>
338.397

> <EXACT_MASS>
338.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.738478143538394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-ol

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
4.237790395666666

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552921963348188

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3971447513832

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
97.30389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031633
     RDKit          3D
Orientanol B
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.3456   -2.4352    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -1.1811    1.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751   -0.7187    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7839   -1.5202    1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.1308    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    0.1039    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    0.8990    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    0.5154    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.4333    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418    1.0265   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    0.8300   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7359    0.4093   -2.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6707    1.0208    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.5174    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.1782   -1.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657    0.0303   -1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.0922   -1.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.3127   -1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2937    0.3817   -2.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5952    0.4727   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    0.4154    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251    0.1946    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    0.0762    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.3823    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -1.8932    1.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4606   -2.5344    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.2217    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -2.5376    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829   -2.4997    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891    1.8765   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    1.5296    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4339    2.4381   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.8795   -2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1379   -0.1918   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0272    1.3417   -2.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6718   -0.0944   -1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5186    2.1038    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3083    0.4259    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.9209    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6102   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7366   -0.0293   -3.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5159    1.2891   -2.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233    0.6494    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816    0.5422    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0497    0.7346    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.4908    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -2.0338    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 23 14  1  0
 25  5  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  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      14.664  -7.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.434  -8.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.974  -4.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.282  -6.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.744  -6.258   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.127  -7.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   23                                                            
CONECT    4    5   12                                                       
CONECT    5    4   13                                                       
CONECT    6    7   14                                                       
CONECT    7    6   15                                                       
CONECT    8   13   16                                                       
CONECT    9   14   20                                                       
CONECT   10   18   19                                                       
CONECT   11   17   24                                                       
CONECT   12    1    2    4                                                  
CONECT   13    5    8   18                                                  
CONECT   14    6    9   22                                                  
CONECT   15    7   17   20                                                  
CONECT   16    8   19   21                                                  
CONECT   17   11   15   21                                                  
CONECT   18   10   13   23                                                  
CONECT   19   10   16   24                                                  
CONECT   20    9   15   25                                                  
CONECT   21   16   17   25                                                  
CONECT   22   14                                                            
CONECT   23    3   18                                                       
CONECT   24   11   19                                                       
CONECT   25   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0031633
HETATM    1  C1  UNL     1      -3.346  -2.435   1.926  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.135  -1.181   1.323  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.875  -0.719   0.983  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.784  -1.520   1.247  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.507  -1.131   0.939  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.676   0.104   0.348  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.418   0.899   0.087  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.730   0.515   0.395  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.865   1.433   0.083  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.642   1.026  -1.093  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.935   0.830  -0.997  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.736   0.409  -2.206  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.671   1.021   0.272  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.054   0.517   0.020  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.576  -0.178  -1.119  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.966   0.030  -1.030  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.960   0.092  -1.993  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.270   0.313  -1.626  1.00  0.00           C  
HETATM   19  O3  UNL     1       7.294   0.382  -2.557  1.00  0.00           O  
HETATM   20  C17 UNL     1       6.595   0.473  -0.298  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.627   0.415   0.675  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.325   0.195   0.292  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.050   0.076   1.080  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.904  -1.382   1.428  1.00  0.00           C  
HETATM   25  O4  UNL     1       1.622  -1.893   1.183  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.461  -2.534   2.056  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.013  -3.222   1.210  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.842  -2.538   2.906  1.00  0.00           H  
HETATM   29  H4  UNL     1      -0.883  -2.500   1.712  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.289   1.877  -0.380  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.534   1.530   0.968  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.434   2.438  -0.129  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.156   0.880  -2.073  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.138  -0.192  -2.901  1.00  0.00           H  
HETATM   35  H10 UNL     1      -6.027   1.342  -2.729  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.672  -0.094  -1.890  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.519   2.104   0.556  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.308   0.426   1.116  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.768   0.921   0.127  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.173   1.610  -0.103  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.737  -0.029  -3.043  1.00  0.00           H  
HETATM   42  H17 UNL     1       7.516   1.289  -2.951  1.00  0.00           H  
HETATM   43  H18 UNL     1       7.623   0.649   0.031  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.882   0.542   1.736  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.050   0.735   1.960  1.00  0.00           H  
HETATM   46  H21 UNL     1       3.155  -1.491   2.500  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.619  -2.034   0.863  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   29
CONECT    5    6    6   25
CONECT    6    7   14
CONECT    7    8    8   30
CONECT    8    9
CONECT    9   10   31   32
CONECT   10   11   11   33
CONECT   11   12   13
CONECT   12   34   35   36
CONECT   13   37   38   39
CONECT   14   15   23   40
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   41
CONECT   18   19   20   20
CONECT   19   42
CONECT   20   21   43
CONECT   21   22   22   44
CONECT   22   23
CONECT   23   24   45
CONECT   24   25   46   47
END

HMDB0031633
     RDKit          3D
Orientanol B
 47 50  0  0  0  0  0  0  0  0999 V2000
   -3.3456   -2.4352    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -1.1811    1.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751   -0.7187    0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7839   -1.5202    1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.1308    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    0.1039    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    0.8990    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    0.5154    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8653    1.4333    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418    1.0265   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    0.8300   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7359    0.4093   -2.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6707    1.0208    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.5174    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.1782   -1.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657    0.0303   -1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596    0.0922   -1.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2697    0.3127   -1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2937    0.3817   -2.5571 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5952    0.4727   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    0.4154    0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251    0.1946    0.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    0.0762    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.3823    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -1.8932    1.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4606   -2.5344    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130   -3.2217    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -2.5376    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829   -2.4997    1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891    1.8765   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5340    1.5296    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4339    2.4381   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.8795   -2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1379   -0.1918   -2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0272    1.3417   -2.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6718   -0.0944   -1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5186    2.1038    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3083    0.4259    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.9209    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.6102   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7366   -0.0293   -3.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5159    1.2891   -2.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233    0.6494    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816    0.5422    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0497    0.7346    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.4908    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191   -2.0338    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 23 14  1  0
 25  5  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-O-Methylcalopocarpin	HMDB
9-Hydroxy-3-methoxy-2-prenylpterocarpan	HMDB

Chemical Formula

C₂₁H₂₂O₄

Average Molecular Weight

338.397

Monoisotopic Molecular Weight

338.151809192

IUPAC Name

5-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-ol

Traditional Name

5-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1CO2

InChI Identifier

InChI=1S/C21H22O4/c1-12(2)4-5-13-8-16-19(10-18(13)23-3)24-11-17-15-7-6-14(22)9-20(15)25-21(16)17/h4,6-10,17,21-22H,5,11H2,1-3H3

InChI Key

FZFGGNNUYSILSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0031633)

Cellular substructure

Membrane (HMDB: HMDB0031633)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031633)

Source

Endogenous

Endogenous (HMDB: HMDB0031633)

Plant

Plant (HMDB: HMDB0031633)

Exogenous

Food

Food (HMDB: HMDB0031633)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	4.01	ALOGPS
logP	4.24	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.3 m³·mol⁻¹	ChemAxon
Polarizability	37.74 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]+	178.785	31661259
DarkChem	[M-H]-	180.595	31661259
DeepCCS	[M+H]+	184.337	30932474
DeepCCS	[M-H]-	181.949	30932474
DeepCCS	[M-2H]-	216.292	30932474
DeepCCS	[M+Na]+	191.917	30932474
AllCCS	[M+H]+	183.3	32859911
AllCCS	[M+H-H2O]+	180.0	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.2	32859911
AllCCS	[M-H]-	187.3	32859911
AllCCS	[M+Na-2H]-	186.8	32859911
AllCCS	[M+HCOO]-	186.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Orientanol B	COC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1CO2	3853.1	Standard polar	33892256
Orientanol B	COC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1CO2	2787.0	Standard non polar	33892256
Orientanol B	COC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1CO2	3070.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Orientanol B,1TMS,isomer #1	COC1=CC2=C(C=C1CC=C(C)C)C1OC3=CC(O[Si](C)(C)C)=CC=C3C1CO2	2961.8	Semi standard non polar	33892256
Orientanol B,1TBDMS,isomer #1	COC1=CC2=C(C=C1CC=C(C)C)C1OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C1CO2	3212.4	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 - Orientanol B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-2957000000-9350144d865fbd7621de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orientanol B GC-MS (1 TMS) - 70eV, Positive	splash10-0007-4519000000-a53e7ce1ac89369541e1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orientanol B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orientanol B 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 - Orientanol B 10V, Positive-QTOF	splash10-000l-1839000000-9c6dfe0c203a23550a88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 20V, Positive-QTOF	splash10-00ll-3966000000-f5395dda17952c5a5448	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 40V, Positive-QTOF	splash10-06dl-5900000000-d9d431e36b17251290da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 10V, Negative-QTOF	splash10-000i-0009000000-cc017c470169dbd5c733	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 20V, Negative-QTOF	splash10-000i-0219000000-11b678c2dc279d38442d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 40V, Negative-QTOF	splash10-00l2-0911000000-d64de7362f502643388d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 10V, Positive-QTOF	splash10-000i-0039000000-5628e154efaecfe85550	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 20V, Positive-QTOF	splash10-0019-0096000000-2c21db4df135bb57455c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 40V, Positive-QTOF	splash10-000w-4791000000-8d52211a4a52ccdab626	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 10V, Negative-QTOF	splash10-000i-0009000000-58aebbe019e7e30272d1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 20V, Negative-QTOF	splash10-000i-0009000000-73f8911c808a8e945fe7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientanol B 40V, Negative-QTOF	splash10-052r-1196000000-a17f5a61f440d7ff2495	2021-09-24	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

FDB008278

KNApSAcK ID

Not Available

Chemspider ID

1617

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1680

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.. .

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

Orientanol B → 3,4,5-trihydroxy-6-{[5-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for Orientanol B (HMDB0031633)

MOL for HMDB0031633 (Orientanol B)

3D MOL for HMDB0031633 (Orientanol B)

3D SDF for HMDB0031633 (Orientanol B)

3D-SDF for HMDB0031633 (Orientanol B)

PDB for HMDB0031633 (Orientanol B)

3D PDB for HMDB0031633 (Orientanol B)

SMILES for HMDB0031633 (Orientanol B)

INCHI for HMDB0031633 (Orientanol B)

Structure for HMDB0031633 (Orientanol B)

3D Structure for HMDB0031633 (Orientanol B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions