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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:07:11 UTC

Update Date

2021-09-23 03:07:11 UTC

HMDB ID

HMDB0301859

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oryzalexin A

Description

Oryzalexin a, also known as 3a,7-oxo-ent-sandaracopimaradiene, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Oryzalexin a is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Oryzalexin a can be found in rice, which makes oryzalexin a a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301859
     RDKit          3D
Oryzalexin A
 52 54  0  0  0  0  0  0  0  0999 V2000
    5.4854    0.9122   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    0.1294   -1.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -0.4793   -0.4551 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0972   -1.2474    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771    0.6373    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.6893   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    1.8888    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    2.8303    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.0041    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522    0.8652   -0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9081    0.8549    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    0.5522    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    2.2247   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432   -0.1778   -0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9075   -0.1842   -0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9858   -1.5389   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5095   -1.6301   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -0.4572    0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4228   -0.5632    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.3616   -0.6921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3186   -1.6535   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696   -1.3647   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3200    1.3715   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888    1.1335    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.0700   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282   -1.5772    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093   -2.1646    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734   -0.6210    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.4574    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1924    2.1920    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827    2.9460   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    1.0349   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.4552    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3703    0.6220    1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    1.3588    2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407    2.1196   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849    2.7372   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913    2.8306    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3914    0.1458   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4029   -0.7637   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748   -1.9223    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -2.2032   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -2.5047    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186   -1.9451   -1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    0.3151    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.6609    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388   -1.5147    1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.1482   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393   -2.0085    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -2.4719   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -2.3268   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -0.8367   -2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 20  6  1  0
 18 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END


  Mrv0541 02241220462D          

 22 24  0  0  1  0            999 V2000
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    0.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  5  8  1  1  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  3  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 12 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0301859

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)[C@H](O)CC[C@@]2(C)[C@@H]3CC[C@@](C)(C=C)C=C3C(=O)C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-6-19(4)9-7-14-13(12-19)15(21)11-16-18(2,3)17(22)8-10-20(14,16)5/h6,12,14,16-17,22H,1,7-11H2,2-5H3/t14-,16-,17-,19-,20+/m1/s1

> <INCHI_KEY>
QOWLIQGNZBOQNG-JECYIRHJSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.824158769981004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4aR,4bS,7S,10aS)-7-ethenyl-2-hydroxy-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-9-one

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.9773975516666673

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.554097164706643

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068223152479964

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.82629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oryzalexin A

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0301859
     RDKit          3D
Oryzalexin A
 52 54  0  0  0  0  0  0  0  0999 V2000
    5.4854    0.9122   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    0.1294   -1.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -0.4793   -0.4551 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0972   -1.2474    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771    0.6373    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.6893   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    1.8888    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    2.8303    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.0041    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522    0.8652   -0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9081    0.8549    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    0.5522    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    2.2247   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432   -0.1778   -0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9075   -0.1842   -0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9858   -1.5389   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5095   -1.6301   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -0.4572    0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4228   -0.5632    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.3616   -0.6921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3186   -1.6535   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696   -1.3647   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3200    1.3715   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888    1.1335    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.0700   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282   -1.5772    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093   -2.1646    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734   -0.6210    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.4574    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1924    2.1920    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827    2.9460   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    1.0349   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.4552    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3703    0.6220    1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    1.3588    2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407    2.1196   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849    2.7372   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913    2.8306    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3914    0.1458   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4029   -0.7637   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748   -1.9223    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -2.2032   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -2.5047    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186   -1.9451   -1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    0.3151    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.6609    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388   -1.5147    1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.1482   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393   -2.0085    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -2.4719   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -2.3268   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -0.8367   -2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 20  6  1  0
 18 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.121   1.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8    9                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13   18   22                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20   21                                             
CONECT   18   17   12   19                                                  
CONECT   19   18    2                                                       
CONECT   20   17                                                            
CONECT   21   17                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0301859
HETATM    1  C1  UNL     1       5.485   0.912  -0.576  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.639   0.129  -1.201  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.514  -0.479  -0.455  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.097  -1.247   0.721  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.677   0.637   0.037  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.381   0.689  -0.066  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.716   1.889   0.486  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.377   2.830   0.979  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.749   2.004   0.469  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.452   0.865  -0.182  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.908   0.855   0.132  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.245   0.552   1.548  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.467   2.225  -0.203  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.543  -0.178  -0.753  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.907  -0.184  -0.517  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.986  -1.539  -0.487  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.510  -1.630  -0.413  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.764  -0.457   0.064  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.423  -0.563   1.530  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.573  -0.362  -0.692  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.319  -1.653  -0.655  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.670  -1.365  -1.326  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.320   1.371  -1.102  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.389   1.133   0.489  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.758  -0.070  -2.247  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.128  -1.577   0.460  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.509  -2.165   0.876  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.173  -0.621   1.626  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.247   1.457   0.518  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.192   2.192   1.476  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.983   2.946  -0.111  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.371   1.035  -1.298  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.990  -0.455   1.892  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.370   0.622   1.633  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.885   1.359   2.253  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.541   2.120  -0.460  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.885   2.737  -0.981  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.391   2.831   0.730  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.391   0.146  -1.812  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.403  -0.764  -1.154  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.475  -1.922   0.441  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.369  -2.203  -1.306  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.258  -2.505   0.258  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.119  -1.945  -1.421  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.729   0.315   2.121  1.00  0.00           H  
HETATM   46  H24 UNL     1       0.688  -0.661   1.703  1.00  0.00           H  
HETATM   47  H25 UNL     1      -0.839  -1.515   1.974  1.00  0.00           H  
HETATM   48  H26 UNL     1       0.367  -0.148  -1.779  1.00  0.00           H  
HETATM   49  H27 UNL     1       1.539  -2.009   0.371  1.00  0.00           H  
HETATM   50  H28 UNL     1       0.863  -2.472  -1.207  1.00  0.00           H  
HETATM   51  H29 UNL     1       3.205  -2.327  -1.474  1.00  0.00           H  
HETATM   52  H30 UNL     1       2.508  -0.837  -2.290  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4    5   22
CONECT    4   26   27   28
CONECT    5    6    6   29
CONECT    6    7   20
CONECT    7    8    8    9
CONECT    9   10   30   31
CONECT   10   11   18   32
CONECT   11   12   13   14
CONECT   12   33   34   35
CONECT   13   36   37   38
CONECT   14   15   16   39
CONECT   15   40
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   19   20
CONECT   19   45   46   47
CONECT   20   21   48
CONECT   21   22   49   50
CONECT   22   51   52
END

HMDB0301859
     RDKit          3D
Oryzalexin A
 52 54  0  0  0  0  0  0  0  0999 V2000
    5.4854    0.9122   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    0.1294   -1.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -0.4793   -0.4551 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0972   -1.2474    0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771    0.6373    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.6893   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162    1.8888    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    2.8303    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.0041    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522    0.8652   -0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9081    0.8549    0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    0.5522    1.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    2.2247   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432   -0.1778   -0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9075   -0.1842   -0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9858   -1.5389   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5095   -1.6301   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -0.4572    0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4228   -0.5632    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.3616   -0.6921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3186   -1.6535   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696   -1.3647   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3200    1.3715   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888    1.1335    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.0700   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282   -1.5772    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5093   -2.1646    0.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734   -0.6210    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.4574    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1924    2.1920    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827    2.9460   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    1.0349   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.4552    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3703    0.6220    1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    1.3588    2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407    2.1196   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849    2.7372   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3913    2.8306    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3914    0.1458   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4029   -0.7637   -1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748   -1.9223    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -2.2032   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -2.5047    0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186   -1.9451   -1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    0.3151    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -0.6609    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388   -1.5147    1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.1482   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393   -2.0085    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630   -2.4719   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -2.3268   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -0.8367   -2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 20  6  1  0
 18 10  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3alpha,7-oxo-ent-Sandaracopimaradiene	ChEBI
3alpha-ent-Sandaracopimaradien-7-one	ChEBI
3a,7-oxo-ent-Sandaracopimaradiene	Generator
3Α,7-oxo-ent-sandaracopimaradiene	Generator
3a-ent-Sandaracopimaradien-7-one	Generator
3Α-ent-sandaracopimaradien-7-one	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

IUPAC Name

(2R,4aR,4bS,7S,10aS)-7-ethenyl-2-hydroxy-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-9-one

Traditional Name

oryzalexin A

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H](O)CC[C@@]2(C)[C@@H]3CC[C@@](C)(C=C)C=C3C(=O)C[C@H]12

InChI Identifier

InChI=1S/C20H30O2/c1-6-19(4)9-7-14-13(12-19)15(21)11-16-18(2,3)17(22)8-10-20(14,16)5/h6,12,14,16-17,22H,1,7-11H2,2-5H3/t14-,16-,17-,19-,20+/m1/s1

InChI Key

QOWLIQGNZBOQNG-JECYIRHJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

tricyclic diterpenoid (CHEBI:78258 )
Pimaranes (C09148 )

Ontology

Not Available

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

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
logP	3.67	ALOGPS
logP	3.98	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.83 m³·mol⁻¹	ChemAxon
Polarizability	35.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	176.532	32859911
AllCCS	[M+H-H2O]+	173.444	32859911
AllCCS	[M+Na]+	180.214	32859911
AllCCS	[M+NH4]+	179.392	32859911
AllCCS	[M-H]-	183.276	32859911
AllCCS	[M+Na-2H]-	183.719	32859911
AllCCS	[M+HCOO]-	184.345	32859911
DeepCCS	[M-2H]-	211.162	30932474
DeepCCS	[M+Na]+	186.167	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oryzalexin A,2TMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C)CC[C@@]3(C)[C@@H]2CC1	2416.5	Semi standard non polar	33892256
Oryzalexin A,2TMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C)CC[C@@]3(C)[C@@H]2CC1	2350.7	Standard non polar	33892256
Oryzalexin A,2TMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C)CC[C@@]3(C)[C@@H]2CC1	2816.8	Standard polar	33892256
Oryzalexin A,2TBDMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C(C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]3(C)[C@@H]2CC1	2867.6	Semi standard non polar	33892256
Oryzalexin A,2TBDMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C(C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]3(C)[C@@H]2CC1	2728.4	Standard non polar	33892256
Oryzalexin A,2TBDMS,isomer #1	C=C[C@@]1(C)C=C2C(O[Si](C)(C)C(C)(C)C)=C[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]3(C)[C@@H]2CC1	3052.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 10V, Positive-QTOF	splash10-0f79-1094000000-fd40020e57de89576e5d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 20V, Positive-QTOF	splash10-0fri-4191000000-990746a32b9980336c02	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 40V, Positive-QTOF	splash10-0udi-9160000000-23e79adbcc5af2ce41f7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 10V, Negative-QTOF	splash10-0udi-0029000000-6212b0a28988a457bda0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 20V, Negative-QTOF	splash10-0udi-0069000000-ca99ce34f88391d19b6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 40V, Negative-QTOF	splash10-0fy9-2190000000-0989484e4aa7a7162768	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 10V, Positive-QTOF	splash10-0udi-0059000000-4d291718f3028fe8774d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 20V, Positive-QTOF	splash10-0uki-2592000000-2d43830b0ad5a09ad9e7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 40V, Positive-QTOF	splash10-007c-5910000000-03814e6614c6b1064b21	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 10V, Negative-QTOF	splash10-0udi-0009000000-16d58525184e918518fa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 20V, Negative-QTOF	splash10-0udi-0019000000-1eeabfa4697915e0ec72	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalexin A 40V, Negative-QTOF	splash10-0udi-0095000000-8c2a0d2ae2d5b9c945d2	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158755

PDB ID

Not Available

ChEBI ID

78258

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

Not Available

Showing metabocard for Oryzalexin A (HMDB0301859)

MOL for HMDB0301859 (Oryzalexin A)

3D MOL for HMDB0301859 (Oryzalexin A)

3D SDF for HMDB0301859 (Oryzalexin A)

3D-SDF for HMDB0301859 (Oryzalexin A)

PDB for HMDB0301859 (Oryzalexin A)

3D PDB for HMDB0301859 (Oryzalexin A)

SMILES for HMDB0301859 (Oryzalexin A)

INCHI for HMDB0301859 (Oryzalexin A)

Structure for HMDB0301859 (Oryzalexin A)

3D Structure for HMDB0301859 (Oryzalexin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra