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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:50:40 UTC

Update Date

2022-03-07 02:55:24 UTC

HMDB ID

HMDB0037591

Secondary Accession Numbers

HMDB37591

Metabolite Identification

Common Name

Oryzalide A

Description

Oryzalide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Oryzalide A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0037591
     RDKit          3D
Oryzalide A
 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.4757    1.5765    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    0.3586   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729    0.4308   -1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -0.8324    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7673   -0.8567    0.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -1.9107    0.9440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -1.9738    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -2.4294   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -0.6105    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -0.0288    1.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    0.3217   -0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.6844   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    1.7574   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2738    0.5470   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    0.3287   -1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -0.6264   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6429   -1.9419   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -1.9110    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -0.7389   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    0.1153    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7919    0.8459    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7048   -0.2016    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    0.7858    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    2.5089    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432    1.6706    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.4190    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.2590   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476    1.4389   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897    0.0369   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8806   -2.6522    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -2.7586   -1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    1.0616    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -0.5170    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -0.2139    2.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.1105   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    2.2048   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181    2.2468    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898    2.6084    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    2.1591   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828    1.2764   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8544   -0.0706   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831   -0.7727   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -2.5670   -1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -2.4723    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513   -2.8337   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -2.0402    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336   -0.9820   -1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6359    1.9079    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348    0.7555    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554    0.4343    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    1.8309    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  2  1  0
 19 14  1  0
 23 20  1  0
 19  9  1  0
 23 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
M  END


  Mrv0541 02241218032D          

 23 27  0  0  0  0            999 V2000
   -2.1406    0.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263    1.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -1.0831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0136   -1.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136    0.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -0.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    0.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    0.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 16  2  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 20  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 21  1  0  0  0  0
 13 14  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037591

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12OC1C13CC2CCC1C1(C)C(O)OC(=O)C(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-16(2)11-7-8-19-9-10(18(4)13(19)23-18)5-6-12(19)17(11,3)15(21)22-14(16)20/h10-13,15,21H,5-9H2,1-4H3

> <INCHI_KEY>
JEZFFKVMFCDTRK-UHFFFAOYSA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.4232

> <EXACT_MASS>
320.198759384

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.779871151163974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-5,5,9,14-tetramethyl-7,15-dioxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-one

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
3.121610039666667

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.799991413821344

> <JCHEM_PKA_STRONGEST_BASIC>
-4.198483755594544

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
83.47919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-5,5,9,14-tetramethyl-7,15-dioxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037591
     RDKit          3D
Oryzalide A
 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.4757    1.5765    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    0.3586   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729    0.4308   -1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -0.8324    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7673   -0.8567    0.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -1.9107    0.9440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -1.9738    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -2.4294   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -0.6105    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -0.0288    1.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    0.3217   -0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.6844   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    1.7574   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2738    0.5470   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    0.3287   -1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -0.6264   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6429   -1.9419   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -1.9110    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -0.7389   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    0.1153    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7919    0.8459    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7048   -0.2016    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    0.7858    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    2.5089    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432    1.6706    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.4190    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.2590   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476    1.4389   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897    0.0369   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8806   -2.6522    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -2.7586   -1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    1.0616    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -0.5170    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -0.2139    2.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.1105   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    2.2048   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181    2.2468    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898    2.6084    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    2.1591   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828    1.2764   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8544   -0.0706   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831   -0.7727   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -2.5670   -1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -2.4723    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513   -2.8337   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -2.0402    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336   -0.9820   -1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6359    1.9079    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348    0.7555    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554    0.4343    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    1.8309    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  2  1  0
 19 14  1  0
 23 20  1  0
 19  9  1  0
 23 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  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      -3.996   0.290   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.996  -1.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.662  -2.022   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.332  -1.251   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.332   0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.662   1.058   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001  -2.022   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.332  -1.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.332   0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.001   1.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.660   1.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.660   2.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.332   3.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.001   2.592   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.662   2.600   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.332  -2.022   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.433  -3.358   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.892  -3.358   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.332   1.832   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.668  -0.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.996   1.821   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.466   0.021   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.332   2.592   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4   17   18                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    1    5   15                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15    6                                                            
CONECT   16    2                                                            
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    9   21   22                                                  
CONECT   21   12   20   22   23                                             
CONECT   22   20   21                                                       
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0037591
HETATM    1  C1  UNL     1      -3.476   1.577   0.673  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.066   0.359  -0.134  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.873   0.431  -1.435  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.552  -0.832   0.597  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.767  -0.857   0.923  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.770  -1.911   0.944  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.443  -1.974   0.459  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.497  -2.429  -0.855  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.829  -0.611   0.460  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.675  -0.029   1.837  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.611   0.322  -0.440  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.990   1.684  -0.491  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.465   1.757  -0.540  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.274   0.547  -0.307  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.314   0.329  -1.426  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.243  -0.626  -0.729  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.643  -1.942  -0.404  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.299  -1.911   0.219  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.523  -0.739  -0.253  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.505   0.115   0.565  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.792   0.846   0.730  1.00  0.00           C  
HETATM   22  O4  UNL     1       2.705  -0.202   1.623  1.00  0.00           O  
HETATM   23  C19 UNL     1       2.189   0.786   0.858  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.465   2.509   0.056  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.943   1.671   1.622  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.566   1.419   0.921  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.386  -0.259  -2.172  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.848   1.439  -1.852  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.890   0.037  -1.242  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.881  -2.652   1.121  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.420  -2.759  -1.095  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.544   1.062   1.803  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.096  -0.517   2.433  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.647  -0.214   2.366  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.503  -0.110  -1.480  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.476   2.205  -1.371  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.418   2.247   0.394  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.790   2.608   0.138  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.762   2.159  -1.559  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.883   1.276  -1.588  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.854  -0.071  -2.330  1.00  0.00           H  
HETATM   42  H19 UNL     1       4.183  -0.773  -1.266  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.663  -2.567  -1.343  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.336  -2.472   0.294  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.751  -2.834  -0.150  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.301  -2.040   1.323  1.00  0.00           H  
HETATM   47  H24 UNL     1       0.234  -0.982  -1.322  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.636   1.908   0.426  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.235   0.755   1.737  1.00  0.00           H  
HETATM   50  H27 UNL     1       5.555   0.434   0.023  1.00  0.00           H  
HETATM   51  H28 UNL     1       2.305   1.831   1.236  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   11
CONECT    3   27   28   29
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    9   30
CONECT    8   31
CONECT    9   10   11   19
CONECT   10   32   33   34
CONECT   11   12   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   19   23
CONECT   15   16   40   41
CONECT   16   17   20   42
CONECT   17   18   43   44
CONECT   18   19   45   46
CONECT   19   47
CONECT   20   21   22   23
CONECT   21   48   49   50
CONECT   22   23
CONECT   23   51
END

HMDB0037591
     RDKit          3D
Oryzalide A
 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.4757    1.5765    0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    0.3586   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729    0.4308   -1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -0.8324    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7673   -0.8567    0.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -1.9107    0.9440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4435   -1.9738    0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -2.4294   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -0.6105    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -0.0288    1.8369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112    0.3217   -0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.6844   -0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    1.7574   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2738    0.5470   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144    0.3287   -1.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -0.6264   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6429   -1.9419   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -1.9110    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -0.7389   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    0.1153    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7919    0.8459    0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7048   -0.2016    1.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    0.7858    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    2.5089    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432    1.6706    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.4190    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.2590   -2.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8476    1.4389   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897    0.0369   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8806   -2.6522    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -2.7586   -1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441    1.0616    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -0.5170    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -0.2139    2.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5026   -0.1105   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    2.2048   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181    2.2468    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898    2.6084    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    2.1591   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828    1.2764   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8544   -0.0706   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831   -0.7727   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -2.5670   -1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356   -2.4723    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513   -2.8337   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -2.0402    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336   -0.9820   -1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6359    1.9079    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348    0.7555    1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554    0.4343    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051    1.8309    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  2  1  0
 19 14  1  0
 23 20  1  0
 19  9  1  0
 23 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₄

Average Molecular Weight

320.4232

Monoisotopic Molecular Weight

320.198759384

IUPAC Name

8-hydroxy-5,5,9,14-tetramethyl-7,15-dioxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-one

Traditional Name

8-hydroxy-5,5,9,14-tetramethyl-7,15-dioxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-one

CAS Registry Number

128500-67-4

SMILES

CC12OC1C13CC2CCC1C1(C)C(O)OC(=O)C(C)(C)C1CC3

InChI Identifier

InChI=1S/C19H28O4/c1-16(2)11-7-8-19-9-10(18(4)13(19)23-18)5-6-12(19)17(11,3)15(21)22-14(16)20/h10-13,15,21H,5-9H2,1-4H3

InChI Key

JEZFFKVMFCDTRK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Pyran
Oxane
Lactone
Hemiacetal
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0037591)
Cell membrane (HMDB: HMDB0037591)

Cellular substructure

Extracellular (HMDB: HMDB0037591)
Membrane (HMDB: HMDB0037591)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037591)

Source

Endogenous

Endogenous (HMDB: HMDB0037591)

Plant

Poaceae (HMDB: HMDB0037591)

Animal

Animal (HMDB: HMDB0037591)

Exogenous

Food

Food (HMDB: HMDB0037591)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037591)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037591)

Cellular process

Cell signaling (HMDB: HMDB0037591)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037591)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037591)

Nutrient

Nutrient (HMDB: HMDB0037591)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037591)

Emulsifier (HMDB: HMDB0037591)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 - 205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.8	ALOGPS
logP	3.12	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.48 m³·mol⁻¹	ChemAxon
Polarizability	34.78 Å³	ChemAxon
Number of Rings	5	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]+	176.272	31661259
DarkChem	[M-H]-	170.508	31661259
DeepCCS	[M-2H]-	206.39	30932474
DeepCCS	[M+Na]+	181.618	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	179.9	32859911
AllCCS	[M+Na]+	180.7	32859911
AllCCS	[M-H]-	185.4	32859911
AllCCS	[M+Na-2H]-	185.4	32859911
AllCCS	[M+HCOO]-	185.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oryzalide A	CC12OC1C13CC2CCC1C1(C)C(O)OC(=O)C(C)(C)C1CC3	2882.4	Standard polar	33892256
Oryzalide A	CC12OC1C13CC2CCC1C1(C)C(O)OC(=O)C(C)(C)C1CC3	2226.8	Standard non polar	33892256
Oryzalide A	CC12OC1C13CC2CCC1C1(C)C(O)OC(=O)C(C)(C)C1CC3	2668.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oryzalide A,1TMS,isomer #1	CC1(C)C(=O)OC(O[Si](C)(C)C)C2(C)C1CCC13CC(CCC12)C1(C)OC31	2647.1	Semi standard non polar	33892256
Oryzalide A,1TBDMS,isomer #1	CC1(C)C(=O)OC(O[Si](C)(C)C(C)(C)C)C2(C)C1CCC13CC(CCC12)C1(C)OC31	2887.1	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 - Oryzalide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f92-1390000000-8db03b88c189d07e1033	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oryzalide A GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9378000000-cfca2394697d3d65d2ac	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oryzalide A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 10V, Positive-QTOF	splash10-00di-0079000000-399f44e57f761c319ba8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 20V, Positive-QTOF	splash10-0uk9-0195000000-cc31b238d5478d2b412b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 40V, Positive-QTOF	splash10-0nmi-3950000000-f2baf43b981ad077a434	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 10V, Negative-QTOF	splash10-014i-0089000000-7abe696d87b35d9a3018	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 20V, Negative-QTOF	splash10-0100-0093000000-56174c190caa4527dcca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 40V, Negative-QTOF	splash10-0ldi-4290000000-17b0e3f6d3458f8aac98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 10V, Positive-QTOF	splash10-00di-0009000000-a1ae1335ad38a52f70ad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 20V, Positive-QTOF	splash10-00di-0069000000-8b2c5cee95ad562105ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 40V, Positive-QTOF	splash10-0g59-2911000000-34812e1c6877520ef0da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 10V, Negative-QTOF	splash10-014i-0009000000-0385a0c55ac9f0aa5ed4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 20V, Negative-QTOF	splash10-014i-0009000000-0385a0c55ac9f0aa5ed4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oryzalide A 40V, Negative-QTOF	splash10-014i-0219000000-313e975a67bd0955f2ea	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB016695

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14634289

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Oryzalide A (HMDB0037591)

MOL for HMDB0037591 (Oryzalide A)

3D MOL for HMDB0037591 (Oryzalide A)

3D SDF for HMDB0037591 (Oryzalide A)

3D-SDF for HMDB0037591 (Oryzalide A)

PDB for HMDB0037591 (Oryzalide A)

3D PDB for HMDB0037591 (Oryzalide A)

SMILES for HMDB0037591 (Oryzalide A)

INCHI for HMDB0037591 (Oryzalide A)

Structure for HMDB0037591 (Oryzalide A)

3D Structure for HMDB0037591 (Oryzalide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra