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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:55:22 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036750

Secondary Accession Numbers

HMDB36750

Metabolite Identification

Common Name

Momilactone C

Description

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

Structure

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

HMDB0036750
     RDKit          3D
Momilactone C
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.4250    2.0036    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.1769   -0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -0.1393    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.9573    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4962    0.0615    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034    0.6230    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798    0.3542   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.9350   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -2.0156   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887   -2.0040   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -2.2169    0.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.3897    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026   -1.1906    2.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183   -0.8429    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523   -1.9019   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946    0.4024    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    1.6625    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414    2.3611    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    1.3950    0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    0.5052   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778    1.3776   -1.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -0.7056   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.9861   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    2.9618   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7395    1.7485    1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    1.4649   -1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0422    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.8170    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3529   -0.6437   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389    0.8282    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -0.8526    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982    0.1316    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620    1.7154    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1242    1.1404   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -2.9921   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -2.8213   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1290   -1.7422   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7880   -1.8301    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4767   -2.9183   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600    0.5173   -0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.2706    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    2.3487   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592    2.0057    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    2.3729    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    1.0323    1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    1.0128   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.4238   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.3259   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802   -0.8049   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.4605   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -2.0140   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  8 23  1  0
 23  3  1  0
 20  7  1  0
 22 10  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END


  Mrv0541 05061309192D          

 23 26  0  0  0  0            999 V2000
    3.8238   -1.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133   -2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -1.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425   -2.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0163   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    1.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16 15  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18  7  1  0  0  0  0
 18  9  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 13  1  0  0  0  0
 22 17  2  0  0  0  0
 23 15  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036750

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC(O)CC3(C)C1C(OC2=O)C=C1CC(C)(CCC31)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-5-18(2)7-6-14-12(9-18)8-15-16-19(14,3)10-13(21)11-20(16,4)17(22)23-15/h5,8,13-16,21H,1,6-7,9-11H2,2-4H3

> <INCHI_KEY>
VSXVHWPQGHHXGS-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.786546880700776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethenyl-14-hydroxy-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-en-11-one

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
3.1920798396666656

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.203045993788649

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7099876823168447

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
89.95059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethenyl-14-hydroxy-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-en-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036750
     RDKit          3D
Momilactone C
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.4250    2.0036    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.1769   -0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -0.1393    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.9573    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4962    0.0615    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034    0.6230    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798    0.3542   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.9350   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -2.0156   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887   -2.0040   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -2.2169    0.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.3897    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026   -1.1906    2.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183   -0.8429    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523   -1.9019   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946    0.4024    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    1.6625    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414    2.3611    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    1.3950    0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    0.5052   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778    1.3776   -1.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -0.7056   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.9861   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    2.9618   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7395    1.7485    1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    1.4649   -1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0422    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.8170    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3529   -0.6437   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389    0.8282    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -0.8526    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982    0.1316    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620    1.7154    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1242    1.1404   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -2.9921   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -2.8213   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1290   -1.7422   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7880   -1.8301    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4767   -2.9183   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600    0.5173   -0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.2706    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    2.3487   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592    2.0057    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    2.3729    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    1.0323    1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    1.0128   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.4238   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.3259   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802   -0.8049   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.4605   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -2.0140   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  8 23  1  0
 23  3  1  0
 20  7  1  0
 22 10  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  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       7.138  -2.421   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.625  -5.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.091  -3.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.426   1.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.613  -3.869   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.429  -4.142   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.764  -4.910   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.095  -2.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.427  -2.602   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.096  -4.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.904  -2.599   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.571   3.336   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.860   2.080   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5    1   18                                                       
CONECT    6    7   14                                                       
CONECT    7    6   18                                                       
CONECT    8   12   15                                                       
CONECT    9   12   18                                                       
CONECT   10   13   19                                                       
CONECT   11   13   20                                                       
CONECT   12    8    9   14                                                  
CONECT   13   10   11   21                                                  
CONECT   14    6   12   19                                                  
CONECT   15    8   16   23                                                  
CONECT   16   15   19   20                                                  
CONECT   17   20   22   23                                                  
CONECT   18    2    5    7    9                                             
CONECT   19    3   10   14   16                                             
CONECT   20    4   11   16   17                                             
CONECT   21   13                                                            
CONECT   22   17                                                            
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0036750
HETATM    1  C1  UNL     1       4.425   2.004   0.207  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.705   1.177  -0.526  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.286  -0.139   0.013  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.522  -0.957   0.425  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.496   0.061   1.250  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.103   0.623   1.063  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.580   0.354  -0.334  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.148  -0.935  -0.728  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.429  -2.016  -0.786  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.989  -2.004  -0.460  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.279  -2.217   0.907  1.00  0.00           O  
HETATM   12  C11 UNL     1      -2.307  -1.390   1.348  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.603  -1.191   2.542  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.918  -0.843   0.120  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.852  -1.902  -0.415  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.695   0.402   0.300  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.903   1.662   0.413  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.341   2.361   1.539  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.426   1.395   0.590  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.877   0.505  -0.507  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.078   1.378  -1.773  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.684  -0.706  -0.758  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.598  -0.986  -1.044  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.714   2.962  -0.223  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.739   1.749   1.236  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.423   1.465  -1.524  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.347  -2.042   0.277  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.745  -0.817   1.497  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.353  -0.644  -0.230  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.039   0.828   1.865  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.503  -0.853   1.912  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.498   0.132   1.851  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.062   1.715   1.240  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.124   1.140  -0.966  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.875  -2.992  -1.087  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.486  -2.821  -1.019  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.129  -1.742  -1.469  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.788  -1.830   0.180  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.477  -2.918  -0.310  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.360   0.517  -0.606  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.376   0.271   1.159  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.033   2.349  -0.451  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.159   2.006   1.923  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.909   2.373   0.496  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.291   1.032   1.600  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.445   1.013  -2.596  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.809   2.424  -1.566  1.00  0.00           H  
HETATM   48  H25 UNL     1      -2.122   1.326  -2.109  1.00  0.00           H  
HETATM   49  H26 UNL     1      -2.080  -0.805  -1.812  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.749  -0.461  -2.012  1.00  0.00           H  
HETATM   51  H28 UNL     1       2.951  -2.014  -1.082  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   26
CONECT    3    4    5   23
CONECT    4   27   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   20   34
CONECT    8    9    9   23
CONECT    9   10   35
CONECT   10   11   22   36
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   16   22
CONECT   15   37   38   39
CONECT   16   17   40   41
CONECT   17   18   19   42
CONECT   18   43
CONECT   19   20   44   45
CONECT   20   21   22
CONECT   21   46   47   48
CONECT   22   49
CONECT   23   50   51
END

HMDB0036750
     RDKit          3D
Momilactone C
 51 54  0  0  0  0  0  0  0  0999 V2000
    4.4250    2.0036    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    1.1769   -0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -0.1393    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.9573    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4962    0.0615    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034    0.6230    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798    0.3542   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -0.9350   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -2.0156   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887   -2.0040   -0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -2.2169    0.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3066   -1.3897    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6026   -1.1906    2.5415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183   -0.8429    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8523   -1.9019   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946    0.4024    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    1.6625    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414    2.3611    1.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4262    1.3950    0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    0.5052   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778    1.3776   -1.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -0.7056   -0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -0.9861   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    2.9618   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7395    1.7485    1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231    1.4649   -1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -2.0422    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -0.8170    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3529   -0.6437   -0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389    0.8282    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -0.8526    1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982    0.1316    1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620    1.7154    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1242    1.1404   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -2.9921   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -2.8213   -1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1290   -1.7422   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7880   -1.8301    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4767   -2.9183   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600    0.5173   -0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758    0.2706    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    2.3487   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592    2.0057    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    2.3729    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912    1.0323    1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    1.0128   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.4238   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220    1.3259   -2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802   -0.8049   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494   -0.4605   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -2.0140   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  8 23  1  0
 23  3  1  0
 20  7  1  0
 22 10  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-7,15-pimaradien-19,6-olide	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

5-ethenyl-14-hydroxy-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-en-11-one

Traditional Name

5-ethenyl-14-hydroxy-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-en-11-one

CAS Registry Number

62394-07-4

SMILES

CC12CC(O)CC3(C)C1C(OC2=O)C=C1CC(C)(CCC31)C=C

InChI Identifier

InChI=1S/C20H28O3/c1-5-18(2)7-6-14-12(9-18)8-15-16-19(14,3)10-13(21)11-20(16,4)17(22)23-15/h5,8,13-16,21H,1,6-7,9-11H2,2-4H3

InChI Key

VSXVHWPQGHHXGS-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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036750)
Membrane (HMDB: HMDB0036750)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036750)

Source

Endogenous

Endogenous (HMDB: HMDB0036750)

Plant

Poaceae (HMDB: HMDB0036750)

Animal

Animal (HMDB: HMDB0036750)

Exogenous

Food

Food (HMDB: HMDB0036750)

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036750)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036750)

Cellular process

Cell signaling (HMDB: HMDB0036750)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036750)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036750)

Nutrient

Nutrient (HMDB: HMDB0036750)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036750)

Emulsifier (HMDB: HMDB0036750)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227 - 228 °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	0.018 g/L	ALOGPS
logP	3.35	ALOGPS
logP	3.19	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.2	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.95 m³·mol⁻¹	ChemAxon
Polarizability	35.79 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]+	171.291	31661259
DarkChem	[M-H]-	170.086	31661259
DeepCCS	[M-2H]-	211.758	30932474
DeepCCS	[M+Na]+	186.985	30932474
AllCCS	[M+H]+	179.3	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	186.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Momilactone C	CC12CC(O)CC3(C)C1C(OC2=O)C=C1CC(C)(CCC31)C=C	3244.9	Standard polar	33892256
Momilactone C	CC12CC(O)CC3(C)C1C(OC2=O)C=C1CC(C)(CCC31)C=C	2497.4	Standard non polar	33892256
Momilactone C	CC12CC(O)CC3(C)C1C(OC2=O)C=C1CC(C)(CCC31)C=C	2623.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Momilactone C,1TMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)CC(O[Si](C)(C)C)CC2(C)C34)C1	2581.1	Semi standard non polar	33892256
Momilactone C,1TBDMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)CC(O[Si](C)(C)C(C)(C)C)CC2(C)C34)C1	2835.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Momilactone C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ul0-3192000000-38c06830ec41c0d625e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Momilactone C GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-4319000000-52fd11e1b7e32c35be1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Momilactone C 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 - Momilactone C 10V, Positive-QTOF	splash10-00kb-0096000000-f07fbdd25830a80f5bd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 20V, Positive-QTOF	splash10-0frt-3192000000-fca16e00bf73edc4f959	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 40V, Positive-QTOF	splash10-0uyi-9340000000-323ad106187559ce6371	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 10V, Negative-QTOF	splash10-014i-0059000000-86df8ab9bf0af6f56313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 20V, Negative-QTOF	splash10-01ba-0095000000-d12325998c1cabed1d31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 40V, Negative-QTOF	splash10-06di-1090000000-032fb67c05202852cb63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 10V, Positive-QTOF	splash10-014i-0009000000-e54cc993678f174093b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 20V, Positive-QTOF	splash10-066s-0091000000-a24b7d293d1db45ff090	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 40V, Positive-QTOF	splash10-053r-3490000000-16b436b71e5e77dc7ecd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 10V, Negative-QTOF	splash10-014i-0009000000-d337ec43015bf5d00be6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 20V, Negative-QTOF	splash10-014i-0019000000-ffe95e369cb44fce3959	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone C 40V, Negative-QTOF	splash10-014j-1095000000-869349f53ebb91ffe3a7	2021-09-23	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

FDB015688

KNApSAcK ID

Not Available

Chemspider ID

26504269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53463366

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 Momilactone C (HMDB0036750)

MOL for HMDB0036750 (Momilactone C)

3D MOL for HMDB0036750 (Momilactone C)

3D SDF for HMDB0036750 (Momilactone C)

3D-SDF for HMDB0036750 (Momilactone C)

PDB for HMDB0036750 (Momilactone C)

3D PDB for HMDB0036750 (Momilactone C)

SMILES for HMDB0036750 (Momilactone C)

INCHI for HMDB0036750 (Momilactone C)

Structure for HMDB0036750 (Momilactone C)

3D Structure for HMDB0036750 (Momilactone C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra