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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:55:13 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036748

Secondary Accession Numbers

HMDB36748

Metabolite Identification

Common Name

Momilactone A

Description

Momilactone A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review a significant number of articles have been published on Momilactone A.

Structure

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

HMDB0036748
     RDKit          3D
Momilactone A
 49 52  0  0  0  0  0  0  0  0999 V2000
    4.7376   -1.6026    1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765   -0.5395    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.2026    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982    1.1258   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317   -0.0925    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.5362    1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -0.7816    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1526   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2671   -1.4113   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.2852   -1.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -1.1319   -2.9143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676   -0.3688   -2.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -0.3342   -3.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431    0.4003   -1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325    1.8684   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024   -0.0773   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.8490   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    0.4373    1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165    0.0954    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823    0.2847    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341    1.6905    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    0.1274   -1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -1.2319   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -2.2518    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732   -1.8751    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804    0.0399    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8289    1.2725   -0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275    1.1639   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    1.9539    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.9584    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.6992    2.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624    0.2634    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -1.4107    2.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5540   -1.7065    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708   -1.6899   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -2.0331   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    2.3656   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    1.9363   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078    2.3815   -0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0817   -0.0594    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    1.5253    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223    0.7227    2.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179   -0.9564    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4310    1.7896    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    2.1386   -0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    2.3644    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7890    0.7743   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -2.2322   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.1688   -1.4748 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  2  0
 16 18  1  0
 18 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
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END


  Mrv0541 05061309182D          

 23 26  0  0  0  0            999 V2000
    4.0736   -2.7041    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
   -0.8411   -0.9804    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
   -0.1286   -1.3929    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
    2.0143   -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
   -0.8411   -0.1554    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    0.2567    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
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 16 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  5  1  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 15  2  0  0  0  0
 22 17  2  0  0  0  0
 23 14  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036748

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C3C(OC1=O)C=C1CC(C)(CCC1C3(C)CCC2=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-5-18(2)8-6-13-12(11-18)10-14-16-19(13,3)9-7-15(21)20(16,4)17(22)23-14/h5,10,13-14,16H,1,6-9,11H2,2-4H3

> <INCHI_KEY>
MPHXYQVSOFGNEN-UHFFFAOYSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.4186

> <EXACT_MASS>
314.188194698

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.94737744287853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethenyl-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-ene-11,13-dione

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.911515005333334

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.852533590756998

> <JCHEM_PKA_STRONGEST_BASIC>
-7.087697656204066

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
88.97429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethenyl-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-ene-11,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036748
     RDKit          3D
Momilactone A
 49 52  0  0  0  0  0  0  0  0999 V2000
    4.7376   -1.6026    1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765   -0.5395    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.2026    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982    1.1258   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317   -0.0925    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.5362    1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -0.7816    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1526   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2671   -1.4113   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.2852   -1.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -1.1319   -2.9143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676   -0.3688   -2.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -0.3342   -3.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431    0.4003   -1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325    1.8684   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024   -0.0773   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.8490   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    0.4373    1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165    0.0954    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823    0.2847    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341    1.6905    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    0.1274   -1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -1.2319   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -2.2518    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732   -1.8751    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804    0.0399    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8289    1.2725   -0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275    1.1639   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    1.9539    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.9584    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.6992    2.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624    0.2634    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -1.4107    2.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5540   -1.7065    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708   -1.6899   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -2.0331   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    2.3656   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    1.9363   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078    2.3815   -0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0817   -0.0594    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    1.5253    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223    0.7227    2.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179   -0.9564    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4310    1.7896    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    2.1386   -0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    2.3644    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7890    0.7743   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -2.2322   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.1688   -1.4748 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  2  0
 16 18  1  0
 18 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
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  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       7.604  -5.048   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      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.764  -4.910   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.095  -2.598   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       2.427  -2.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.570  -0.290   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   0.479   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    8   13                                                       
CONECT    7    9   15                                                       
CONECT    8    6   18                                                       
CONECT    9    7   19                                                       
CONECT   10   12   14                                                       
CONECT   11   12   18                                                       
CONECT   12   10   11   13                                                  
CONECT   13    6   12   19                                                  
CONECT   14   10   16   23                                                  
CONECT   15    7   20   21                                                  
CONECT   16   14   19   20                                                  
CONECT   17   20   22   23                                                  
CONECT   18    2    5    8   11                                             
CONECT   19    3    9   13   16                                             
CONECT   20    4   15   16   17                                             
CONECT   21   15                                                            
CONECT   22   17                                                            
CONECT   23   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0036748
HETATM    1  C1  UNL     1       4.738  -1.603   1.379  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.377  -0.539   0.650  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.927  -0.203   0.466  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.898   1.126  -0.278  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.232  -0.092   1.770  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.832  -0.536   1.858  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.084  -0.782   0.603  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.877  -1.153  -0.568  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.267  -1.411  -1.708  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.246  -1.285  -1.660  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.829  -1.132  -2.914  1.00  0.00           O  
HETATM   12  C11 UNL     1      -2.968  -0.369  -2.700  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.957  -0.334  -3.464  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.843   0.400  -1.435  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.133   1.868  -1.652  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.702  -0.077  -0.351  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.610  -0.849  -0.520  1.00  0.00           O  
HETATM   18  C15 UNL     1      -3.408   0.437   1.005  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.016   0.095   1.367  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.982   0.285   0.302  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.434   1.690   0.453  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.425   0.127  -1.081  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.336  -1.232  -0.461  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.004  -2.252   1.858  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.773  -1.875   1.532  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.180   0.040   0.217  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.829   1.272  -0.872  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.027   1.164  -0.988  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.736   1.954   0.451  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.400   0.958   2.158  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.848  -0.699   2.501  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.262   0.263   2.423  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.767  -1.411   2.573  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.554  -1.706   0.800  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.771  -1.690  -2.610  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.696  -2.033  -1.011  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.329   2.366  -2.232  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.103   1.936  -2.185  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.208   2.382  -0.695  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.082  -0.059   1.762  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.616   1.525   1.104  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.722   0.723   2.254  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.018  -0.956   1.780  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.431   1.790   1.092  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.172   2.139  -0.541  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.241   2.364   0.862  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.789   0.774  -1.755  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.684  -2.232  -0.066  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.802  -1.169  -1.475  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   17   18
CONECT   18   19   40   41
CONECT   19   20   42   43
CONECT   20   21   22
CONECT   21   44   45   46
CONECT   22   47
CONECT   23   48   49
END

HMDB0036748
     RDKit          3D
Momilactone A
 49 52  0  0  0  0  0  0  0  0999 V2000
    4.7376   -1.6026    1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765   -0.5395    0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.2026    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982    1.1258   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317   -0.0925    1.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.5362    1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0841   -0.7816    0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1526   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2671   -1.4113   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459   -1.2852   -1.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -1.1319   -2.9143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676   -0.3688   -2.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -0.3342   -3.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431    0.4003   -1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325    1.8684   -1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024   -0.0773   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102   -0.8490   -0.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081    0.4373    1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0165    0.0954    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823    0.2847    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4341    1.6905    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    0.1274   -1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -1.2319   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -2.2518    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732   -1.8751    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804    0.0399    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8289    1.2725   -0.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275    1.1639   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356    1.9539    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004    0.9584    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.6992    2.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624    0.2634    2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -1.4107    2.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5540   -1.7065    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708   -1.6899   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -2.0331   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    2.3656   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032    1.9363   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2078    2.3815   -0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0817   -0.0594    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    1.5253    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223    0.7227    2.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179   -0.9564    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4310    1.7896    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    2.1386   -0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    2.3644    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7890    0.7743   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841   -2.2322   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.1688   -1.4748 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  2  0
 16 18  1  0
 18 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
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-oxo-7,15-Pimaradien-19,6-olide	HMDB
3-oxo-9beta-Pimara-7,15-dien-19,6beta-olide	HMDB, ChEBI
6beta,18-Epoxy-9beta-pimara-7,15-diene-3,18-dione	HMDB
Momilacton a	HMDB, ChEBI
3-oxo-9b-Pimara-7,15-dien-19,6b-olide	Generator
3-oxo-9Β-pimara-7,15-dien-19,6β-olide	Generator

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

5-ethenyl-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-ene-11,13-dione

Traditional Name

5-ethenyl-1,5,12-trimethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-7-ene-11,13-dione

CAS Registry Number

51415-07-7

SMILES

CC12C3C(OC1=O)C=C1CC(C)(CCC1C3(C)CCC2=O)C=C

InChI Identifier

InChI=1S/C20H26O3/c1-5-18(2)8-6-13-12(11-18)10-14-16-19(13,3)9-7-15(21)20(16,4)17(22)23-14/h5,10,13-14,16H,1,6-9,11H2,2-4H3

InChI Key

MPHXYQVSOFGNEN-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
Pimarane diterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-7092 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036748)

Source

Endogenous

Endogenous (HMDB: HMDB0036748)

Plant

Poaceae (HMDB: HMDB0036748)

Animal

Animal (HMDB: HMDB0036748)

Exogenous

Food

Food (HMDB: HMDB0036748)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Rice (FooDB: FOOD00125)

Cereals and cereal products (FooDB: FOOD00858)

Exogenous (HMDB: HMDB0036748)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036748)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036748)

Lipid metabolism pathway (HMDB: HMDB0036748)

Cellular process

Cell signaling (HMDB: HMDB0036748)

Biochemical process

Lipid transport (HMDB: HMDB0036748)

Role

Biological role

Energy source (HMDB: HMDB0036748)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036748)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 236 °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	0.0027 g/L	ALOGPS
logP	3.42	ALOGPS
logP	3.91	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.97 m³·mol⁻¹	ChemAxon
Polarizability	34.95 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]+	171.664	31661259
DarkChem	[M-H]-	170.839	31661259
DeepCCS	[M-2H]-	209.588	30932474
DeepCCS	[M+Na]+	184.815	30932474
AllCCS	[M+H]+	178.1	32859911
AllCCS	[M+H-H2O]+	175.0	32859911
AllCCS	[M+NH4]+	181.0	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	185.3	32859911
AllCCS	[M+Na-2H]-	185.2	32859911
AllCCS	[M+HCOO]-	185.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.4 minutes	32390414
Predicted by Siyang on May 30, 2022	18.8565 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2952.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	513.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	387.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	688.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	930.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1589.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	534.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1647.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	534.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	474.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Momilactone A	CC12C3C(OC1=O)C=C1CC(C)(CCC1C3(C)CCC2=O)C=C	3112.8	Standard polar	33892256
Momilactone A	CC12C3C(OC1=O)C=C1CC(C)(CCC1C3(C)CCC2=O)C=C	2443.0	Standard non polar	33892256
Momilactone A	CC12C3C(OC1=O)C=C1CC(C)(CCC1C3(C)CCC2=O)C=C	2555.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Momilactone A,1TMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C(O[Si](C)(C)C)=CCC2(C)C34)C1	2568.1	Semi standard non polar	33892256
Momilactone A,1TMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C(O[Si](C)(C)C)=CCC2(C)C34)C1	2411.3	Standard non polar	33892256
Momilactone A,1TBDMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C34)C1	2827.0	Semi standard non polar	33892256
Momilactone A,1TBDMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C34)C1	2614.7	Standard non polar	33892256

Spectra

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18336661

PDB ID

Not Available

ChEBI ID

49191

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1453931

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 A (HMDB0036748)

MOL for HMDB0036748 (Momilactone A)

3D MOL for HMDB0036748 (Momilactone A)

3D SDF for HMDB0036748 (Momilactone A)

3D-SDF for HMDB0036748 (Momilactone A)

PDB for HMDB0036748 (Momilactone A)

3D PDB for HMDB0036748 (Momilactone A)

SMILES for HMDB0036748 (Momilactone A)

INCHI for HMDB0036748 (Momilactone A)

Structure for HMDB0036748 (Momilactone A)

3D Structure for HMDB0036748 (Momilactone A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized