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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:55:17 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036749

Secondary Accession Numbers

HMDB36749

Metabolite Identification

Common Name

Momilactone B

Description

Momilactone B is found in cereals and cereal products. Momilactone B is a constituent of Oryza sativa (rice) Momilactone B is an allelopathic agent produced from the roots of rice (Oryza sativa L.) (100 mg from 200 kg dry rice husk). It has been shown to be produced in high concentrations by the roots of rice seedlings. The production of momilactone B has also been induced in response to infection by blast fungus (Pyricularia oryzae) or irradiated with UV light. More recently is has been shown to be a potential chemotherapeutic agent against human colon cancer. The second step is the cyclization of syn-CDP to 9 -pimara-7,15-diene. This step is initiated by the elimination of the diphosphate group, a type A cyclization. The genes encoding for the type A cyclase were found by Otomo et al. in 2004. It is suggested that OsKS4, located on chromosome 4 (14.3cM) is one of the genes responsible for phytoalexin biosynthesis. After UV-radiation, OsKS4 mRNA levels rise drastically in response to the attack.

Structure

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

HMDB0036749
     RDKit          3D
Momilactone B
 50 54  0  0  0  0  0  0  0  0999 V2000
    3.2032    2.2823    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203    1.2488    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.0499   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.0069   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.1069   -1.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047    0.1181   -1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6699   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063   -0.2676    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    0.3023    1.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083    0.6167    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5489   -0.2084    2.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -0.6419    2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.5548    2.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8858    0.1470    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.3629    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    0.5381    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -0.5376   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.2465   -1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9721   -0.0812   -1.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178   -0.6683   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.7805   -0.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602   -1.9545   -0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.9092   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -0.5727    0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    3.2405    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.1457    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.3375    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855   -1.4836    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -0.5030   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3257   -1.8319   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    1.0587   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.6894   -2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -0.2995   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.1488   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.7440   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    0.5503    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162    1.6852    2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    1.6022    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131    2.2269    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.1932    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.5076   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -1.1065   -2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.6909   -2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4978   -0.5619   -2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    1.0144   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344    0.0309   -0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1537   -2.2358    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -2.6146   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859   -0.2360    1.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308   -1.6997    0.9174 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8 24  1  0
 24  3  1  0
 17  7  1  0
 16 10  1  0
 23 17  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
M  END


  Mrv0541 05061309182D          

 24 28  0  0  0  0            999 V2000
    4.4816   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045    0.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511    2.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4999    2.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    3.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    3.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2023    0.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3932    2.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740    1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228    1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    1.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7933    1.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9795    0.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565    2.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9376    2.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304    2.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314    1.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6978    2.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2857    0.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15 14  1  0  0  0  0
 17  2  1  0  0  0  0
 17  4  1  0  0  0  0
 17  6  1  0  0  0  0
 17 10  1  0  0  0  0
 18  3  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  2  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 23 20  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036749

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-4-17(2)6-5-13-12(10-17)9-14-15-18(3,16(21)24-14)20(22)8-7-19(13,15)11-23-20/h4,9,13-15,22H,1,5-8,10-11H2,2-3H3

> <INCHI_KEY>
SONPFFIKLYCKOY-UHFFFAOYSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.418

> <EXACT_MASS>
330.18310932

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.794542259757925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.8105342076666666

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.417107408633273

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345382150519913

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
89.6389

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036749
     RDKit          3D
Momilactone B
 50 54  0  0  0  0  0  0  0  0999 V2000
    3.2032    2.2823    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203    1.2488    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.0499   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.0069   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.1069   -1.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047    0.1181   -1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6699   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063   -0.2676    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    0.3023    1.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083    0.6167    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5489   -0.2084    2.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -0.6419    2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.5548    2.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8858    0.1470    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.3629    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    0.5381    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -0.5376   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.2465   -1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9721   -0.0812   -1.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178   -0.6683   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.7805   -0.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602   -1.9545   -0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.9092   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -0.5727    0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    3.2405    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.1457    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.3375    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855   -1.4836    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -0.5030   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3257   -1.8319   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    1.0587   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.6894   -2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -0.2995   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.1488   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.7440   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    0.5503    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162    1.6852    2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    1.6022    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131    2.2269    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.1932    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.5076   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -1.1065   -2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.6909   -2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4978   -0.5619   -2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    1.0144   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344    0.0309   -0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1537   -2.2358    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -2.6146   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859   -0.2360    1.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308   -1.6997    0.9174 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8 24  1  0
 24  3  1  0
 17  7  1  0
 16 10  1  0
 23 17  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  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       8.366  -1.091   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.835   1.399   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.842   4.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.552  -0.109   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.400   3.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.573   2.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.317   5.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.632   6.274   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.406   0.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.844   0.893   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.467   5.101   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.671   1.891   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.949   3.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.932   1.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.002   3.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.481   2.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.295   1.409   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.345   3.756   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.484   4.088   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.110   5.499   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.059   2.369   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.746   6.215   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.169   4.595   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.400   1.139   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4    1   17                                                       
CONECT    5    6   13                                                       
CONECT    6    5   17                                                       
CONECT    7    8   19                                                       
CONECT    8    7   20                                                       
CONECT    9   12   14                                                       
CONECT   10   12   17                                                       
CONECT   11   19   23                                                       
CONECT   12    9   10   13                                                  
CONECT   13    5   12   19                                                  
CONECT   14    9   15   24                                                  
CONECT   15   14   18   19                                                  
CONECT   16   18   21   24                                                  
CONECT   17    2    4    6   10                                             
CONECT   18    3   15   16   20                                             
CONECT   19    7   11   13   15                                             
CONECT   20    8   18   22   23                                             
CONECT   21   16                                                            
CONECT   22   20                                                            
CONECT   23   11   20                                                       
CONECT   24   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0036749
HETATM    1  C1  UNL     1       3.203   2.282   0.358  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.020   1.249   0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.426  -0.050  -0.299  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.590  -1.007  -0.494  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.664   0.107  -1.550  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.205   0.118  -1.526  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.551  -0.670  -0.427  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.206  -0.268   0.842  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.619   0.302   1.858  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.808   0.617   1.850  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.549  -0.208   2.714  1.00  0.00           O  
HETATM   12  C11 UNL     1      -2.716  -0.642   2.097  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.432  -1.555   2.584  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.886   0.147   0.865  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.721   1.363   1.151  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.451   0.538   0.504  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.917  -0.538  -0.381  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.472  -0.246  -1.783  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.972  -0.081  -1.607  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.418  -0.668  -0.283  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.796  -0.780  -0.266  1.00  0.00           O  
HETATM   22  O4  UNL     1      -2.860  -1.955  -0.181  1.00  0.00           O  
HETATM   23  C19 UNL     1      -1.500  -1.909  -0.010  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.661  -0.573   0.884  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.617   3.240   0.674  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.145   2.146   0.222  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.095   1.337   0.256  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.885  -1.484   0.465  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.475  -0.503  -0.930  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.326  -1.832  -1.185  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.021   1.059  -2.050  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.002  -0.689  -2.276  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.779  -0.300  -2.489  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.778   1.149  -1.476  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.840  -1.744  -0.595  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.204   0.550   2.734  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.916   1.685   2.201  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.618   1.602   2.246  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.313   2.227   0.591  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.784   1.193   0.976  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.520   1.508  -0.022  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.239  -1.106  -2.438  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.072   0.691  -2.196  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.498  -0.562  -2.443  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.234   1.014  -1.641  1.00  0.00           H  
HETATM   46  H22 UNL     1      -5.234   0.031  -0.641  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.154  -2.236   0.978  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.047  -2.615  -0.761  1.00  0.00           H  
HETATM   49  H25 UNL     1       3.086  -0.236   1.850  1.00  0.00           H  
HETATM   50  H26 UNL     1       2.731  -1.700   0.917  1.00  0.00           H  
CONECT    1    2    2   25   26
CONECT    2    3   27
CONECT    3    4    5   24
CONECT    4   28   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   17   35
CONECT    8    9    9   24
CONECT    9   10   36
CONECT   10   11   16   37
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   16   20
CONECT   15   38   39   40
CONECT   16   17   41
CONECT   17   18   23
CONECT   18   19   42   43
CONECT   19   20   44   45
CONECT   20   21   22
CONECT   21   46
CONECT   22   23
CONECT   23   47   48
CONECT   24   49   50
END

HMDB0036749
     RDKit          3D
Momilactone B
 50 54  0  0  0  0  0  0  0  0999 V2000
    3.2032    2.2823    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203    1.2488    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.0499   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.0069   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    0.1069   -1.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047    0.1181   -1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6699   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2063   -0.2676    0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    0.3023    1.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083    0.6167    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5489   -0.2084    2.7138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -0.6419    2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320   -1.5548    2.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8858    0.1470    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.3629    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    0.5381    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -0.5376   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.2465   -1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9721   -0.0812   -1.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178   -0.6683   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7964   -0.7805   -0.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602   -1.9545   -0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.9092   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -0.5727    0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    3.2405    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.1457    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954    1.3375    0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855   -1.4836    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -0.5030   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3257   -1.8319   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    1.0587   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.6894   -2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -0.2995   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.1488   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8395   -1.7440   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039    0.5503    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162    1.6852    2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    1.6022    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131    2.2269    0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    1.1932    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201    1.5076   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388   -1.1065   -2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.6909   -2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4978   -0.5619   -2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    1.0144   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344    0.0309   -0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1537   -2.2358    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -2.6146   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859   -0.2360    1.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308   -1.6997    0.9174 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8 24  1  0
 24  3  1  0
 17  7  1  0
 16 10  1  0
 23 17  1  0
 20 14  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3b,20-Epoxy-3a-hydroxy-7,15-pimaradien-19,6b-olide	HMDB
Momilacton b	HMDB
Momilactone b	MeSH

Chemical Formula

C₂₀H₂₆O₄

Average Molecular Weight

330.418

Monoisotopic Molecular Weight

330.18310932

IUPAC Name

5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one

Traditional Name

5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one

CAS Registry Number

51415-08-8

SMILES

CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C

InChI Identifier

InChI=1S/C20H26O4/c1-4-17(2)6-5-13-12(10-17)9-14-15-18(3,16(21)24-14)20(22)8-7-19(13,15)11-23-20/h4,9,13-15,22H,1,5-8,10-11H2,2-3H3

InChI Key

SONPFFIKLYCKOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthofuran
Naphthalene
Furopyran
Gamma butyrolactone
Oxane
Pyran
Furan
Cyclic alcohol
Tetrahydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036749)

Cellular substructure

Extracellular (HMDB: HMDB0036749)
Membrane (HMDB: HMDB0036749)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036749)

Source

Endogenous

Endogenous (HMDB: HMDB0036749)

Plant

Poaceae (HMDB: HMDB0036749)

Exogenous

Food

Food (HMDB: HMDB0036749)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Rice (FooDB: FOOD00125)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036749)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036749)

Nutrient

Nutrient (HMDB: HMDB0036749)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036749)

Emulsifier (HMDB: HMDB0036749)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	242 °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	0.045 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.81	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	35.79 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]+	173.169	31661259
DarkChem	[M-H]-	170.52	31661259
DeepCCS	[M-2H]-	210.302	30932474
DeepCCS	[M+Na]+	185.55	30932474
AllCCS	[M+H]+	181.4	32859911
AllCCS	[M+H-H2O]+	178.4	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	186.9	32859911
AllCCS	[M+HCOO]-	187.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Momilactone B	CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C	3179.4	Standard polar	33892256
Momilactone B	CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C	2499.6	Standard non polar	33892256
Momilactone B	CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C	2669.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Momilactone B,1TMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C3C23CCC4(O[Si](C)(C)C)OC3)C1	2659.9	Semi standard non polar	33892256
Momilactone B,1TBDMS,isomer #1	C=CC1(C)CCC2C(=CC3OC(=O)C4(C)C3C23CCC4(O[Si](C)(C)C(C)(C)C)OC3)C1	2898.1	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 - Momilactone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-7594000000-262e9a486816a49966ed	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Momilactone B GC-MS (1 TMS) - 70eV, Positive	splash10-000i-9204000000-01083810d31bad04f17a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Momilactone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 10V, Positive-QTOF	splash10-001i-0029000000-efd9dd6471fec372d203	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 20V, Positive-QTOF	splash10-00lr-5259000000-4d21f007a0c800a54780	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 40V, Positive-QTOF	splash10-0gb9-9441000000-d1bb689b6f85a17a1415	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 10V, Negative-QTOF	splash10-004i-0009000000-71a231edd4c086920a1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 20V, Negative-QTOF	splash10-004i-0019000000-dcaf394ed89d9e3d9fba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 40V, Negative-QTOF	splash10-00li-0590000000-28abb07c252c401a32ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 10V, Positive-QTOF	splash10-001i-0009000000-00a7d712e9bc4f24f659	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 20V, Positive-QTOF	splash10-001j-0095000000-c0ceddbd2548e575cfc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 40V, Positive-QTOF	splash10-001a-2960000000-51d1f38d076c94076b61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 10V, Negative-QTOF	splash10-004i-0009000000-f547833d1942b8c5fe90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 20V, Negative-QTOF	splash10-004i-0009000000-f547833d1942b8c5fe90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Momilactone B 40V, Negative-QTOF	splash10-01t9-1059000000-487b3e63f89e0fc52e7a	2021-09-22	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

FDB015687

KNApSAcK ID

C00000260

Chemspider ID

24785551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Momilactone B

METLIN ID

Not Available

PubChem Compound

73018629

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Momilactone B (HMDB0036749)

MOL for HMDB0036749 (Momilactone B)

3D MOL for HMDB0036749 (Momilactone B)

3D SDF for HMDB0036749 (Momilactone B)

3D-SDF for HMDB0036749 (Momilactone B)

PDB for HMDB0036749 (Momilactone B)

3D PDB for HMDB0036749 (Momilactone B)

SMILES for HMDB0036749 (Momilactone B)

INCHI for HMDB0036749 (Momilactone B)

Structure for HMDB0036749 (Momilactone B)

3D Structure for HMDB0036749 (Momilactone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra