NP-MRD: Showing NP-Card for Momordic acid (NP0075877)

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Record Information

Version

2.0

Created at

2022-04-28 21:05:37 UTC

Updated at

2022-04-28 21:05:37 UTC

NP-MRD ID

NP0075877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Momordic acid

Description

Virgatic acid, also known as virgatate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Momordic acid is found in Cousinia canescens, Cyclotrichium niveum, Juglans regia, Lagerstroemia speciosa, Momordica cochinchinensis , Salvia palaestina, Salvia pinnata, Salvia tomentosa, Salvia verticillata, Salvia virgata, Scapholeberis mucronata and Viburnum suspensum. Momordic acid was first documented in 2002 (PMID: 12150795). Based on a literature review very few articles have been published on virgatic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223052D          

 34 38  0  0  1  0            999 V2000
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 15  1  6  0  0  0
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 17 26  1  6  0  0  0
 26 27  2  0  0  0  0
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 12 29  1  1  0  0  0
  9 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282223052D          

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 10 11  1  0  0  0  0
  4 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  6  0  0  0
 16 13  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 17 26  1  6  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 12 29  1  1  0  0  0
  9 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@@H](O)CC(=O)[C@]43C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-25(2)12-14-30(24(33)34)15-13-27(5)18(19(30)17-25)8-9-21-28(27,6)11-10-20-26(3,4)22(31)16-23(32)29(20,21)7/h8,19-22,31H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21-,22-,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
IZWBODJDDBCDFA-DXEZAUPJSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.190692812571754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8aS,10S,12aR,12bS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-12-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
6.18

> <JCHEM_LOGP>
6.083457532000001

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.520718880632664

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.579235484431248

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006574355126326

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
134.1637

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,6bR,8aS,10S,12aR,12bS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-12-oxo-3,4,5,6,7,8,8a,10,11,12b,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.034   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.885  -2.095   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   31                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   15                                                  
CONECT    9    8   10   12   30                                             
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13   19   29                                             
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16   13   17   23                                                  
CONECT   17   16   18   20   26                                             
CONECT   18   17   19                                                       
CONECT   19   18   12                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   16                                                       
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   12                                                            
CONECT   30    9                                                            
CONECT   31    5                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Virgatate	Generator
Vergatic acid	MeSH

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(4aS,6aS,6bR,8aS,10S,12aR,12bS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-12-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aS,10S,12aR,12bS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-12-oxo-3,4,5,6,7,8,8a,10,11,12b,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@@H](O)CC(=O)[C@]43C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H46O4/c1-25(2)12-14-30(24(33)34)15-13-27(5)18(19(30)17-25)8-9-21-28(27,6)11-10-20-26(3,4)22(31)16-23(32)29(20,21)7/h8,19-22,31H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21-,22-,27+,28+,29-,30-/m0/s1

InChI Key

IZWBODJDDBCDFA-DXEZAUPJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cousinia canescens	LOTUS Database	35616633
Cyclotrichium niveum	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Momordica cochinchinensis	Plant	KNApSAcK
Salvia palaestina	LOTUS Database	35616633
Salvia pinnata	LOTUS Database	35616633
Salvia tomentosa	LOTUS Database	35616633
Salvia verticillata	LOTUS Database	35616633
Salvia virgata	Plant	KNApSAcK
Scapholeberis mucronata	LOTUS Database	35616633
Viburnum suspensum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:67945 )
pentacyclic triterpenoid (CHEBI:67945 )
cyclic terpene ketone (CHEBI:67945 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.18	ALOGPS
logP	6.08	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.16 m³·mol⁻¹	ChemAxon
Polarizability	55.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037990

Chemspider ID

30785555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14489125

PDB ID

Not Available

ChEBI ID

67945

Good Scents ID

Not Available

References

General References

Fukuyama Y, Minami H, Fujii H, Tajima M: Triterpenoids from Viburnum suspensum. Phytochemistry. 2002 Aug;60(8):765-8. doi: 10.1016/s0031-9422(02)00153-x. [PubMed:12150795 ]

Showing NP-Card for Momordic acid (NP0075877)

MOL for NP0075877 (Momordic acid)

3D MOL for NP0075877 (Momordic acid)

3D SDF for NP0075877 (Momordic acid)

3D-SDF for NP0075877 (Momordic acid)

PDB for NP0075877 (Momordic acid)

3D PDB for NP0075877 (Momordic acid)

SMILES for NP0075877 (Momordic acid)

INCHI for NP0075877 (Momordic acid)

Structure for NP0075877 (Momordic acid)

3D Structure for NP0075877 (Momordic acid)