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Showing NP-Card for Momordicinin (NP0048054)

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Record Information
Version2.0
Created at2022-03-17 20:50:21 UTC
Updated at2022-03-17 20:50:21 UTC
NP-MRD IDNP0048054
Secondary Accession NumbersNone
Natural Product Identification
Common NameMomordicinin
DescriptionMomordicinin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Momordicinin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, momordicinin has been detected, but not quantified in, bitter gourds and fruits. This could make momordicinin a potential biomarker for the consumption of these foods. Momordicinin or 13β,28-epoxy-urs-11-en-3-one is chemical compound, a triterpene with formula C30H46O2, found in the fresh fruit of the bitter melon (Momordica charantia). The compound is soluble in ethyl acetate and chloroform but not in petrol. It was isolated in 1997 by S. Begum and others. It crystallizes as irregular plates that melt at 146−147 °C.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048054 (Momordicinin)


  Mrv0541 05061308022D          

 32 37  0  0  1  0            999 V2000
    4.3010   -1.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -4.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -1.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4386   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4386   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -4.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -2.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -2.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1 10  1  0  0  0  0
  2 17  1  0  0  0  0
  2 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  3 25  1  0  0  0  0
  4  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  6 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 27  1  0  0  0  0
  7 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 11 10  1  0  0  0  0
 11 20  1  0  0  0  0
 11 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 28  1  0  0  0  0
 14 15  1  0  0  0  0
 14 29  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  2  0  0  0  0
 24 32  1  0  0  0  0
 24 31  1  0  0  0  0
M  END
Download

3D MOL for NP0048054 (Momordicinin)

Download
3D SDF for NP0048054 (Momordicinin)

  Mrv0541 05061308022D          

 32 37  0  0  1  0            999 V2000
    4.3010   -1.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -4.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -1.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4386   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4386   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588   -2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -3.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -4.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -4.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -2.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1440   -2.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2945   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1 10  1  0  0  0  0
  2 17  1  0  0  0  0
  2 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  3 25  1  0  0  0  0
  4  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  6 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 27  1  0  0  0  0
  7 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 11 10  1  0  0  0  0
 11 20  1  0  0  0  0
 11 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 28  1  0  0  0  0
 14 15  1  0  0  0  0
 14 29  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  2  0  0  0  0
 24 32  1  0  0  0  0
 24 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC23COC4(C=CC5C6(C)CCC(=O)C(C)(C)C6CCC5(C)C4(C)CC2)C3C1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O2/c1-19-8-14-29-17-16-28(7)27(6)13-9-21-25(3,4)23(31)11-12-26(21,5)22(27)10-15-30(28,32-18-29)24(29)20(19)2/h10,15,19-22,24H,8-9,11-14,16-18H2,1-7H3

> <INCHI_KEY>
PKMBOLUTQNQQBP-UHFFFAOYSA-N

> <FORMULA>
C30H46O2

> <MOLECULAR_WEIGHT>
438.685

> <EXACT_MASS>
438.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
53.189186252455414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-one

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
6.952792181666665

> <ALOGPS_LOGS>
-7.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.915882722137045

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203642211167734

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
130.9868

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0048054 (Momordicinin)
Download
PDB for NP0048054 (Momordicinin)
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  O   UNK     0       8.029  -3.113   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.016  -4.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.016  -6.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.682  -6.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.336  -6.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.002  -6.935   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.002  -8.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.336  -9.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.682  -8.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.685  -3.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.685  -4.615   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.351  -3.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.351  -2.295   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.685  -1.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.019  -2.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.019  -3.846   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.682  -3.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.336  -4.615   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.351  -6.935   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.685  -6.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.668  -6.153   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -6.935   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -8.461   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.668  -9.242   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.101  -7.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.682  -5.420   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.002  -5.396   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.016  -1.538   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.685   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -9.242   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.911 -10.577   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.437 -10.577   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1   17   12    3                                             
CONECT    3    2    4   19   25                                             
CONECT    4    3    9    5   26                                             
CONECT    5    4    6   18                                                  
CONECT    6    5   21    7   27                                             
CONECT    7    6   24    8                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    1   11                                                       
CONECT   11   10   20   16   12                                             
CONECT   12    2   11   13                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17    2   18                                                       
CONECT   18    5   17                                                       
CONECT   19    3   20                                                       
CONECT   20   11   19                                                       
CONECT   21    6   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24    7   23   32   31                                             
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

Download
3D PDB for NP0048054 (Momordicinin)
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SMILES for NP0048054 (Momordicinin)
CC1CCC23COC4(C=CC5C6(C)CCC(=O)C(C)(C)C6CCC5(C)C4(C)CC2)C3C1C
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INCHI for NP0048054 (Momordicinin)
InChI=1S/C30H46O2/c1-19-8-14-29-17-16-28(7)27(6)13-9-21-25(3,4)23(31)11-12-26(21,5)22(27)10-15-30(28,32-18-29)24(29)20(19)2/h10,15,19-22,24H,8-9,11-14,16-18H2,1-7H3
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View in JSmol
Synonyms
ValueSource
13b,28-Epoxy-11-ursen-3-oneHMDB
Chemical FormulaC30H46O2
Average Mass438.6850 Da
Monoisotopic Mass438.34978 Da
IUPAC Name4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-one
Traditional Name4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-one
CAS Registry Number128529-78-2
SMILES
CC1CCC23COC4(C=CC5C6(C)CCC(=O)C(C)(C)C6CCC5(C)C4(C)CC2)C3C1C
InChI Identifier
InChI=1S/C30H46O2/c1-19-8-14-29-17-16-28(7)27(6)13-9-21-25(3,4)23(31)11-12-26(21,5)22(27)10-15-30(28,32-18-29)24(29)20(19)2/h10,15,19-22,24H,8-9,11-14,16-18H2,1-7H3
InChI KeyPKMBOLUTQNQQBP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Momordica charantiaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.64ALOGPS
logP6.95ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)19.92ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity130.99 m³·mol⁻¹ChemAxon
Polarizability53.19 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034726  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013263  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMomordicinin  
METLIN IDNot Available
PubChem Compound14526924  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References