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Showing NP-Card for Momordicin I (NP0048313)

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Record Information
Version2.0
Created at2022-03-17 20:54:28 UTC
Updated at2022-03-17 20:54:28 UTC
NP-MRD IDNP0048313
Secondary Accession NumbersNone
Natural Product Identification
Common NameMomordicin I
Description(1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol has been detected, but not quantified in, fats and oils and herbs and spices. This could make (1S,2S,4R,8R)-p-menthane-1,2,8,9-tetrol a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048313 (Momordicin I)


  Mrv0541 02241209562D          

 34 37  0  0  0  0            999 V2000
    2.8955    2.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1722    1.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    1.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4655    2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452    1.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0371    2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452    0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -1.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253   -1.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398    0.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533    1.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    1.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    2.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035    1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661   -2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 30  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 23  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  0  0  0  0
 12 13  1  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 33  1  0  0  0  0
 17 18  1  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 33  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
Download

3D MOL for NP0048313 (Momordicin I)

Download
3D SDF for NP0048313 (Momordicin I)

  Mrv0541 02241209562D          

 34 37  0  0  0  0            999 V2000
    2.8955    2.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1722    1.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    1.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4655    2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452    1.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0371    2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452    0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466   -0.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -1.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253   -1.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398    0.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533    1.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    0.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    1.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    2.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035    1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5883    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4274   -2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   -1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661   -2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 30  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 23  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  0  0  0  0
 12 13  1  0  0  0  0
 12 26  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 33  1  0  0  0  0
 17 18  1  0  0  0  0
 17 26  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 33  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(O)C=C(C)C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(CCC12C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18(2)14-20(32)15-19(3)21-10-11-29(7)26-24(33)16-23-22(8-9-25(34)27(23,4)5)30(26,17-31)13-12-28(21,29)6/h14,16-17,19-22,24-26,32-34H,8-13,15H2,1-7H3

> <INCHI_KEY>
QBXNBPFTVLJTMK-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.6997

> <EXACT_MASS>
472.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
56.33869966061218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,9-dihydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.399738288333333

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.32361870168723

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.51556573104218

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7449659246158226

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
138.55709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,9-dihydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048313 (Momordicin I)
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PDB for NP0048313 (Momordicin I)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.405   4.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.055   3.579   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.034   2.036   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.736   4.369   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.391   3.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.069   4.415   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.391   1.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.297   0.612   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.391  -0.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.074  -0.158   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.087  -1.687   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.406  -0.928   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.406  -2.468   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.074  -3.237   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.741  -3.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.075  -2.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.075  -0.928   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.407  -0.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.742  -0.928   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.742  -2.468   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.074  -3.237   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.087   2.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.074   1.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.406   2.152   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.741   1.382   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.741  -0.158   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.075   0.612   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.075   2.152   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.074   4.274   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.727   3.532   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.698   1.990   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.398  -4.415   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.407  -3.237   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.417  -4.415   0.000  0.00  0.00           C+0
CONECT    1    2   30                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   23                                             
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23    7   10   22   24                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   12   17   25   27                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30    1   29   31                                                  
CONECT   31   30                                                            
CONECT   32   33                                                            
CONECT   33   16   20   32   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

Download
3D PDB for NP0048313 (Momordicin I)
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SMILES for NP0048313 (Momordicin I)
CC(CC(O)C=C(C)C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(CCC12C)C=O
Download
INCHI for NP0048313 (Momordicin I)
InChI=1S/C30H48O4/c1-18(2)14-20(32)15-19(3)21-10-11-29(7)26-24(33)16-23-22(8-9-25(34)27(23,4)5)30(26,17-31)13-12-28(21,29)6/h14,16-17,19-22,24-26,32-34H,8-13,15H2,1-7H3
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View in JSmol
Synonyms
ValueSource
(+)-Momordicine IHMDB
Momordicine IHMDB
Chemical FormulaC30H48O4
Average Mass472.6997 Da
Monoisotopic Mass472.35526 Da
IUPAC Name5,9-dihydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde
Traditional Name5,9-dihydroxy-14-(4-hydroxy-6-methylhept-5-en-2-yl)-6,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-1-carbaldehyde
CAS Registry Number91590-76-0
SMILES
CC(CC(O)C=C(C)C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)C)C3(CCC12C)C=O
InChI Identifier
InChI=1S/C30H48O4/c1-18(2)14-20(32)15-19(3)21-10-11-29(7)26-24(33)16-23-22(8-9-25(34)27(23,4)5)30(26,17-31)13-12-28(21,29)6/h14,16-17,19-22,24-26,32-34H,8-13,15H2,1-7H3
InChI KeyQBXNBPFTVLJTMK-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 menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMenthane monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
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  • Monocyclic monoterpenoid
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  • Cyclohexanol
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  • Tertiary alcohol
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  • Cyclic alcohol
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  • Secondary alcohol
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  • Organic oxygen compound
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  • Hydrocarbon derivative
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  • Primary alcohol
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  • Organooxygen compound
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  • Alcohol
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  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP4.41ALOGPS
logP4.4ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.52ChemAxon
pKa (Strongest Basic)-0.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity138.56 m³·mol⁻¹ChemAxon
Polarizability56.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039974  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019648  
KNApSAcK IDNot Available
Chemspider ID99340  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound110677  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References