NP-MRD: Showing NP-Card for Ambonic acid (NP0048391)

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Record Information

Version

2.0

Created at

2022-03-17 20:55:45 UTC

Updated at

2022-03-17 20:55:45 UTC

NP-MRD ID

NP0048391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ambonic acid

Description

Ambonic acid, also known as ambonate, belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. Ambonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ambonic acid has been detected, but not quantified in, fruits and mango. This could make ambonic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308492D          

 34 38  0  0  0  0            999 V2000
    6.2589   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -1.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495   -0.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -0.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104   -1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363   -1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5078   -1.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    0.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924    0.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    0.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -0.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -0.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945    0.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.5811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -1.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 16  1  0  0  0  0
 19  1  2  0  0  0  0
 19  8  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 21  3  1  0  0  0  0
 21 19  1  0  0  0  0
 22 12  1  0  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 13  1  0  0  0  0
 26 21  1  0  0  0  0
 27  4  1  0  0  0  0
 27  5  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28  6  1  0  0  0  0
 28 16  1  0  0  0  0
 28 22  1  0  0  0  0
 29  7  1  0  0  0  0
 29 14  1  0  0  0  0
 29 24  1  0  0  0  0
 29 28  1  0  0  0  0
 30 15  1  0  0  0  0
 30 18  1  0  0  0  0
 30 23  1  0  0  0  0
 31 17  1  0  0  0  0
 31 18  1  0  0  0  0
 31 24  1  0  0  0  0
 31 30  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 26  1  0  0  0  0
M  END


  Mrv0541 05061308492D          

 34 38  0  0  0  0            999 V2000
    6.2589   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734    0.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -1.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495   -0.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -0.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104   -1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5445   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363   -1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5078   -1.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285    0.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3924    0.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    0.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -0.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -1.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -0.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945    0.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.5811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -1.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 16  1  0  0  0  0
 19  1  2  0  0  0  0
 19  8  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 21  3  1  0  0  0  0
 21 19  1  0  0  0  0
 22 12  1  0  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 13  1  0  0  0  0
 26 21  1  0  0  0  0
 27  4  1  0  0  0  0
 27  5  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28  6  1  0  0  0  0
 28 16  1  0  0  0  0
 28 22  1  0  0  0  0
 29  7  1  0  0  0  0
 29 14  1  0  0  0  0
 29 24  1  0  0  0  0
 29 28  1  0  0  0  0
 30 15  1  0  0  0  0
 30 18  1  0  0  0  0
 30 23  1  0  0  0  0
 31 17  1  0  0  0  0
 31 18  1  0  0  0  0
 31 24  1  0  0  0  0
 31 30  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(=C)C(C)C(O)=O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(=O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O3/c1-19(21(3)26(33)34)8-9-20(2)22-12-14-29(7)24-11-10-23-27(4,5)25(32)13-15-30(23)18-31(24,30)17-16-28(22,29)6/h20-24H,1,8-18H2,2-7H3,(H,33,34)

> <INCHI_KEY>
HTNUCKDQVIZWMJ-UHFFFAOYSA-N

> <FORMULA>
C31H48O3

> <MOLECULAR_WEIGHT>
468.711

> <EXACT_MASS>
468.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
56.307368768301515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-methylidene-6-{7,7,12,16-tetramethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}heptanoic acid

> <ALOGPS_LOGP>
5.90

> <JCHEM_LOGP>
7.391868268666668

> <ALOGPS_LOGS>
-6.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.88177363646541

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.629695432797136

> <JCHEM_PKA_STRONGEST_BASIC>
-7.470897114855402

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
136.37829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.24e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-3-methylidene-6-{7,7,12,16-tetramethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.683  -3.395   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.682   0.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.017   0.455   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.168  -2.631   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.639  -1.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.086  -0.198   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.006  -3.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.350  -1.085   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.016  -1.855   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.132  -2.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.374  -3.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.188  -3.386   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.560   1.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.681  -3.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.053   1.197   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.466   0.236   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.960   0.556   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.453   0.877   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.683  -1.855   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.682  -1.085   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.017  -1.085   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.349  -1.855   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.608  -1.412   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.405  -2.053   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.590   0.373   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.351  -1.855   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.114  -1.092   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.942  -1.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.911  -2.373   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.423  -0.268   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.929  -0.588   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.096   0.693   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      15.684  -1.085   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.351  -3.395   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   27                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   19                                                       
CONECT    9    8   20                                                       
CONECT   10   11   23                                                       
CONECT   11   10   24                                                       
CONECT   12   14   22                                                       
CONECT   13   15   25                                                       
CONECT   14   12   29                                                       
CONECT   15   13   30                                                       
CONECT   16   17   28                                                       
CONECT   17   16   31                                                       
CONECT   18   30   31                                                       
CONECT   19    1    8   21                                                  
CONECT   20    2    9   22                                                  
CONECT   21    3   19   26                                                  
CONECT   22   12   20   28                                                  
CONECT   23   10   27   30                                                  
CONECT   24   11   29   31                                                  
CONECT   25   13   27   32                                                  
CONECT   26   21   33   34                                                  
CONECT   27    4    5   23   25                                             
CONECT   28    6   16   22   29                                             
CONECT   29    7   14   24   28                                             
CONECT   30   15   18   23   31                                             
CONECT   31   17   18   24   30                                             
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Ambonate	Generator
2-Methyl-3-methylidene-6-{7,7,12,16-tetramethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}heptanoate	Generator

Chemical Formula

C₃₁H₄₈O₃

Average Mass

468.7110 Da

Monoisotopic Mass

468.36035 Da

IUPAC Name

2-methyl-3-methylidene-6-{7,7,12,16-tetramethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}heptanoic acid

Traditional Name

2-methyl-3-methylidene-6-{7,7,12,16-tetramethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}heptanoic acid

CAS Registry Number

17984-17-7

SMILES

CC(CCC(=C)C(C)C(O)=O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(=O)C4(C)C

InChI Identifier

InChI=1S/C31H48O3/c1-19(21(3)26(33)34)8-9-20(2)22-12-14-29(7)24-11-10-23-27(4,5)25(32)13-15-30(23)18-31(24,30)17-16-28(22,29)6/h20-24H,1,8-18H2,2-7H3,(H,33,34)

InChI Key

HTNUCKDQVIZWMJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mangifera indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Triterpenoid
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Bile acid, alcohol, or derivatives
Steroid acid
3-oxosteroid
Oxosteroid
Medium-chain fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	5.9	ALOGPS
logP	7.39	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.38 m³·mol⁻¹	ChemAxon
Polarizability	56.31 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0035972

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014776

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78385012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ambonic acid (NP0048391)

MOL for NP0048391 (Ambonic acid)

3D MOL for NP0048391 (Ambonic acid)

3D SDF for NP0048391 (Ambonic acid)

3D-SDF for NP0048391 (Ambonic acid)

PDB for NP0048391 (Ambonic acid)

3D PDB for NP0048391 (Ambonic acid)

SMILES for NP0048391 (Ambonic acid)

INCHI for NP0048391 (Ambonic acid)

Structure for NP0048391 (Ambonic acid)

3D Structure for NP0048391 (Ambonic acid)