NP-MRD: Showing NP-Card for Mangiferolic acid (NP0048304)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:20 UTC

Updated at

2022-03-17 20:54:20 UTC

NP-MRD ID

NP0048304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mangiferolic acid

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216342D          

 33 37  0  0  0  0            999 V2000
    1.0908   -2.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -1.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -1.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579    0.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    0.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379    1.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    2.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794    2.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273   -1.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321   -3.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962   -1.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -1.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7820   -1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -2.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -3.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256   -3.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923   -3.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279    2.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306    3.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315    3.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 32  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  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
 21 22  1  0  0  0  0
 21 29  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 26 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END


  Mrv0541 02241216342D          

 33 37  0  0  0  0            999 V2000
    1.0908   -2.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -1.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -1.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8837   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579    0.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    0.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4379    1.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    2.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794    2.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1304   -0.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273   -1.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321   -3.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962   -1.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -1.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7820   -1.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -2.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794   -3.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256   -3.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750   -3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923   -3.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279    2.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306    3.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315    3.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 32  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  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
 21 22  1  0  0  0  0
 21 29  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 26 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048304

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-19(8-7-9-20(2)25(32)33)21-12-14-28(6)23-11-10-22-26(3,4)24(31)13-15-29(22)18-30(23,29)17-16-27(21,28)5/h9,19,21-24,31H,7-8,10-18H2,1-6H3,(H,32,33)/b20-9+

> <INCHI_KEY>
CYHOTEDWAOHQLA-AWQFTUOYSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.94926354376361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
5.89

> <JCHEM_LOGP>
6.739354978333335

> <ALOGPS_LOGS>
-6.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489408976606935

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.772299891466471

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351335860213535

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.75039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       2.036  -4.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.489  -2.995   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.041  -3.473   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.882  -2.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.062  -1.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650  -1.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.415   0.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.726   1.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.626   0.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.006   0.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.567   2.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.551   3.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.994   4.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.495   5.043   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.243  -0.727   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.005  -1.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.171  -2.935   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.154  -3.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.071  -5.203   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.180  -5.908   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.586  -5.147   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.420  -3.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.375  -2.210   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.826  -2.879   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.193  -3.664   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.041  -5.123   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.495  -5.792   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.714  -7.338   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.873  -6.048   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.972  -7.335   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.479   5.551   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.977   5.899   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.539   7.338   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    2    5    7   15                                             
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    5    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22   23                                             
CONECT   18    2   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   17   21   23   24                                             
CONECT   23   17   22                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   21   26   28   30                                             
CONECT   30   29                                                            
CONECT   31   32                                                            
CONECT   32   13   31   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Isomangiferolate	Generator
(2E)-6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7003 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(2E)-6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylhept-2-enoic acid

Traditional Name

(2E)-6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylhept-2-enoic acid

CAS Registry Number

13878-92-7

SMILES

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

InChI Identifier

InChI=1S/C30H48O3/c1-19(8-7-9-20(2)25(32)33)21-12-14-28(6)23-11-10-22-26(3,4)24(31)13-15-29(22)18-30(23,29)17-16-27(21,28)5/h9,19,21-24,31H,7-8,10-18H2,1-6H3,(H,32,33)/b20-9+

InChI Key

CYHOTEDWAOHQLA-AWQFTUOYSA-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
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
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	5.89	ALOGPS
logP	6.74	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.75 m³·mol⁻¹	ChemAxon
Polarizability	55.95 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

HMDB0035119

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013752

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

14034465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Mangiferolic acid (NP0048304)

MOL for NP0048304 (Mangiferolic acid)

3D MOL for NP0048304 (Mangiferolic acid)

3D SDF for NP0048304 (Mangiferolic acid)

3D-SDF for NP0048304 (Mangiferolic acid)

PDB for NP0048304 (Mangiferolic acid)

3D PDB for NP0048304 (Mangiferolic acid)

SMILES for NP0048304 (Mangiferolic acid)

INCHI for NP0048304 (Mangiferolic acid)

Structure for NP0048304 (Mangiferolic acid)

3D Structure for NP0048304 (Mangiferolic acid)