NP-MRD: Showing NP-Card for Ambolic acid (NP0048298)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:14 UTC

Updated at

2022-03-17 20:54:14 UTC

NP-MRD ID

NP0048298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ambolic acid

Description

Isobiflorin, also known as clove 3, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Isobiflorin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isobiflorin has been detected, but not quantified in, cloves and herbs and spices. This could make isobiflorin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308402D          

 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  1  0  0  0  0
 33 26  2  0  0  0  0
 34 26  1  0  0  0  0
M  END


  Mrv0541 05061308402D          

 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  1  0  0  0  0
 33 26  2  0  0  0  0
 34 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048298

> <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/C31H50O3/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/h20-25,32H,1,8-18H2,2-7H3,(H,33,34)

> <INCHI_KEY>
FCQSIIVNJCMJLB-UHFFFAOYSA-N

> <FORMULA>
C31H50O3

> <MOLECULAR_WEIGHT>
470.7269

> <EXACT_MASS>
470.375995466

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.440197227368095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methyl-3-methylideneheptanoic acid

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
6.828340563000001

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489408976606935

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.629696922005682

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351340028410171

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.20059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methyl-3-methylideneheptanoic 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
8-b-D-Glucopyranosyl-5,7-dihydroxy-2-methyl-4H-1-benzopyran-4-one	HMDB
8-C-Glucopyranosylnoreugenin	HMDB
8-Glucosyl-5,7-dihydroxy-2-methylchromone	HMDB
Clove 3	HMDB
3b-Hydroxy-24-methylene-25R-cycloartan-26-Oic acid	HMDB
6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methyl-3-methylideneheptanoate	Generator
Ambolate	Generator

Chemical Formula

C₃₁H₅₀O₃

Average Mass

470.7269 Da

Monoisotopic Mass

470.37600 Da

IUPAC Name

6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methyl-3-methylideneheptanoic acid

Traditional Name

6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methyl-3-methylideneheptanoic acid

CAS Registry Number

13878-93-8

SMILES

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

InChI Identifier

InChI=1S/C31H50O3/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/h20-25,32H,1,8-18H2,2-7H3,(H,33,34)

InChI Key

FCQSIIVNJCMJLB-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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.74	ALOGPS
logP	6.83	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.63	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	6	ChemAxon
Refractivity	137.2 m³·mol⁻¹	ChemAxon
Polarizability	57.44 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

HMDB0040632

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020423

KNApSAcK ID

C00030518

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

85114699

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ambolic acid (NP0048298)

MOL for NP0048298 (Ambolic acid)

3D MOL for NP0048298 (Ambolic acid)

3D SDF for NP0048298 (Ambolic acid)

3D-SDF for NP0048298 (Ambolic acid)

PDB for NP0048298 (Ambolic acid)

3D PDB for NP0048298 (Ambolic acid)

SMILES for NP0048298 (Ambolic acid)

INCHI for NP0048298 (Ambolic acid)

Structure for NP0048298 (Ambolic acid)

3D Structure for NP0048298 (Ambolic acid)