NP-MRD: Showing NP-Card for Asiatic acid (NP0137191)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:34 UTC

Updated at

2026-02-17 08:01:28 UTC

NP-MRD ID

NP0137191

Natural Product DOI

https://doi.org/10.57994/7388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asiatic acid

Description

Esculentic acid (Diplazium) belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Asiatic acid is found in Actinidia chinensis, Actinidia polygama, Calyptranthes pallens, Centella asiatica, Centella erecta, Combretum laxum, Cornus kousa, Craibiodendron yunnanense, Dipterocarpus hispidus, Eucalyptus perriniana, Gentiana dahurica, Hedyotis lawsoniae, Schefflera heptaphylla, Ilex cornuta, Juglans regia, Melaleuca ericifolia, Mucuna birdwoodiana, Prunella vulgaris, Prunus africana, Prunus serrulata, Psidium guajava, Punica granatum, Shorea robusta, Siphoneugena densiflora, Symplocos lancifolia, Syzygium crebrinerve, Terminalia brassii, Terminalia catappa, Terminalia glabrescens, Ugni molinae and Vitex altissima. Asiatic acid was first documented in 2013 (PMID: 23379693). Esculentic acid (Diplazium) is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308422D          

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M  END

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M  END


  Mrv0541 05061308422D          

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   -1.3226    3.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088    3.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515    6.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804    5.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    0.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354    0.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14 13  1  0  0  0  0
 17  1  1  0  0  0  0
 17  9  1  0  0  0  0
 18  2  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  2  0  0  0  0
 20 15  1  0  0  0  0
 21 10  1  0  0  0  0
 22  8  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  1  0  0  0  0
 26  3  1  0  0  0  0
 26 15  1  0  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27  4  1  0  0  0  0
 27 16  1  0  0  0  0
 27 21  1  0  0  0  0
 27 24  1  0  0  0  0
 28  5  1  0  0  0  0
 28 13  1  0  0  0  0
 28 19  1  0  0  0  0
 29  6  1  0  0  0  0
 29 11  1  0  0  0  0
 29 22  1  0  0  0  0
 29 28  1  0  0  0  0
 30 12  1  0  0  0  0
 30 14  1  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31 16  1  0  0  0  0
 32 20  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  2  0  0  0  0
 35 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)

> <INCHI_KEY>
JXSVIVRDWWRQRT-UHFFFAOYSA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.6991

> <EXACT_MASS>
488.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
56.63011346915526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
4.2261306460000005

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.553793907295333

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744125421269486

> <JCHEM_PKA_STRONGEST_BASIC>
-2.787482617442854

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
136.83419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asiatic 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       5.533   5.606   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.866   7.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.469   8.686   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.997   6.469   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.101   6.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.502   4.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.199   7.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.135   7.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.200   3.296   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.136   5.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.802   4.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.866   2.526   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.135   3.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.199   2.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.802   9.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.987   8.184   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.200   4.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.866   5.606   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.199   5.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.136  10.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.136   7.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.469   7.146   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.532   4.836   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.470   9.456   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.532   1.756   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.802   7.916   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.470   7.916   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.135   4.836   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.469   5.606   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.532   3.296   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.976   7.004   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.136  11.766   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -7.803  10.226   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.199   0.986   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.866   0.986   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    8   19                                                       
CONECT    8    7   22                                                       
CONECT    9   12   17                                                       
CONECT   10   11   21                                                       
CONECT   11   10   29                                                       
CONECT   12    9   30                                                       
CONECT   13   14   28                                                       
CONECT   14   13   30                                                       
CONECT   15   20   26                                                       
CONECT   16   27   31                                                       
CONECT   17    1    9   18                                                  
CONECT   18    2   17   23                                                  
CONECT   19    7   23   28                                                  
CONECT   20   15   24   32                                                  
CONECT   21   10   26   27                                                  
CONECT   22    8   26   29                                                  
CONECT   23   18   19   30                                                  
CONECT   24   20   27   33                                                  
CONECT   25   30   34   35                                                  
CONECT   26    3   15   21   22                                             
CONECT   27    4   16   21   24                                             
CONECT   28    5   13   19   29                                             
CONECT   29    6   11   22   28                                             
CONECT   30   12   14   23   25                                             
CONECT   31   16                                                            
CONECT   32   20                                                            
CONECT   33   24                                                            
CONECT   34   25                                                            
CONECT   35   25                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Esculentate (diplazium)	Generator
10,11-Dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.6991 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

asiatic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5CCC34C)C2C1C)C(O)=O

InChI Identifier

InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)

InChI Key

JXSVIVRDWWRQRT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia chinensis	LOTUS Database	35616633
Actinidia polygama	LOTUS Database	35616633
Calyptranthes pallens	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Centella erecta	LOTUS Database	35616633
Combretum laxum	LOTUS Database	35616633
Cornus kousa	LOTUS Database	35616633
Craibiodendron yunnanense	LOTUS Database	35616633
Cyrtomium fortunei		Not Available
Dipterocarpus hispidus	LOTUS Database	35616633
Eucalyptus perriniana	LOTUS Database	35616633
Gentiana dahurica	LOTUS Database	35616633
Hedyotis lawsoniae	LOTUS Database	35616633
Heptapleurum heptaphyllum	LOTUS Database	35616633
Ilex cornuta	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Melaleuca ericifolia	LOTUS Database	35616633
Mucuna birdwoodiana	LOTUS Database	35616633
Prunella vulgaris	LOTUS Database	35616633
Prunus africana	LOTUS Database	35616633
Prunus serrulata	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Shorea robusta	LOTUS Database	35616633
Siphoneugena densiflora	LOTUS Database	35616633
Symplocos lancifolia	LOTUS Database	35616633
Syzygium crebrinerve	LOTUS Database	35616633
Terminalia brassii	LOTUS Database	35616633
Terminalia catappa	LOTUS Database	35616633
Terminalia glabrescens	LOTUS Database	35616633
Ugni molinae	LOTUS Database	35616633
Vitex altissima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
12-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
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	4.81	ALOGPS
logP	4.23	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.83 m³·mol⁻¹	ChemAxon
Polarizability	56.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035782

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014529

KNApSAcK ID

Not Available

Chemspider ID

261424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

296191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang S, Liu M, Liang N, Zhao Q, Zhang Y, Xue W, Yang S: Discovery and antitumor activities of constituents from Cyrtomium fortumei (J.) Smith rhizomes. Chem Cent J. 2013 Feb 4;7(1):24. doi: 10.1186/1752-153X-7-24. [PubMed:23379693 ]
DOI: 10.1186/1752-153x-7-24

Showing NP-Card for Asiatic acid (NP0137191)

MOL for NP0137191 (Asiatic acid)

3D MOL for NP0137191 (Asiatic acid)

3D SDF for NP0137191 (Asiatic acid)

3D-SDF for NP0137191 (Asiatic acid)

PDB for NP0137191 (Asiatic acid)

3D PDB for NP0137191 (Asiatic acid)

SMILES for NP0137191 (Asiatic acid)

INCHI for NP0137191 (Asiatic acid)

Structure for NP0137191 (Asiatic acid)

3D Structure for NP0137191 (Asiatic acid)