NP-MRD: Showing NP-Card for Aleuritolic acid (NP0076141)

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Record Information

Version

2.0

Created at

2022-04-28 21:18:24 UTC

Updated at

2022-04-28 21:18:25 UTC

NP-MRD ID

NP0076141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aleuritolic acid

Description

Maprounic acid, also known as aleuritolic acid or aleuritolate, belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. Aleuritolic acid is found in Aleurites montana, Elateriospermum tapos , Euphorbia guyoniana, Euphorbia portlandica, Jatropha macrorhiza, Maprounea africana and Triadica sebifera. Aleuritolic acid was first documented in 2013 (PMID: 22493952). Based on a literature review very few articles have been published on maprounic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223182D          

 33 37  0  0  1  0            999 V2000
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223182D          

 33 37  0  0  1  0            999 V2000
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
 14 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  8 29  1  1  0  0  0
  5 30  1  1  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  2 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
BHHPRAFMEFGOLZ-QVUWEPBXSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.15512275866956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
6.93

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48943324166892

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.743996982639648

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351230447263248

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.6245

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   18                                                  
CONECT    8    7    9   11   29                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23   26                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17   19                                             
CONECT   17   16   18                                                       
CONECT   18   17    7                                                       
CONECT   19   16                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   24   25                                             
CONECT   22   21   23                                                       
CONECT   23   22   14                                                       
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26   14   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    2                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Aleuritolic acid	ChEBI
Aleuritolate	Generator
Maprounate	Generator
3-Hydroxyurs-12-en-29-Oic acid	MeSH

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6bR,8aR,10S,12aR,12bR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1

InChI Key

BHHPRAFMEFGOLZ-QVUWEPBXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aleurites montana	Plant	KNApSAcK
Elateriospermum tapos	Plant	KNApSAcK
Euphorbia guyoniana	LOTUS Database	35616633
Euphorbia portlandica	LOTUS Database	35616633
Jatropha macrorhiza	Plant	KNApSAcK
Maprounea africana	LOTUS Database	35616633
Triadica sebifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:73107 )
pentacyclic triterpenoid (CHEBI:73107 )

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	6.93	ALOGPS
logP	6.59	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.74	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	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	55.16 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038406

Chemspider ID

141879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161527

PDB ID

Not Available

ChEBI ID

73107

Good Scents ID

Not Available

References

General References

Momo IJ, Dufat TH, Wandji J, Michel S, Chiozem DD: New triterpenoids from the stem bark of Hypodaphnis zenkeri. Nat Prod Res. 2013;27(2):137-45. doi: 10.1080/14786419.2012.662647. Epub 2012 Apr 11. [PubMed:22493952 ]

Showing NP-Card for Aleuritolic acid (NP0076141)

MOL for NP0076141 (Aleuritolic acid)

3D MOL for NP0076141 (Aleuritolic acid)

3D SDF for NP0076141 (Aleuritolic acid)

3D-SDF for NP0076141 (Aleuritolic acid)

PDB for NP0076141 (Aleuritolic acid)

3D PDB for NP0076141 (Aleuritolic acid)

SMILES for NP0076141 (Aleuritolic acid)

INCHI for NP0076141 (Aleuritolic acid)

Structure for NP0076141 (Aleuritolic acid)

3D Structure for NP0076141 (Aleuritolic acid)