NP-MRD: Showing NP-Card for dihydrobetulinic acid (NP0241135)

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Record Information

Version

2.0

Created at

2022-09-07 01:07:43 UTC

Updated at

2022-09-07 01:07:44 UTC

NP-MRD ID

NP0241135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydrobetulinic acid

Description

Dihydrobetulinic acid, also known as 20,29-dihydrobetulinate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. dihydrobetulinic acid is found in Calophyllum inophyllum. dihydrobetulinic acid was first documented in 2004 (PMID: 15149668). Based on a literature review a small amount of articles have been published on dihydrobetulinic acid (PMID: 33353300) (PMID: 30453551) (PMID: 28987603) (PMID: 25942059).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072203072D          

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  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  6  0  0  0
 15 33  1  0  0  0  0
 33  4  1  6  0  0  0
  7 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241135

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
PZXJOHSZQAEJFE-FZFNOLFKSA-N

> <FORMULA>
C30H50O3

> <MOLECULAR_WEIGHT>
458.727

> <EXACT_MASS>
458.37599547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.56726372473472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8S,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <JCHEM_LOGP>
6.987384891

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48943339017772

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.774351250596012

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351229024983197

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.848

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8S,9R,10R,13R,14R,17S,19R)-17-hydroxy-8-isopropyl-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.977  -4.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.105  -5.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.577  -5.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.985  -9.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.061 -10.670   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.666 -12.086   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.468 -10.485   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.663 -10.127   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.934 -11.090   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11   33                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   18   13   32                                             
CONECT   32   31                                                            
CONECT   33   15    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
20,29-Dihydrobetulinic acid	ChEBI
20,29-Dihydrobetulinate	Generator
Dihydrobetulinate	Generator

Chemical Formula

C₃₀H₅₀O₃

Average Mass

458.7270 Da

Monoisotopic Mass

458.37600 Da

IUPAC Name

(1R,2R,5S,8S,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

Traditional Name

(1R,2R,5S,8S,9R,10R,13R,14R,17S,19R)-17-hydroxy-8-isopropyl-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

InChI Identifier

InChI=1S/C30H50O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h18-24,31H,8-17H2,1-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

InChI Key

PZXJOHSZQAEJFE-FZFNOLFKSA-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, 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
Calophyllum inophyllum	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
18-oxosteroid
18-hydroxysteroid
Oxosteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:65485 )
pentacyclic triterpenoid (CHEBI:65485 )

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	6.99	ChemAxon
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	2	ChemAxon
Refractivity	132.85 m³·mol⁻¹	ChemAxon
Polarizability	55.57 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

Not Available

Chemspider ID

58804

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65319

PDB ID

Not Available

ChEBI ID

65485

Good Scents ID

Not Available

References

General References

Pakulski Z, Cmoch P, Korda A, Luboradzki R, Gwardiak K, Karczewski R: Rearrangements of the Betulin Core. Synthesis of Terpenoids Possessing the Bicyclo[3.3.1]nonane Fragment by Rearrangement of Lupane-Type Epoxides. J Org Chem. 2021 Jan 1;86(1):1084-1095. doi: 10.1021/acs.joc.0c02560. Epub 2020 Dec 23. [PubMed:33353300 ]
Spivak A, Khalitova R, Nedopekina D, Dzhemileva L, Yunusbaeva M, Odinokov V, D'yakonov V, Dzhemilev U: Synthesis and Evaluation of Anticancer Activities of Novel C-28 Guanidine-Functionalized Triterpene Acid Derivatives. Molecules. 2018 Nov 16;23(11):3000. doi: 10.3390/molecules23113000. [PubMed:30453551 ]
Eignerova B, Tichy M, Krasulova J, Kvasnica M, Rarova L, Christova R, Urban M, Bednarczyk-Cwynar B, Hajduch M, Sarek J: Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids. Eur J Med Chem. 2017 Nov 10;140:403-420. doi: 10.1016/j.ejmech.2017.09.041. Epub 2017 Sep 21. [PubMed:28987603 ]
Borkova L, Jasikova L, Rehulka J, Frisonsova K, Urban M, Frydrych I, Popa I, Hajduch M, Dickinson NJ, Vlk M, Dzubak P, Sarek J: Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells. Eur J Med Chem. 2015;96:482-90. doi: 10.1016/j.ejmech.2015.03.068. Epub 2015 Apr 1. [PubMed:25942059 ]
Mukherjee R, Jaggi M, Rajendran P, Srivastava SK, Siddiqui MJ, Vardhan A, Burman AC: Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3169-72. doi: 10.1016/j.bmcl.2004.04.010. [PubMed:15149668 ]
LOTUS database [Link]

Showing NP-Card for dihydrobetulinic acid (NP0241135)

MOL for NP0241135 (dihydrobetulinic acid)

3D MOL for NP0241135 (dihydrobetulinic acid)

3D SDF for NP0241135 (dihydrobetulinic acid)

3D-SDF for NP0241135 (dihydrobetulinic acid)

PDB for NP0241135 (dihydrobetulinic acid)

3D PDB for NP0241135 (dihydrobetulinic acid)

SMILES for NP0241135 (dihydrobetulinic acid)

INCHI for NP0241135 (dihydrobetulinic acid)

Structure for NP0241135 (dihydrobetulinic acid)

3D Structure for NP0241135 (dihydrobetulinic acid)