NP-MRD: Showing NP-Card for beta-Sitosterol acetate (NP0082291)

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Record Information

Version

2.0

Created at

2022-04-29 03:20:02 UTC

Updated at

2022-04-29 03:20:02 UTC

NP-MRD ID

NP0082291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Sitosterol acetate

Description

Beta-sitosterol 3-O-acetate, also known as b-sitosterol acetic acid or 3beta-acetoxystigmast-5-ene, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. beta-Sitosterol acetate is found in Acacia leucophloea , Allium victorialis, Baccharoides anthelmintica, Cajanus cajan, Cassia nigricans , Cynomorium songaricum, Dioscorea polystachya, Ekebergia pterophylla, Lordhowea insularis, Neolitsea sericea, Ophiocordyceps sinensis, Pyrosoma atlanticum, Toona ciliata, Wrightia tinctoria and Zea mays. beta-Sitosterol acetate was first documented in 2001 (PMID: 11429262). Based on a literature review a small amount of articles have been published on beta-sitosterol 3-O-acetate (PMID: 12774386) (PMID: 16276968).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205202D          

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M  END

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M  END


  Mrv1652304292205202D          

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   -9.5042    0.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6757    1.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4603    1.7742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0626    2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9788   -0.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  6  0  0  0
  7 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  1  0  0  0
  5 20  1  6  0  0  0
  3 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  2 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
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 24 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O2/c1-8-23(20(2)3)10-9-21(4)27-13-14-28-26-12-11-24-19-25(33-22(5)32)15-17-30(24,6)29(26)16-18-31(27,28)7/h11,20-21,23,25-29H,8-10,12-19H2,1-7H3/t21-,23-,25+,26+,27-,28+,29+,30+,31-/m1/s1

> <INCHI_KEY>
PBWOIPCULUXTNY-LBKBYZTLSA-N

> <FORMULA>
C31H52O2

> <MOLECULAR_WEIGHT>
456.755

> <EXACT_MASS>
456.396730914

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.84129808563004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetate

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
8.285602202333337

> <ALOGPS_LOGS>
-7.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003272146910708

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
138.91759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.78e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0     -11.562  -2.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.883  -0.574   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.738   0.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.274  -0.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.953  -1.526   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.098  -2.556   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.422  -1.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.795  -0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.940   0.751   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.652  -3.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.112  -3.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.342  -4.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.802  -4.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.032  -5.688   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.492  -5.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.032  -3.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.802  -1.687   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.492  -3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.422  -4.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.478  -2.990   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.058   1.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.523   2.439   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.667   1.408   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.347  -0.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.492  -1.128   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -15.956  -0.653   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.277   0.854   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -15.132   1.884   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -17.741   1.330   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -18.061   2.836   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -19.526   3.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -16.917   3.867   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -13.027  -1.604   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10                                                            
CONECT   20    5                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23    2   25   33                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3beta-Acetoxystigmast-5-ene	ChEBI
beta-Sitosterol acetate	ChEBI
beta-Sitosteryl acetate	ChEBI
3b-Acetoxystigmast-5-ene	Generator
3Β-acetoxystigmast-5-ene	Generator
b-Sitosterol acetate	Generator
b-Sitosterol acetic acid	Generator
beta-Sitosterol acetic acid	Generator
Β-sitosterol acetate	Generator
Β-sitosterol acetic acid	Generator
b-Sitosteryl acetate	Generator
b-Sitosteryl acetic acid	Generator
beta-Sitosteryl acetic acid	Generator
Β-sitosteryl acetate	Generator
Β-sitosteryl acetic acid	Generator
b-Sitosterol 3-O-acetate	Generator
b-Sitosterol 3-O-acetic acid	Generator
beta-Sitosterol 3-O-acetic acid	Generator
Β-sitosterol 3-O-acetate	Generator
Β-sitosterol 3-O-acetic acid	Generator

Chemical Formula

C₃₁H₅₂O₂

Average Mass

456.7550 Da

Monoisotopic Mass

456.39673 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetate

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O)C(C)C

InChI Identifier

InChI=1S/C31H52O2/c1-8-23(20(2)3)10-9-21(4)27-13-14-28-26-12-11-24-19-25(33-22(5)32)15-17-30(24,6)29(26)16-18-31(27,28)7/h11,20-21,23,25-29H,8-10,12-19H2,1-7H3/t21-,23-,25+,26+,27-,28+,29+,30+,31-/m1/s1

InChI Key

PBWOIPCULUXTNY-LBKBYZTLSA-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
Acacia leucophloea	Plant	KNApSAcK
Allium victorialis	LOTUS Database	35616633
Baccharoides anthelmintica	LOTUS Database	35616633
Cajanus cajan	LOTUS Database	35616633
Cassia nigricans	Plant	KNApSAcK
Cynomorium songaricum	LOTUS Database	35616633
Dioscorea polystachya	LOTUS Database	35616633
Ekebergia pterophylla	Plant	KNApSAcK
Lordhowea insularis	LOTUS Database	35616633
Neolitsea sericea	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Pyrosoma atlanticum	LOTUS Database	35616633
Toona ciliata	LOTUS Database	35616633
Wrightia tinctoria	LOTUS Database	35616633
Zea mays	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
C24-propyl-sterol-skeleton
Steroid ester
Steroid
Delta-5-steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

acetate ester (CHEBI:69433 )
steroid ester (CHEBI:69433 )

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	7.71	ALOGPS
logP	8.29	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	138.92 m³·mol⁻¹	ChemAxon
Polarizability	58.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049121

Chemspider ID

4510688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354503

PDB ID

Not Available

ChEBI ID

69433

Good Scents ID

rw1364841

References

General References

Olivier M, Renault JH, Richard B, Moretti C, Zeches-Hanrot M: Constituents of the stem bark of Ormosia wayana. Fitoterapia. 2001 Jun;72(5):583-4. doi: 10.1016/s0367-326x(00)00319-1. [PubMed:11429262 ]
Wang GL, Hou QY, Zhang J, Xu JM, Peng JF, Lin RC: [Studies on the chemical constituents of the stems of Alyxia sinensis (I)]. Zhongguo Zhong Yao Za Zhi. 2002 Feb;27(2):125-7. [PubMed:12774386 ]
Thuong PT, Jin W, Lee J, Seong R, Lee YM, Seong Y, Song K, Bae K: Inhibitory effect on TNF-alpha-induced IL-8 production in the HT29 cell of constituents from the leaf and stem of Weigela subsessilis. Arch Pharm Res. 2005 Oct;28(10):1135-41. doi: 10.1007/BF02972975. [PubMed:16276968 ]

Showing NP-Card for beta-Sitosterol acetate (NP0082291)

MOL for NP0082291 (beta-Sitosterol acetate)

3D MOL for NP0082291 (beta-Sitosterol acetate)

3D SDF for NP0082291 (beta-Sitosterol acetate)

3D-SDF for NP0082291 (beta-Sitosterol acetate)

PDB for NP0082291 (beta-Sitosterol acetate)

3D PDB for NP0082291 (beta-Sitosterol acetate)

SMILES for NP0082291 (beta-Sitosterol acetate)

INCHI for NP0082291 (beta-Sitosterol acetate)

Structure for NP0082291 (beta-Sitosterol acetate)

3D Structure for NP0082291 (beta-Sitosterol acetate)