NP-MRD: Showing NP-Card for beta-Sitosterone (NP0071986)

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Record Information

Version

2.0

Created at

2022-04-28 17:22:31 UTC

Updated at

2022-04-28 17:22:31 UTC

NP-MRD ID

NP0071986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Sitosterone

Description

Beta-Sitosterone, also known as β-sitosterone, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. beta-Sitosterone is found in Abies spectabilis, Aristolochia zollingeriana, Bistorta officinalis, Boswellia ovalifoliolata, Cassia multijuga, Dendrobium loddigesii, Engelhardia roxburghiana, Euphorbia plumerioides, Flemingia paniculata, Gynura japonica, Gynura segetum, Hernandia nymphaeifolia, Kadsura heteroclita, Microtropis fokienensis, Microtropis japonica, Parahancornia fasciculata, Pieris japonica, Polygonum bistorta , Sargentodoxa cuneata, Spiraea formosana , Tabebuia rosea, Taxus mairei, Trichilia hirta, Zanthoxylum simulans and Zanthoxylum wutaiense. beta-Sitosterone was first documented in 2005 (PMID: 16112695). Based on a literature review a small amount of articles have been published on beta-Sitosterone (PMID: 17348850) (PMID: 32071612) (PMID: 25495689) (PMID: 23479194).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219222D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219222D          

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M  END
> <DATABASE_ID>
NP0071986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,24-27H,7-9,11-18H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
KYOFIJXMVNQYFC-XJZKHKOHSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.32997049834303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,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-one

> <ALOGPS_LOGP>
7.20

> <JCHEM_LOGP>
8.051977593666667

> <ALOGPS_LOGS>
-7.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.227856548613076

> <JCHEM_PKA_STRONGEST_BASIC>
-7.429976128468029

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
128.73799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,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-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       7.210  12.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.065  13.753   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.385  15.259   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.601  13.277   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.280  11.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.816  11.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.496   9.788   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.640   8.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.105   9.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.425  10.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.889  11.216   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.569   9.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.249   8.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.929   6.697   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.464   6.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.320   7.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.986   6.482   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.306   4.975   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.838   4.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.148   3.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.918   2.147   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.458   2.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.228   0.813   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.768   0.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.458  -0.521   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.228   3.481   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.768   3.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.838   2.147   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.495   5.077   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    5   11   12                                             
CONECT   11   10    1                                                       
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19   30                                             
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27                                                            
CONECT   29   20                                                            
CONECT   30   15                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
b-Sitosterone	Generator
Β-sitosterone	Generator

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(1S,2R,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-one

Traditional Name

(1S,2R,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-one

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,24-27H,7-9,11-18H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KYOFIJXMVNQYFC-XJZKHKOHSA-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
Abies spectabilis	LOTUS Database	35616633
Aristolochia zollingeriana	LOTUS Database	35616633
Bistorta officinalis	LOTUS Database	35616633
Boswellia ovalifoliolata	LOTUS Database	35616633
Cassia multijuga	Plant	KNApSAcK
Dendrobium loddigesii	LOTUS Database	35616633
Engelhardia roxburghiana	LOTUS Database	35616633
Euphorbia plumerioides	LOTUS Database	35616633
Flemingia paniculata	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Gynura segetum	Plant	KNApSAcK
Hernandia nymphaeifolia	LOTUS Database	35616633
Kadsura heteroclita	LOTUS Database	35616633
Microtropis fokienensis	LOTUS Database	35616633
Microtropis japonica	LOTUS Database	35616633
Parahancornia fasciculata	LOTUS Database	35616633
Pieris japonica	LOTUS Database	35616633
Polygonum bistorta	Plant	KNApSAcK
Sargentodoxa cuneata	LOTUS Database	35616633
Spiraea formosana	Plant	KNApSAcK
Tabebuia rosea	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Trichilia hirta	LOTUS Database	35616633
Zanthoxylum simulans	Plant	KNApSAcK
Zanthoxylum wutaiense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Oxosteroid
3-oxosteroid
3-oxo-delta-5-steroid
Delta-5-steroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.2	ALOGPS
logP	8.05	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.74 m³·mol⁻¹	ChemAxon
Polarizability	53.33 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

C00031627

Chemspider ID

7977573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9801811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Manoharan KP, Yang D, Hsu A, Huat BT: Evaluation of Polygonum bistorta for anticancer potential using selected cancer cell lines. Med Chem. 2007 Mar;3(2):121-6. doi: 10.2174/157340607780059495. [PubMed:17348850 ]
Manoharan KP, Benny TK, Yang D: Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta. Phytochemistry. 2005 Oct;66(19):2304-8. doi: 10.1016/j.phytochem.2005.07.008. [PubMed:16112695 ]
Li Z, Du Y, Yuan Y, Zhang X, Wang Z, Tian X: Integrated quality evaluation strategy for multi-species resourced herb medicine of Qinjiao by metabolomics analysis and genetic comparation. Chin Med. 2020 Feb 11;15:16. doi: 10.1186/s13020-020-0292-3. eCollection 2020. [PubMed:32071612 ]
Hou YL, Chang HS, Wang HC, Wang SY, Chen TY, Lin CH, Chen IS: Sassarandainol: a new neolignan and anti-inflammatory constituents from the stem of Sassafras randaiense. Nat Prod Res. 2015;29(9):827-32. doi: 10.1080/14786419.2014.988713. Epub 2014 Dec 11. [PubMed:25495689 ]
Joycharat N, Thammavong S, Limsuwan S, Homlaead S, Voravuthikunchai SP, Yingyongnarongkul BE, Dej-Adisai S, Subhadhirasakul S: Antibacterial substances from Albizia myriophylla wood against cariogenic Streptococcus mutans. Arch Pharm Res. 2013 Jun;36(6):723-30. doi: 10.1007/s12272-013-0085-7. Epub 2013 Mar 12. [PubMed:23479194 ]

Showing NP-Card for beta-Sitosterone (NP0071986)

MOL for NP0071986 (beta-Sitosterone)

3D MOL for NP0071986 (beta-Sitosterone)

3D SDF for NP0071986 (beta-Sitosterone)

3D-SDF for NP0071986 (beta-Sitosterone)

PDB for NP0071986 (beta-Sitosterone)

3D PDB for NP0071986 (beta-Sitosterone)

SMILES for NP0071986 (beta-Sitosterone)

INCHI for NP0071986 (beta-Sitosterone)

Structure for NP0071986 (beta-Sitosterone)

3D Structure for NP0071986 (beta-Sitosterone)