NP-MRD: Showing NP-Card for (1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0219531)

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Record Information

Version

2.0

Created at

2022-09-05 20:32:48 UTC

Updated at

2022-09-05 20:32:49 UTC

NP-MRD ID

NP0219531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

Description

CHOLESTANOL, also known as beta cholestanol or coprostanol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. (1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol is found in Actinia equina, Aiolochroia crassa, Avena sativa, Cinachyrella schulzei, Cribricellina cribraria, Dioscorea polystachya, Dysidea fragilis, Gastrothylax crumenifer, Gleichenia japonica, Kalanchoe petitiana, Nicotiana tabacum, Osteolaemus tetraspis, Rubus crataegifolius, Salpa thompsoni, Suberites massa, Tedania anhelans, Verongula gigantea and Volkameria inermis. (1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol was first documented in 2022 (PMID: 35967798). Based on a literature review a small amount of articles have been published on CHOLESTANOL (PMID: 35926102) (PMID: 35870600) (PMID: 35745232) (PMID: 35714521).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052222322D          

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M  END
> <DATABASE_ID>
NP0219531

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22-,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
QYIXCDOBOSTCEI-PNIPQYGLSA-N

> <FORMULA>
C27H48O

> <MOLECULAR_WEIGHT>
388.68

> <EXACT_MASS>
388.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
50.70458997443345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_LOGP>
7.518468512000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413656

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
119.76649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   13   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12    9   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
5 alpha Cholestan 3 beta ol	MeSH
5 beta Cholestan 3 beta ol	MeSH
beta Cholestanol	MeSH
beta-Ol, 5 beta-cholestan-3	MeSH
5 alpha Cholestan 3 alpha ol	MeSH
5 beta-Cholestan-3 alpha-ol	MeSH
5 beta-Cholestan-3 beta-ol	MeSH
Coprostanol	MeSH
5 alpha-Cholestan-3 beta-ol	MeSH
Cholestan 3 ol	MeSH
Cholestanol, (3alpha, 5beta)-isomer	MeSH
Coprosterol	MeSH
beta-Cholestanol	MeSH
5 alpha-Cholestan-3 alpha-ol	MeSH
Cholestan-3-ol	MeSH
Dihydrocholesterol	MeSH
beta-Cholestan-3 beta-ol, 5	MeSH

Chemical Formula

C₂₇H₄₈O

Average Mass

388.6800 Da

Monoisotopic Mass

388.37052 Da

IUPAC Name

(1S,2S,5S,7S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

Traditional Name

(1S,2S,5S,7S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22-,23-,24+,25+,26+,27-/m1/s1

InChI Key

QYIXCDOBOSTCEI-PNIPQYGLSA-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
Actinia equina	LOTUS Database	35616633
Aiolochroia crassa	LOTUS Database	35616633
Avena sativa	LOTUS Database	35616633
Cinachyrella schulzei	LOTUS Database	35616633
Cribricellina cribraria	LOTUS Database	35616633
Dioscorea polystachya	LOTUS Database	35616633
Dysidea fragilis	LOTUS Database	35616633
Gastrothylax crumenifer	LOTUS Database	35616633
Gleichenia japonica	LOTUS Database	35616633
Kalanchoe petitiana	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Osteolaemus tetraspis	LOTUS Database	35616633
Rubus crataegifolius	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633
Suberites massa	LOTUS Database	35616633
Tedania anhelans	LOTUS Database	35616633
Verongula gigantea	LOTUS Database	35616633
Volkameria inermis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Cholesterol
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	7.52	ChemAxon
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.77 m³·mol⁻¹	ChemAxon
Polarizability	50.7 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042080

Chemspider ID

5496309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7157118

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhu Q, Wu J, Li J, Wang S, He D, Lian X: Effects of phytosterols' intake on systemic and tissue-specific lipid metabolism in C57BL/6J mice. Front Nutr. 2022 Jul 27;9:924236. doi: 10.3389/fnut.2022.924236. eCollection 2022. [PubMed:35967798 ]
Schlag S, Gotz S, Ruttler F, Schmockel SM, Vetter W: Quantitation of 20 Phytosterols in 34 Different Accessions of Quinoa (Chenopodium quinoa). J Agric Food Chem. 2022 Aug 17;70(32):9856-9864. doi: 10.1021/acs.jafc.2c03374. Epub 2022 Aug 4. [PubMed:35926102 ]
Jaukovic Z, Grujic S, Bujagic IM, Petkovic A, Lausevic M: Steroid-based tracing of sewage-sourced pollution of river water and wastewater treatment efficiency: Dissolved and suspended water phase distribution. Sci Total Environ. 2022 Nov 10;846:157510. doi: 10.1016/j.scitotenv.2022.157510. Epub 2022 Jul 20. [PubMed:35870600 ]
Stanasila L, Marques-Vidal P: Serum Phytosterols Are Not Associated with Inflammatory Markers in Two Cross-Sectional, Swiss Population-Based Studies (The CoLaus|PsyCoLaus Study). Nutrients. 2022 Jun 16;14(12):2500. doi: 10.3390/nu14122500. [PubMed:35745232 ]
Contreras MJ, Arias ME, Silva M, Cabrera P, Felmer R: Effect of cholestanol and cholesterol-loaded cyclodextrin on stallion sperm function and capacitation post-cryopreservation. Theriogenology. 2022 Sep 1;189:1-10. doi: 10.1016/j.theriogenology.2022.06.005. Epub 2022 Jun 8. [PubMed:35714521 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0219531)

MOL for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0219531 ((1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)