NP-MRD: Showing NP-Card for methost-8-enol (NP0142925)

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Record Information

Version

2.0

Created at

2022-09-01 21:34:42 UTC

Updated at

2022-09-01 21:34:42 UTC

NP-MRD ID

NP0142925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methost-8-enol

Description

4Alpha-methyl-5alpha-cholest-8-en-3beta-ol, also known as methost-8-enol or 4α-methylcholesta-8-en-3β-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4alpha-methyl-5alpha-cholest-8-en-3beta-ol is considered to be a sterol lipid molecule. methost-8-enol is found in Agelas oroides, Agelas sceptrum and Scrippsiella trochoidea. methost-8-enol was first documented in 1982 (PMID: 7104833). 4Alpha-methyl-5alpha-cholest-8-en-3beta-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

6452640
  Mrv1652301231920092D          

 29 32  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

6452640
  Mrv1652301231920092D          

 29 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0142925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24,26,29H,7-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1

> <INCHI_KEY>
SCEZIHJVTBQOLS-YIJYGBTNSA-N

> <FORMULA>
C28H48O

> <MOLECULAR_WEIGHT>
400.691

> <EXACT_MASS>
400.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.52366068389644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.73

> <JCHEM_LOGP>
7.434204032333334

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.95724607071678

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0679005686684793

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.82149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.81e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-JAN-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6452640                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-19         0                                  
HETATM    1  O   UNK     0       3.905  -4.866   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.211  -0.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.211  -1.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.668   0.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.142  -2.486   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.877  -2.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.543  -1.705   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.129  -4.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.877   0.605   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.668  -2.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.567  -0.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.543  -0.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.902  -4.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.519  -4.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.689  -4.937   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.146   1.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.714  -1.617   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.211   1.375   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.242  -4.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.254  -2.430   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.154  -0.946   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.653   2.085   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.695  -6.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.118   2.914   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.132   3.549   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.639   3.867   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.117   5.330   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.624   5.648   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.088   6.477   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    3    4    9   18                                             
CONECT    3    2    6   10                                                  
CONECT    4    2   11   16                                                  
CONECT    5    7    8   17   21                                             
CONECT    6    3    7   13                                                  
CONECT    7    5    6   12                                                  
CONECT    8    5   14   15                                                  
CONECT    9    2   12                                                       
CONECT   10    3   11                                                       
CONECT   11    4   10                                                       
CONECT   12    7    9                                                       
CONECT   13    6   14                                                       
CONECT   14    8   13                                                       
CONECT   15    8   19   23                                                  
CONECT   16    4   22   24                                                  
CONECT   17    5   20                                                       
CONECT   18    2                                                            
CONECT   19    1   15   20                                                  
CONECT   20   17   19                                                       
CONECT   21    5                                                            
CONECT   22   16   25                                                       
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
4alpha-Methylcholesta-8-en-3beta-ol	ChEBI
Methost-8-enol	ChEBI
4a-Methylcholesta-8-en-3b-ol	Generator
4Α-methylcholesta-8-en-3β-ol	Generator
4a-Methyl-5a-cholest-8-en-3b-ol	Generator
4Α-methyl-5α-cholest-8-en-3β-ol	Generator

Chemical Formula

C₂₈H₄₈O

Average Mass

400.6910 Da

Monoisotopic Mass

400.37052 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@@H]1CC3

InChI Identifier

InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24,26,29H,7-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1

InChI Key

SCEZIHJVTBQOLS-YIJYGBTNSA-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
Agelas oroides	LOTUS Database	35616633
Agelas sceptrum	LOTUS Database	35616633
Scrippsiella trochoidea	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
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

cholestanoid (CHEBI:87051 )
3beta-sterol (CHEBI:87051 )
Cholesterol and derivatives (LMST01010197 )

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	6.73	ALOGPS
logP	7.43	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-1.1	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	124.82 m³·mol⁻¹	ChemAxon
Polarizability	52.52 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

HMDB0062394

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452640

PDB ID

Not Available

ChEBI ID

87051

Good Scents ID

Not Available

References

General References

Masse R, Huang YS, Eid K, Laliberte C, Davignon J: Plasma methyl sterol sulfates in familial hypercholesterolemia after partial ileal bypass. Can J Biochem. 1982 May;60(5):556-63. doi: 10.1139/o82-068. [PubMed:7104833 ]
LOTUS database [Link]

Showing NP-Card for methost-8-enol (NP0142925)

MOL for NP0142925 (methost-8-enol)

3D MOL for NP0142925 (methost-8-enol)

3D SDF for NP0142925 (methost-8-enol)

3D-SDF for NP0142925 (methost-8-enol)

PDB for NP0142925 (methost-8-enol)

3D PDB for NP0142925 (methost-8-enol)

SMILES for NP0142925 (methost-8-enol)

INCHI for NP0142925 (methost-8-enol)

Structure for NP0142925 (methost-8-enol)

3D Structure for NP0142925 (methost-8-enol)