NP-MRD: Showing NP-Card for 4alpha-Methylfecosterol (NP0044307)

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Record Information

Version

2.0

Created at

2022-02-14 20:48:22 UTC

Updated at

2022-03-10 22:17:34 UTC

NP-MRD ID

NP0044307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4alpha-Methylfecosterol

Description

4A-Methylfecosterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 4a-methylfecosterol is considered to be a sterol lipid molecule. 4A-Methylfecosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4Alpha-Methylfecosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042000332D          

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 15 19  1  0  0  0  0
 19  4  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044307

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1

> <INCHI_KEY>
QLDNWJOJCDIMKK-XLFBYWHPSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.6908

> <EXACT_MASS>
412.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.45054455315034

> <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-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

> <ALOGPS_LOGP>
6.64

> <JCHEM_LOGP>
7.373577317666668

> <ALOGPS_LOGS>
-5.78

> <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>
129.14759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.90e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.3038661.210   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6368662.754   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8666.6228668.943   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8662.6338661.985   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8661.3028665.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9688665.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9688663.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.3028662.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6308665.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6308663.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.9648662.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.2948668.166   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9608667.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9608665.856   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.2948665.086   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0928665.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.9978666.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0928667.872   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0928669.412   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4288670.178   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8666.7608670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0968670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4328669.412   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.0968671.718   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8673.4328667.872   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8669.4288668.638   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   10                                                            
CONECT    3    9                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6   12                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9    2   12                                                  
CONECT   11   12    7    1   17                                             
CONECT   12   11   13   10    6                                             
CONECT   13   12   14                                                       
CONECT   14   13   18                                                       
CONECT   15   16   19                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   11                                                  
CONECT   18   17   14   20                                                  
CONECT   19   20   23   15    4                                             
CONECT   20   19   21   18    5                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   33   19   22                                             
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   31   32                                                  
CONECT   30   28                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
4alpha-Methylfecosterol	HMDB
4 alpha-Methyl-5 alpha-ergosta-8,24(28)-dien-3 beta-ol	MeSH, HMDB
4a-Methylfecosterol	Generator
4Α-methylfecosterol	Generator, HMDB
(3beta,4alpha,5alpha)-4-Methylergosta-8,24(28)-dien-3-ol	HMDB
(3β,4α,5α)-4-Methylergosta-8,24(28)-dien-3-ol	HMDB
24,25-Dihydro-4alpha-methyl-24-methylenezymosterol	HMDB
24,25-Dihydro-4α-methyl-24-methylenezymosterol	HMDB
4α-Methylfecosterol	HMDB

Chemical Formula

C₂₉H₄₈O

Average Mass

412.6908 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

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

CAS Registry Number

17757-07-2

SMILES

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

InChI Identifier

InChI=1S/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1

InChI Key

QLDNWJOJCDIMKK-XLFBYWHPSA-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
Agaricus campestris	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Cannabis sativa	CannabisDB	Not Available
Eutypa lata	LOTUS Database	35616633
Leptosphaeria maculans	LOTUS Database	35616633
Neofibularia nolitangere	LOTUS Database	35616633
Triticum aestivum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-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

ergostanoid (CHEBI:80094 )
Ergosterols and C24-methyl derivatives (C15776 )
Ergosterols and C24-methyl derivatives (LMST01031019 )

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	6.64	ALOGPS
logP	7.37	ChemAxon
logS	-5.8	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	129.15 m³·mol⁻¹	ChemAxon
Polarizability	53.45 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