NP-MRD: Showing NP-Card for Delta 8,14 -Sterol (NP0044551)

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Record Information

Version

2.0

Created at

2022-02-14 20:58:43 UTC

Updated at

2022-03-10 22:21:56 UTC

NP-MRD ID

NP0044551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Delta 8,14 -Sterol

Description

Delta 8,14-Sterol, also known as Œ¥8,14 -sterol, 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, Delta 8,14 -sterol is considered to be a sterol lipid molecule. Delta 8,14 -Sterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Œ¥ 8,14 -Sterol 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


  Mrv1652306222023582D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306222023582D          

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 25 22  1  0  0  0  0
 26 14  1  0  0  0  0
 26 22  2  0  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  6  0  0  0
 28 16  1  0  0  0  0
 28 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29  7  1  6  0  0  0
 29 17  1  0  0  0  0
 29 24  1  0  0  0  0
 29 26  1  0  0  0  0
 27 30  1  6  0  0  0
 20 31  1  6  0  0  0
 21 32  1  6  0  0  0
 23 33  1  1  0  0  0
 24 34  1  1  0  0  0
 27 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CCC(=C)C(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C)[C@]1([H])CC3

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O/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/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1

> <INCHI_KEY>
HLAWVOWADPNAGN-BAHZUFOISA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.6749

> <EXACT_MASS>
410.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.05747553131935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.00

> <JCHEM_LOGP>
6.967997836333335

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.957245922127218

> <JCHEM_PKA_STRONGEST_BASIC>
-1.067900633661555

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.99759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      15.277  -3.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.944  -5.791   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.610  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.609  -5.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.218  -3.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.013  -5.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.380  -6.212   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.276  -4.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.943  -3.481   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.301  -2.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.795  -2.458   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.114  -1.949   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.608  -1.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.886  -5.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.633  -6.852   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.392  -5.571   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.873  -6.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.944  -4.251   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.610  -3.481   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.188  -4.243   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.332  -3.283   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.275  -3.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.319  -3.923   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.838  -2.962   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.856  -4.747   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.663  -5.708   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.868  -4.107   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.349  -5.067   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.170  -6.028   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       9.943  -5.021   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.712  -2.779   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.567  -2.642   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.157  -5.388   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.694  -4.563   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   19                                                       
CONECT    9    8   20                                                       
CONECT   10   11   22                                                       
CONECT   11   10   24                                                       
CONECT   12   13   23                                                       
CONECT   13   12   25                                                       
CONECT   14   16   26                                                       
CONECT   15   17   27                                                       
CONECT   16   14   28                                                       
CONECT   17   15   29                                                       
CONECT   18    1    2   19                                                  
CONECT   19    3    8   18                                                  
CONECT   20    4    9   23   31                                             
CONECT   21    5   24   27   32                                             
CONECT   22   10   25   26                                                  
CONECT   23   12   20   28   33                                             
CONECT   24   11   21   29   34                                             
CONECT   25   13   22   28                                                  
CONECT   26   14   22   29                                                  
CONECT   27   15   21   30   35                                             
CONECT   28    6   16   23   25                                             
CONECT   29    7   17   24   26                                             
CONECT   30   27                                                            
CONECT   31   20                                                            
CONECT   32   21                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   27                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
delta8,14 -Sterol	ChEBI
delta8,14-Sterol	ChEBI
Δ8,14 -sterol	Generator
Δ8,14-sterol	Generator
Δ 8,14 -sterol	Generator
4-alpha-Methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol	HMDB
4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-ol	HMDB
4a-Methylergosta-8,14,24(241)-trien-3b-ol	HMDB
4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol	HMDB
(3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-ol	HMDB
(3β,4α,5α)-4-Methylergosta-8,14,24(28)-trien-3-ol	HMDB
4alpha-Methylergosta-8,14,24(241)-trien-3beta-ol	HMDB
4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-ol	HMDB
4α-Methylergosta-8,14,24(241)-trien-3β-ol	HMDB

Chemical Formula

C₂₉H₄₆O

Average Mass

410.6749 Da

Monoisotopic Mass

410.35487 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

74635-33-9

SMILES

[H][C@@](C)(CCC(=C)C(C)C)[C@@]1([H])CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@]([H])(O)[C@@]([H])(C)[C@]1([H])CC3

InChI Identifier

InChI=1S/C29H46O/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/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1

InChI Key

HLAWVOWADPNAGN-BAHZUFOISA-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
Arabidopsis thaliana	Plant	KNApSAcK
Cannabis sativa	CannabisDB	Not Available

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

3beta-sterol (CHEBI:30109 )
Ergosterols and C24-methyl derivatives (C11508 )
Ergosterols and C24-methyl derivatives (LMST01031020 )

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	ALOGPS
logP	6.97	ChemAxon
logS	-5.4	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	130 m³·mol⁻¹	ChemAxon
Polarizability	53.06 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