NP-MRD: Showing NP-Card for (24S)-24-Methyl-25-dehydrocholesterol (NP0046855)

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Record Information

Version

2.0

Created at

2022-03-17 20:30:37 UTC

Updated at

2022-03-17 20:30:37 UTC

NP-MRD ID

NP0046855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(24S)-24-Methyl-25-dehydrocholesterol

Description

(24S)-24-Methyl-25-dehydrocholesterol 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. (24S)-24-Methyl-25-dehydrocholesterol is found in Aplysina fistularis and Kalanchoe marmorata. Thus, (24S)-24-methyl-25-dehydrocholesterol is considered to be a sterol lipid molecule (24S)-24-Methyl-25-dehydrocholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212322D          

 32 35  0  0  1  0            999 V2000
    2.6741    5.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9596    5.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9596    4.2246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    3.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    4.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    5.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1030    5.4621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1030    3.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    4.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    5.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8175    6.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030    6.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    6.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5319    6.2871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5319    5.4621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9608    5.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9608    6.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    3.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    5.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    7.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    7.5246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6753    7.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    7.9371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1043    7.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8187    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1043    6.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030    4.6371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    5.8746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    4.6371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    8.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 29  1  6  0  0  0
 10 30  1  1  0  0  0
 15 31  1  6  0  0  0
 13 22  1  1  0  0  0
 24 32  1  1  0  0  0
M  END


  Mrv0541 02241212322D          

 32 35  0  0  1  0            999 V2000
    2.6741    5.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9596    5.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9596    4.2246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6741    3.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    4.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    5.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1030    5.4621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1030    3.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    4.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    5.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8175    6.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030    6.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    6.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5319    6.2871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5319    5.4621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9608    5.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9608    6.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    3.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    5.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    7.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    7.5246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6753    7.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    7.9371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1043    7.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8187    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1043    6.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    7.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030    4.6371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    5.8746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319    4.6371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    8.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  2  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 29  1  6  0  0  0
 10 30  1  1  0  0  0
 15 31  1  6  0  0  0
 13 22  1  1  0  0  0
 24 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](C)C(C)=C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,19-20,22-26,29H,1,7-8,10-17H2,2-6H3/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
IBAFJAONJZIYIT-PODYLUTMSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.30310895321575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-6-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
6.81

> <JCHEM_LOGP>
7.052262316

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.94259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-6-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.992  10.196   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.658   9.426   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.658   7.886   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.992   7.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.325   7.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.325   9.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.659  10.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.659   7.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.993   7.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.993   9.426   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.993  12.506   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.659  11.736   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.660  12.506   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.326  11.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.326  10.196   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.993  10.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.993  11.736   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.324   7.116   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.325  10.966   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.326  13.276   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.994  14.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.660  14.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.327  14.046   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.661  14.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.995  14.046   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.328  14.816   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.995  12.506   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.326  14.816   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       7.659   8.656   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.993  10.966   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      10.326   8.656   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      15.661  16.356   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10   29                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15   30                                             
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   17   22                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16   31                                             
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   21   28   13                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29    7                                                            
CONECT   30   10                                                            
CONECT   31   15                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6642 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-6-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-6-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](C)C(C)=C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,19-20,22-26,29H,1,7-8,10-17H2,2-6H3/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

InChI Key

IBAFJAONJZIYIT-PODYLUTMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysina fistularis	LOTUS Database	35616633
Kalanchoe marmorata	LOTUS Database	35616633
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Ergosterols and C24-methyl derivatives (LMST01030111 )

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	6.81	ALOGPS
logP	7.05	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.2	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	124.94 m³·mol⁻¹	ChemAxon
Polarizability	51.3 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

FDB006226

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

5283653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (24S)-24-Methyl-25-dehydrocholesterol (NP0046855)

MOL for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

3D MOL for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

3D SDF for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

3D-SDF for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

PDB for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

3D PDB for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

SMILES for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

INCHI for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

Structure for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)

3D Structure for NP0046855 ((24S)-24-Methyl-25-dehydrocholesterol)