NP-MRD: Showing NP-Card for (3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol (NP0336012)

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Record Information

Version

2.0

Created at

2024-09-11 04:19:20 UTC

Updated at

2024-09-11 04:19:20 UTC

NP-MRD ID

NP0336012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol

Description

(3Beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Based on a literature review very few articles have been published on (3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262306512D          

 31 34  0  0  0  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392    0.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5628   -0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 20  4  1  0  0  0  0
 20  9  1  0  0  0  0
 21  5  1  0  0  0  0
 22  8  2  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 23 11  1  0  0  0  0
 24 13  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27 15  1  0  0  0  0
 27 23  2  0  0  0  0
 28 16  1  0  0  0  0
 28 21  1  0  0  0  0
 29  6  1  0  0  0  0
 29 17  1  0  0  0  0
 29 24  1  0  0  0  0
 29 26  1  0  0  0  0
 30  7  1  0  0  0  0
 30 18  1  0  0  0  0
 30 25  1  0  0  0  0
 30 27  1  0  0  0  0
 31 28  1  0  0  0  0
M  END


  Mrv2104 05262306512D          

 31 34  0  0  0  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392    0.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5628   -0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 20  4  1  0  0  0  0
 20  9  1  0  0  0  0
 21  5  1  0  0  0  0
 22  8  2  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 23 11  1  0  0  0  0
 24 13  1  0  0  0  0
 24 20  1  0  0  0  0
 25 12  1  0  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27 15  1  0  0  0  0
 27 23  2  0  0  0  0
 28 16  1  0  0  0  0
 28 21  1  0  0  0  0
 29  6  1  0  0  0  0
 29 17  1  0  0  0  0
 29 24  1  0  0  0  0
 29 26  1  0  0  0  0
 30  7  1  0  0  0  0
 30 18  1  0  0  0  0
 30 25  1  0  0  0  0
 30 27  1  0  0  0  0
 31 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\CCC(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C

> <INCHI_IDENTIFIER>
InChI=1/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,19-21,24-26,28,31H,9-18H2,1-7H3/b22-8-

> <INCHI_KEY>
MPTIJFTWLPEOOP-UYOCIXKTNA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.552546885470385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,9a,11a-trimethyl-1-[(5Z)-5-(propan-2-yl)hept-5-en-2-yl]-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
7.760212312333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.95724607071678

> <JCHEM_PKA_STRONGEST_BASIC>
-1.067900568668479

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
134.82109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-[(5Z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.513   0.368   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.984  -0.637   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.287   3.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.458  -0.848   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.811   2.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.397  -0.314   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    1   22                                                       
CONECT    9   10   20                                                       
CONECT   10    9   22                                                       
CONECT   11   12   23                                                       
CONECT   12   11   25                                                       
CONECT   13   14   24                                                       
CONECT   14   13   26                                                       
CONECT   15   17   27                                                       
CONECT   16   18   28                                                       
CONECT   17   15   29                                                       
CONECT   18   16   30                                                       
CONECT   19    2    3   22                                                  
CONECT   20    4    9   24                                                  
CONECT   21    5   25   28                                                  
CONECT   22    8   10   19                                                  
CONECT   23   11   26   27                                                  
CONECT   24   13   20   29                                                  
CONECT   25   12   21   30                                                  
CONECT   26   14   23   29                                                  
CONECT   27   15   23   30                                                  
CONECT   28   16   21   31                                                  
CONECT   29    6   17   24   26                                             
CONECT   30    7   18   25   27                                             
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(3b,4a,5a,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol	Generator
(3Β,4α,5α,24Z)-4-methylstigmasta-8,24(28)-dien-3-ol	Generator

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

6,9a,11a-trimethyl-1-[(5Z)-5-(propan-2-yl)hept-5-en-2-yl]-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

Traditional Name

1-[(5Z)-5-isopropylhept-5-en-2-yl]-6,9a,11a-trimethyl-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-ol

CAS Registry Number

Not Available

SMILES

C\C=C(\CCC(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C

InChI Identifier

InChI=1/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,19-21,24-26,28,31H,9-18H2,1-7H3/b22-8-

InChI Key

MPTIJFTWLPEOOP-UYOCIXKTNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
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	7.76	ChemAxon
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	134.82 m³·mol⁻¹	ChemAxon
Polarizability	55.55 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol (NP0336012)

MOL for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

3D MOL for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

3D SDF for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

3D-SDF for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

PDB for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

3D PDB for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

SMILES for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

INCHI for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

Structure for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)

3D Structure for NP0336012 ((3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-8,24(28)-dien-3-ol)