NP-MRD: Showing NP-Card for 4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol (NP0046478)

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Record Information

Version

2.0

Created at

2022-03-17 20:03:02 UTC

Updated at

2022-03-17 20:03:02 UTC

NP-MRD ID

NP0046478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol

Description

4Alpha,24-Dimethylcholesta-7,24-dien-3beta-ol 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. 4Alpha,24-Dimethylcholesta-7,24-dien-3beta-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212342D          

 30 33  0  0  0  0            999 V2000
   -2.1620   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.5695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1620   -1.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4476   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7331   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331   -1.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    0.4930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6958   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -1.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476    0.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.7305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8392    1.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    1.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -2.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    2.9680    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  1  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  2  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
 22 13  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  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  4 29  1  6  0  0  0
 24 30  1  0  0  0  0
M  END


  Mrv0541 02241212342D          

 30 33  0  0  0  0            999 V2000
   -2.1620   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -1.5695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1620   -1.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4476   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7331   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331   -1.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    0.4930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6958   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5910   -1.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476    0.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.7305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8392    1.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    1.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682    0.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    2.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -2.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537    2.9680    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  1  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  2  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
 22 13  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  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  4 29  1  6  0  0  0
 24 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(C)=C(C)C)C1CCC2C3=CCC4[C@H](C)[C@@H](O)CC[C@]4(C)C3CC[C@]12C

> <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/h10,20-21,23-27,30H,8-9,11-17H2,1-7H3/t20-,21+,23?,24?,25?,26?,27+,28-,29+/m1/s1

> <INCHI_KEY>
KPIRFXVTLHBVFL-TXTDMRFKSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.6908

> <EXACT_MASS>
412.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
52.950285952991365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,6S,15R)-14-[(2R)-5,6-dimethylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
7.315643647333333

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.957638198850066

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0677290518229814

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.2201

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6S,15R)-14-[(2R)-5,6-dimethylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-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      -4.036  -0.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.369  -1.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.369  -2.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.036  -3.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.702  -2.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.702  -1.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.368  -0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.368  -3.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.035  -2.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.035  -1.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.035   1.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.368   0.920   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.633   1.690   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.299   0.920   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.299  -0.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.966  -0.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.966   0.920   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.703  -3.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.702   0.150   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.299   2.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.966   4.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.633   3.230   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.300   3.230   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.634   4.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.967   3.230   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.301   4.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.967   1.690   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.299   4.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.036  -5.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.634   5.540   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   29                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29    4                                                            
CONECT   30   24                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
4a,24-Dimethylcholesta-7,24-dien-3b-ol	Generator
4Α,24-dimethylcholesta-7,24-dien-3β-ol	Generator

Chemical Formula

C₂₉H₄₈O

Average Mass

412.6908 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(2S,5S,6S,15R)-14-[(2R)-5,6-dimethylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

Traditional Name

(2S,5S,6S,15R)-14-[(2R)-5,6-dimethylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(C)=C(C)C)C1CCC2C3=CCC4[C@H](C)[C@@H](O)CC[C@]4(C)C3CC[C@]12C

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/h10,20-21,23-27,30H,8-9,11-17H2,1-7H3/t20-,21+,23?,24?,25?,26?,27+,28-,29+/m1/s1

InChI Key

KPIRFXVTLHBVFL-TXTDMRFKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum lycopersicum var. lycopersicum	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
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
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	6.62	ALOGPS
logP	7.32	ChemAxon
logS	-6.1	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	4	ChemAxon
Refractivity	130.22 m³·mol⁻¹	ChemAxon
Polarizability	52.95 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

FDB004627

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 4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol (NP0046478)

MOL for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

3D MOL for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

3D SDF for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

3D-SDF for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

PDB for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

3D PDB for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

SMILES for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

INCHI for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

Structure for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)

3D Structure for NP0046478 (4alpha,24-Dimethylcholesta-7,24-dien-3beta-ol)