NP-MRD: Showing NP-Card for (24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol (NP0046853)

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Record Information

Version

2.0

Created at

2022-03-17 20:30:35 UTC

Updated at

2022-03-17 20:30:36 UTC

NP-MRD ID

NP0046853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol

Description

(24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-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 (24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212322D          

 32 35  0  0  0  0            999 V2000
    1.4143    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -1.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4143   -1.4143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1288   -1.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1288   -0.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8432    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432    1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    1.0608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2721    0.2357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7010    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    2.2983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4155    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1300    2.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8445    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5589    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8445    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -1.8268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1300    3.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 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
 16 17  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
  3 18  1  1  0  0  0
  6 19  1  1  0  0  0
 14 20  1  1  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  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
 22 28  1  6  0  0  0
  4 29  1  6  0  0  0
 15 30  1  6  0  0  0
  5 31  1  6  0  0  0
 24 32  1  6  0  0  0
M  END


  Mrv0541 02241212322D          

 32 35  0  0  0  0            999 V2000
    1.4143    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -1.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4143   -1.4143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1288   -1.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1288   -0.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8432    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432   -1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8432    1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    1.0608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2721    0.2357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7010    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    2.2983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4155    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1300    2.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8445    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5589    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8445    1.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721    2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -1.8268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1300    3.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 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
 16 17  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
  3 18  1  1  0  0  0
  6 19  1  1  0  0  0
 14 20  1  1  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  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
 22 28  1  6  0  0  0
  4 29  1  6  0  0  0
 15 30  1  6  0  0  0
  5 31  1  6  0  0  0
 24 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0046853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC3=C(CC[C@]4(C)C(CC[C@@]34C)[C@H](C)CC[C@H](C)C(C)=C)[C@@]1(C)CC[C@H](O)[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h20-24,27,31H,1,9-18H2,2-8H3/t20-,21+,22-,23?,24-,27-,28-,29+,30-/m0/s1

> <INCHI_KEY>
ZNGUCFLTOCTQKJ-AOHCPOOUSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.593280781087834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.08

> <JCHEM_LOGP>
7.6736244376666685

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.95724607023405

> <JCHEM_PKA_STRONGEST_BASIC>
-1.067900568879626

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
133.62269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6S,7S,11R,15R)-14-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-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       2.640   0.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.306  -0.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.306  -1.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.640  -2.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.974  -1.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.974  -0.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.307   0.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.307  -2.640   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.641  -1.870   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.641  -0.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.641   2.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.307   1.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.308   2.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.975   1.980   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.975   0.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.642   0.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.642   1.980   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.027  -2.640   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.974   1.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.975   3.520   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.642   5.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.308   4.290   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.976   4.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.309   5.060   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.643   4.290   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.977   5.060   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.643   2.750   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.975   5.060   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.640  -4.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.975  -1.100   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       3.974  -3.410   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      13.309   6.600   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   31                                             
CONECT    6    1    7    5   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    7   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   16   14   30                                             
CONECT   16   17   15                                                       
CONECT   17   16   13                                                       
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   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29    4                                                            
CONECT   30   15                                                            
CONECT   31    5                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(24R)-4a,14a,24-Trimethyl-5a-cholesta-8,25(27)-dien-3b-ol	Generator
(24R)-4Α,14α,24-trimethyl-5α-cholesta-8,25(27)-dien-3β-ol	Generator

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7174 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

7235-40-7

SMILES

[H][C@@]12CCC3=C(CC[C@]4(C)C(CC[C@@]34C)[C@H](C)CC[C@H](C)C(C)=C)[C@@]1(C)CC[C@H](O)[C@H]2C

InChI Identifier

InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h20-24,27,31H,1,9-18H2,2-8H3/t20-,21+,22-,23?,24-,27-,28-,29+,30-/m0/s1

InChI Key

ZNGUCFLTOCTQKJ-AOHCPOOUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
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
14-alpha-methylsteroid
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

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	7.08	ALOGPS
logP	7.67	ChemAxon
logS	-6	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	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.59 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

FDB006224

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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Showing NP-Card for (24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol (NP0046853)

MOL for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

3D MOL for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

3D SDF for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

3D-SDF for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

PDB for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

3D PDB for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

SMILES for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

INCHI for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

Structure for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)

3D Structure for NP0046853 ((24R)-4alpha,14alpha,24-trimethyl-5alpha-cholesta-8,25(27)-dien-3beta-ol)