NP-MRD: Showing NP-Card for 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol (NP0334680)

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Record Information

Version

2.0

Created at

2024-09-10 19:29:29 UTC

Updated at

2024-09-10 19:29:30 UTC

NP-MRD ID

NP0334680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol

Description

4A-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol, also known as 4a-methylzymosterol-4-carboxylate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4A-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, 4a-carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol is involved in bloch pathway (cholesterol biosynthesis).

Structure

MOL SDF PDB SMILES InChI

23724596
  Mrv1652301181921162D          

 32 35  0  0  1  0            999 V2000
    2.0919   -2.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5888   -3.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -2.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    0.4353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5414   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617   -0.8078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3220    0.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.6671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8269   -0.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8269    0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3220   -0.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8035    0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -2.1207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0992   -2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402   -1.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969   -0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5783    1.4709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5414    1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -1.6731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8149   -0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -2.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3856    1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1735   -2.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274    2.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6419    2.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4492    2.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7055    3.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5127    3.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1545    3.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21  1  1  1  0  0  0
  2 26  1  0  0  0  0
  3 26  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 20  1  1  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 18  1  0  0  0  0
  6 23  1  1  0  0  0
  7 13  1  0  0  0  0
  7 19  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  1  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 14  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 15 21  1  0  0  0  0
 15 24  1  1  0  0  0
 15 26  1  0  0  0  0
 16 17  1  0  0  0  0
 18 22  1  0  0  0  0
 19 25  1  0  0  0  0
 19 27  1  6  0  0  0
 21 22  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

23724596
  Mrv1652301181921162D          

 32 35  0  0  1  0            999 V2000
    2.0919   -2.0829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5888   -3.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -2.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    0.4353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5414   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617   -0.8078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3220    0.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.6671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8269   -0.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8269    0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3220   -0.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8035    0.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124    0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -2.1207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0992   -2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402   -1.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969   -0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5783    1.4709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5414    1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -1.6731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8149   -0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -2.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3856    1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1735   -2.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0274    2.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6419    2.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4492    2.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7055    3.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5127    3.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1545    3.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21  1  1  1  0  0  0
  2 26  1  0  0  0  0
  3 26  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 20  1  1  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 18  1  0  0  0  0
  6 23  1  1  0  0  0
  7 13  1  0  0  0  0
  7 19  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  1  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 14  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 15 21  1  0  0  0  0
 15 24  1  1  0  0  0
 15 26  1  0  0  0  0
 16 17  1  0  0  0  0
 18 22  1  0  0  0  0
 19 25  1  0  0  0  0
 19 27  1  6  0  0  0
 21 22  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1

> <INCHI_KEY>
MYWAIWDQTCHPTH-YCIQJMEESA-N

> <FORMULA>
C29H46O3

> <MOLECULAR_WEIGHT>
442.6737

> <EXACT_MASS>
442.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.65357575633656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

> <ALOGPS_LOGP>
6.64

> <JCHEM_LOGP>
6.598317999999999

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.716008813949259

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590055980466473

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0380298101870595

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
131.7868

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-JAN-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 23724596                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JAN-19         0                                  
HETATM    1  O   UNK     0       3.905  -3.888   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.699  -6.626   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.384  -5.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.211   0.813   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.211  -0.727   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.142  -1.508   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.668   1.282   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.129  -3.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.877  -1.497   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.543  -0.727   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.877   1.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.668  -1.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.567   0.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.543   0.813   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.689  -3.959   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.519  -3.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.902  -3.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.714  -0.639   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.146   2.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.211   2.352   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.242  -3.123   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.254  -1.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.154   0.032   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.464  -5.289   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.653   3.063   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.924  -5.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.118   3.892   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.132   4.527   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.639   4.845   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.117   6.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.624   6.626   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.088   7.455   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4    5    7   11   20                                             
CONECT    5    4    9   12                                                  
CONECT    6    8   10   18   23                                             
CONECT    7    4   13   19                                                  
CONECT    8    6   15   16                                                  
CONECT    9    5   10   17                                                  
CONECT   10    6    9   14                                                  
CONECT   11    4   14                                                       
CONECT   12    5   13                                                       
CONECT   13    7   12                                                       
CONECT   14   10   11                                                       
CONECT   15    8   21   24   26                                             
CONECT   16    8   17                                                       
CONECT   17    9   16                                                       
CONECT   18    6   22                                                       
CONECT   19    7   25   27                                                  
CONECT   20    4                                                            
CONECT   21    1   15   22                                                  
CONECT   22   18   21                                                       
CONECT   23    6                                                            
CONECT   24   15                                                            
CONECT   25   19   28                                                       
CONECT   26    2    3   15                                                  
CONECT   27   19                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol	Kegg
4Α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol	Generator
4a-Methylzymosterol-4-carboxylate	HMDB
4a-Methylzymosterol-4-carboxylic acid	HMDB
4alpha-Methylzymosterol-4-carboxylic acid	HMDB
4Α-methylzymosterol-4-carboxylate	HMDB
4Α-methylzymosterol-4-carboxylic acid	HMDB
4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol	Generator

Chemical Formula

C₂₉H₄₆O₃

Average Mass

442.6737 Da

Monoisotopic Mass

442.34470 Da

IUPAC Name

(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

Traditional Name

(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=O

InChI Identifier

InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1

InChI Key

MYWAIWDQTCHPTH-YCIQJMEESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholesterol-skeleton
Cholestane-skeleton
4-carboxy steroid
Steroid acid
3-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
15-hydroxysteroid
Steroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	6.64	ALOGPS
logP	6.6	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.79 m³·mol⁻¹	ChemAxon
Polarizability	53.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001181

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022471

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15808

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6062

PubChem Compound

23724596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol (NP0334680)

MOL for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

3D MOL for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

3D SDF for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

3D-SDF for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

PDB for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

3D PDB for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

SMILES for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

INCHI for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

Structure for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)

3D Structure for NP0334680 (4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol)