NP-MRD: Showing NP-Card for Isolithocholic acid (NP0334658)

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Record Information

Version

2.0

Created at

2024-09-10 19:20:51 UTC

Updated at

2024-09-10 19:20:51 UTC

NP-MRD ID

NP0334658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isolithocholic acid

Description

Isolithocholic acid is also known as isolithocholate. Isolithocholic acid was first documented in 2024 (PMID: 39057717). Based on a literature review a small amount of articles have been published on Isolithocholic acid (PMID: 38815838) (PMID: 38701355) (PMID: 38514730) (PMID: 38357569).

Structure

MOL SDF PDB SMILES InChI

Isolithocholic acid.mol
  Mrv2104 05252321532D          

 31 34  0  0  0  0            999 V2000
   -2.4539   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4539   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3105   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    2.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    3.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -3.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.9214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.9214    0.0000 H   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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  1  1  0  0  0
  5 28  1  1  0  0  0
 22 29  1  6  0  0  0
  8 30  1  1  0  0  0
  9 31  1  6  0  0  0
M  END

Isolithocholic acid.mol
  Mrv2104 05252321532D          

 31 34  0  0  0  0            999 V2000
   -2.4539   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4539   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.3339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3105   -2.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -2.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1184   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9030   -1.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030   -0.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1580    0.7682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881    2.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9650    0.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0250   -0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    3.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1684    1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684   -2.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -3.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -1.9214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -1.9214    0.0000 H   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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  1  0  0  0
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 16 25  2  0  0  0  0
 16 26  1  0  0  0  0
  1 27  1  1  0  0  0
  5 28  1  1  0  0  0
 22 29  1  6  0  0  0
  8 30  1  1  0  0  0
  9 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334658

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/s2

> <INCHI_KEY>
SMEROWZSTRWXGI-JNAGDMDVNA-N

> <FORMULA>
C24H40O3

> <MOLECULAR_WEIGHT>
376.581

> <EXACT_MASS>
376.297745148

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
45.892648691618156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

> <JCHEM_LOGP>
5.022070320666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396321121705

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.791043111632056

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569565580180343

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
107.68129999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
isolithocholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isolithocholic acid.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -4.581  -4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.581  -2.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.247  -2.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.247  -5.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.913  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.580  -5.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.754  -4.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.754  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.088  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -2.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.458  -1.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.552  -0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.028   1.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.939   2.523   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.338   4.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.825   4.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.535   1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.088  -0.507   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.088   1.033   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.754   0.263   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.580  -0.507   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.580  -2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.913  -2.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.913  -1.277   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.224   5.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.914   3.320   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.914  -5.127   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.913  -5.897   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.580  -3.587   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.754  -1.277   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.088  -3.587   0.000  0.00  0.00           H+0
CONECT    1    2    4   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   23   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22   30                                             
CONECT    9    8   10   18   31                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   25   26                                                  
CONECT   17   13                                                            
CONECT   18   12    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23   29                                             
CONECT   23   22    3    5   24                                             
CONECT   24   23                                                            
CONECT   25   16                                                            
CONECT   26   16                                                            
CONECT   27    1                                                            
CONECT   28    5                                                            
CONECT   29   22                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Isolithocholate	Generator

Chemical Formula

C₂₄H₄₀O₃

Average Mass

376.5810 Da

Monoisotopic Mass

376.29775 Da

IUPAC Name

(4R)-4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid

Traditional Name

isolithocholic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/s2

InChI Key

SMEROWZSTRWXGI-JNAGDMDVNA-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 monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:81253 )
C24 bile acids, alcohols, and derivatives (LMST04010004 )

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	5.02	ChemAxon
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-1.4	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	4	ChemAxon
Refractivity	107.68 m³·mol⁻¹	ChemAxon
Polarizability	45.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Chiang PI, Chang KH, Tang HY, Wu YR, Cheng ML, Chen CM: Diagnostic Potential of Alternations of Bile Acid Profiles in the Plasma of Patients with Huntington's Disease. Metabolites. 2024 Jul 20;14(7):394. doi: 10.3390/metabo14070394. [PubMed:39057717 ]
Bao S, Wang W, Deng Z, Zhou R, Zeng S, Hou D, He J, Huang Z: Changes of bacterial communities and bile acid metabolism reveal the potential "intestine-hepatopancreas axis" in shrimp. Sci Total Environ. 2024 Aug 15;938:173384. doi: 10.1016/j.scitotenv.2024.173384. Epub 2024 May 28. [PubMed:38815838 ]
Choucair I, Mallela DP, Hilser JR, Hartiala JA, Nemet I, Gogonea V, Li L, Lusis AJ, Fischbach MA, Tang WHW, Allayee H, Hazen SL: Comprehensive Clinical and Genetic Analyses of Circulating Bile Acids and Their Associations With Diabetes and Its Indices. Diabetes. 2024 Aug 1;73(8):1215-1228. doi: 10.2337/db23-0676. [PubMed:38701355 ]
Myszor IT, Lapka K, Hermannsson K, Rekha RS, Bergman P, Gudmundsson GH: Bile acid metabolites enhance expression of cathelicidin antimicrobial peptide in airway epithelium through activation of the TGR5-ERK1/2 pathway. Sci Rep. 2024 Mar 21;14(1):6750. doi: 10.1038/s41598-024-57251-3. [PubMed:38514730 ]
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Showing NP-Card for Isolithocholic acid (NP0334658)

MOL for NP0334658 (Isolithocholic acid)

3D MOL for NP0334658 (Isolithocholic acid)

3D SDF for NP0334658 (Isolithocholic acid)

3D-SDF for NP0334658 (Isolithocholic acid)

PDB for NP0334658 (Isolithocholic acid)

3D PDB for NP0334658 (Isolithocholic acid)

SMILES for NP0334658 (Isolithocholic acid)

INCHI for NP0334658 (Isolithocholic acid)

Structure for NP0334658 (Isolithocholic acid)

3D Structure for NP0334658 (Isolithocholic acid)