NP-MRD: Showing NP-Card for Allolithocholic acid (NP0334631)

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Record Information

Version

2.0

Created at

2024-09-10 19:13:35 UTC

Updated at

2024-09-10 19:13:36 UTC

NP-MRD ID

NP0334631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Allolithocholic acid

Description

Allolithocholic acid, also known as allolithocholate, 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. Allolithocholic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Allolithocholic acid is a bile acid present in normal serum and feces, with a tendency to be at higher concentrations in patients with colon cancer, particularly in men (PMID 16548228 ). Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231218292D          

 27 30  0  0  1  0            999 V2000
    9.7767   -5.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -7.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1014   -5.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3938   -5.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7270   -9.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4156   -8.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2976   -7.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534   -7.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135   -8.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -6.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021   -7.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2679   -6.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3006   -9.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9814   -5.6033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9892   -8.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627   -8.9751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3663   -7.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7737   -6.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0549   -7.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6285   -7.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0108   -4.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399   -8.0663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0057   -6.7031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8741   -9.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2185   -3.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155   -4.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  6  0  0  0
 23  2  1  1  0  0  0
 24  3  1  1  0  0  0
  4 15  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
 16  5  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
  7  8  1  0  0  0  0
 20  8  1  0  0  0  0
  9 22  1  0  0  0  0
 10 17  1  0  0  0  0
 10 12  1  0  0  0  0
 21 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 23  1  0  0  0  0
 17 25  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 24  1  0  0  0  0
 20 24  1  0  0  0  0
 21 23  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  2  0  0  0  0
M  END


  Mrv0541 02231218292D          

 27 30  0  0  1  0            999 V2000
    9.7767   -5.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -7.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1014   -5.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3938   -5.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7270   -9.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4156   -8.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2976   -7.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534   -7.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135   -8.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -6.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021   -7.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2679   -6.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3006   -9.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9814   -5.6033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9892   -8.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627   -8.9751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3663   -7.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7737   -6.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0549   -7.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6285   -7.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0108   -4.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399   -8.0663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0057   -6.7031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8741   -9.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2185   -3.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2155   -4.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  6  0  0  0
 23  2  1  1  0  0  0
 24  3  1  1  0  0  0
  4 15  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
 16  5  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
  7  8  1  0  0  0  0
 20  8  1  0  0  0  0
  9 22  1  0  0  0  0
 10 17  1  0  0  0  0
 10 12  1  0  0  0  0
 21 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 23  1  0  0  0  0
 17 25  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 24  1  0  0  0  0
 20 24  1  0  0  0  0
 21 23  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/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+/m0/s1

> <INCHI_KEY>
SMEROWZSTRWXGI-IBUNROKMSA-N

> <FORMULA>
C24H40O3

> <MOLECULAR_WEIGHT>
376.5726

> <EXACT_MASS>
376.297745146

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.12080129039343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
5.022070320666666

> <ALOGPS_LOGS>
-5.87

> <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>
107.68129999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.05e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allolithocholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      18.250 -10.050   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.996 -13.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.123 -10.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.668  -9.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.557 -17.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.842 -16.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.356 -13.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.526 -14.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.184  -9.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.425 -15.216   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.281 -12.672   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.711 -14.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.567 -11.823   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.894 -17.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.765 -10.459   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.180 -16.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.517 -16.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.750 -14.898   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.378 -11.950   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.036 -14.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.373 -14.209   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.087  -8.707   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.088 -15.057   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.944 -12.512   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.232 -17.602   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.475  -7.217   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.602  -9.117   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   15    9                                                       
CONECT    5    6   16                                                       
CONECT    6    5   18                                                       
CONECT    7   19    8                                                       
CONECT    8    7   20                                                       
CONECT    9    4   22                                                       
CONECT   10   17   12                                                       
CONECT   11   21   13                                                       
CONECT   12   10   23                                                       
CONECT   13   11   24                                                       
CONECT   14   16   17                                                       
CONECT   15    1    4   19                                                  
CONECT   16    5   14   23                                                  
CONECT   17   10   14   25                                                  
CONECT   18    6   20   21                                                  
CONECT   19    7   15   24                                                  
CONECT   20    8   18   24                                                  
CONECT   21   11   18   23                                                  
CONECT   22    9   26   27                                                  
CONECT   23    2   12   16   21                                             
CONECT   24    3   13   19   20                                             
CONECT   25   17                                                            
CONECT   26   22                                                            
CONECT   27   22                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
Allolithocholate	Generator
3a-Hydroxy-5a-cholan-24-Oate	HMDB
3a-Hydroxy-5a-cholan-24-Oic acid	HMDB
3a-Hydroxy-5a-cholanoate	HMDB
3a-Hydroxy-5a-cholanoic acid	HMDB
(4S)-4-[(2S,5R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Chemical Formula

C₂₄H₄₀O₃

Average Mass

376.5726 Da

Monoisotopic Mass

376.29775 Da

IUPAC Name

(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

allolithocholic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/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+/m0/s1

InChI Key

SMEROWZSTRWXGI-IBUNROKMSA-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 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-alpha-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

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	4.38	ALOGPS
logP	5.02	ChemAxon
logS	-5.9	ALOGPS
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	45.12 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

HMDB0000381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021999

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

5370

PubChem Compound

53477689

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Allolithocholic acid (NP0334631)

MOL for NP0334631 (Allolithocholic acid)

3D MOL for NP0334631 (Allolithocholic acid)

3D SDF for NP0334631 (Allolithocholic acid)

3D-SDF for NP0334631 (Allolithocholic acid)

PDB for NP0334631 (Allolithocholic acid)

3D PDB for NP0334631 (Allolithocholic acid)

SMILES for NP0334631 (Allolithocholic acid)

INCHI for NP0334631 (Allolithocholic acid)

Structure for NP0334631 (Allolithocholic acid)

3D Structure for NP0334631 (Allolithocholic acid)