NP-MRD: Showing NP-Card for allocholic acid (NP0220212)

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Record Information

Version

2.0

Created at

2022-09-05 21:27:42 UTC

Updated at

2022-09-05 21:27:43 UTC

NP-MRD ID

NP0220212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

allocholic acid

Description

Allocholic acid, also known as allocholate or 5alpha-cholate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. allocholic acid is found in Petromyzon marinus. allocholic acid was first documented in 1962 (PMID: 14012853). Allocholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 2079611) (PMID: 11344576) (PMID: 11041240) (PMID: 3660436) (PMID: 6825311) (PMID: 7150258).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652305021922112D          

 34 37  0  0  0  0            999 V2000
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627010001.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652305021922112D          

 34 37  0  0  0  0            999 V2000
10000.3421 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0220212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
BHQCQFFYRZLCQQ-PGHAKIONSA-N

> <FORMULA>
C24H40O5

> <MOLECULAR_WEIGHT>
408.579

> <EXACT_MASS>
408.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.19560447759984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.482494456666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475012423758966

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944265438213734

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
110.78929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAY-19         0                                  
HETATM    1  O   UNK     0    8667.3058662.405   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0    8665.9708669.372   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.1068669.832   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8671.4388669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.7748669.832   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0    8674.1068669.062   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0    8672.7748671.372   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8667.4378669.832   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8670.1068668.292   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5   18                                                            
CONECT    6   12                                                            
CONECT    7   10                                                            
CONECT    8   23                                                            
CONECT    9   13                                                            
CONECT   10   11    7   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18    6                                             
CONECT   13   12   21    9   23                                             
CONECT   14   15   18                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    3                                                  
CONECT   17   16   19                                                       
CONECT   18   19   14    5   12                                             
CONECT   19   18   20   17    4                                             
CONECT   20   19   21                                                       
CONECT   21   20    1   13                                                  
CONECT   22   23   26   10    2                                             
CONECT   23   22   24   13    8                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   27   34   22   25                                             
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27                                                            
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoic acid	ChEBI
5alpha-Cholic acid	ChEBI
Allocholate	Kegg
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5alpha,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
3a,7a,12a-Trihydroxy-5a-cholanoate	Generator
3a,7a,12a-Trihydroxy-5a-cholanoic acid	Generator
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoate	Generator
5a-Cholate	Generator
5a-Cholic acid	Generator
5alpha-Cholate	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	HMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	HMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	HMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	HMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate	HMDB
(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oate	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acid	HMDB
3a,7a,12a-Trihydroxycholanate	HMDB
3a,7a,12a-Trihydroxycholanic acid	HMDB
5alpha-Allocholic acid	HMDB
5Α-allocholic acid	HMDB
Allocholic acid	HMDB

Chemical Formula

C₂₄H₄₀O₅

Average Mass

408.5790 Da

Monoisotopic Mass

408.28757 Da

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

BHQCQFFYRZLCQQ-PGHAKIONSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petromyzon marinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:81308 )
C24 bile acids, alcohols, and derivatives (C17737 )
C24 bile acids, alcohols, and derivatives (LMST04010092 )

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	2.26	ALOGPS
logP	2.48	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	47.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011602

KNApSAcK ID

Not Available

Chemspider ID

141151

KEGG Compound ID

C17737

BioCyc ID

CPD-16581

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5491

PubChem Compound

160636

PDB ID

Not Available

ChEBI ID

81308

Good Scents ID

Not Available

References

General References

Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]
Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. [PubMed:11344576 ]
Kuramoto T, Miyamoto J, Konishi M, Hoshita T, Masul T, Une M: Bile acids in porcine fetal bile. Biol Pharm Bull. 2000 Oct;23(10):1143-6. doi: 10.1248/bpb.23.1143. [PubMed:11041240 ]
Kihira K, Shimazu K, Kuwabara M, Yoshii M, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. Steroids. 1986 Jul-Aug;48(1-2):109-19. doi: 10.1016/0039-128x(86)90045-0. [PubMed:3660436 ]
Amuro Y, Hayashi E, Endo T, Higashino K, Kishimoto S: Unusual trihydroxylated bile acids in urine of patients with liver cirrhosis. Clin Chim Acta. 1983 Jan 7;127(1):61-7. doi: 10.1016/0009-8981(83)90075-x. [PubMed:6825311 ]
Clayton PT, Muller DP, Lawson AM: The bile acid composition of gastric contents from neonates with high intestinal obstruction. Biochem J. 1982 Sep 15;206(3):489-98. doi: 10.1042/bj2060489. [PubMed:7150258 ]
Yun SS, Scott AP, Siefkes MJ, Li W: Development and application of an ELISA for a sex pheromone released by the male sea lamprey (Petromyzon marinus L.). Gen Comp Endocrinol. 2002 Dec;129(3):163-70. doi: 10.1016/s0016-6480(02)00517-8. [PubMed:12460600 ]
Ali SS, Farhat H, Elliott WH: Bile acids. XLIX. Allocholic acid, the major bile acid of Uromastix hardwickii. J Lipid Res. 1976 Jan;17(1):21-4. [PubMed:1255017 ]
Goto T, Holzinger F, Hagey LR, Cerre C, Ton-Nu HT, Schteingart CD, Steinbach JH, Shneider BL, Hofmann AF: Physicochemical and physiological properties of 5alpha-cyprinol sulfate, the toxic bile salt of cyprinid fish. J Lipid Res. 2003 Sep;44(9):1643-51. doi: 10.1194/jlr.M300155-JLR200. Epub 2003 Jun 16. [PubMed:12810826 ]
ANDERSON IG, HASLEWOOD GA: Comparative studiesof 'bile salts'. 15. The natural occurrence and preparation of allocholic acid. Biochem J. 1962 Oct;85(1):236-42. doi: 10.1042/bj0850236. [PubMed:14012853 ]
KARAVOLAS HJ, ELLIOTT WH, HSIA SL, DOISY EA Jr, MATSCHINER JT, THAYER SA, DOISY EA: BILE ACIDS. XXII. ALLOCHOLIC ACID, A METABOLITE OF 5-ALPHA-CHOLESTAN-3-BET-A-OL IN THE RAT. J Biol Chem. 1965 Apr;240:1568-72. [PubMed:14285492 ]
Siefkes MJ, Li W: Electrophysiological evidence for detection and discrimination of pheromonal bile acids by the olfactory epithelium of female sea lampreys ( Petromyzon marinus). J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2004 Mar;190(3):193-9. doi: 10.1007/s00359-003-0484-1. Epub 2003 Dec 20. [PubMed:14689221 ]
Venkatachalam KV: Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey. Bioessays. 2005 Feb;27(2):222-8. doi: 10.1002/bies.20155. [PubMed:15666352 ]
Fine JM, Vrieze LA, Sorensen PW: Evidence that petromyzontid lampreys employ a common migratory pheromone that is partially comprised of bile acids. J Chem Ecol. 2004 Nov;30(11):2091-110. doi: 10.1023/b:joec.0000048776.16091.b1. [PubMed:15672658 ]
LOTUS database [Link]

Showing NP-Card for allocholic acid (NP0220212)

MOL for NP0220212 (allocholic acid)

3D MOL for NP0220212 (allocholic acid)

3D SDF for NP0220212 (allocholic acid)

3D-SDF for NP0220212 (allocholic acid)

PDB for NP0220212 (allocholic acid)

3D PDB for NP0220212 (allocholic acid)

SMILES for NP0220212 (allocholic acid)

INCHI for NP0220212 (allocholic acid)

Structure for NP0220212 (allocholic acid)

3D Structure for NP0220212 (allocholic acid)