NP-MRD: Showing NP-Card for Sulfolithocholylglycine (NP0086996)

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Record Information

Version

2.0

Created at

2022-05-11 16:36:51 UTC

Updated at

2022-05-11 16:36:51 UTC

NP-MRD ID

NP0086996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sulfolithocholylglycine

Description

Sulfolithocholylglycine, also known as glca-sul or glycolithocholate 3-sulfate, belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. Sulfolithocholylglycine was first documented in 1975 (PMID: 1097294). Sulfolithocholylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 832799) (PMID: 1150035).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219332D          

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 12 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 27  1  0  0  0  0
 15 24  1  0  0  0  0
 16 20  1  0  0  0  0
 17 25  1  0  0  0  0
 18 34  1  1  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 26  1  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 23 28  2  0  0  0  0
 23 27  1  0  0  0  0
 24 29  1  0  0  0  0
 24 30  2  0  0  0  0
 31 35  1  0  0  0  0
 32 35  2  0  0  0  0
 33 35  2  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086996

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17?,18+,19?,20?,21?,22?,25+,26-/m1/s1

> <INCHI_KEY>
FHXBAFXQVZOILS-JWOIRZCRSA-N

> <FORMULA>
C26H43NO7S

> <MOLECULAR_WEIGHT>
513.687

> <EXACT_MASS>
513.276023425

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
56.96783684314634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
2.5726574248775305

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.773289633791134

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.414656042550539

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5755994195823376

> <JCHEM_POLAR_SURFACE_AREA>
130

> <JCHEM_REFRACTIVITY>
130.4765999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic 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      20.407 -10.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.485 -14.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.762 -11.853   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.942 -11.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.808 -17.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.144 -17.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.856 -14.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.947 -15.389   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.969 -12.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.814 -15.660   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.821 -13.361   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.150 -14.894   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.157 -12.595   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.141 -17.974   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.011 -12.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.434 -11.434   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.477 -17.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.809 -17.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.148 -15.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.954 -12.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.484 -14.909   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.817 -14.901   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.476 -11.949   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.038 -13.928   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.481 -15.667   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.489 -13.369   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      26.503 -13.096   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      25.956 -10.486   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      30.545 -13.612   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      28.558 -15.391   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.009 -19.511   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.929 -19.502   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.465 -21.046   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      11.474 -17.966   0.000  0.00  0.00           O+0
HETATM   35  S   UNK     0      11.469 -19.506   0.000  0.00  0.00           S+0
CONECT    1   16                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   16    9                                                       
CONECT    5    6   17                                                       
CONECT    6    5   19                                                       
CONECT    7   20    8                                                       
CONECT    8    7   21                                                       
CONECT    9    4   23                                                       
CONECT   10   18   12                                                       
CONECT   11   22   13                                                       
CONECT   12   10   25                                                       
CONECT   13   11   26                                                       
CONECT   14   17   18                                                       
CONECT   15   27   24                                                       
CONECT   16    1    4   20                                                  
CONECT   17    5   14   25                                                  
CONECT   18   10   14   34                                                  
CONECT   19    6   21   22                                                  
CONECT   20    7   16   26                                                  
CONECT   21    8   19   26                                                  
CONECT   22   11   19   25                                                  
CONECT   23    9   28   27                                                  
CONECT   24   15   29   30                                                  
CONECT   25    2   12   17   22                                             
CONECT   26    3   13   20   21                                             
CONECT   27   15   23                                                       
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   24                                                            
CONECT   31   35                                                            
CONECT   32   35                                                            
CONECT   33   35                                                            
CONECT   34   18   35                                                       
CONECT   35   31   32   33   34                                             
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Sulpholithocholylglycine	Generator
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetate	HMDB
2-{[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene]amino}acetic acid	HMDB
GLCA-sul	HMDB
Glycine amidated	HMDB
Glycolithocholate 3-sulfate	HMDB
Glycolithocholate 3-sulphate	HMDB
Glycolithocholate sulfate	HMDB
Glycolithocholate sulphate	HMDB
Glycolithocholic acid 3-sulfate	HMDB
Glycolithocholic acid 3-sulphate	HMDB
Glycolithocholic acid sulfate	HMDB
Glycolithocholic acid sulphate	HMDB
LCA-sul	HMDB
Sulfoglycolithocholate	HMDB
Sulfoglycolithocholic acid	HMDB

Chemical Formula

C₂₆H₄₃NO₇S

Average Mass

513.6870 Da

Monoisotopic Mass

513.27602 Da

IUPAC Name

2-[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(2S,5S,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17?,18+,19?,20?,21?,22?,25+,26-/m1/s1

InChI Key

FHXBAFXQVZOILS-JWOIRZCRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Sulfated steroid skeleton
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Fatty acyl
Organic sulfuric acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
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	1.1	ALOGPS
logP	2.57	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.48 m³·mol⁻¹	ChemAxon
Polarizability	56.97 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0002639

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023034

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11301

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6725

PubChem Compound

53477756

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW, Coffin SB: Metabolism of lithocholate in healthy man. II. Enterohepatic circulation. Gastroenterology. 1975 Jul;69(1):67-76. [PubMed:1097294 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW: Metabolism of lethocholate in healthy man. I. Biotransformation and biliary excretion of intravenously administered lithocholate, lithocholylglycine, and their sulfates. Gastroenterology. 1975 Jul;69(1):59-66. [PubMed:1150035 ]

Showing NP-Card for Sulfolithocholylglycine (NP0086996)

MOL for NP0086996 (Sulfolithocholylglycine)

3D MOL for NP0086996 (Sulfolithocholylglycine)

3D SDF for NP0086996 (Sulfolithocholylglycine)

3D-SDF for NP0086996 (Sulfolithocholylglycine)

PDB for NP0086996 (Sulfolithocholylglycine)

3D PDB for NP0086996 (Sulfolithocholylglycine)

SMILES for NP0086996 (Sulfolithocholylglycine)

INCHI for NP0086996 (Sulfolithocholylglycine)

Structure for NP0086996 (Sulfolithocholylglycine)

3D Structure for NP0086996 (Sulfolithocholylglycine)