NP-MRD: Showing NP-Card for ethyl cholate (NP0310040)

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Record Information

Version

2.0

Created at

2022-09-11 05:02:30 UTC

Updated at

2022-09-11 05:02:30 UTC

NP-MRD ID

NP0310040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl cholate

Description

Ethyl cholate, also known as ethyl cholic acid, 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. ethyl cholate is found in Streptomyces parvulus. ethyl cholate was first documented in 2019 (PMID: 31717987). Based on a literature review a small amount of articles have been published on ethyl cholate (PMID: 34674527) (PMID: 33842888).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112207022D          

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M  END
> <DATABASE_ID>
NP0310040

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O5/c1-5-31-23(30)9-6-15(2)18-7-8-19-24-20(14-22(29)26(18,19)4)25(3)11-10-17(27)12-16(25)13-21(24)28/h15-22,24,27-29H,5-14H2,1-4H3/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

> <INCHI_KEY>
FPDXMWHJGOCDQJ-HZAMXZRMSA-N

> <FORMULA>
C26H44O5

> <MOLECULAR_WEIGHT>
436.633

> <EXACT_MASS>
436.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.34451843282873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (4R)-4-[(1S,2S,5R,7S,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]pentanoate

> <JCHEM_LOGP>
2.9851964673333313

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963399055959

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15943466982205112

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
120.30699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (4R)-4-[(1S,2S,5R,7S,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]pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.153 -13.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.819 -14.029   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.486 -13.259   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.848 -14.029   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.848 -15.569   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.182 -13.259   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.515 -14.029   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.849 -13.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.849 -11.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.183 -14.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.344 -15.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.850 -15.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.620 -14.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.126 -14.227   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.602 -12.762   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.572 -11.618   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.065 -11.938   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.035 -10.793   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.590 -13.403   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.445 -12.372   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.109 -12.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.078 -11.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.584 -10.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.091 -10.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.121 -11.802   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.628 -11.481   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.645 -13.266   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.139 -13.586   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.663 -15.051   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.157 -15.371   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.681 -16.836   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   10   20                                             
CONECT   20   19                                                            
CONECT   21   15   22   23   28                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   14   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Ethyl cholic acid	Generator

Chemical Formula

C₂₆H₄₄O₅

Average Mass

436.6330 Da

Monoisotopic Mass

436.31887 Da

IUPAC Name

ethyl (4R)-4-[(1S,2S,5R,7S,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]pentanoate

Traditional Name

ethyl (4R)-4-[(1S,2S,5R,7S,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]pentanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H44O5/c1-5-31-23(30)9-6-15(2)18-7-8-19-24-20(14-22(29)26(18,19)4)25(3)11-10-17(27)12-16(25)13-21(24)28/h15-22,24,27-29H,5-14H2,1-4H3/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

InChI Key

FPDXMWHJGOCDQJ-HZAMXZRMSA-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
Streptomyces parvulus	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
7-hydroxysteroid
3-alpha-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	2.99	ChemAxon
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.31 m³·mol⁻¹	ChemAxon
Polarizability	51.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

4954537

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bera A, Sahoo S, Goswami K, Das SK, Ghosh P, De P: Modulating Insulin Aggregation with Charge Variable Cholic Acid-Derived Polymers. Biomacromolecules. 2021 Nov 8;22(11):4833-4845. doi: 10.1021/acs.biomac.1c01107. Epub 2021 Oct 22. [PubMed:34674527 ]
Sahoo S, Ur Rehman J, Shah MR, De P, Tecilla P: Cholate Conjugated Polymeric Amphiphiles as Efficient Artificial Ionophores. ACS Appl Polym Mater. 2021 Feb 12;3(2):588-593. doi: 10.1021/acsapm.0c01182. Epub 2021 Jan 4. [PubMed:33842888 ]
Castro-Hernandez A, Cortez-Lemus NA: Thermo/pH Responsive Star and Linear Copolymers Containing a Cholic Acid-Derived Monomer, N-Isopropylacrylamide and Acrylic Acid: Synthesis and Solution Properties. Polymers (Basel). 2019 Nov 11;11(11):1859. doi: 10.3390/polym11111859. [PubMed:31717987 ]
LOTUS database [Link]

Showing NP-Card for ethyl cholate (NP0310040)

MOL for NP0310040 (ethyl cholate)

3D MOL for NP0310040 (ethyl cholate)

3D SDF for NP0310040 (ethyl cholate)

3D-SDF for NP0310040 (ethyl cholate)

PDB for NP0310040 (ethyl cholate)

3D PDB for NP0310040 (ethyl cholate)

SMILES for NP0310040 (ethyl cholate)

INCHI for NP0310040 (ethyl cholate)

Structure for NP0310040 (ethyl cholate)

3D Structure for NP0310040 (ethyl cholate)