NP-MRD: Showing NP-Card for Cortolone 3-glucuronide (NP0090876)

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Record Information

Version

2.0

Created at

2022-05-11 18:24:50 UTC

Updated at

2022-05-11 18:24:50 UTC

NP-MRD ID

NP0090876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cortolone 3-glucuronide

Description

Cortolone-3-glucuronide belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Cortolone 3-glucuronide was first documented in 1984 (PMID: 6549383). Cortolone-3-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241200502D          

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M  END

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  Mrv0541 02241200502D          

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   17.1085   -5.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1085   -4.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6795   -5.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2925   -5.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361   -6.4712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6701   -6.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  1  0  0  0
  2 10  1  6  0  0  0
  6 11  1  6  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 18 20  1  0  0  0  0
 21 17  1  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 22  1  0  0  0  0
 25 22  1  0  0  0  0
 23 25  1  0  0  0  0
 26 19  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 28  1  0  0  0  0
 28 24  1  0  0  0  0
 24 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 33  1  0  0  0  0
 35 32  1  0  0  0  0
 36 31  1  0  0  0  0
 37 26  2  0  0  0  0
 38 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0090876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(=O)C3C(CCC4CCC(CC34C)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C1CCC2(O)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O11/c1-25-9-13(37-24-21(33)19(31)20(32)22(38-24)23(34)35)5-3-12(25)4-6-14-15-7-8-27(36,17(30)11-28)26(15,2)10-16(29)18(14)25/h12-15,17-22,24,28,30-33,36H,3-11H2,1-2H3,(H,34,35)/t12?,13?,14?,15?,17?,18?,19-,20-,21+,22-,24+,25?,26?,27?/m0/s1

> <INCHI_KEY>
OKNSFVSKHQJVRN-XAYCFROHSA-N

> <FORMULA>
C27H42O11

> <MOLECULAR_WEIGHT>
542.6158

> <EXACT_MASS>
542.272712186

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
56.6029565422804

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-0.566723060333334

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.158422809532459

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5636990019876422

> <JCHEM_PKA_STRONGEST_BASIC>
-2.976535816909254

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
129.72359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.933 -15.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.933 -16.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      18.599 -14.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.599 -17.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.265 -15.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.265 -16.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      21.266 -14.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.932 -14.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.599 -19.010   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      21.266 -17.470   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.931 -17.470   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.931 -12.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      14.598 -15.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      22.600 -15.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.934 -14.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.600 -16.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.267 -15.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.934 -17.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.601 -14.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.267 -16.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.267 -13.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.935 -15.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.601 -17.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.268 -14.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.935 -16.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.601 -12.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.935 -12.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.268 -12.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      31.936 -12.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      31.936 -14.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.602 -12.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.602 -10.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.936  -9.769   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      31.936  -8.229   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      29.268  -9.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      32.279 -11.181   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      25.267 -12.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      29.251 -11.361   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4   10                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6    8                                                  
CONECT    6    4    5   11                                                  
CONECT    7    1   14                                                       
CONECT    8    5   12   13                                                  
CONECT    9    4                                                            
CONECT   10    2                                                            
CONECT   11    6                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    7   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19   20   21                                             
CONECT   18   16   20                                                       
CONECT   19   17   22   26                                                  
CONECT   20   17   18   23                                                  
CONECT   21   17                                                            
CONECT   22   19   24   25                                                  
CONECT   23   20   25                                                       
CONECT   24   22   28   30                                                  
CONECT   25   22   23                                                       
CONECT   26   19   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   31   24   38                                             
CONECT   29   30   31                                                       
CONECT   30   29   24                                                       
CONECT   31   29   28   32   36                                             
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31                                                            
CONECT   37   26                                                            
CONECT   38   28                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
20alpha-Cortolone-3-glucuronide	HMDB
20beta-Cortolone-3-glucuronide	HMDB
20 alpha-Cortolone-3-glucuronide	MeSH
20 beta-Cortolone-3-glucuronide	MeSH
(2S,3S,4S,5R,6R)-6-{[14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
Cortolone-3-glucuronide	MeSH

Chemical Formula

C₂₇H₄₂O₁₁

Average Mass

542.6158 Da

Monoisotopic Mass

542.27271 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CC(=O)C3C(CCC4CCC(CC34C)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C1CCC2(O)C(O)CO

InChI Identifier

InChI=1S/C27H42O11/c1-25-9-13(37-24-21(33)19(31)20(32)22(38-24)23(34)35)5-3-12(25)4-6-14-15-7-8-27(36,17(30)11-28)26(15,2)10-16(29)18(14)25/h12-15,17-22,24,28,30-33,36H,3-11H2,1-2H3,(H,34,35)/t12?,13?,14?,15?,17?,18?,19-,20-,21+,22-,24+,25?,26?,27?/m0/s1

InChI Key

OKNSFVSKHQJVRN-XAYCFROHSA-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 steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Steroidal glycoside
21-hydroxysteroid
20-hydroxysteroid
Pregnane-skeleton
Diterpenoid
Hydroxysteroid
17-hydroxysteroid
11-oxosteroid
Oxosteroid
Terpene glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Acetal
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.01	ALOGPS
logP	-0.57	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.72 m³·mol⁻¹	ChemAxon
Polarizability	56.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010320

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027472

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

53480447

PDB ID

Not Available

ChEBI ID

88773

Good Scents ID

Not Available

References

General References

Hosoda H, Yokohama H, Nambara T: Synthesis of cortol 3-glucuronides and cortolone 3-glucuronides. Chem Pharm Bull (Tokyo). 1984 Oct;32(10):4023-8. doi: 10.1248/cpb.32.4023. [PubMed:6549383 ]

Showing NP-Card for Cortolone 3-glucuronide (NP0090876)

MOL for NP0090876 (Cortolone 3-glucuronide)

3D MOL for NP0090876 (Cortolone 3-glucuronide)

3D SDF for NP0090876 (Cortolone 3-glucuronide)

3D-SDF for NP0090876 (Cortolone 3-glucuronide)

PDB for NP0090876 (Cortolone 3-glucuronide)

3D PDB for NP0090876 (Cortolone 3-glucuronide)

SMILES for NP0090876 (Cortolone 3-glucuronide)

INCHI for NP0090876 (Cortolone 3-glucuronide)

Structure for NP0090876 (Cortolone 3-glucuronide)

3D Structure for NP0090876 (Cortolone 3-glucuronide)