NP-MRD: Showing NP-Card for 11-Hydroxyprogesterone 11-glucuronide (NP0090916)

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Record Information

Version

2.0

Created at

2022-05-11 18:25:54 UTC

Updated at

2022-05-11 18:25:54 UTC

NP-MRD ID

NP0090916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxyprogesterone 11-glucuronide

Description

11-Hydroxyprogesterone 11-glucuronide, also known as 11-HPG or 11alpha-glucuronylprogesterone, belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, 11-hydroxyprogesterone 11-glucuronide is considered to be a steroid conjugate lipid molecule. 11-Hydroxyprogesterone 11-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241200522D          

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M  END

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  Mrv0541 02241200522D          

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 14 15  1  0  0  0  0
 16 21  1  0  0  0  0
 16 24  1  0  0  0  0
 16 25  1  1  0  0  0
 17 20  1  0  0  0  0
 17 26  1  1  0  0  0
 18 20  1  0  0  0  0
 19 23  1  0  0  0  0
 21 23  1  0  0  0  0
 21 28  2  0  0  0  0
 24 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 30  1  0  0  0  0
 28 30  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 35  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0090916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@H]1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3C(C[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O9/c1-12(28)16-6-7-17-15-5-4-13-10-14(29)8-9-26(13,2)19(15)18(11-27(16,17)3)35-25-22(32)20(30)21(31)23(36-25)24(33)34/h10,15-23,25,30-32H,4-9,11H2,1-3H3,(H,33,34)/t15?,16-,17?,18?,19?,20+,21+,22-,23+,25-,26+,27-/m1/s1

> <INCHI_KEY>
WVTMNZAPPOMZST-UCMXSJKRSA-N

> <FORMULA>
C27H38O9

> <MOLECULAR_WEIGHT>
506.5852

> <EXACT_MASS>
506.251582814

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
52.55528650676624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.389278496000001

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.227603458486843

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5949182406725573

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6864993663319456

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
126.57849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(2R,14S,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-17-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  O   UNK     0      30.741 -12.124   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.649  -9.814   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.074  -9.814   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      26.436 -17.594   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      28.073 -10.584   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      28.073  -7.504   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      30.741  -5.964   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.408  -5.964   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      34.742  -8.274   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      34.742 -12.894   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.742 -14.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.408 -15.204   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.074 -14.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.408 -12.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.074 -12.894   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.673 -15.214   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.199 -12.424   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.199 -14.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.433 -16.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.098 -13.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.661 -16.818   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.742 -11.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.050 -17.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.246 -14.346   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      30.685 -13.674   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.677 -10.961   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.786 -15.158   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.220 -17.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.741 -10.584   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.773 -16.829   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.184 -10.643   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.407  -9.814   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      29.407  -8.274   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.074  -8.274   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      30.741  -7.504   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.408  -7.504   0.000  0.00  0.00           C+0
CONECT    1   15   29                                                       
CONECT    2   26                                                            
CONECT    3   29   34                                                       
CONECT    4   30                                                            
CONECT    5   32                                                            
CONECT    6   33                                                            
CONECT    7   35                                                            
CONECT    8   36                                                            
CONECT    9   36                                                            
CONECT   10   11   14   17   22                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   15   16                                                  
CONECT   14   10   15                                                       
CONECT   15    1   13   14                                                  
CONECT   16   13   21   24   25                                             
CONECT   17   10   20   26                                                  
CONECT   18   11   20                                                       
CONECT   19   12   23                                                       
CONECT   20   17   18                                                       
CONECT   21   16   23   28                                                  
CONECT   22   10                                                            
CONECT   23   19   21                                                       
CONECT   24   16   27                                                       
CONECT   25   16                                                            
CONECT   26    2   17   31                                                  
CONECT   27   24   30                                                       
CONECT   28   21   30                                                       
CONECT   29    1    3   32                                                  
CONECT   30    4   27   28                                                  
CONECT   31   26                                                            
CONECT   32    5   29   33                                                  
CONECT   33    6   32   35                                                  
CONECT   34    3   35   36                                                  
CONECT   35    7   33   34                                                  
CONECT   36    8    9   34                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
11-HPG	HMDB
11-Hydroxyprogesterone 11-glucuronoside	HMDB
11alpha-Glucuronylprogesterone	HMDB
11alpha-Hydroxyprogesterone 11-glucuronide	HMDB
11alpha-Hydroxyprogesterone 11-glucuronoside	HMDB

Chemical Formula

C₂₇H₃₈O₉

Average Mass

506.5852 Da

Monoisotopic Mass

506.25158 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2R,14S,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-17-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(2R,14S,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-17-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)[C@H]1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3C(C[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C27H38O9/c1-12(28)16-6-7-17-15-5-4-13-10-14(29)8-9-26(13,2)19(15)18(11-27(16,17)3)35-25-22(32)20(30)21(31)23(36-25)24(33)34/h10,15-23,25,30-32H,4-9,11H2,1-3H3,(H,33,34)/t15?,16-,17?,18?,19?,20+,21+,22-,23+,25-,26+,27-/m1/s1

InChI Key

WVTMNZAPPOMZST-UCMXSJKRSA-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 steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety 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

Steroid glucuronide conjugates

Alternative Parents

Substituents

Steroid-glucuronide-skeleton
Progestogin-skeleton
20-oxosteroid
Pregnane-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Glucuronides (LMST05010031 )

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	1.63	ALOGPS
logP	1.39	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.58 m³·mol⁻¹	ChemAxon
Polarizability	52.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027516

KNApSAcK ID

Not Available

Chemspider ID

24850122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42621273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 11-Hydroxyprogesterone 11-glucuronide (NP0090916)

MOL for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

3D MOL for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

3D SDF for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

3D-SDF for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

PDB for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

3D PDB for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

SMILES for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

INCHI for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

Structure for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)

3D Structure for NP0090916 (11-Hydroxyprogesterone 11-glucuronide)