NP-MRD: Showing NP-Card for Dehydroepiandrosterone 3-glucuronide (NP0090902)

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Record Information

Version

2.0

Created at

2022-05-11 18:25:33 UTC

Updated at

2022-05-11 18:25:33 UTC

NP-MRD ID

NP0090902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydroepiandrosterone 3-glucuronide

Description

Dehydroepiandrosterone 3-glucuronide 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, dehydroepiandrosterone 3-glucuronide is considered to be a steroid conjugate lipid molecule. Dehydroepiandrosterone 3-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241200512D          

 36 40  0  0  1  0            999 V2000
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   13.4418   -7.5842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7321   -6.3439    0.0000 O   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

  Mrv0541 02241200512D          

 36 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0090902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h3,13-16,18-21,23,27-29H,4-11H2,1-2H3,(H,30,31)/t13-,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1

> <INCHI_KEY>
GLONBVCUAVPJFV-PCDHEYSGSA-N

> <FORMULA>
C25H36O8

> <MOLECULAR_WEIGHT>
464.5485

> <EXACT_MASS>
464.241018128

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
49.630043162443066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.9111439476666658

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.227603500497686

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.432307689263852

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6864993700354454

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
116.93959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-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      40.672  -6.004   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.432 -12.638   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.764 -12.627   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      30.444  -9.558   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.783  -8.007   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      25.109  -9.537   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      25.091 -14.157   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.767 -11.842   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      36.070  -9.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.403 -10.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.737  -9.477   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.737  -7.937   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.668 -10.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.070  -7.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.403  -7.167   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.194  -9.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.428 -11.851   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.656 -11.862   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.241  -9.389   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.194  -7.468   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.093  -8.707   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.045 -12.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.737  -6.397   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.680  -8.718   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.215 -12.708   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.781 -10.202   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.768 -11.873   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.101 -11.863   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.107 -10.323   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.776  -9.547   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.440 -10.312   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.434 -11.852   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.097 -12.617   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      36.177 -11.056   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      37.310  -8.429   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      38.875 -10.779   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   27   28                                                       
CONECT    3   28   32                                                       
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   33                                                            
CONECT    8   33                                                            
CONECT    9   10   13   14   34                                             
CONECT   10    9   11   17   35                                             
CONECT   11   10   12   16   36                                             
CONECT   12   11   15   20   23                                             
CONECT   13    9   18   19   24                                             
CONECT   14    9   15                                                       
CONECT   15   12   14                                                       
CONECT   16   11   21                                                       
CONECT   17   10   22                                                       
CONECT   18   13   22   25                                                  
CONECT   19   13   26                                                       
CONECT   20    1   12   21                                                  
CONECT   21   16   20                                                       
CONECT   22   17   18                                                       
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   18   27                                                       
CONECT   26   19   27                                                       
CONECT   27    2   25   26                                                  
CONECT   28    2    3   29                                                  
CONECT   29    4   28   30                                                  
CONECT   30    5   29   31                                                  
CONECT   31    6   30   32                                                  
CONECT   32    3   31   33                                                  
CONECT   33    7    8   32                                                  
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Dehydroepiandrosterone glucopyranuronoside	ChEBI
Dehydroisoandrosterone glucopyranuronoside	ChEBI
3-(Glucuronide)-(3-beta)-androst-5-en-17-one	HMDB
Dehydroepiandrosterone 3-beta-D-glucuronide	HMDB
Dehydroepiandrosterone 3-glucuronoside	HMDB

Chemical Formula

C₂₅H₃₆O₈

Average Mass

464.5485 Da

Monoisotopic Mass

464.24102 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C25H36O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h3,13-16,18-21,23,27-29H,4-11H2,1-2H3,(H,30,31)/t13-,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1

InChI Key

GLONBVCUAVPJFV-PCDHEYSGSA-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
Androstane-skeleton
17-oxosteroid
Oxosteroid
Delta-5-steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Hydroxy acid
Monosaccharide
Oxane
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

steroid glucosiduronic acid (CHEBI:68834 )
Glucuronides (LMST05010045 )

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	2.09	ALOGPS
logP	1.91	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.94 m³·mol⁻¹	ChemAxon
Polarizability	49.63 Å³	ChemAxon
Number of Rings	5	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

HMDB0010348

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027500

KNApSAcK ID

Not Available

Chemspider ID

413525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

470824

PDB ID

Not Available

ChEBI ID

68834

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dehydroepiandrosterone 3-glucuronide (NP0090902)

MOL for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

3D MOL for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

3D SDF for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

3D-SDF for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

PDB for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

3D PDB for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

SMILES for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

INCHI for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

Structure for NP0090902 (Dehydroepiandrosterone 3-glucuronide)

3D Structure for NP0090902 (Dehydroepiandrosterone 3-glucuronide)