NP-MRD: Showing NP-Card for 4-Hydroxyandrostenedione glucuronide (NP0090872)

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Record Information

Version

2.0

Created at

2022-05-11 18:24:44 UTC

Updated at

2022-05-11 18:24:44 UTC

NP-MRD ID

NP0090872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxyandrostenedione glucuronide

Description

4,4-Dimethylcholesta-8,14,24-trienol, also known as FF-MAS or follicular fluid meiosis activating sterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4,4-dimethylcholesta-8,14,24-trienol is considered to be a sterol lipid molecule. 4,4-Dimethylcholesta-8,14,24-trienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4,4-Dimethylcholesta-8,14,24-trienol exists in all eukaryotes, ranging from yeast to humans. Within humans, 4,4-dimethylcholesta-8,14,24-trienol participates in a number of enzymatic reactions. In particular, 4,4-dimethylcholesta-8,14,24-trienol and formic acid can be biosynthesized from lanosterol through its interaction with the enzyme lanosterol 14-alpha demethylase. In addition, 4,4-dimethylcholesta-8,14,24-trienol can be converted into 4,4-dimethyl-5a-cholesta-8,24-dien-3-b-ol through its interaction with the enzyme Delta(14)-sterol reductase. 4-Hydroxyandrostenedione glucuronide was first documented in 1998 (PMID: 9788247). In humans, 4,4-dimethylcholesta-8,14,24-trienol is involved in the metabolic disorder called the child syndrome pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241200502D          

 34 38  0  0  1  0            999 V2000
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M  END

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  Mrv0541 02241200502D          

 34 38  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0090872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4=C(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)C(O)=O)C(=O)CC[C@]34C)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c1-24-10-8-15(26)20(33-23-19(30)17(28)18(29)21(34-23)22(31)32)14(24)4-3-11-12-5-6-16(27)25(12,2)9-7-13(11)24/h11-13,17-19,21,23,28-30H,3-10H2,1-2H3,(H,31,32)/t11?,12?,13?,17-,18-,19+,21-,23+,24+,25-/m0/s1

> <INCHI_KEY>
JIKFCHILHFFTSH-NRIFOQJISA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.5321

> <EXACT_MASS>
478.220282686

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
49.35710479542668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.429433100000002

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216648770283344

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4999583535579823

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868283467138827

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
117.85559999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-{[(2R,15S)-2,15-dimethyl-5,14-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-6-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      39.270  -6.053   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.819 -14.297   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.029 -12.687   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      29.151 -14.307   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.831 -17.377   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      29.169 -18.927   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      26.496 -17.398   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      26.478 -12.778   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.153 -15.093   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      36.001 -10.296   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.667  -9.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.334  -9.526   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.334  -7.986   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.266 -10.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.667  -7.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.001  -7.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.025 -11.900   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.792  -9.995   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.253 -11.911   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.642 -12.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.792  -7.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.690  -8.756   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.838  -9.438   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.334  -6.446   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.277  -8.767   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.378 -10.251   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.812 -12.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.366 -11.922   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.488 -15.072   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.494 -16.612   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.163 -17.387   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.826 -16.623   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.820 -15.083   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.484 -14.318   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   27   29                                                       
CONECT    3   28                                                            
CONECT    4   29   33                                                       
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   32                                                            
CONECT    8   34                                                            
CONECT    9   34                                                            
CONECT   10   11   12   17                                                  
CONECT   11   10   14   15                                                  
CONECT   12   10   13   18                                                  
CONECT   13   12   16   21   24                                             
CONECT   14   11   19   23   25                                             
CONECT   15   11   16                                                       
CONECT   16   13   15                                                       
CONECT   17   10   20                                                       
CONECT   18   12   22                                                       
CONECT   19   14   20   27                                                  
CONECT   20   17   19                                                       
CONECT   21    1   13   22                                                  
CONECT   22   18   21                                                       
CONECT   23   14   26                                                       
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   23   28                                                       
CONECT   27    2   19   28                                                  
CONECT   28    3   26   27                                                  
CONECT   29    2    4   30                                                  
CONECT   30    5   29   31                                                  
CONECT   31    6   30   32                                                  
CONECT   32    7   31   33                                                  
CONECT   33    4   32   34                                                  
CONECT   34    8    9   33                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
4,4-Dimechol-8,14,24-trienol	ChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3beta-ol	ChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3b-ol	Generator
4,4-Dimethylcholesta-8(9),14,24-trien-3β-ol	Generator
(3beta,5alpha)-4,4-Dimethyl-cholesta-8,14,24-trien-3-ol	HMDB
(3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol	HMDB
4,4'-Dimethyl cholesta-8,14,24-triene-3-beta-ol	HMDB
4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol	HMDB
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-ol	HMDB
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol	HMDB
4,4-Dimethyl-cholesta-8,14,24-trienol	HMDB
FF-MAS	HMDB
Follicular fluid meiosis activating sterol	HMDB
4-HADG	MeSH, HMDB
4-Hydroxy-4-androstene-3,17-dione glucuronide	MeSH, HMDB
4-Hydroxyandrost-4-ene-3,17-dione glucuronide	MeSH, HMDB
(2S,3S,4S,5R,6S)-6-{[(2R,15S)-2,15-dimethyl-5,14-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
HAD-glucuronide	MeSH
4-Hydroxyandrostenedione glucuronide	MeSH

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5321 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CCC4=C(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)C(O)=O)C(=O)CC[C@]34C)C1CCC2=O

InChI Identifier

InChI=1S/C25H34O9/c1-24-10-8-15(26)20(33-23-19(30)17(28)18(29)21(34-23)22(31)32)14(24)4-3-11-12-5-6-16(27)25(12,2)9-7-13(11)24/h11-13,17-19,21,23,28-30H,3-10H2,1-2H3,(H,31,32)/t11?,12?,13?,17-,18-,19+,21-,23+,24+,25-/m0/s1

InChI Key

JIKFCHILHFFTSH-NRIFOQJISA-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 cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:17813 )
Cholesterol and derivatives (C11455 )
Cholesterol and derivatives (LMST01010149 )

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	1.49	ALOGPS
logP	1.43	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.5	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	3	ChemAxon
Refractivity	117.86 m³·mol⁻¹	ChemAxon
Polarizability	49.36 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

HMDB0001023

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022376

KNApSAcK ID

Not Available

Chemspider ID

391478

KEGG Compound ID

C11455

BioCyc ID

Not Available

BiGG ID

1454719

Wikipedia Link

Not Available

METLIN ID

5952

PubChem Compound

443212

PDB ID

Not Available

ChEBI ID

17813

Good Scents ID

Not Available

References

General References

Ruan B, Watanabe S, Eppig JJ, Kwoh C, Dzidic N, Pang J, Wilson WK, Schroepfer GJ Jr: Sterols affecting meiosis: novel chemical syntheses and the biological activity and spectral properties of the synthetic sterols. J Lipid Res. 1998 Oct;39(10):2005-20. [PubMed:9788247 ]

Showing NP-Card for 4-Hydroxyandrostenedione glucuronide (NP0090872)

MOL for NP0090872 (4-Hydroxyandrostenedione glucuronide)

3D MOL for NP0090872 (4-Hydroxyandrostenedione glucuronide)

3D SDF for NP0090872 (4-Hydroxyandrostenedione glucuronide)

3D-SDF for NP0090872 (4-Hydroxyandrostenedione glucuronide)

PDB for NP0090872 (4-Hydroxyandrostenedione glucuronide)

3D PDB for NP0090872 (4-Hydroxyandrostenedione glucuronide)

SMILES for NP0090872 (4-Hydroxyandrostenedione glucuronide)

INCHI for NP0090872 (4-Hydroxyandrostenedione glucuronide)

Structure for NP0090872 (4-Hydroxyandrostenedione glucuronide)

3D Structure for NP0090872 (4-Hydroxyandrostenedione glucuronide)