NP-MRD: Showing NP-Card for Androsterone sulfate (NP0087008)

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Record Information

Version

2.0

Created at

2022-05-11 16:37:13 UTC

Updated at

2022-05-11 16:37:13 UTC

NP-MRD ID

NP0087008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Androsterone sulfate

Description

Androsterone sulfate, also known as andros-S, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Androsterone sulfate is found in Homo sapiens. Androsterone sulfate was first documented in 1965 (PMID: 14328399). Androsterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 14573603) (PMID: 8380602) (PMID: 1254687).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-3
  Mrv0541 02231219352D          

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M  END

     RDKit          3D

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 16 43  1  0
M  END

Untitled Document-3
  Mrv0541 02231219352D          

 29 32  0  0  0  0            999 V2000
   -1.3492   -0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
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 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 17 12  1  0  0  0  0
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  5 24  1  1  0  0  0
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 11 28  1  6  0  0  0
 10 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/t12-,13+,14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
ZMITXKRGXGRMKS-HLUDHZFRSA-N

> <FORMULA>
C19H30O5S

> <MOLECULAR_WEIGHT>
370.504

> <EXACT_MASS>
370.18139476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.01089322333445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
3.8222703046666666

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.961719950339404

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3307185708846694

> <JCHEM_PKA_STRONGEST_BASIC>
-7.475645879362316

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
93.80069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dheas

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-3                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.519  -0.585   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.519  -2.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.185  -2.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.149  -2.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.149  -0.585   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185   0.185   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.483  -2.895   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.816  -2.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.816  -0.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.483   0.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.150   0.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.150   1.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.816   2.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.483   1.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.614  -0.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.520   0.955   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.614   2.201   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.090   3.665   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.852  -2.895   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0      -5.186  -2.125   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0      -4.416  -0.792   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.520  -1.355   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.956  -3.459   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.149   0.955   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.548   3.212   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       2.816   0.955   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.149  -3.665   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.150  -1.355   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.483  -1.355   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   27                                             
CONECT    5    4    6   10   24                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   26                                             
CONECT   10    9    5   14   29                                             
CONECT   11    9   12   15   28                                             
CONECT   12   11   13   17   25                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24    5                                                            
CONECT   25   12                                                            
CONECT   26    9                                                            
CONECT   27    4                                                            
CONECT   28   11                                                            
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulfate	ChEBI
5alpha-Androstane-3alpha-ol-17-one sulfate	ChEBI
3a-Hydroxy-5a-androstan-17-one 3-sulfate	Generator
3a-Hydroxy-5a-androstan-17-one 3-sulfuric acid	Generator
3a-Hydroxy-5a-androstan-17-one 3-sulphate	Generator
3a-Hydroxy-5a-androstan-17-one 3-sulphuric acid	Generator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulfuric acid	Generator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphate	Generator
3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphuric acid	Generator
3Α-hydroxy-5α-androstan-17-one 3-sulfate	Generator
3Α-hydroxy-5α-androstan-17-one 3-sulfuric acid	Generator
3Α-hydroxy-5α-androstan-17-one 3-sulphate	Generator
3Α-hydroxy-5α-androstan-17-one 3-sulphuric acid	Generator
5a-Androstane-3a-ol-17-one sulfate	Generator
5a-Androstane-3a-ol-17-one sulfuric acid	Generator
5a-Androstane-3a-ol-17-one sulphate	Generator
5a-Androstane-3a-ol-17-one sulphuric acid	Generator
5alpha-Androstane-3alpha-ol-17-one sulfuric acid	Generator
5alpha-Androstane-3alpha-ol-17-one sulphate	Generator
5alpha-Androstane-3alpha-ol-17-one sulphuric acid	Generator
5Α-androstane-3α-ol-17-one sulfate	Generator
5Α-androstane-3α-ol-17-one sulfuric acid	Generator
5Α-androstane-3α-ol-17-one sulphate	Generator
5Α-androstane-3α-ol-17-one sulphuric acid	Generator
Androsterone sulfuric acid	Generator
Androsterone sulphate	Generator
Androsterone sulphuric acid	Generator
3alpha-Sulfate-5alpha-androstan-17-one	HMDB
5alpha-Androsterone sulfate	HMDB
5alpha-Androsterone sulphate	HMDB
Andros-S	HMDB
Androsterone 3alpha-sulfate	HMDB
Androsterone 3alpha-sulphate	HMDB
Androsterone monosulfate	HMDB
Androsterone monosulphate	HMDB
Androsterone sulfate, (3alpha,5beta)-isomer	HMDB
Androsterone sulfate, (3beta,5alpha)-isomer	HMDB
Androsterone sulfate, (3beta,5beta)-isomer	HMDB
Androsterone sulfate, sodium salt	HMDB
Androsterone sulfate, sodium salt, (3alpha,5beta)-isomer	HMDB
Androsterone sulfate, sodium salt, (3beta,5alpha)-isomer	HMDB
Epiandrosterone sulfate	HMDB
Androsterone sulfate	MeSH

Chemical Formula

C₁₉H₃₀O₅S

Average Mass

370.5040 Da

Monoisotopic Mass

370.18139 Da

IUPAC Name

[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid

Traditional Name

dheas

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/t12-,13+,14-,15-,16-,18-,19-/m0/s1

InChI Key

ZMITXKRGXGRMKS-HLUDHZFRSA-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
Homo sapiens	LOTUS Database	35616633
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 sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Androstane-skeleton
17-oxosteroid
Oxosteroid
Sulfuric acid ester
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Ketone
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:83037 )
17-oxo steroid (CHEBI:83037 )
androstanoid (CHEBI:83037 )
Sulfates (LMST05020001 )

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	0.45	ALOGPS
logP	3.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.8 m³·mol⁻¹	ChemAxon
Polarizability	40.01 Å³	ChemAxon
Number of Rings	4	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

HMDB0002759

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023062

KNApSAcK ID

Not Available

Chemspider ID

140383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Androsterone sulfate

METLIN ID

3559

PubChem Compound

159663

PDB ID

Not Available

ChEBI ID

83037

Good Scents ID

Not Available

References

General References

Chang HJ, Shi R, Rehse P, Lin SX: Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex. J Biol Chem. 2004 Jan 23;279(4):2689-96. doi: 10.1074/jbc.M310446200. Epub 2003 Oct 21. [PubMed:14573603 ]
PLAGER JE: THE BINDING OF ANDROSTERONE SULFATE, ETHIOCHOLANOLONE SULFATE, AND DEHYDROISOANDROSTERONE SULFATE BY HUMAN PLASMA PROTEIN. J Clin Invest. 1965 Jul;44:1234-9. doi: 10.1172/JCI105229. [PubMed:14328399 ]
Zwicker H, Rittmaster RS: Androsterone sulfate: physiology and clinical significance in hirsute women. J Clin Endocrinol Metab. 1993 Jan;76(1):112-6. doi: 10.1210/jcem.76.1.8380602. [PubMed:8380602 ]
Rosenfeld RS, Kream J, Hellman L: Androsterone sulfate concentrations in plasma in hypo- and hyperthyroidism. J Clin Endocrinol Metab. 1976 Mar;42(3):464-7. doi: 10.1210/jcem-42-3-464. [PubMed:1254687 ]

Showing NP-Card for Androsterone sulfate (NP0087008)

MOL for NP0087008 (Androsterone sulfate)

3D MOL for NP0087008 (Androsterone sulfate)

3D SDF for NP0087008 (Androsterone sulfate)

3D-SDF for NP0087008 (Androsterone sulfate)

PDB for NP0087008 (Androsterone sulfate)

3D PDB for NP0087008 (Androsterone sulfate)

SMILES for NP0087008 (Androsterone sulfate)

INCHI for NP0087008 (Androsterone sulfate)

Structure for NP0087008 (Androsterone sulfate)

3D Structure for NP0087008 (Androsterone sulfate)