NP-MRD: Showing NP-Card for 5a-Dihydrotestosterone sulfate (NP0087480)

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Record Information

Version

2.0

Created at

2022-05-11 16:50:50 UTC

Updated at

2022-05-11 16:50:50 UTC

NP-MRD ID

NP0087480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5a-Dihydrotestosterone sulfate

Description

5A-Dihydrotestosterone sulfate, also known as DHT-sulfate or DHT-sulfuric acid, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. 5A-Dihydrotestosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DHT is a C19 steroid and possesses androgenic activity. 5A-Dihydrotestosterone sulfate is a sulfate derivative of 5a-Dihydrotestosterone produced through phase II metabolism. DHT has at least three times the binding affinity for SHBG than testosterone. About 70% of DHT is derived from peripheral conversion of testosterone in males, while most of the DHT is derived from androstenedione in females. Androgen production takes place mainly in the Leydig cells of the testes. 5a-Dihydrotestosterone sulfate was first documented in 1972 (PMID: 4648789). Androgens circulate in the blood bound to proteins, especially sex hormone binding globulin (SHBG) and albumin (PMID: 21890434) (PMID: 133773) (PMID: 133774) (PMID: 24428203) (PMID: 26239050) (PMID: 27480913).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-2
  Mrv0541 02231220352D          

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M  END

     RDKit          3D

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M  END

Untitled Document-2
  Mrv0541 02231220352D          

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M  END
> <DATABASE_ID>
NP0087480

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
KYVPWJSGFKNNLD-ABEVXSGRSA-N

> <FORMULA>
C19H30O5S

> <MOLECULAR_WEIGHT>
370.504

> <EXACT_MASS>
370.18139476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.40638560465992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
3.4662434006666665

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2716174889906044

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352809112126309

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
93.59489999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5α-dihydrotestosterone sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-2                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
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HETATM    2  C   UNK     0      -5.144  -1.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.810  -0.729   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.478  -3.809   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.810  -3.809   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.477  -3.039   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.143  -3.809   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.191  -3.039   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.191  -1.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.525  -0.729   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.989  -1.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.894   0.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.989   1.287   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.525   0.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.525   2.351   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.191   1.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.143   0.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.143  -0.729   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.477  -1.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.477   0.041   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0       4.971   3.072   0.000  0.00  0.00           S+0
HETATM   22  O   UNK     0       4.651   4.579   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.291   1.566   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.465   2.752   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.478   3.392   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -2.477  -4.579   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.143  -2.269   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.191   0.041   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.525  -2.269   0.000  0.00  0.00           H+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3                                                       
CONECT    3    2   19                                                       
CONECT    4    1                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7   19   26                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18   28                                             
CONECT   10    9   11   14   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   10   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    9   19   27                                             
CONECT   19   18    3    6   20                                             
CONECT   20   19                                                            
CONECT   21   22   23   24   25                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   13                                                       
CONECT   25   21                                                            
CONECT   26    6                                                            
CONECT   27   18                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfate	ChEBI
5alpha-Dihydrotestosterone 17-sulfate	ChEBI
DHT-Sulfate	ChEBI
DHT-Sulphate	ChEBI
Dihydrotestosterone sulfate	ChEBI
Dihydrotestosterone sulphate	ChEBI
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfate	Generator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfuric acid	Generator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphate	Generator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphuric acid	Generator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfuric acid	Generator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphate	Generator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphuric acid	Generator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfate	Generator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfuric acid	Generator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphate	Generator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphuric acid	Generator
5a-Dihydrotestosterone 17-sulfate	Generator
5a-Dihydrotestosterone 17-sulfuric acid	Generator
5a-Dihydrotestosterone 17-sulphate	Generator
5a-Dihydrotestosterone 17-sulphuric acid	Generator
5alpha-Dihydrotestosterone 17-sulfuric acid	Generator
5alpha-Dihydrotestosterone 17-sulphate	Generator
5alpha-Dihydrotestosterone 17-sulphuric acid	Generator
5Α-dihydrotestosterone 17-sulfate	Generator
5Α-dihydrotestosterone 17-sulfuric acid	Generator
5Α-dihydrotestosterone 17-sulphate	Generator
5Α-dihydrotestosterone 17-sulphuric acid	Generator
DHT-Sulfuric acid	Generator
DHT-Sulphuric acid	Generator
Dihydrotestosterone sulfuric acid	Generator
Dihydrotestosterone sulphuric acid	Generator
5a-Dihydrotestosterone sulfuric acid	Generator
5a-Dihydrotestosterone sulphate	Generator
5a-Dihydrotestosterone sulphuric acid	Generator
5alpha-Dihydrotestosterone sulfate	HMDB
5alpha-Dihydrotestosterone sulphate	HMDB

Chemical Formula

C₁₉H₃₀O₅S

Average Mass

370.5040 Da

Monoisotopic Mass

370.18139 Da

IUPAC Name

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

Traditional Name

5α-dihydrotestosterone sulfate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

KYVPWJSGFKNNLD-ABEVXSGRSA-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 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
Androgen-skeleton
Androstane-skeleton
3-oxosteroid
Oxosteroid
3-oxo-5-alpha-steroid
Sulfuric acid ester
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Organic sulfuric acid or derivatives
Cyclic ketone
Ketone
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	0.27	ALOGPS
logP	3.47	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	-7.4	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	93.59 m³·mol⁻¹	ChemAxon
Polarizability	40.41 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

HMDB0006278

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023873

KNApSAcK ID

Not Available

Chemspider ID

18915389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2794980

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18665256

PDB ID

Not Available

ChEBI ID

138026

Good Scents ID

Not Available

References

General References

Wang C, Feng R, Sun D, Li Y, Bi X, Sun C: Metabolic profiling of urine in young obese men using ultra performance liquid chromatography and Q-TOF mass spectrometry (UPLC/Q-TOF MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Oct 1;879(27):2871-6. doi: 10.1016/j.jchromb.2011.08.014. Epub 2011 Aug 22. [PubMed:21890434 ]
Purvis K, Saksena SK, Landgren BM, Cekan Z, Diczfalusy E: Steroid conjugates in human seminal plasma. Clin Endocrinol (Oxf). 1976 May;5(3):253-61. doi: 10.1111/j.1365-2265.1976.tb01951.x. [PubMed:133773 ]
Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72. doi: 10.1111/j.1365-2265.1976.tb01952.x. [PubMed:133774 ]
Zhao X, Xu F, Qi B, Hao S, Li Y, Li Y, Zou L, Lu C, Xu G, Hou L: Serum metabolomics study of polycystic ovary syndrome based on liquid chromatography-mass spectrometry. J Proteome Res. 2014 Feb 7;13(2):1101-11. doi: 10.1021/pr401130w. Epub 2014 Jan 24. [PubMed:24428203 ]
Sanchez-Guijo A, Oji V, Hartmann MF, Traupe H, Wudy SA: Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS. J Lipid Res. 2015 Sep;56(9):1843-51. doi: 10.1194/jlr.D061499. Epub 2015 Aug 2. [PubMed:26239050 ]
Xu H, Zheng X, Qian Y, Guan J, Yi H, Zou J, Wang Y, Meng L, Zhao A, Yin S, Jia W: Metabolomics Profiling for Obstructive Sleep Apnea and Simple Snorers. Sci Rep. 2016 Aug 2;6:30958. doi: 10.1038/srep30958. [PubMed:27480913 ]
Dehennin L, Jondet M, Scholler R: Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J Steroid Biochem. 1987 Mar;26(3):399-405. doi: 10.1016/0022-4731(87)90107-5. [PubMed:3586654 ]
Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51. doi: 10.1016/0005-2760(72)90144-0. [PubMed:4648789 ]
de la Torre B, Hedman M, Jensen F, Pedersen PH, Diczfalusy E: Lack of effect of vasectomy on peripheral gonadotrophin and steroid levels. Int J Androl. 1983 Apr;6(2):125-34. doi: 10.1111/j.1365-2605.1983.tb00331.x. [PubMed:6408012 ]
de la Torre B, Noren S, Hedman M, Ritzen M, Diczfalusy E: Intratesticular and plasma steroid profiles in fertile and infertile men. Int J Androl. 1982 Aug;5(4):367-78. doi: 10.1111/j.1365-2605.1982.tb00267.x. [PubMed:7141722 ]

Showing NP-Card for 5a-Dihydrotestosterone sulfate (NP0087480)

MOL for NP0087480 (5a-Dihydrotestosterone sulfate)

3D MOL for NP0087480 (5a-Dihydrotestosterone sulfate)

3D SDF for NP0087480 (5a-Dihydrotestosterone sulfate)

3D-SDF for NP0087480 (5a-Dihydrotestosterone sulfate)

PDB for NP0087480 (5a-Dihydrotestosterone sulfate)

3D PDB for NP0087480 (5a-Dihydrotestosterone sulfate)

SMILES for NP0087480 (5a-Dihydrotestosterone sulfate)

INCHI for NP0087480 (5a-Dihydrotestosterone sulfate)

Structure for NP0087480 (5a-Dihydrotestosterone sulfate)

3D Structure for NP0087480 (5a-Dihydrotestosterone sulfate)