NP-MRD: Showing NP-Card for 2beta-Hydroxytestosterone (NP0339083)

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Record Information

Version

2.0

Created at

2024-09-11 19:36:24 UTC

Updated at

2024-09-11 19:36:25 UTC

NP-MRD ID

NP0339083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2beta-Hydroxytestosterone

Description

SM(d18:0/24:1(15Z)(OH)), also known as C24:1-OH sphingomyelin or hydroxysphingomyeline C24:1, Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. SM(d18:0/24:1(15Z)(OH)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, SM(d18:0/24:1(15Z)(OH)) has been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make SM(D18:0/24:1(15Z)(OH)) a potential biomarker for the consumption of these foods. 2beta-Hydroxytestosterone was first documented in 1994 (PMID: 8106344). An N-hydroxytetracosenoylsphingosine-1-phosphocholine in which the N-acyl group is specified as (15Z)-3-hydroxytetracos-15-enoyl (PMID: 9034165).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 22 25  0  0  1  0            999 V2000
   14.3314  -10.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1798  -11.2401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.4692  -10.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7506  -11.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7438  -12.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4544  -12.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4473  -13.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7293  -13.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0184  -13.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3004  -13.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5897  -13.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8717  -13.6773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5965  -12.4461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8860  -12.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3146  -12.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0258  -12.4587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0403  -11.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1730  -12.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9551  -12.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4461  -11.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9668  -10.9922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2697  -10.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0339083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4=CC(=O)[C@@H](O)C[C@]34C)C1CC[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-18-8-7-14-12(13(18)5-6-17(18)22)4-3-11-9-15(20)16(21)10-19(11,14)2/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12?,13?,14?,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
ZOIPFFUVGMVQGE-MYLKINFHSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.4238

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.91793718629539

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4S,14S,15S)-4,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.494357377

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.151645304922337

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.38481347059577

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839825042993489

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.92199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S,14S,15S)-4,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      26.752 -19.467   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.469 -20.982   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.143 -20.199   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.801 -20.958   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.788 -22.498   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.115 -23.280   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.102 -24.819   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.761 -25.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.434 -24.797   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.094 -25.555   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.767 -24.773   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.427 -25.531   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.780 -23.233   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.454 -22.452   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.121 -22.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.448 -23.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.475 -21.475   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.456 -22.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.916 -23.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.833 -21.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.938 -20.519   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.503 -19.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16    5    9   15   17                                             
CONECT   17   16                                                            
CONECT   18    2    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    2   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
C24:1-OH Sphingomyelin	ChEBI
Hydroxysphingomyeline C24:1	ChEBI
N-[(15Z)-3-Hydroxytetracos-15-enoyl]sphing-4-enine-1-phosphocholine	ChEBI
SM(D18:1/24:1(15Z)(OH))	ChEBI
N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine	HMDB
Sphingomyelin	MetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-sphinganine	MetBuilder
Sphingomyelin(D18:0/24:1(15Z)(OH))	MetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-dihydrosphingosine	MetBuilder
N-(3-Hydroxy-15Z-tetracosenoyl)-1-phosphocholine-D-erythro-sphinganine	MetBuilder
2beta,17beta-Dihydroxyandrost-4-en-3-one	HMDB
2b-Hydroxytestosterone	Generator
2Β-hydroxytestosterone	Generator

Chemical Formula

C₁₉H₂₈O₃

Average Mass

304.4238 Da

Monoisotopic Mass

304.20384 Da

IUPAC Name

(2R,4S,14S,15S)-4,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,4S,14S,15S)-4,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CCC4=CC(=O)[C@@H](O)C[C@]34C)C1CC[C@@H]2O

InChI Identifier

InChI=1S/C19H28O3/c1-18-8-7-14-12(13(18)5-6-17(18)22)4-3-11-9-15(20)16(21)10-19(11,14)2/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12?,13?,14?,16-,17-,18-,19-/m0/s1

InChI Key

ZOIPFFUVGMVQGE-MYLKINFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic zwitterion
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.18	ALOGPS
logP	2.49	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.92 m³·mol⁻¹	ChemAxon
Polarizability	34.92 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

HMDB0013469

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029469

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingomyelin

METLIN ID

Not Available

PubChem Compound

53481791

PDB ID

Not Available

ChEBI ID

90006

Good Scents ID

Not Available

References

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. [PubMed:8106344 ]

Showing NP-Card for 2beta-Hydroxytestosterone (NP0339083)

MOL for NP0339083 (2beta-Hydroxytestosterone)

3D MOL for NP0339083 (2beta-Hydroxytestosterone)

3D SDF for NP0339083 (2beta-Hydroxytestosterone)

3D-SDF for NP0339083 (2beta-Hydroxytestosterone)

PDB for NP0339083 (2beta-Hydroxytestosterone)

3D PDB for NP0339083 (2beta-Hydroxytestosterone)

SMILES for NP0339083 (2beta-Hydroxytestosterone)

INCHI for NP0339083 (2beta-Hydroxytestosterone)

Structure for NP0339083 (2beta-Hydroxytestosterone)

3D Structure for NP0339083 (2beta-Hydroxytestosterone)