NP-MRD: Showing NP-Card for Androstanediol (NP0334648)

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Record Information

Version

2.0

Created at

2024-09-10 19:18:18 UTC

Updated at

2024-09-10 19:18:18 UTC

NP-MRD ID

NP0334648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Androstanediol

Description

PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) Through the action of the enzyme choline/ethanolaminephosphotransferase. In humans, PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is involved in phosphatidylcholine biosynthesis. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PCs can be synthesized via three different routes. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Fatty acids containing 16, 18 and 20 carbons are the most common. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the docosapentaenoic acid moiety is derived from animal fats and brain. It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. A third route to PC synthesis involves the conversion of either PS or PE to PC. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231218332D          

 25 28  0  0  1  0            999 V2000
   23.0815  -14.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0815  -15.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -15.0231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.5105  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.7960  -13.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -15.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -15.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -14.1981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2249  -13.7856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.6539  -13.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6539  -12.9606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9394  -12.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -12.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -14.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9235  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4385  -12.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3670  -15.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -12.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6935  -11.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2249  -14.6106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5105  -13.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9394  -13.3731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.7401  -14.6061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5302  -15.8676    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  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
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334648

> <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](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1

> <INCHI_KEY>
CBMYJHIOYJEBSB-UNPXRYTGSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.34320962303727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.2037568309999997

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705356554483

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7580100340749988

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
84.63119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      43.085 -26.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.085 -28.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      44.419 -28.813   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      45.753 -28.043   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.753 -26.503   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      44.419 -25.733   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.086 -28.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.420 -28.043   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.420 -26.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.086 -25.733   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.754 -25.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.754 -24.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      48.420 -23.423   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.086 -24.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.219 -26.209   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.124 -24.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.219 -23.717   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      41.752 -28.813   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      49.915 -22.662   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      51.695 -22.253   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      47.086 -27.273   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      45.753 -24.963   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      48.420 -24.963   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      49.915 -27.265   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      45.790 -29.620   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
Androstane-3,17-diol	KEGG
3-a-Androstanediol	HMDB
3-alpha-Androstanediol	HMDB
3alpha-Androstanediol	HMDB
5 a-Androstane-3 a, 17 b-diol	HMDB
5 alpha-Androstane-3 alpha, 17 beta-diol	HMDB
5-a-Androstane-3-a, 17-b-diol	HMDB
5-alpha-Androstan-3-alpha,17-beta-diol	HMDB
5-alpha-Androstane-3-a, 17-beta-diol	HMDB
5-alpha-Androstane-3-alpha-17-beta-diol	HMDB
5 Androstane 3,17 diol	MeSH, HMDB
5 alpha Androstane 3 alpha,17 beta diol	MeSH, HMDB
5 alpha Androstane 3 beta,17 alpha diol	MeSH, HMDB
5 alpha Androstane 3 beta,17 beta diol	MeSH, HMDB
5 alpha Androstane 3alpha,17 beta diol	MeSH, HMDB
5 alpha-Androstane-3 alpha,17 beta-diol	MeSH, HMDB
5 alpha-Androstane-3 beta,17 alpha-diol	MeSH, HMDB
5 alpha-Androstane-3 beta,17 beta-diol	MeSH, HMDB
5 alpha-Androstane-3alpha,17 beta-diol	MeSH, HMDB
5 beta Androstane 3 alpha,17 beta diol	MeSH, HMDB
5 beta-Androstane-3 alpha,17 beta-diol	MeSH, HMDB
5-Androstane-3,17-diol	MeSH, HMDB
5alpha Androstane 3beta,17alpha diol	MeSH, HMDB
5alpha-Androstane-3beta,17alpha-diol	MeSH, HMDB
Androstane 3,17 diol	MeSH, HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Mass

292.4562 Da

Monoisotopic Mass

292.24023 Da

IUPAC Name

(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

Traditional Name

(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol

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](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1

InChI Key

CBMYJHIOYJEBSB-UNPXRYTGSA-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 phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
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	3.56	ALOGPS
logP	3.2	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.63 m³·mol⁻¹	ChemAxon
Polarizability	35.34 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025706

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Androstanediol (NP0334648)

MOL for NP0334648 (Androstanediol)

3D MOL for NP0334648 (Androstanediol)

3D SDF for NP0334648 (Androstanediol)

3D-SDF for NP0334648 (Androstanediol)

PDB for NP0334648 (Androstanediol)

3D PDB for NP0334648 (Androstanediol)

SMILES for NP0334648 (Androstanediol)

INCHI for NP0334648 (Androstanediol)

Structure for NP0334648 (Androstanediol)

3D Structure for NP0334648 (Androstanediol)