NP-MRD: Showing NP-Card for Etiocholanediol (NP0334651)

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Record Information

Version

2.0

Created at

2024-09-10 19:19:03 UTC

Updated at

2024-09-10 19:19:03 UTC

NP-MRD ID

NP0334651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Etiocholanediol

Description

Etiocholanediol belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, etiocholanediol is considered to be a steroid lipid molecule. Etiocholanediol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305231918042D          

 25 28  0  0  1  0            999 V2000
   10.4450  -10.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4450  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739  -11.3104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8739  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1595  -10.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -11.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -11.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028  -10.4854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5884  -10.0729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0173  -10.0729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0173   -9.2479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3028   -8.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884   -9.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020  -10.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2869   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8020   -8.9930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7305  -11.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036   -8.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0569   -8.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5884  -10.8979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8739   -9.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3028   -9.6604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1036  -10.8934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8937  -12.1549    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  1  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  1  0  0  0
M  END
> <DATABASE_ID>
NP0334651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](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+/m1/s1

> <INCHI_KEY>
CBMYJHIOYJEBSB-GCXXXECGSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.4562

> <EXACT_MASS>
292.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19525567353625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      19.497 -19.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.497 -21.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.831 -21.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.165 -21.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.165 -19.573   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.831 -18.803   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.498 -21.883   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.832 -21.113   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.832 -19.573   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.498 -18.803   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.166 -18.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.166 -17.263   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.832 -16.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.498 -17.263   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.630 -19.279   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.536 -18.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.630 -16.787   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.164 -21.883   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      26.327 -15.731   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.106 -15.322   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      23.498 -20.343   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      22.165 -18.033   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      24.832 -18.033   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      26.327 -20.334   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      22.202 -22.689   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
(3alpha,5beta,17beta)-Androstane-3,17-diol	ChEBI
3alpha,17beta-Dihydroxyetiocholane	ChEBI
(3a,5b,17b)-Androstane-3,17-diol	Generator
(3Α,5β,17β)-androstane-3,17-diol	Generator
3a,17b-Dihydroxyetiocholane	Generator
3Α,17β-dihydroxyetiocholane	Generator
5b-Androstane-3a,17b-diol	HMDB
b-Androstane-3a,17b-diol	HMDB
beta-Androstane-3a,17b-diol	HMDB
5Β-androstane-3α,17β-diol	HMDB

Chemical Formula

C₁₉H₃₂O₂

Average Mass

292.4562 Da

Monoisotopic Mass

292.24023 Da

IUPAC Name

(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

Traditional Name

(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](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+/m1/s1

InChI Key

CBMYJHIOYJEBSB-GCXXXECGSA-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 androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
17-hydroxysteroid
3-alpha-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

androstane-3alpha,17beta-diol (CHEBI:36714 )
C19 steroids (androgens) and derivatives (LMST02020077 )

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	35.2 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