NP-MRD: Showing NP-Card for Calusterone (NP0334592)

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Record Information

Version

2.0

Created at

2024-09-10 19:03:22 UTC

Updated at

2024-09-10 19:03:22 UTC

NP-MRD ID

NP0334592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calusterone

Description

Calusterone, also known as methosarb, 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. Calusterone is an extremely weak basic (essentially neutral) compound (based on its pKa). Calusterone was first documented in 1979 (PMID: 153787). It is a 17α-alkylated AAS similar in structure to bolasterone (which is its 7α-isomer) (PMID: 2325376).

Structure

MOL SDF PDB SMILES InChI

1564
  Mrv0541 02231215342D          

 26 29  0  0  1  0            999 V2000
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3606    0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 24  1  6  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 16  1  1  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 25  1  1  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  6  0  0  0
  7 13  1  0  0  0  0
  7 18  1  0  0  0  0
  8 15  1  0  0  0  0
  8 17  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  1  0  0  0
 14 15  1  0  0  0  0
 15 22  2  0  0  0  0
 17 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END

1564
  Mrv0541 02231215342D          

 26 29  0  0  1  0            999 V2000
    7.5474    1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.0653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0987    0.7597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3843   -0.4777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6698   -0.0653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8793    1.0111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9192   -0.4833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3843    1.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6698    0.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8793   -0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3975   -1.3368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3606    0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6257    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727   -0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685   -0.7215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583   -0.8032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2415    0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 23  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3 11  1  0  0  0  0
  3 24  1  6  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 16  1  1  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 25  1  1  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 26  1  6  0  0  0
  7 13  1  0  0  0  0
  7 18  1  0  0  0  0
  8 15  1  0  0  0  0
  8 17  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  1  0  0  0
 14 15  1  0  0  0  0
 15 22  2  0  0  0  0
 17 21  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](C)CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16-,17-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
IVFYLRMMHVYGJH-PVPPCFLZSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.77128360682956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.933019062333334

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.564040768992434

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280731514980953

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.61659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calusterone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1564                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.088   2.790   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.282   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.384  -0.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.384   1.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.051  -0.892   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.717  -0.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.841   1.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.316  -0.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.051   2.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.717   1.418   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.841  -0.591   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.075  -2.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.740   0.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.693  -3.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.304  -2.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.384   2.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -0.034   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.368   3.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.328   0.638   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.418  -3.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.429  -0.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.863  -3.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.416  -2.517   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      11.514  -1.347   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      11.122  -1.499   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       9.784   0.494   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   23                                                            
CONECT    3    4    5   11   24                                             
CONECT    4    3    7    9   16                                             
CONECT    5    3    6   12   25                                             
CONECT    6    5    8   10   26                                             
CONECT    7    1    4   13   18                                             
CONECT    8    6   15   17   19                                             
CONECT    9    4   10                                                       
CONECT   10    6    9                                                       
CONECT   11    3   13                                                       
CONECT   12    5   14   20                                                  
CONECT   13    7   11                                                       
CONECT   14   12   15                                                       
CONECT   15    8   14   22                                                  
CONECT   16    4                                                            
CONECT   17    8   21                                                       
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   12                                                            
CONECT   21   17   23                                                       
CONECT   22   15   23                                                       
CONECT   23    2   21   22                                                  
CONECT   24    3                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(7b,17b)-17-Hydroxy-7,17-dimethyl-androst-4-en-3-one	HMDB
17-beta-Hydroxy-7-beta,17-alpha-dimethylandrost-4-ene-3-one	HMDB
17-beta-Hydroxy-7-beta-17-dimethyl androst-4-en-3-one	HMDB
17-Dimethyl-17beta-hydroxy-7beta-androst-4-en-3-one	HMDB
17-Hydroxy-7,17-dimethylandrost-4-en-3-one	HMDB
17b-Hydroxy-7b,17-dimethyl-androst-4-en-3-one	HMDB
17b-Hydroxy-7b,17-dimethylandrost-4-en-3-one	HMDB
17beta-Dimethyl testosterone	HMDB
17beta-Hydroxy-7beta-17-dimethylandrost-4-en-3-one	HMDB
17beta-Hydroxy-7beta-17alpha-dimethylandrost-4-ene-3-one	HMDB
7-beta,17-alpha-Dimethyl testosterone	HMDB
7-beta,17-Dimethyltestosterone	HMDB
7-beta-17-alpha-Dimethyltestosterone	HMDB
7beta,17alpha-Dimethyltestosterone	HMDB
7beta,17beta-Dimethyltestosterone	HMDB
7beta-Dimethyltestosterone	HMDB
Calusteron	HMDB
Calusterona	HMDB
Calusteronum	HMDB
Dimethyltestosterone	HMDB
Methosarb	HMDB
7 beta,17 alpha-Dimethyltestosterone	HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Mass

316.4776 Da

Monoisotopic Mass

316.24023 Da

IUPAC Name

(1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

calusterone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](C)CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16-,17-,18+,19-,20-,21-/m0/s1

InChI Key

IVFYLRMMHVYGJH-PVPPCFLZSA-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
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	3.55	ALOGPS
logP	3.93	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	19.56	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.62 m³·mol⁻¹	ChemAxon
Polarizability	37.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004627

DrugBank ID

DB01564

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023386

KNApSAcK ID

Not Available

Chemspider ID

26239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calusterone

METLIN ID

Not Available

PubChem Compound

28204

PDB ID

Not Available

ChEBI ID

554295

Good Scents ID

Not Available

References

General References

Lloyd RE, Jones SE, Salmon SE: Comparative trial of low-dose adriamycin plus cyclophosphamide with or without additive hormonal therapy in advanced breast cancer. Cancer. 1979 Jan;43(1):60-5. doi: 10.1002/1097-0142(197901)43:1<60::aid-cncr2820430108>3.0.co;2-m. [PubMed:153787 ]
Choo HY, Kwon OS, Park J: Quantitative determination of stanozolol and its metabolite in urine by gas chromatography/mass spectrometry. J Anal Toxicol. 1990 Mar-Apr;14(2):109-12. doi: 10.1093/jat/14.2.109. [PubMed:2325376 ]

Showing NP-Card for Calusterone (NP0334592)

MOL for NP0334592 (Calusterone)

3D MOL for NP0334592 (Calusterone)

3D SDF for NP0334592 (Calusterone)

3D-SDF for NP0334592 (Calusterone)

PDB for NP0334592 (Calusterone)

3D PDB for NP0334592 (Calusterone)

SMILES for NP0334592 (Calusterone)

INCHI for NP0334592 (Calusterone)

Structure for NP0334592 (Calusterone)

3D Structure for NP0334592 (Calusterone)