NP-MRD: Showing NP-Card for (22alpha)-Hydroxy-campest-4-en-3-one (NP0334802)

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Record Information

Version

2.0

Created at

2024-09-10 20:01:45 UTC

Updated at

2024-09-10 20:01:46 UTC

NP-MRD ID

NP0334802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(22alpha)-Hydroxy-campest-4-en-3-one

Description

(22Alpha)-hydroxy-campest-4-en-3-one belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group (22Alpha)-hydroxy-campest-4-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241203392D          

 30 33  0  0  1  0            999 V2000
    8.8850   -8.8514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8850   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1704   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1704  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560   -8.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -8.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5994   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5994  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0285   -7.6139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0285   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -7.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5995   -7.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8131   -7.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2980   -8.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8132   -8.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8849   -8.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9955   -6.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -6.5743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8750   -6.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5160   -5.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4270   -7.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1300   -5.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2340   -6.8444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7860   -7.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4890   -6.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5310   -8.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5930   -7.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7415  -10.0888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  1 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 15  1  0  0  0  0
 21 20  1  0  0  0  0
 20 22  1  6  0  0  0
 23 21  1  0  0  0  0
 21 24  1  1  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 25 27  1  1  0  0  0
 28 26  1  0  0  0  0
 29 26  1  0  0  0  0
  6 30  2  0  0  0  0
M  END


  Mrv0541 02241203392D          

 30 33  0  0  1  0            999 V2000
    8.8850   -8.8514    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8850   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1704   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1704  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560   -8.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -8.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -9.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5994   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5994  -10.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0285   -7.6139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0285   -8.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139   -7.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5995   -7.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8131   -7.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2980   -8.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8132   -8.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8849   -8.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9955   -6.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0680   -6.5743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8750   -6.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5160   -5.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4270   -7.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1300   -5.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2340   -6.8444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7860   -7.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4890   -6.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5310   -8.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5930   -7.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7415  -10.0888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 13 11  1  0  0  0  0
  7 12  1  0  0  0  0
 14 13  1  0  0  0  0
  9  7  1  0  0  0  0
  9 14  1  0  0  0  0
 15 11  1  0  0  0  0
 12 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
  1 18  1  1  0  0  0
 11 19  1  1  0  0  0
 20 15  1  0  0  0  0
 21 20  1  0  0  0  0
 20 22  1  6  0  0  0
 23 21  1  0  0  0  0
 21 24  1  1  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 25 27  1  1  0  0  0
 28 26  1  0  0  0  0
 29 26  1  0  0  0  0
  6 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](C)C[C@H](O)[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O2/c1-17(2)18(3)15-26(30)19(4)23-9-10-24-22-8-7-20-16-21(29)11-13-27(20,5)25(22)12-14-28(23,24)6/h16-19,22-26,30H,7-15H2,1-6H3/t18-,19+,22?,23?,24?,25?,26+,27+,28-/m1/s1

> <INCHI_KEY>
FMFAICDKESPFNH-HSKWBYRYSA-N

> <FORMULA>
C28H46O2

> <MOLECULAR_WEIGHT>
414.6636

> <EXACT_MASS>
414.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.6135442315281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
6.658389278000001

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.83565000081592

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.08782611778911

> <JCHEM_PKA_STRONGEST_BASIC>
-0.683654773176371

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
125.70619999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      16.585 -16.523   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.585 -18.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.251 -15.753   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.251 -18.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.918 -16.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.918 -18.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.253 -16.523   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.253 -18.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.919 -15.753   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.919 -18.833   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.587 -14.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.587 -15.753   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.253 -13.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.919 -14.213   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.051 -13.737   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.956 -14.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.051 -16.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.585 -14.983   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.525 -12.681   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.527 -12.272   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.033 -11.952   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.497 -11.128   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.064 -13.096   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      24.509 -10.487   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      26.570 -12.776   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.601 -13.921   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.046 -11.312   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.125 -15.385   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.107 -13.601   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.584 -18.832   0.000  0.00  0.00           O+0
CONECT    1    3    9    2   18                                             
CONECT    2    4   10    1                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   30                                                  
CONECT    7    8   12    9                                                  
CONECT    8    7   10                                                       
CONECT    9    1    7   14                                                  
CONECT   10    8    2                                                       
CONECT   11   13   15   12   19                                             
CONECT   12    7   11   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18    1                                                            
CONECT   19   11                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20   23   24                                                  
CONECT   22   20                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   28   29                                                  
CONECT   27   25                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30    6                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(22a)-Hydroxy-campest-4-en-3-one	Generator
(22Α)-hydroxy-campest-4-en-3-one	Generator

Chemical Formula

C₂₈H₄₆O₂

Average Mass

414.6636 Da

Monoisotopic Mass

414.34978 Da

IUPAC Name

(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,15S)-14-[(2S,3S,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)C[C@H](O)[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C28H46O2/c1-17(2)18(3)15-26(30)19(4)23-9-10-24-22-8-7-20-16-21(29)11-13-27(20,5)25(22)12-14-28(23,24)6/h16-19,22-26,30H,7-15H2,1-6H3/t18-,19+,22?,23?,24?,25?,26+,27+,28-/m1/s1

InChI Key

FMFAICDKESPFNH-HSKWBYRYSA-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 monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Ergostane-skeleton
Monohydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
3-oxosteroid
Hydroxysteroid
3-oxo-delta-4-steroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Ketone
Secondary alcohol
Cyclic ketone
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	5.13	ALOGPS
logP	6.66	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-0.68	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	5	ChemAxon
Refractivity	125.71 m³·mol⁻¹	ChemAxon
Polarizability	51.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012113

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028777

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

25201842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (22alpha)-Hydroxy-campest-4-en-3-one (NP0334802)

MOL for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D MOL for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D SDF for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D-SDF for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

PDB for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D PDB for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

SMILES for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

INCHI for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

Structure for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)

3D Structure for NP0334802 ((22alpha)-Hydroxy-campest-4-en-3-one)