NP-MRD: Showing NP-Card for (1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0146478)

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Record Information

Version

2.0

Created at

2022-09-02 01:53:20 UTC

Updated at

2022-09-02 01:53:20 UTC

NP-MRD ID

NP0146478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

Description

3Alpha-Acetoxy-25-hydroxycholesta-4-ene-6-one belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. (1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate is found in Dasystenella acanthina. Based on a literature review very few articles have been published on 3alpha-Acetoxy-25-hydroxycholesta-4-ene-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203532D          

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  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 12 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC(=O)C4=C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-18(8-7-13-27(3,4)32)22-9-10-23-21-17-26(31)25-16-20(33-19(2)30)11-14-29(25,6)24(21)12-15-28(22,23)5/h16,18,20-24,32H,7-15,17H2,1-6H3/t18-,20-,21+,22-,23+,24+,28-,29-/m1/s1

> <INCHI_KEY>
FTEIQSAGHHOQFO-FAXUZTPQSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.70767068416359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-yl acetate

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.571523854666666

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.5307684666132

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2544348164001105

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
132.1433

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.208  -1.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.169   0.544   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.205  -5.343   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.352   1.715   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.877   1.505   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.822   2.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.767   3.936   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.038   1.775   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.606   3.666   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   12    7   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    5                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3a-Acetoxy-25-hydroxycholesta-4-ene-6-one	Generator
3Α-acetoxy-25-hydroxycholesta-4-ene-6-one	Generator

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC(=O)C4=C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O

InChI Identifier

InChI=1S/C29H46O4/c1-18(8-7-13-27(3,4)32)22-9-10-23-21-17-26(31)25-16-20(33-19(2)30)11-14-29(25,6)24(21)12-15-28(22,23)5/h16,18,20-24,32H,7-15,17H2,1-6H3/t18-,20-,21+,22-,23+,24+,28-,29-/m1/s1

InChI Key

FTEIQSAGHHOQFO-FAXUZTPQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dasystenella acanthina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholestane steroids

Alternative Parents

Substituents

Cholestane-skeleton
25-hydroxysteroid
Steroid ester
Oxosteroid
6-oxosteroid
Delta-4-steroid
Tertiary alcohol
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	5.01	ALOGPS
logS	-6.1	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9640133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11465294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0146478)

MOL for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D MOL for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D SDF for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D-SDF for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

PDB for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D PDB for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

SMILES for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

INCHI for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

Structure for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D Structure for NP0146478 ((1r,3as,3bs,7r,9ar,9bs,11ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,3bh,4h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)