NP-MRD: Showing NP-Card for 1-(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 (NP0206418)

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Record Information

Version

2.0

Created at

2022-09-05 02:39:25 UTC

Updated at

2022-09-05 02:39:25 UTC

NP-MRD ID

NP0206418

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(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

14-(6-Hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-en-5-yl acetate belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. 1-(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. 14-(6-Hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-en-5-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517112D          

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M  END

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M  END


  Mrv1533004151517112D          

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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 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 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCCC(C)(C)O)C1CCC2C3CC(=O)C4=CC(CCC4(C)C3CCC12C)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

> <INCHI_KEY>
FTEIQSAGHHOQFO-UHFFFAOYSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.190724840263336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(6-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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>
63.6

> <JCHEM_REFRACTIVITY>
132.14329999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(6-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.057  -8.818   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.375  -6.928   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   14   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   10   13   29                                             
CONECT   29   28                                                            
CONECT   30   20   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
14-(6-Hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0,.0,]heptadec-6-en-5-yl acetic acid	Generator
14-(6-Hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-yl acetic acid	Generator

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

14-(6-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-yl acetate

Traditional Name

14-(6-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(CCCC(C)(C)O)C1CCC2C3CC(=O)C4=CC(CCC4(C)C3CCC12C)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

InChI Key

FTEIQSAGHHOQFO-UHFFFAOYSA-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
logP	5.57	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	18.53	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.14 m³·mol⁻¹	ChemAxon
Polarizability	55.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

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

72972009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(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 (NP0206418)

MOL for NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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 NP0206418 (1-(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)