NP-MRD: Showing NP-Card for 3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol (NP0248432)

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Record Information

Version

2.0

Created at

2022-09-07 10:41:57 UTC

Updated at

2022-09-07 10:41:57 UTC

NP-MRD ID

NP0248432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol

Description

14-(5-Ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 14-(5-Ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310091706402D          

 31 34  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652310091706402D          

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 24 10  1  0  0  0  0
 25 11  1  0  0  0  0
 25 19  1  0  0  0  0
 26 12  1  0  0  0  0
 26 24  1  0  0  0  0
 27 14  1  0  0  0  0
 27 24  1  0  0  0  0
 28  4  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29  5  1  0  0  0  0
 29 16  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  1  0  0  0  0
 30 18  1  0  0  0  0
 31 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O2/c1-6-21(20(3)18-30)8-7-19(2)25-11-12-26-24-10-9-22-17-23(31)13-15-28(22,4)27(24)14-16-29(25,26)5/h9,19-21,23-27,30-31H,6-8,10-18H2,1-5H3

> <INCHI_KEY>
OCFKVMGCLMOOPD-UHFFFAOYSA-N

> <FORMULA>
C29H50O2

> <MOLECULAR_WEIGHT>
430.717

> <EXACT_MASS>
430.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.681940726385804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5-ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
6.55

> <JCHEM_LOGP>
6.485751905333334

> <ALOGPS_LOGS>
-6.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.681531210101035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1956634541938387

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
131.61779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5-ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0       8.572  -8.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.907  -3.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.572  -3.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.136  -3.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.503  -4.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.906  -7.820   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.573  -6.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.240  -5.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.721  -7.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.215  -7.622   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.402  -7.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.908  -8.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.149  -2.908   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.630  -3.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.643  -3.229   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.123  -4.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.703  -5.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.239  -6.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.907  -5.510   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.906  -6.280   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.197  -5.838   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.179  -4.053   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.184  -6.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.241  -6.280   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.678  -6.798   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.660  -5.013   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.167  -4.693   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.648  -5.654   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.905  -5.510   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      25.686  -3.733   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6    1   21                                                       
CONECT    7    8   19                                                       
CONECT    8    7   21                                                       
CONECT    9   10   22                                                       
CONECT   10    9   24                                                       
CONECT   11   12   25                                                       
CONECT   12   11   26                                                       
CONECT   13   15   23                                                       
CONECT   14   16   27                                                       
CONECT   15   13   28                                                       
CONECT   16   14   29                                                       
CONECT   17   22   23                                                       
CONECT   18   20   30                                                       
CONECT   19    2    7   25                                                  
CONECT   20    3   18   21                                                  
CONECT   21    6    8   20                                                  
CONECT   22    9   17   28                                                  
CONECT   23   13   17   31                                                  
CONECT   24   10   26   27                                                  
CONECT   25   11   19   29                                                  
CONECT   26   12   24   29                                                  
CONECT   27   14   24   28                                                  
CONECT   28    4   15   22   27                                             
CONECT   29    5   16   25   26                                             
CONECT   30   18                                                            
CONECT   31   23                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀O₂

Average Mass

430.7170 Da

Monoisotopic Mass

430.38108 Da

IUPAC Name

14-(5-ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

14-(5-ethyl-7-hydroxy-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)CO

InChI Identifier

InChI=1S/C29H50O2/c1-6-21(20(3)18-30)8-7-19(2)25-11-12-26-24-10-9-22-17-23(31)13-15-28(22,4)27(24)14-16-29(25,26)5/h9,19-21,23-27,30-31H,6-8,10-18H2,1-5H3

InChI Key

OCFKVMGCLMOOPD-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	6.55	ALOGPS
logP	6.49	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	17.68	ChemAxon
pKa (Strongest Basic)	-1.2	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	7	ChemAxon
Refractivity	131.62 m³·mol⁻¹	ChemAxon
Polarizability	54.68 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

HMDB0168481

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

14562763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol (NP0248432)

MOL for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

3D MOL for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

3D SDF for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

3D-SDF for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

PDB for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

3D PDB for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

SMILES for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

INCHI for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

Structure for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)

3D Structure for NP0248432 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-1-ol)