NP-MRD: Showing NP-Card for (1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0258815)

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Record Information

Version

2.0

Created at

2022-09-08 00:27:31 UTC

Updated at

2022-09-08 00:27:31 UTC

NP-MRD ID

NP0258815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

CHEMBL1085679 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. (1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Theonella swinhoei. Based on a literature review very few articles have been published on CHEMBL1085679.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082202272D          

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  Mrv1652309082202272D          

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 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 10 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0258815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](CC[C@@H](C)[C@H]1CCC2=C3CCC4C(=C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h19-20,22,24-25,27-28,31H,5,8-18H2,1-4,6-7H3/t20-,22+,24-,25?,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
CVZFQTIJNREPCP-MZTSSLHVSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.58235779594347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
7.8960997126666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.09585379735507

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4446735490368923

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
133.67159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.741   9.891   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.421   8.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.956   7.909   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.812   8.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.347   8.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.027   6.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.562   6.482   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.229   7.252   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.084   6.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.711   4.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.711   2.147   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.401   3.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.369   2.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.909   2.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.679   0.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.219   0.813   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.679   3.481   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.909   4.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.219   3.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.242   4.975   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.766   3.511   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.387   3.945   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.851   4.421   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.171   5.927   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.636   6.403   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.316   4.896   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.780   5.372   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.245   5.848   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.565   7.355   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -13.030   7.830   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   10    7   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    6   26                                                  
CONECT   26   25    3   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(1R,2R,5S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

Traditional Name

(1R,2R,5S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

CAS Registry Number

Not Available

SMILES

CC[C@@H](CC[C@@H](C)[C@H]1CCC2=C3CCC4C(=C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h19-20,22,24-25,27-28,31H,5,8-18H2,1-4,6-7H3/t20-,22+,24-,25?,27+,28+,29-,30+/m1/s1

InChI Key

CVZFQTIJNREPCP-MZTSSLHVSA-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
Theonella swinhoei	LOTUS Database	35616633

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

Triterpenoid
Stigmastane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	7.9	ChemAxon
pKa (Strongest Acidic)	18.1	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.67 m³·mol⁻¹	ChemAxon
Polarizability	55.58 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	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

24666544

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46881117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0258815)

MOL for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0258815 ((1r,7s,9ar,9br,11ar)-1-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-6-methylidene-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)