NP-MRD: Showing NP-Card for 9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0311892)

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Record Information

Version

2.0

Created at

2022-09-11 08:12:11 UTC

Updated at

2022-09-11 08:12:11 UTC

NP-MRD ID

NP0311892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate

Description

2,15-Dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-16-yl acetate belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate is found in Gersemia rubiformis. 2,15-Dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-16-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506542D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251506542D          

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M  END
> <DATABASE_ID>
NP0311892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C=CC(C)C1CCC2C3CCC4=CC(=O)C=CC4(C)C3CC(OC(C)=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O3/c1-17(2)7-8-18(3)23-11-12-24-22-10-9-20-15-21(30)13-14-27(20,5)25(22)16-26(28(23,24)6)31-19(4)29/h7-8,13-15,17-18,22-26H,9-12,16H2,1-6H3

> <INCHI_KEY>
NACRYBSGHPQZTL-UHFFFAOYSA-N

> <FORMULA>
C28H40O3

> <MOLECULAR_WEIGHT>
424.625

> <EXACT_MASS>
424.297745148

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.20287286304936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,15-dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-16-yl acetate

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
6.081782490000002

> <ALOGPS_LOGS>
-6.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.86113426549753

> <JCHEM_PKA_STRONGEST_BASIC>
-4.999229844865211

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
127.84099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25    8   11   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
2,15-Dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,6-dien-16-yl acetic acid	Generator
2,15-Dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-16-yl acetic acid	Generator

Chemical Formula

C₂₈H₄₀O₃

Average Mass

424.6250 Da

Monoisotopic Mass

424.29775 Da

IUPAC Name

2,15-dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-16-yl acetate

Traditional Name

2,15-dimethyl-14-(5-methylhex-3-en-2-yl)-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-16-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C=CC(C)C1CCC2C3CCC4=CC(=O)C=CC4(C)C3CC(OC(C)=O)C12C

InChI Identifier

InChI=1S/C28H40O3/c1-17(2)7-8-18(3)23-11-12-24-22-10-9-20-15-21(30)13-14-27(20,5)25(22)16-26(28(23,24)6)31-19(4)29/h7-8,13-15,17-18,22-26H,9-12,16H2,1-6H3

InChI Key

NACRYBSGHPQZTL-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
Gersemia rubiformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
Steroid ester
3-oxo-delta-1,4-steroid
3-oxosteroid
Oxosteroid
Delta-1,4-steroid
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	4.98	ALOGPS
logP	6.08	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	50.2 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	No	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

73999922

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0311892)

MOL for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D MOL for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D SDF for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D-SDF for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

PDB for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D PDB for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

SMILES for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

INCHI for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

Structure for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D Structure for NP0311892 (9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)