NP-MRD: Showing NP-Card for 6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid (NP0330821)

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Record Information

Version

1.0

Created at

2022-09-12 16:33:27 UTC

Updated at

2022-09-12 16:33:27 UTC

NP-MRD ID

NP0330821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid

Description

NSC681144 belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. 6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid is found in Taiwanofungus camphoratus. Based on a literature review very few articles have been published on NSC681144.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218332D          

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  Mrv1652309122218332D          

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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0330821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(=C)C(C)C(O)=O)C1CCC2C3=C(C(=O)CC12C)C1(C)CCC(=O)[C@@H](C)C1CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O4/c1-16(19(4)28(33)34)8-9-17(2)21-10-11-22-26-18(3)14-23-20(5)24(31)12-13-29(23,6)27(26)25(32)15-30(21,22)7/h17,19-23H,1,3,8-15H2,2,4-7H3,(H,33,34)/t17?,19?,20-,21?,22?,23?,29?,30?/m0/s1

> <INCHI_KEY>
AOHVXUIUIGQIIP-TZPKLYSRSA-N

> <FORMULA>
C30H42O4

> <MOLECULAR_WEIGHT>
466.662

> <EXACT_MASS>
466.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.403184834270924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-3-methylidene-6-[(6S)-2,6,15-trimethyl-9-methylidene-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

> <JCHEM_LOGP>
5.966906912333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.82179431615452

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.845053571767633

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0908013483875125

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
134.93299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-3-methylidene-6-[(6S)-2,6,15-trimethyl-9-methylidene-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.797   2.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.767   1.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.242  -0.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.212  -1.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.688  -3.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.194  -3.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.657  -4.214   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.133  -5.679   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.151  -3.894   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.325  -2.429   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.706  -1.285   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.801  -0.965   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.230   0.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.260   1.324   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.784   2.789   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.554   4.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.524   5.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.883   4.641   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.217   5.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.217   6.951   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.550   4.641   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.884   5.411   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.218   4.641   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.218   3.101   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.551   5.411   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.551   6.951   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.885   4.641   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.219   5.411   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.885   3.101   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.722   3.109   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.187   3.585   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.752   1.965   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.277   0.500   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.307  -0.644   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   33                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   18   15   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   13   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₄

Average Mass

466.6620 Da

Monoisotopic Mass

466.30831 Da

IUPAC Name

2-methyl-3-methylidene-6-[(6S)-2,6,15-trimethyl-9-methylidene-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

Traditional Name

2-methyl-3-methylidene-6-[(6S)-2,6,15-trimethyl-9-methylidene-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]heptanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(=C)C(C)C(O)=O)C1CCC2C3=C(C(=O)CC12C)C1(C)CCC(=O)[C@@H](C)C1CC3=C

InChI Identifier

InChI=1S/C30H42O4/c1-16(19(4)28(33)34)8-9-17(2)21-10-11-22-26-18(3)14-23-20(5)24(31)12-13-29(23,6)27(26)25(32)15-30(21,22)7/h17,19-23H,1,3,8-15H2,2,4-7H3,(H,33,34)/t17?,19?,20-,21?,22?,23?,29?,30?/m0/s1

InChI Key

AOHVXUIUIGQIIP-TZPKLYSRSA-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
Taiwanofungus camphoratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Bile acid, alcohol, or derivatives
Steroid acid
3-oxosteroid
11-oxosteroid
Oxosteroid
Medium-chain fatty acid
Cyclohexenone
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	5.97	ChemAxon
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.93 m³·mol⁻¹	ChemAxon
Polarizability	54.4 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

343352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

387396

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid (NP0330821)

MOL for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

3D MOL for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

3D SDF for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

3D-SDF for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

PDB for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

3D PDB for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

SMILES for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

INCHI for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

Structure for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)

3D Structure for NP0330821 (6-[(6s)-6,9a,11a-trimethyl-4-methylidene-7,10-dioxo-1h,2h,3h,3ah,5h,5ah,6h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptanoic acid)