NP-MRD: Showing NP-Card for (2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid (NP0143751)

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Record Information

Version

2.0

Created at

2022-09-01 22:35:14 UTC

Updated at

2022-09-01 22:35:14 UTC

NP-MRD ID

NP0143751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid

Description

(2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid is found in Kadsura heteroclita.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200352D          

 33 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309022200352D          

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 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC\C=C(/C)C(O)=O)C1CCC2(C)C3CCC4C(C)(C)C(=O)CCC4(C)C3=CC2C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O3/c1-18(9-8-10-19(2)27(32)33)21-13-15-29(6)22-11-12-25-28(4,5)26(31)14-16-30(25,7)24(22)17-23(29)20(21)3/h10,17-18,21-23,25H,3,8-9,11-16H2,1-2,4-7H3,(H,32,33)/b19-10+

> <INCHI_KEY>
BQCSILLZKUEZCI-VXLYETTFSA-N

> <FORMULA>
C30H44O3

> <MOLECULAR_WEIGHT>
452.679

> <EXACT_MASS>
452.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.608941877252505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-methyl-6-{2,6,6,11-tetramethyl-15-methylidene-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadec-1(17)-en-14-yl}hept-2-enoic acid

> <ALOGPS_LOGP>
6.90

> <JCHEM_LOGP>
7.144876815666668

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.69273444915176

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.938206079802007

> <JCHEM_PKA_STRONGEST_BASIC>
-7.471286963006843

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
135.55719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-methyl-6-{2,6,6,11-tetramethyl-15-methylidene-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadec-1(17)-en-14-yl}hept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.254   3.847   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.845   2.181   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.919   3.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.141   1.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.510   2.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.805   1.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.732  -0.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.363  -1.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.028  -1.149   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.955  -2.687   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.397  -0.443   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.506  -1.458   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.372   2.147   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.024  -1.805   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.179  -0.517   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.995  -2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.774  -1.214   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.741   0.594   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.564   2.234   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   20   24   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₃

Average Mass

452.6790 Da

Monoisotopic Mass

452.32905 Da

IUPAC Name

(2E)-2-methyl-6-{2,6,6,11-tetramethyl-15-methylidene-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadec-1(17)-en-14-yl}hept-2-enoic acid

Traditional Name

(2E)-2-methyl-6-{2,6,6,11-tetramethyl-15-methylidene-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadec-1(17)-en-14-yl}hept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CC\C=C(/C)C(O)=O)C1CCC2(C)C3CCC4C(C)(C)C(=O)CCC4(C)C3=CC2C1=C

InChI Identifier

InChI=1S/C30H44O3/c1-18(9-8-10-19(2)27(32)33)21-13-15-29(6)22-11-12-25-28(4,5)26(31)14-16-30(25,7)24(22)17-23(29)20(21)3/h10,17-18,21-23,25H,3,8-9,11-16H2,1-2,4-7H3,(H,32,33)/b19-10+

InChI Key

BQCSILLZKUEZCI-VXLYETTFSA-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
Kadsura heteroclita	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	6.9	ALOGPS
logP	7.14	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.56 m³·mol⁻¹	ChemAxon
Polarizability	54.61 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid (NP0143751)

MOL for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

3D MOL for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

3D SDF for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

3D-SDF for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

PDB for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

3D PDB for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

SMILES for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

INCHI for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

Structure for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)

3D Structure for NP0143751 ((2e)-6-{4,4,6b,11b-tetramethyl-10-methylidene-3-oxo-1h,2h,4ah,5h,6h,6ah,7h,8h,9h,10ah-cyclohexa[a]fluoren-9-yl}-2-methylhept-2-enoic acid)