NP-MRD: Showing NP-Card for (4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid (NP0244373)

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Record Information

Version

2.0

Created at

2022-09-07 05:09:01 UTC

Updated at

2022-09-07 05:09:01 UTC

NP-MRD ID

NP0244373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid

Description

(4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid is found in Meiogyne cylindrocarpa.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207092D          

 34 36  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 32  1  1  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072207092D          

 34 36  0  0  1  0            999 V2000
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 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 33 32  1  1  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC=C(C)C)[C@H]1C[C@@H]2CC(C)=C[C@@H](\C=C(/C)[C@H]3CC[C@@H](CC3)C(O)=O)[C@@]2(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-19(2)7-6-8-21(4)25-13-14-30(29(33)34)26(15-20(3)16-27(30)18-25)17-22(5)23-9-11-24(12-10-23)28(31)32/h7,13-15,17,21,23-27H,6,8-12,16,18H2,1-5H3,(H,31,32)(H,33,34)/b22-17+/t21-,23-,24-,25+,26-,27-,30+/m0/s1

> <INCHI_KEY>
OTBMTWUPWVANPM-BNAFIAHISA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.12171205433441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aR,5S,8aR)-7-methyl-2-[(2S)-6-methylhept-5-en-2-yl]-5-[(1E)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-1,2,4a,5,8,8a-hexahydronaphthalene-4a-carboxylic acid

> <JCHEM_LOGP>
7.238348828333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.9628696346374515

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.324169540237944

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
140.8508

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,7R,8aR)-2-methyl-7-[(2S)-6-methylhept-5-en-2-yl]-4-[(1E)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1H-naphthalene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.627   2.177   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   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                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   33                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28                                                       
CONECT   28   27   20                                                       
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   12   34                                                  
CONECT   34   33    9                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

(2R,4aR,5S,8aR)-7-methyl-2-[(2S)-6-methylhept-5-en-2-yl]-5-[(1E)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-1,2,4a,5,8,8a-hexahydronaphthalene-4a-carboxylic acid

Traditional Name

(4S,4aR,7R,8aR)-2-methyl-7-[(2S)-6-methylhept-5-en-2-yl]-4-[(1E)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1H-naphthalene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC=C(C)C)[C@H]1C[C@@H]2CC(C)=C[C@@H](\C=C(/C)[C@H]3CC[C@@H](CC3)C(O)=O)[C@@]2(C=C1)C(O)=O

InChI Identifier

InChI=1S/C30H44O4/c1-19(2)7-6-8-21(4)25-13-14-30(29(33)34)26(15-20(3)16-27(30)18-25)17-22(5)23-9-11-24(12-10-23)28(31)32/h7,13-15,17,21,23-27H,6,8-12,16,18H2,1-5H3,(H,31,32)(H,33,34)/b22-17+/t21-,23-,24-,25+,26-,27-,30+/m0/s1

InChI Key

OTBMTWUPWVANPM-BNAFIAHISA-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
Meiogyne cylindrocarpa	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	7.24	ChemAxon
pKa (Strongest Acidic)	4.32	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.85 m³·mol⁻¹	ChemAxon
Polarizability	56.12 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid (NP0244373)

MOL for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

3D MOL for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

3D SDF for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

3D-SDF for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

PDB for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

3D PDB for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

SMILES for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

INCHI for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

Structure for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)

3D Structure for NP0244373 ((4s,4ar,7r,8ar)-2-methyl-7-[(2s)-6-methylhept-5-en-2-yl]-4-[(1e)-2-[(1r,4r)-4-carboxycyclohexyl]prop-1-en-1-yl]-4,7,8,8a-tetrahydro-1h-naphthalene-4a-carboxylic acid)