NP-MRD: Showing NP-Card for 6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid (NP0330948)

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Record Information

Version

1.0

Created at

2022-09-12 16:47:43 UTC

Updated at

2022-09-12 16:47:43 UTC

NP-MRD ID

NP0330948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

Description

Kadsuric acid 3-methylester belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid is found in Dicranopteris ampla. Kadsuric acid 3-methylester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522582D          

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M  END

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M  END


  Mrv1533004191522582D          

 35 37  0  0  0  0            999 V2000
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   -4.9208    5.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    4.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3201    5.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5629    3.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485    0.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182    0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC1(C)C(CCC2C1=CCC1(C)C(CCC21C)C(C)CCC=C(C)C(O)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O4/c1-20(2)23-12-13-26-25(29(23,5)17-16-27(32)35-8)15-19-30(6)24(14-18-31(26,30)7)21(3)10-9-11-22(4)28(33)34/h11,15,21,23-24,26H,1,9-10,12-14,16-19H2,2-8H3,(H,33,34)

> <INCHI_KEY>
NLLYXLDQSXMKSE-UHFFFAOYSA-N

> <FORMULA>
C31H48O4

> <MOLECULAR_WEIGHT>
484.721

> <EXACT_MASS>
484.355260026

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
58.0739842606574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,6H,7H,8H,9H,9aH,9bH-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
7.88

> <JCHEM_LOGP>
7.259087939333334

> <ALOGPS_LOGS>
-6.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.812292391087667

> <JCHEM_PKA_STRONGEST_BASIC>
-7.024322452818603

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
143.1531

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,4H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -5.981   1.589   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.647   0.819   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.313   1.589   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.313   3.129   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.980   0.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.646   1.589   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.646   3.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.163   2.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.870   2.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.860   4.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.183   5.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.173   4.577   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.689   4.844   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.216   6.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.226   7.471   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.707   7.895   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.441   8.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.056   9.671   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.013   8.563   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.710   7.203   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.827   7.096   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.800   9.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.854  11.258   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.106   8.903   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.466   9.626   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.772   8.810   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.132   9.533   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.186  11.072   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.438   8.717   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -11.798   9.440   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -10.384   7.177   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.397   1.415   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.914   1.147   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.407   0.235   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   16   22                                             
CONECT   22   21                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    9   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
Kadsate 3-methylester	Generator
Kadsic acid 3-methylester	Generator
6-[6-(3-Methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,3ah,4H,6H,7H,8H,9H,9ah,9BH-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₁H₄₈O₄

Average Mass

484.7210 Da

Monoisotopic Mass

484.35526 Da

IUPAC Name

6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,6H,7H,8H,9H,9aH,9bH-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

Traditional Name

6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,4H,7H,8H,9H,9aH-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CCC1(C)C(CCC2C1=CCC1(C)C(CCC21C)C(C)CCC=C(C)C(O)=O)C(C)=C

InChI Identifier

InChI=1S/C31H48O4/c1-20(2)23-12-13-26-25(29(23,5)17-16-27(32)35-8)15-19-30(6)24(14-18-31(26,30)7)21(3)10-9-11-22(4)28(33)34/h11,15,21,23-24,26H,1,9-10,12-14,16-19H2,2-8H3,(H,33,34)

InChI Key

NLLYXLDQSXMKSE-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
Dicranopteris ampla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Medium-chain fatty acid
Branched fatty acid
Fatty acid ester
Methyl-branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Methyl ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	7.88	ALOGPS
logP	7.26	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.15 m³·mol⁻¹	ChemAxon
Polarizability	58.07 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

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

137796304

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid (NP0330948)

MOL for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

PDB for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

SMILES for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

INCHI for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

Structure for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0330948 (6-[6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h,9ah-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid)