NP-MRD: Showing NP-Card for 2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid (NP0194092)

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Record Information

Version

2.0

Created at

2022-09-04 11:41:05 UTC

Updated at

2022-09-04 11:41:05 UTC

NP-MRD ID

NP0194092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid

Description

2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]Dodec-10-en-4-yl]-2-methylpropanoic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid is found in Excoecaria agallocha. Based on a literature review very few articles have been published on 2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]Dodec-10-en-4-yl]-2-methylpropanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042213412D          

 25 27  0  0  1  0            999 V2000
    3.1719    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -0.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135    0.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885   -0.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913   -0.1453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0182   -0.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1934   -0.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930   -0.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0114   -0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    0.4298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3673    0.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948    0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    1.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842    1.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426    1.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003    0.5291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9420    0.5545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9405    1.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    1.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    1.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174    2.1998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423    2.3077    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 10 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END


  Mrv1652309042213412D          

 25 27  0  0  1  0            999 V2000
    3.1719    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -0.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135    0.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885   -0.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3913   -0.1453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0182   -0.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1934   -0.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930   -0.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0114   -0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    0.4298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3673    0.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948    0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    1.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842    1.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6426    1.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1003    0.5291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9420    0.5545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9405    1.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    1.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    1.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174    2.1998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2423    2.3077    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 10 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)([C@H]1CC[C@@]23C[C@@](C)(C=C2)C(=O)C[C@H]3[C@]1(C)CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-17(2,16(24)25)12-5-6-20-8-7-18(3,11-20)14(21)9-13(20)19(12,4)10-15(22)23/h7-8,12-13H,5-6,9-11H2,1-4H3,(H,22,23)(H,24,25)/t12-,13+,18-,19-,20+/m1/s1

> <INCHI_KEY>
NTNYEJFDYFYWKG-LOAVNOHISA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.08098861411908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

> <JCHEM_LOGP>
3.2827837186666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.828855830663324

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.151786177974667

> <JCHEM_PKA_STRONGEST_BASIC>
-7.5542495951389785

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
92.78999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.921   1.347   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.002  -0.190   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.083  -1.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.540  -0.110   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.238   1.263   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.379  -1.401   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.464  -0.271   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.767  -1.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.228  -1.751   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.294  -0.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.021  -1.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.397  -0.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.089   0.802   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.552   1.281   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.177   0.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.401   2.263   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.277   3.530   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.200   2.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.054   0.988   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.625   1.035   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.622   2.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.897   1.904   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.781   3.439   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.393   4.106   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.052   4.308   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   19                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13   10                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-[(1R,4S,5S,6S,9S)-5-(Carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0,]dodec-10-en-4-yl]-2-methylpropanoate	Generator

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

Traditional Name

2-[(1R,4S,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)([C@H]1CC[C@@]23C[C@@](C)(C=C2)C(=O)C[C@H]3[C@]1(C)CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C20H28O5/c1-17(2,16(24)25)12-5-6-20-8-7-18(3,11-20)14(21)9-13(20)19(12,4)10-15(22)23/h7-8,12-13H,5-6,9-11H2,1-4H3,(H,22,23)(H,24,25)/t12-,13+,18-,19-,20+/m1/s1

InChI Key

NTNYEJFDYFYWKG-LOAVNOHISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Excoecaria agallocha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Ketone
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.28	ChemAxon
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.79 m³·mol⁻¹	ChemAxon
Polarizability	37.08 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162909971

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid (NP0194092)

MOL for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

3D MOL for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

3D SDF for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

3D-SDF for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

PDB for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

3D PDB for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

SMILES for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

INCHI for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

Structure for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)

3D Structure for NP0194092 (2-[(1r,4s,5s,6s,9s)-5-(carboxymethyl)-5,9-dimethyl-8-oxotricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid)