NP-MRD: Showing NP-Card for (1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid (NP0224248)

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Record Information

Version

2.0

Created at

2022-09-06 02:33:54 UTC

Updated at

2022-09-06 02:33:54 UTC

NP-MRD ID

NP0224248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid

Description

Echinoic acid, also known as echinoate, belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. (1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid is found in Echinodorus grandiflorus and Echinodorus macrophyllus. Based on a literature review very few articles have been published on Echinoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204332D          

 22 22  0  0  0  0            999 V2000
    2.0562    0.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064    0.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4866   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -2.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843   -1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9143   -0.0503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  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
 11 13  2  0  0  0  0
 13 14  1  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
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C/C=C(C)/CC\C=C(\CC\C=C(C)\CC\1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-15(2)18-13-11-16(3)7-5-9-19(20(21)22)10-6-8-17(4)12-14-18/h7,10,12,14-15H,5-6,8-9,11,13H2,1-4H3,(H,21,22)/b16-7+,17-12+,18-14+,19-10-

> <INCHI_KEY>
WPJBQAROQHYNMO-LFFOPEAISA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.55030077096134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z,5E,7E,11E)-5,11-dimethyl-8-(propan-2-yl)cyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid

> <JCHEM_LOGP>
5.6730001303333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.004502589984495

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
96.87519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,5E,7E,11E)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.838   0.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334   1.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.342   2.816   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.855   2.525   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.359   1.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.871   0.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.879   1.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.375  -0.676   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.351  -0.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.855  -1.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.846  -2.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.351  -4.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334  -2.422   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -3.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.814  -3.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.310  -1.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.203  -1.549   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.211  -2.713   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.707  -0.094   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.318  -0.676   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.814   0.779   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.822   1.943   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
Echinoate	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1Z,5E,7E,11E)-5,11-dimethyl-8-(propan-2-yl)cyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid

Traditional Name

(1Z,5E,7E,11E)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=C/C=C(C)/CC\C=C(\CC\C=C(C)\CC\1)C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-15(2)18-13-11-16(3)7-5-9-19(20(21)22)10-6-8-17(4)12-14-18/h7,10,12,14-15H,5-6,8-9,11,13H2,1-4H3,(H,21,22)/b16-7+,17-12+,18-14+,19-10-

InChI Key

WPJBQAROQHYNMO-LFFOPEAISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Echinodorus grandiflorus	LOTUS Database	35616633
Echinodorus macrophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	5.67	ChemAxon
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.88 m³·mol⁻¹	ChemAxon
Polarizability	35.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

102066452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid (NP0224248)

MOL for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

3D MOL for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

3D SDF for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

3D-SDF for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

PDB for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

3D PDB for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

SMILES for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

INCHI for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

Structure for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)

3D Structure for NP0224248 ((1z,5e,7e,11e)-8-isopropyl-5,11-dimethylcyclotetradeca-1,5,7,11-tetraene-1-carboxylic acid)