NP-MRD: Showing NP-Card for ent-6,16-Kauradien-19-oic acid (NP0335438)

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Record Information

Version

2.0

Created at

2024-09-11 01:36:43 UTC

Updated at

2024-09-11 01:36:43 UTC

NP-MRD ID

NP0335438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-6,16-Kauradien-19-oic acid

Description

Ent-6,16-Kauradien-19-oic acid belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review very few articles have been published on ent-6,16-Kauradien-19-oic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262304082D          

 22 25  0  0  0  0            999 V2000
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  2  0  0  0  0
 13  1  2  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 16  6  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1C=CC13CC(CCC21)C(=C)C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C20H28O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h7,10,14-16H,1,4-6,8-9,11-12H2,2-3H3,(H,21,22)

> <INCHI_KEY>
CZTZKVUEUYRGFD-UHFFFAOYNA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.88380572607378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-2-ene-5-carboxylic acid

> <JCHEM_LOGP>
4.445909107666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.800314485394872

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.48019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-2-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.108   0.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.934   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.616   4.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.904   6.373   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.282   4.089   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    8    9                                                       
CONECT    5    6   14                                                       
CONECT    6    5   16                                                       
CONECT    7   10   15                                                       
CONECT    8    4   18                                                       
CONECT    9    4   19                                                       
CONECT   10    7   20                                                       
CONECT   11   13   20                                                       
CONECT   12   14   20                                                       
CONECT   13    1   11   14                                                  
CONECT   14    5   12   13                                                  
CONECT   15    7   18   19                                                  
CONECT   16    6   18   20                                                  
CONECT   17   19   21   22                                                  
CONECT   18    2    8   15   16                                             
CONECT   19    3    9   15   17                                             
CONECT   20   10   11   12   16                                             
CONECT   21   17                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
ent-6,16-Kauradien-19-Oate	Generator

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-2-ene-5-carboxylic acid

Traditional Name

5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-2-ene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1C=CC13CC(CCC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1/C20H28O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h7,10,14-16H,1,4-6,8-9,11-12H2,2-3H3,(H,21,22)

InChI Key

CZTZKVUEUYRGFD-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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	4.45	ChemAxon
pKa (Strongest Acidic)	4.8	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	1	ChemAxon
Refractivity	88.48 m³·mol⁻¹	ChemAxon
Polarizability	34.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ent-6,16-Kauradien-19-oic acid (NP0335438)

MOL for NP0335438 (ent-6,16-Kauradien-19-oic acid)

3D MOL for NP0335438 (ent-6,16-Kauradien-19-oic acid)

3D SDF for NP0335438 (ent-6,16-Kauradien-19-oic acid)

3D-SDF for NP0335438 (ent-6,16-Kauradien-19-oic acid)

PDB for NP0335438 (ent-6,16-Kauradien-19-oic acid)

3D PDB for NP0335438 (ent-6,16-Kauradien-19-oic acid)

SMILES for NP0335438 (ent-6,16-Kauradien-19-oic acid)

INCHI for NP0335438 (ent-6,16-Kauradien-19-oic acid)

Structure for NP0335438 (ent-6,16-Kauradien-19-oic acid)

3D Structure for NP0335438 (ent-6,16-Kauradien-19-oic acid)