MiMeDB: Showing metabocard for ent-kaur-16-en-19-oic acid (MMDBc0054474)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:14:28 UTC

Update Date

2022-08-12 20:09:00 UTC

MiMeDB ID

MMDBc0054474

Metabolite Identification

Common Name

ent-kaur-16-en-19-oic acid

Description

ent-kaurenoate 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. ent-kaurenoate is a weakly acidic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303082008092D          

 25 28  0  0  1  0            999 V2000
   -0.6777    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
    3.7828    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
    1.1622    0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6019    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
    1.9120    2.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    0.6389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2703    2.0040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1835    1.0612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7861    2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5714    1.6962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7702    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5083    2.1905    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1035    0.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600    1.8491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    0.8382    0.0000 H   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  1  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  6  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  1  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  6  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  6  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 14 23  1  6  0  0  0
 15 24  1  1  0  0  0
 16 25  1  1  0  0  0
M  CHG  1  22  -1
M  END


  Mrv1652303082008092D          

 25 28  0  0  1  0            999 V2000
   -0.6777    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
    3.7828    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
    1.1622    0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6019    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
    1.9120    2.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    0.6389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2703    2.0040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1835    1.0612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7861    2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5714    1.6962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7702    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5083    2.1905    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1035    0.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600    1.8491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    0.8382    0.0000 H   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  1  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  6  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  1  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  6  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  6  0  0  0
 20 16  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 14 23  1  6  0  0  0
 15 24  1  1  0  0  0
 16 25  1  1  0  0  0
M  CHG  1  22  -1
M  END
> <DATABASE_ID>
MMDBc0054474

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12C[C@]3(CC1=C)CC[C@]1([H])[C@@](C)(CCC[C@@]1(C)[C@]3([H])CC2)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/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/h14-16H,1,4-12H2,2-3H3,(H,21,22)/p-1/t14-,15+,16+,18-,19-,20-/m1/s1

> <INCHI_KEY>
NIKHGUQULKYIGE-OTCXFQBHSA-M

> <FORMULA>
C20H29O2

> <MOLECULAR_WEIGHT>
301.451

> <EXACT_MASS>
301.217303754

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.896089237573435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.8078307643333345

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.839023750520022

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
98.20069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         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   0.827   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       2.169   0.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.723   0.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.098   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-1
HETATM   23  H   UNK     0      -0.193   0.277   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.592   3.452   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.593   1.565   0.000  0.00  0.00           H+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   23                                             
CONECT   15    7   18   19   24                                             
CONECT   16    6   18   20   25                                             
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                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

Synonyms

Value	Source
ent-Kaurenoic acid	Generator
ent-Kaur-16-en-19-Oic acid	Generator

Chemical Formula

C₂₀H₂₉O₂

Average Molecular Weight

301.451

Monoisotopic Molecular Weight

301.217303754

IUPAC Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

Traditional Name

(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3(CC1=C)CC[C@]1([H])[C@@](C)(CCC[C@@]1(C)[C@]3([H])CC2)C([O-])=O

InChI Identifier

InChI=1S/C20H30O2/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/h14-16H,1,4-12H2,2-3H3,(H,21,22)/p-1/t14-,15+,16+,18-,19-,20-/m1/s1

InChI Key

NIKHGUQULKYIGE-OTCXFQBHSA-M

Chemical Taxonomy

Description

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
Organic anion
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid anion (CHEBI:57297 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00035 g/L	ALOGPS
logP	4.21	ALOGPS
logP	4.81	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.2 m³·mol⁻¹	ChemAxon
Polarizability	34.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	3	Human Feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD1F-132

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25200785

PDB ID

Not Available

ChEBI ID

57297

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for ent-kaur-16-en-19-oic acid (MMDBc0054474)

MOL for #<Metabolite:0x000055b76dc81070>

3D MOL for #<Metabolite:0x000055b76dc81070>

3D SDF for #<Metabolite:0x000055b76dc81070>

3D-SDF for #<Metabolite:0x000055b76dc81070>

PDB for #<Metabolite:0x000055b76dc81070>

3D PDB for #<Metabolite:0x000055b76dc81070>

SMILES for #<Metabolite:0x000055b76dc81070>

INCHI for #<Metabolite:0x000055b76dc81070>

Structure for #<Metabolite:0x000055b76dc81070>

3D Structure for #<Metabolite:0x000055b76dc81070>