MiMeDB: Showing metabocard for ent-kaur-16-ene (MMDBc0054475)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:14:29 UTC

Update Date

2024-10-17 05:47:48 UTC

Metabolite ID

MMDBc0054475

Metabolite Identification

Common Name

ent-kaur-16-ene

Description

ent-Kaurene, also known as ent kaurane, 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. Thus, ent-kaurene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on ent-Kaurene.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304232017582D          

 22 25  0  0  1  0            999 V2000
   -1.2933    0.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078    0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5789    0.0337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5738    1.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6180    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7497    1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501    0.0337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8612    1.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    1.8052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0126    1.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356    0.4463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1356   -0.3787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5789    0.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    1.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -1.5037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -0.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.7911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8094   -1.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -1.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2932   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0  0  0  0
 12  4  1  0  0  0  0
  8 12  1  0  0  0  0
  4  1  1  0  0  0  0
  2  1  1  0  0  0  0
  8  3  1  0  0  0  0
 11  5  1  0  0  0  0
 10  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
  8  7  1  6  0  0  0
 10  9  1  0  0  0  0
 10  7  1  6  0  0  0
 12 13  1  1  0  0  0
  4 14  1  6  0  0  0
  9 15  2  0  0  0  0
 19 17  1  1  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 19  1  0  0  0  0
 19 16  1  0  0  0  0
 18  2  1  0  0  0  0
 16  3  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054475

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])C(C)(C)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-12-20-11-8-16-18(2,3)9-5-10-19(16,4)17(20)7-6-15(14)13-20/h15-17H,1,5-13H2,2-4H3/t15-,16-,17+,19-,20-/m1/s1

> <INCHI_KEY>
ONVABDHFQKWOSV-HPUSYDDDSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.43330307639061

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.14

> <JCHEM_LOGP>
5.616138165333334

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
85.64639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.03e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-20         0                                  
HETATM    1  C   UNK     0      -2.414   0.833   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.748   0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.587  -1.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.081   0.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.071   3.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.020   0.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.399   1.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.587   0.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.474   2.097   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.607   3.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.024   2.356   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.253   0.833   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       0.253  -0.707   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -1.081   1.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.997   2.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.252  -2.247   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -1.082  -2.807   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -3.747  -1.477   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.081  -1.477   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.378  -3.448   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.432  -3.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.414  -2.246   0.000  0.00  0.00           C+0
CONECT    1    4    2                                                       
CONECT    2    1   18                                                       
CONECT    3    8   16                                                       
CONECT    4   12    1   14   19                                             
CONECT    5   11   10                                                       
CONECT    6    8    9                                                       
CONECT    7    8   10                                                       
CONECT    8   12    3    6    7                                             
CONECT    9    6   10   15                                                  
CONECT   10    5    9    7                                                  
CONECT   11   12    5                                                       
CONECT   12   11    4    8   13                                             
CONECT   13   12                                                            
CONECT   14    4                                                            
CONECT   15    9                                                            
CONECT   16   19    3                                                       
CONECT   17   19                                                            
CONECT   18   22    2                                                       
CONECT   19   17   22   16    4                                             
CONECT   20   22                                                            
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

Synonyms

Value	Source
(5beta,8alpha,9beta,10alpha,13alpha)-Kaur-16-ene	ChEBI
ent-Kaur-16-ene	ChEBI
(5b,8a,9b,10a,13a)-Kaur-16-ene	Generator
(5Β,8α,9β,10α,13α)-kaur-16-ene	Generator
Diterpenoids, kaurane	MeSH
ent-Kauranes	MeSH
Kaurane	MeSH
Kaurane diterpenes	MeSH
Kauranes	MeSH
Diterpenes, kaurane	MeSH
Diterpenoid, kaurane	MeSH
ent-Kaurane	MeSH
Kaurane diterpenoids	MeSH
ent Kaurane	MeSH
ent Kaurene	MeSH
ent-Kaurenes	MeSH
Kaurane diterpenoid	MeSH

Molecular Formula

C₂₀H₃₂

Average Mass

272.476

Monoisotopic Mass

272.25040103

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])C(C)(C)CCC[C@@]21C

InChI Identifier

InChI=1S/C20H32/c1-14-12-20-11-8-16-18(2,3)9-5-10-19(16,4)17(20)7-6-15(14)13-20/h15-17H,1,5-13H2,2-4H3/t15-,16-,17+,19-,20-/m1/s1

InChI Key

ONVABDHFQKWOSV-HPUSYDDDSA-N

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
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpene (CHEBI:15415 )
Kaurane and phyllocladane diterpenoids (LMPR0104130002 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	5.14	ALOGPS
logP	5.62	ChemAxon
logS	-6.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.65 m³·mol⁻¹	ChemAxon
Polarizability	34.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	4	Human feces

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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

16737395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966109

PDB ID

Not Available

ChEBI ID

15415

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-ene (MMDBc0054475)

MOL for #<Metabolite:0x00007fdb4885ce08>

3D MOL for #<Metabolite:0x00007fdb4885ce08>

3D SDF for #<Metabolite:0x00007fdb4885ce08>

3D-SDF for #<Metabolite:0x00007fdb4885ce08>

PDB for #<Metabolite:0x00007fdb4885ce08>

3D PDB for #<Metabolite:0x00007fdb4885ce08>

SMILES for #<Metabolite:0x00007fdb4885ce08>

INCHI for #<Metabolite:0x00007fdb4885ce08>

Structure for #<Metabolite:0x00007fdb4885ce08>

3D Structure for #<Metabolite:0x00007fdb4885ce08>