MiMeDB: Showing metabocard for (+)-kaurene (MMDBc0004665)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:34:12 UTC

Update Date

2022-08-31 06:22:49 UTC

Metabolite ID

MMDBc0004665

Metabolite Identification

Common Name

(+)-kaurene

Description

(+)-kaurene 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 (+)-kaurene is possibly neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100342D          

 23 26  0  0  1  0            999 V2000
   -0.6778    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3553    0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225    1.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    2.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999    1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2706    2.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1837    1.0614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0801    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034    1.2236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5716    1.6964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1036    0.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5416    2.7834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    0.8384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 14  1  2  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  7  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 18 16  1  0  0  0  0
 19  4  1  1  0  0  0
 19 10  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  1  0  0  0
 20 17  1  0  0  0  0
 15 21  1  6  0  0  0
 16 22  1  6  0  0  0
 17 23  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004665

> <DATABASE_NAME>
MIME

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

> <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-YSDSKTICSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
52.31828438294071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,9S,10S,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>
85.6464

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.03e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.935   4.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.062   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.109   0.827   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.130   1.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.723   0.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.099   4.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.629   2.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.619   1.124   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.263   2.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.934   3.167   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -0.193   0.277   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.611   5.196   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.593   1.565   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5    9   10                                                       
CONECT    6    7   15                                                       
CONECT    7    6   17                                                       
CONECT    8   11   16                                                       
CONECT    9    5   18                                                       
CONECT   10    5   19                                                       
CONECT   11    8   20                                                       
CONECT   12   14   20                                                       
CONECT   13   15   20                                                       
CONECT   14    1   12   15                                                  
CONECT   15    6   13   14   21                                             
CONECT   16    8   18   19   22                                             
CONECT   17    7   19   20   23                                             
CONECT   18    2    3    9   16                                             
CONECT   19    4   10   16   17                                             
CONECT   20   11   12   13   17                                             
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₃₂

Average Mass

272.476

Monoisotopic Mass

272.25040103

IUPAC Name

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

Traditional Name

(1R,4S,9S,10S,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@@]12C[C@@]3(CC1=C)CC[C@@]1([H])C(C)(C)CCC[C@]1(C)[C@@]3([H])CC2

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-YSDSKTICSA-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

Not Available

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	52.32 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

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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	3	Human feces	Metabolic reconstruction

Exposure Sources

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

78436700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304781

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for (+)-kaurene (MMDBc0004665)

MOL for #<Metabolite:0x00007fdb58137730>

3D MOL for #<Metabolite:0x00007fdb58137730>

3D SDF for #<Metabolite:0x00007fdb58137730>

3D-SDF for #<Metabolite:0x00007fdb58137730>

PDB for #<Metabolite:0x00007fdb58137730>

3D PDB for #<Metabolite:0x00007fdb58137730>

SMILES for #<Metabolite:0x00007fdb58137730>

INCHI for #<Metabolite:0x00007fdb58137730>

Structure for #<Metabolite:0x00007fdb58137730>

3D Structure for #<Metabolite:0x00007fdb58137730>