NP-MRD: Showing NP-Card for ent-kaurene (NP0184762)

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Record Information

Version

1.0

Created at

2022-09-03 23:58:14 UTC

Updated at

2022-09-03 23:58:14 UTC

NP-MRD ID

NP0184762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-kaurene

Description

Ent-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. Thus, ent-kaurene is considered to be an isoprenoid lipid molecule. ent-kaurene is found in Aristolochia triangularis, Baccharis minutiflora, Balsamorhiza sagittata, Chamaecyparis formosensis, Cryptomeria japonica, Espeletia schultzii, Coespeletia timotensis, Espeletiopsis guacharaca, Guarea kunthiana, Helichrysum schimperi, Hordeum vulgare, Manihot esculenta, Marah macrocarpa, Plagiochila pulcherrima, Pleurozia gigantea, Porella densifolia, Sapium stylare, Sideritis ferrensis, Sideritis lotsyi, Spinacia oleracea, Thapsia tenuifolia and Triticum aestivum. It was first documented in 2006 (PMID: 16714024). Ent-kaurene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21122070) (PMID: 21228464).

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>
NP0184762

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aristolochia triangularis	LOTUS Database	35616633
Baccharis minutiflora	LOTUS Database	35616633
Balsamorhiza sagittata	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Espeletia schultzii	LOTUS Database	35616633
Espeletia timotensis	LOTUS Database	35616633
Espeletiopsis guacharaca	LOTUS Database	35616633
Guarea kunthiana	LOTUS Database	35616633
Helichrysum schimperi	LOTUS Database	35616633
Hordeum vulgare	LOTUS Database	35616633
Manihot esculenta	LOTUS Database	35616633
Marah macrocarpa	LOTUS Database	35616633
Plagiochila pulcherrima	LOTUS Database	35616633
Pleurozia gigantea	LOTUS Database	35616633
Porella densifolia	LOTUS Database	35616633
Sapium stylare	LOTUS Database	35616633
Sideritis ferrensis	LOTUS Database	35616633
Sideritis lotsyi	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633
Thapsia tenuifolia	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633

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 )

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	5.14	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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007253

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

Good Scents ID

Not Available

References

General References

Gamero-Pasadas A, Viera Alcaide I, Rios JJ, Graciani Constante E, Vicario IM, Leon-Camacho M: Characterization and quantification of the hydrocarbons fraction of the subcutaneous fresh fat of Iberian pig by off-line combination of high performance liquid chromatography and gas chromatography. J Chromatogr A. 2006 Aug 4;1123(1):82-91. doi: 10.1016/j.chroma.2006.04.081. Epub 2006 May 22. [PubMed:16714024 ]
Kawaide H, Hayashi K, Kawanabe R, Sakigi Y, Matsuo A, Natsume M, Nozaki H: Identification of the single amino acid involved in quenching the ent-kauranyl cation by a water molecule in ent-kaurene synthase of Physcomitrella patens. FEBS J. 2011 Jan;278(1):123-33. doi: 10.1111/j.1742-4658.2010.07938.x. Epub 2010 Dec 1. [PubMed:21122070 ]
Sugai Y, Miyazaki S, Mukai S, Yumoto I, Natsume M, Kawaide H: Enzymatic total synthesis of gibberellin A(4) from acetate. Biosci Biotechnol Biochem. 2011;75(1):128-35. doi: 10.1271/bbb.100733. Epub 2011 Jan 7. [PubMed:21228464 ]
LOTUS database [Link]

Showing NP-Card for ent-kaurene (NP0184762)

MOL for NP0184762 (ent-kaurene)

3D MOL for NP0184762 (ent-kaurene)

3D SDF for NP0184762 (ent-kaurene)

3D-SDF for NP0184762 (ent-kaurene)

PDB for NP0184762 (ent-kaurene)

3D PDB for NP0184762 (ent-kaurene)

SMILES for NP0184762 (ent-kaurene)

INCHI for NP0184762 (ent-kaurene)

Structure for NP0184762 (ent-kaurene)

3D Structure for NP0184762 (ent-kaurene)