NP-MRD: Showing NP-Card for Clavukerin A (NP0064064)

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Record Information

Version

2.0

Created at

2022-04-28 08:21:30 UTC

Updated at

2022-04-28 08:21:30 UTC

NP-MRD ID

NP0064064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clavukerin A

Description

Clavukerin A belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. Clavukerin A is found in Cespitularia sp. and Clavularia koellikeri. Clavukerin A was first documented in 2002 (PMID: 12467385). Based on a literature review a small amount of articles have been published on Clavukerin A (PMID: 16933886) (PMID: 27333451) (PMID: 21804869) (PMID: 20028120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    2.9704   -1.2186   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170   -0.1979   -0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7207   -0.4260    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.7291    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1654   -2.0478    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -1.2856    0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623    0.0459    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193    1.0057    0.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5828    0.9608   -1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    0.8327    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0124    1.8856    0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3679    1.2196    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802   -0.7544   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -1.9420   -1.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -1.8480    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.5202   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590   -3.1176   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734   -1.8932    1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884   -1.2260   -0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1862    0.5146    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -0.0133    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101    2.0357    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.9976   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8709    0.3393   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    0.5738   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    0.9117    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    2.1159   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0031    2.8136    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    1.3495    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885    1.6176   -0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
 10  3  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
  8 22  1  1
  7 20  1  0
  7 21  1  0
  6 18  1  0
  6 19  1  0
  5 17  1  0
  4 16  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
 12 29  1  0
 12 30  1  0
 11 27  1  0
 11 28  1  0
 10 26  1  1
M  END

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.706   1.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.205   1.119   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.001   2.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.464   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.369   2.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.464   4.095   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001   3.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.205   4.579   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.706   4.236   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.375   2.849   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.862   6.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.939   0.138   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1                                                       
CONECT   11    8                                                            
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	Source
(-)-(S,S)-Clavukerin a	MeSH

Chemical Formula

C₁₂H₁₈

Average Mass

162.2760 Da

Monoisotopic Mass

162.14085 Da

IUPAC Name

(8S,8aS)-3,8-dimethyl-1,2,6,7,8,8a-hexahydroazulene

Traditional Name

(3aS,4S)-1,4-dimethyl-2,3,3a,4,5,6-hexahydroazulene

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC=CC2=C(C)CC[C@@H]12

InChI Identifier

InChI=1S/C12H18/c1-9-5-3-4-6-11-10(2)7-8-12(9)11/h4,6,9,12H,3,5,7-8H2,1-2H3/t9-,12-/m0/s1

InChI Key

WLTLKQLUBPNLAM-CABZTGNLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cespitularia sp.	Animalia	KNApSAcK
Clavularia koellikeri	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Unsaturated hydrocarbons

Sub Class

Branched unsaturated hydrocarbons

Direct Parent

Branched unsaturated hydrocarbons

Alternative Parents

Substituents

Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Olefin
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	4.74	ALOGPS
logP	3.43	ChemAxon
logS	-3.2	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	54.9 m³·mol⁻¹	ChemAxon
Polarizability	20.42 Å³	ChemAxon
Number of Rings	2	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

C00020988

Chemspider ID

9063504

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10888240

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Blay G, Garcia B, Molina E, Pedro JR: A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A. J Nat Prod. 2006 Aug;69(8):1234-6. doi: 10.1021/np060184g. [PubMed:16933886 ]
Barthel A, Kaden F, Jager A, Metz P: Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis. Org Lett. 2016 Jul 1;18(13):3298-301. doi: 10.1021/acs.orglett.6b01619. Epub 2016 Jun 22. [PubMed:27333451 ]
Cheong JY, Rhee YH: A racemic formal total synthesis of clavukerin A using gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes as the key strategy. Beilstein J Org Chem. 2011;7:740-3. doi: 10.3762/bjoc.7.84. Epub 2011 Jun 1. [PubMed:21804869 ]
Li W, Liu X, Zhou X, Lee CS: Amine-induced Michael/Conia-ene cascade reaction: application to a formal synthesis of (+/-)-Clavukerin A. Org Lett. 2010 Feb 5;12(3):548-51. doi: 10.1021/ol902567e. [PubMed:20028120 ]
Alexakis A, March S: Tandem enantioselective conjugate addition--cyclopropanation. Application to natural products synthesis. J Org Chem. 2002 Dec 13;67(25):8753-7. doi: 10.1021/jo026262w. [PubMed:12467385 ]

Showing NP-Card for Clavukerin A (NP0064064)

MOL for NP0064064 (Clavukerin A)

3D MOL for NP0064064 (Clavukerin A)

3D SDF for NP0064064 (Clavukerin A)

3D-SDF for NP0064064 (Clavukerin A)

PDB for NP0064064 (Clavukerin A)

3D PDB for NP0064064 (Clavukerin A)

SMILES for NP0064064 (Clavukerin A)

INCHI for NP0064064 (Clavukerin A)

Structure for NP0064064 (Clavukerin A)

3D Structure for NP0064064 (Clavukerin A)