NP-MRD: Showing NP-Card for (+)-clovene (NP0146096)

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Record Information

Version

2.0

Created at

2022-09-02 01:25:36 UTC

Updated at

2022-09-02 01:25:36 UTC

NP-MRD ID

NP0146096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-clovene

Description

Cloven belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (+)-clovene is found in Arctium lappa and Pulicaria arabica. (+)-clovene was first documented in 2022 (PMID: 36046508). Based on a literature review a significant number of articles have been published on Cloven (PMID: 36016432) (PMID: 36016403) (PMID: 36016348) (PMID: 36005757) (PMID: 35937300) (PMID: 35863499).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.0640   -1.1316    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053   -0.0636    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    0.2342   -1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597    1.1965    0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    1.7218    0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806    0.9069    0.0730 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2770    1.4169   -1.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    1.2866   -1.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.1119   -1.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9579   -0.3887    0.3848 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3023   -0.5308    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950   -1.6681    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -1.3885    0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776   -0.4317   -0.1145 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1463    0.7417    0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -1.2600    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181   -0.7679    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953   -2.0579    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    1.2186   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.5233   -2.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376    0.1340   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    1.6114    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150    2.6579    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.8085   -2.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    2.4500   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    1.3876   -2.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070    2.0601   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -0.8632   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.1485   -1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8235   -1.3760    0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2178   -0.7889    2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9290    0.3627    0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2742   -2.3692   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742   -2.2161    1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4290   -1.0888    1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942   -2.3775    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -0.8664   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6961    1.6820    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.5411    1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 14  2  1  0
 14  6  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652309022203252D          

 15 17  0  0  1  0            999 V2000
   -1.4450   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    0.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0763   -1.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -0.8165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2701   -1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -1.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031   -0.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8680    0.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5264    0.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3698    0.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197    0.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -0.0828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2607   -0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  2 14  1  0  0  0  0
  6 14  1  0  0  0  0
 10 15  1  0  0  0  0
  6 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0146096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C=C[C@]23CCC[C@](C)(CC[C@@H]12)C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-13(2)9-10-15-7-4-6-14(3,11-15)8-5-12(13)15/h9-10,12H,4-8,11H2,1-3H3/t12-,14+,15-/m0/s1

> <INCHI_KEY>
MKZIRHIVARSBHI-CFVMTHIKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.573624140020517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{1,5}]dodec-2-ene

> <ALOGPS_LOGP>
5.12

> <JCHEM_LOGP>
4.315393603333334

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.9399

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{1,5}]dodec-2-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.697  -0.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.158  -0.570   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.388   0.953   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.296  -2.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.142  -2.679   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.255  -1.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.371  -2.763   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.967  -2.577   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.486  -1.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.487   0.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.716   1.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.557   1.481   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.970   1.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.346  -0.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.353  -0.688   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   14                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14   15                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    2    6                                                  
CONECT   15   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1R,5S,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{1,5}]dodec-2-ene

Traditional Name

(1R,5S,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{1,5}]dodec-2-ene

CAS Registry Number

Not Available

SMILES

CC1(C)C=C[C@]23CCC[C@](C)(CC[C@@H]12)C3

InChI Identifier

InChI=1S/C15H24/c1-13(2)9-10-15-7-4-6-14(3,11-15)8-5-12(13)15/h9-10,12H,4-8,11H2,1-3H3/t12-,14+,15-/m0/s1

InChI Key

MKZIRHIVARSBHI-CFVMTHIKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Arctium lappa	LOTUS Database	35616633
Pulicaria arabica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Clovane sesquiterpenoid
Sesquiterpenoid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
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	5.12	ALOGPS
logP	4.32	ChemAxon
logS	-5.8	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	65.94 m³·mol⁻¹	ChemAxon
Polarizability	25.57 Å³	ChemAxon
Number of Rings	3	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

C00021776

Chemspider ID

9404534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11229486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shurbe M, Simeon B, Seyoum W, Muluneh A, Tora E, Abayneh E: Seroprevalence and associated risk factors for foot and mouth disease virus seropositivity in cattle in selected districts of Gamo zone, Southern Ethiopia. Front Vet Sci. 2022 Aug 15;9:931643. doi: 10.3389/fvets.2022.931643. eCollection 2022. [PubMed:36046508 ]
Luo C, Yan Q, Huang J, Liu J, Li Y, Wu K, Li B, Zhao M, Fan S, Ding H, Chen J: Using Self-Assembling ADDomer Platform to Display B and T Epitopes of Type O Foot-and-Mouth Disease Virus. Viruses. 2022 Aug 18;14(8):1810. doi: 10.3390/v14081810. [PubMed:36016432 ]
Di Giacomo S, Bucafusco D, Schammas JM, Pega J, Miraglia MC, Barrionuevo F, Capozzo AV, Perez-Filgueira DM: Assessment on Different Vaccine Formulation Parameters in the Protection against Heterologous Challenge with FMDV in Cattle. Viruses. 2022 Aug 15;14(8):1781. doi: 10.3390/v14081781. [PubMed:36016403 ]
Kim H, Seo HW, Cho HS, Oh Y: A Vaccine Based on Asia1 Shamir of the Foot-and-Mouth Disease Virus Offers Low Levels of Protection to Pigs against Asia1/MOG/05, Circulating in East Asia. Viruses. 2022 Aug 4;14(8):1726. doi: 10.3390/v14081726. [PubMed:36016348 ]
Wu X, Hu Y, Sui C, Pan L, Yoo D, Miller LC, Lee C, Cong X, Li J, Du Y, Qi J: Multiple-Site SUMOylation of FMDV 3C Protease and Its Negative Role in Viral Replication. J Virol. 2022 Sep 14;96(17):e0061222. doi: 10.1128/jvi.00612-22. Epub 2022 Aug 25. [PubMed:36005757 ]
Yang L, Chen H, Liu L, Song J, Feng T, Li Y, Shen C, Kong L, Xin X: Foot-and-mouth disease virus VP1 promotes viral replication by regulating the expression of chemokines and GBP1. Front Vet Sci. 2022 Jul 22;9:937409. doi: 10.3389/fvets.2022.937409. eCollection 2022. [PubMed:35937300 ]
Lee G, Kang HR, Kim A, Park JH, Lee MJ, Kim SM: Antiviral effect of vesatolimod (GS-9620) against foot-and-mouth disease virus both in vitro and invivo. Antiviral Res. 2022 Sep;205:105384. doi: 10.1016/j.antiviral.2022.105384. Epub 2022 Jul 19. [PubMed:35863499 ]
Sahoo M, Kondabattula G, Thakor JC, Dinesh M, Kumar P, Singh R, Singh K, Saminathan M, Sahoo NR: Novel pathological findings and immunohistochemical detection of FMDV antigens in the brain of calves naturally infected with foot-and-mouth disease. Microb Pathog. 2022 Aug;169:105650. doi: 10.1016/j.micpath.2022.105650. Epub 2022 Jun 25. [PubMed:35764187 ]
Emami SJ, Bahonar AR, Mehrabadi MHF, Lotfollazadeh S, Amiri K, Abdollahi D: Evaluation of foot and mouth disease (FMD) vaccine using registered surveillance data. Trop Anim Health Prod. 2022 Jun 20;54(4):215. doi: 10.1007/s11250-022-03204-9. [PubMed:35723776 ]
Brown E, Nelson N, Gubbins S, Colenutt C: Airborne Transmission of Foot-and-Mouth Disease Virus: A Review of Past and Present Perspectives. Viruses. 2022 May 9;14(5):1009. doi: 10.3390/v14051009. [PubMed:35632750 ]
LOTUS database [Link]

Showing NP-Card for (+)-clovene (NP0146096)

MOL for NP0146096 ((+)-clovene)

3D MOL for NP0146096 ((+)-clovene)

3D SDF for NP0146096 ((+)-clovene)

3D-SDF for NP0146096 ((+)-clovene)

PDB for NP0146096 ((+)-clovene)

3D PDB for NP0146096 ((+)-clovene)

SMILES for NP0146096 ((+)-clovene)

INCHI for NP0146096 ((+)-clovene)

Structure for NP0146096 ((+)-clovene)

3D Structure for NP0146096 ((+)-clovene)