NP-MRD: Showing NP-Card for Cuparene (NP0046790)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:36 UTC

Updated at

2022-03-17 20:29:36 UTC

NP-MRD ID

NP0046790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cuparene

Description

Cuparene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, cuparene is considered to be an isoprenoid lipid molecule. Cuparene is found in Acorus calamus, Aloysia triphylla, Angelica archangelica, Atalantia buxifolia, Bazzania fauriana, Bazzania praerupta, Bazzania tridens, Bazzania trilobata, Biota orientalis, Carpesium abrotanoides, Chamaecyparis thyoides, Chuquiraga spinosa, Cupressus spp., Cupressus torulosa, Cymbopogon schoenanthus, Erigeron canadensis, Frullania falciloba, Gymnomitrion obtusum, Heteroscyphus aselliformis, Jungermannia rosulans, Juniperus cedrus, Juniperus communis, Juniperus horizontalis, Juniperus osteosperma, Juniperus phoenicea, Juniperus procera, Juniperus spp., Juniperus thurifera, Lepechinia chamaedryoides, Lepidozia vitrea, Marchantia polymorpha, Marsupella emarginata, Mastigophora diclados, Metacalypogeia alternifolia, Metacalypogeia cordifolia, Pallavicinia subciliata, Perilla frutescens, Platycladus orientalis, Radula perrottetii, Ricciocarpos natans, Jungermannia infusca, Targionia hypophylla, Thuja standishii, Thujopsis dolabrata, Tordylium apulum, Torulopsis spp., Trachyspermum anethifolium, Vaccinium vitis-idaea, Vitex agnus-castus, Wettsteinia inversa, Widdringtonia spp. and Widdringtonia whytei. Cuparene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221072D          

 15 16  0  0  1  0            999 V2000
    1.6110   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -1.6320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4172   -1.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -1.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -0.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837    0.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8421    0.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786    0.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798   -0.2375    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C(C=C1)[C@]1(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-12-6-8-13(9-7-12)15(4)11-5-10-14(15,2)3/h6-9H,5,10-11H2,1-4H3/t15-/m0/s1

> <INCHI_KEY>
SLKPBCXNFNIJSV-HNNXBMFYSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.3352

> <EXACT_MASS>
202.172150704

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.503259300195005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-[(1R)-1,2,2-trimethylcyclopentyl]benzene

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
5.044201119666666

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.18860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cuparene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.007  -0.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.977  -2.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.946  -0.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.223  -3.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.747  -4.511   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.207  -4.511   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.731  -3.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.779  -3.351   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.312  -1.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.814  -2.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.857  -1.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.396   0.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.439   1.488   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.893   0.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.149  -0.443   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂

Average Mass

202.3352 Da

Monoisotopic Mass

202.17215 Da

IUPAC Name

1-methyl-4-[(1R)-1,2,2-trimethylcyclopentyl]benzene

Traditional Name

cuparene

CAS Registry Number

Not Available

SMILES

CC1=CC=C(C=C1)[C@]1(C)CCCC1(C)C

InChI Identifier

InChI=1S/C15H22/c1-12-6-8-13(9-7-12)15(4)11-5-10-14(15,2)3/h6-9H,5,10-11H2,1-4H3/t15-/m0/s1

InChI Key

SLKPBCXNFNIJSV-HNNXBMFYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acorus calamus	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Angelica archangelica	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Bazzania fauriana	LOTUS Database	35616633
Bazzania praerupta	LOTUS Database	35616633
Bazzania tridens	LOTUS Database	35616633
Bazzania trilobata	LOTUS Database	35616633
Biota orientalis	Plant	KNApSAcK
Carpesium abrotanoides	LOTUS Database	35616633
Chamaecyparis thyoides	Plant	KNApSAcK
Chuquiraga spinosa	LOTUS Database	35616633
Cupressus spp.	Plant	KNApSAcK
Cupressus torulosa	LOTUS Database	35616633
Cymbopogon schoenanthus	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	12926889
Erigeron canadensis	LOTUS Database	35616633
Frullania falciloba	LOTUS Database	35616633
Gymnomitrion obtusum	LOTUS Database	35616633
Heteroscyphus aselliformis	LOTUS Database	35616633
Jungermannia rosulans	Plant	KNApSAcK
Juniperus cedrus	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Juniperus horizontalis	LOTUS Database	35616633
Juniperus osteosperma	LOTUS Database	35616633
Juniperus phoenicea	LOTUS Database	35616633
Juniperus procera	LOTUS Database	35616633
Juniperus spp.	Plant	KNApSAcK
Juniperus thurifera	LOTUS Database	35616633
Lepechinia chamaedryoides	LOTUS Database	35616633
Lepidozia vitrea	LOTUS Database	35616633
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Marchantia polymorpha	LOTUS Database	35616633
Marsupella emarginata	LOTUS Database	35616633
Mastigophora diclados	LOTUS Database	35616633
Metacalypogeia alternifolia	LOTUS Database	35616633
Metacalypogeia cordifolia	LOTUS Database	35616633
Pallavicinia subciliata	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Platycladus orientalis	LOTUS Database	35616633
Radula perrottetii	LOTUS Database	35616633
Ricciocarpos natans	LOTUS Database	35616633
Solenostoma infuscum	LOTUS Database	35616633
Targionia hypophylla	LOTUS Database	35616633
Thuja standishii	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Tordylium apulum	LOTUS Database	35616633
Torulopsis spp.	Fungi	KNApSAcK
Trachyspermum anethifolium	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Wettsteinia inversa	LOTUS Database	35616633
Widdringtonia spp.	Plant	KNApSAcK
Widdringtonia whytei	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

Cuparane sesquiterpenoid
Sesquiterpenoid
Toluene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Cuparane sesquiterpenoids (LMPR0103140001 )

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	6.06	ALOGPS
logP	5.04	ChemAxon
logS	-5.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.19 m³·mol⁻¹	ChemAxon
Polarizability	25.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

FDB005922

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cuparene (NP0046790)

MOL for NP0046790 (Cuparene)

3D MOL for NP0046790 (Cuparene)

3D SDF for NP0046790 (Cuparene)

3D-SDF for NP0046790 (Cuparene)

PDB for NP0046790 (Cuparene)

3D PDB for NP0046790 (Cuparene)

SMILES for NP0046790 (Cuparene)

INCHI for NP0046790 (Cuparene)

Structure for NP0046790 (Cuparene)

3D Structure for NP0046790 (Cuparene)