NP-MRD: Showing NP-Card for (+)-calarene (NP0045075)

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Record Information

Version

2.0

Created at

2022-03-10 18:57:33 UTC

Updated at

2022-03-10 22:16:21 UTC

NP-MRD ID

NP0045075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-calarene

Description

(+)-Calarene or Calarene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6, C11 cyclization of the bicyclic eremophilane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. It was identified in the essential oil of leaves of Rhododendron aureum (rosebay) (10.4% - 66.4% Relative to total oil constituents) (DOI: 10.2298/JSC1002209O), the essential oil from Valeriana jatamansi Jones (Indian valerian or Tagar) (DOI: 10.1080/10412905.2013.767757), The essential oil from Humulus lupulus (hop) (PMID: 24152289 ), The essential oil of Piper sarmentosum (wild pepper) (0.81%) (DOI: 10.1016/S2095-3119(17)61693-9), agarwood oil (24.7% Relative to total volatile compounds), spikenard (PMID: 18404340 ), And cannabis (PMID: 26657499 ). It has been shown to have a sedative effect (PMID: 18404340 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.9280   -1.1433   -1.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -0.2456   -0.8354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6937   -0.5623   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    0.3606    0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0759    1.1321    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077    0.8438    1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433    1.6227    1.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.9084    1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2502    0.9915   -0.1477 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0336   -0.2436    0.3467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9506   -0.0824   -0.7139 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2859   -1.4897   -0.9331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673    0.7323   -1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610   -0.3937    0.4007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8893   -1.6088    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8178   -2.2062   -1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0365   -0.8300   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8008   -1.0922   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025    0.7880   -1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356   -0.4738   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -1.6212   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.1312    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7718   -0.1293    1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3856    2.0000    1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.1641    2.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738    2.6213    2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548    2.9593    0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    1.5345    1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5390    1.5389   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -0.5659    1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -2.2579   -0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0459   -1.9052   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -1.6762   -1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    0.1507   -1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.2227   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    1.5148   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0537   -1.8787    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7302   -1.3216    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734   -2.4892    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 10 14  1  0
 14 15  1  1
 14  2  1  0
 14  6  1  0
 11  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  6
 10 30  1  1
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652303192001393D          

 15 17  0  0  0  0            999 V2000
   -1.2306   -2.1885    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7199   -2.0233   -1.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -0.6337   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -0.0835    1.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948    1.0293    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7723   -0.3797   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    1.9335    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4397    2.4917   -0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    1.8687   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -0.7650   -0.2725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6411    1.5130    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3525    0.4527   -1.0047 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0291   -0.1425    0.4157 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9342   -0.7445   -0.4827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4182    0.0821    0.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
  2 14  1  0  0  0  0
  3 14  1  0  0  0  0
 15  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1

> <INCHI_KEY>
MBIPADCEHSKJDQ-XTWPYSKKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.85844876584825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1aH,2H,3H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.231  -2.188   0.303  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.720  -2.023  -1.289  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.442  -0.634  -0.153  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.845  -0.084   1.987  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.995   1.029   0.311  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.772  -0.380  -0.151  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.882   1.934   0.065  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.440   2.492  -0.113  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.684   1.869  -0.738  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.321  -0.765  -0.273  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.641   1.513   0.151  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.353   0.453  -1.005  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.029  -0.143   0.416  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.934  -0.745  -0.483  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.418   0.082   0.516  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    1    6   15                                                  
CONECT   11    7    8   15                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12   14   15                                                  
CONECT   14    2    3   12   13                                             
CONECT   15    4   10   11   13                                             
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

(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

Traditional Name

(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1aH,2H,3H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C

InChI Identifier

InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1

InChI Key

MBIPADCEHSKJDQ-XTWPYSKKSA-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
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Classification

Not classified

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	4.58	ALOGPS
logP	4.1	ChemAxon
logS	-5	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	65.69 m³·mol⁻¹	ChemAxon
Polarizability	25.86 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takemoto H, Ito M, Shiraki T, Yagura T, Honda G: Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components. J Nat Med. 2008 Jan;62(1):41-6. doi: 10.1007/s11418-007-0177-0. Epub 2007 Aug 23. [PubMed:18404340 ]

Showing NP-Card for (+)-calarene (NP0045075)

MOL for NP0045075 ((+)-calarene)

3D MOL for NP0045075 ((+)-calarene)

3D SDF for NP0045075 ((+)-calarene)

3D-SDF for NP0045075 ((+)-calarene)

PDB for NP0045075 ((+)-calarene)

3D PDB for NP0045075 ((+)-calarene)

SMILES for NP0045075 ((+)-calarene)

INCHI for NP0045075 ((+)-calarene)

Structure for NP0045075 ((+)-calarene)

3D Structure for NP0045075 ((+)-calarene)