NP-MRD: Showing NP-Card for 2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene (NP0324680)

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Record Information

Version

1.0

Created at

2022-09-12 04:54:34 UTC

Updated at

2022-09-12 04:54:34 UTC

NP-MRD ID

NP0324680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene

Description

Thujopsadiene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene is found in Widdringtonia whytei and Zea mays. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on Thujopsadiene (PMID: 27253005) (PMID: 24135886) (PMID: 27583328) (PMID: 36127157).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    2.1682    2.2270   -0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587    0.8851   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603   -0.1585   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265   -1.4982   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2116   -1.3995    0.3430 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5343   -2.1982    1.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -2.1005   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609   -1.3458   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065   -0.0483   -1.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0973    0.6566   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781    0.6091    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    2.1087   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626    0.0203    0.6400 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2675    0.8027    1.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3341    0.6000    0.9414 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9022    2.9902   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923    2.3027   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    2.4914   -1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681   -0.0613   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -2.1249   -1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976   -2.0091   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0184   -1.6103    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -3.0635    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -2.6505    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930   -2.2999    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -3.1109   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560   -1.9191   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    0.5235   -2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4390    1.5606    1.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2797    0.5946    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163   -0.1952    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633    2.7336    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0001    2.5222   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972    2.2739   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278    1.8098    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1708    0.2075    2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034   -0.1255    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 13 10  1  6
 13 14  1  0
 14 15  1  0
 15  2  1  0
 13  5  1  0
 15 13  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
M  END


  Mrv1652309122206542D          

 15 17  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2(C)CC=CC(C)(C)C22CC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h5-7,12H,8-10H2,1-4H3

> <INCHI_KEY>
HIRCZOSUMSSTDU-UHFFFAOYSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.341

> <EXACT_MASS>
202.172150708

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.03772545779327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4a,8,8-tetramethyl-1H,4H,4aH,5H,8H,8bH-cyclopropa[e]naphthalene

> <JCHEM_LOGP>
3.7522645533333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
66.7375

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,4a,8,8-tetramethyl-1H,4H,5H,8bH-cyclopropa[e]naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.991  -1.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.011  -1.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    5   14   15                                             
CONECT   14   13   15                                                       
CONECT   15   14    2   13                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂

Average Mass

202.3410 Da

Monoisotopic Mass

202.17215 Da

IUPAC Name

2,4a,8,8-tetramethyl-1H,4H,4aH,5H,8H,8bH-cyclopropa[e]naphthalene

Traditional Name

2,4a,8,8-tetramethyl-1H,4H,5H,8bH-cyclopropa[e]naphthalene

CAS Registry Number

Not Available

SMILES

CC1=CCC2(C)CC=CC(C)(C)C22CC12

InChI Identifier

InChI=1S/C15H22/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h5-7,12H,8-10H2,1-4H3

InChI Key

HIRCZOSUMSSTDU-UHFFFAOYSA-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
Widdringtonia whytei	LOTUS Database	35616633
Zea mays	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

Thujopsane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
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	3.75	ChemAxon
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	66.74 m³·mol⁻¹	ChemAxon
Polarizability	25.04 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

C00021880

Chemspider ID

4934338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428961

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Kim KH, Moon E, Kim SY, Choi SU, Son MW, Choi SZ, Lee KR: Bioactive sesquiterpenes from the essential oil of Thuja orientalis. Planta Med. 2013 Nov;79(17):1680-4. doi: 10.1055/s-0033-1350952. Epub 2013 Oct 17. [PubMed:24135886 ]
Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387 ]
Authors unspecified: Financial Toxicity and Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:27583328 ]
Gadot R, Najera R, Hirani S, Anand A, Storch E, Goodman WK, Shofty B, Sheth SA: Efficacy of deep brain stimulation for treatment-resistant obsessive-compulsive disorder: systematic review and meta-analysis. J Neurol Neurosurg Psychiatry. 2022 Sep 20. pii: jnnp-2021-328738. doi: 10.1136/jnnp-2021-328738. [PubMed:36127157 ]
LOTUS database [Link]

Showing NP-Card for 2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene (NP0324680)

MOL for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

3D MOL for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

3D SDF for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

3D-SDF for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

PDB for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

3D PDB for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

SMILES for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

INCHI for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

Structure for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)

3D Structure for NP0324680 (2,4a,8,8-tetramethyl-1h,1ah,4h,5h-cyclopropa[e]naphthalene)