NP-MRD: Showing NP-Card for 1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene (NP0236911)

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Record Information

Version

2.0

Created at

2022-09-06 19:55:32 UTC

Updated at

2022-09-06 19:55:32 UTC

NP-MRD ID

NP0236911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene

Description

Aristolene 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. Aristolene is possibly neutral. Outside of the human body, Aristolene has been detected, but not quantified in, herbs and spices and root vegetables. 1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene is found in Acanthella cavernosa, Aquilaria sinensis, Bazzania tridens, Calypogeia muelleriana, Calypogeia suecica, Nardostachys jatamansi, Pallavicinia subciliata, Teucrium polium, Teucrium scorodonia and Valeriana jatamansi. This could make aristolene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.6271   -1.4082   -0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4594   -1.0020    0.2339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9990   -0.3681    1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5444    0.9998    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3404    1.8926    0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.2268    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    1.9112   -0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8382    1.3954   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9801   -0.0926   -1.1325 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8653   -0.8527   -0.5887 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0274   -0.6738    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145    0.2399    1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108   -1.8515    0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.1451   -0.4654 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9620   -0.0043   -1.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -2.3298   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176   -0.5777   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815   -1.6772    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9512   -1.9583    0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -0.2199    2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7652   -1.0022    1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1398    0.9770    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494    1.4108    1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866    2.8503    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751    2.0321    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    2.9299    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.7229   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134    1.8235   -0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5753   -0.5377   -1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -1.8910   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.4145    1.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -0.1951    2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004    1.2098    1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -2.3982   -0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -2.4882    1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   -1.4387    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    0.7958   -1.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1181    0.2725   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3141   -0.9926   -2.2929 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  6
 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  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  6
 10 30  1  6
 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


  Mrv0541 05061308152D          

 15 17  0  0  0  0            999 V2000
    0.6556    3.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5078    2.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1474    2.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196    1.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917    2.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3278    0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835    0.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278    2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1308    1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6391    1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    1.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2=CCC3C(C3(C)C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3

> <INCHI_KEY>
FOBXOZMHEKILEY-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.61616342239818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.224   5.906   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.088   3.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.681   5.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.142   4.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.530   2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.918   4.316   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.612   1.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.836   0.607   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.366   0.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.612   4.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.918   1.844   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.977   2.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.060   3.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.590   3.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.530   3.257   0.000  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

Value	Source
(-)-9-Aristolene	HMDB
(-)-Aristolene	HMDB
Aristol-9-ene	HMDB
Aristolen	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

Traditional Name

1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

CAS Registry Number

Not Available

SMILES

CC1CCCC2=CCC3C(C3(C)C)C12C

InChI Identifier

InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3

InChI Key

FOBXOZMHEKILEY-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
Acanthella cavernosa	LOTUS Database	35616633
Aquilaria sinensis	LOTUS Database	35616633
Bazzania tridens	LOTUS Database	35616633
Calypogeia muelleriana	LOTUS Database	35616633
Calypogeia suecica	LOTUS Database	35616633
Nardostachys jatamansi	LOTUS Database	35616633
Pallavicinia subciliata	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Teucrium scorodonia	LOTUS Database	35616633
Valeriana jatamansi	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Aristolane sesquiterpenoids

Alternative Parents

Substituents

Aristolane 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	4.65	ALOGPS
logP	4.1	ChemAxon
logS	-5.1	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	25.62 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

HMDB0035146

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013783

KNApSAcK ID

C00017471

Chemspider ID

462023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

530421

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene (NP0236911)

MOL for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

3D MOL for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

3D SDF for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

3D-SDF for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

PDB for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

3D PDB for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

SMILES for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

INCHI for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

Structure for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)

3D Structure for NP0236911 (1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene)