NP-MRD: Showing NP-Card for (2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene (NP0175492)

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Record Information

Version

2.0

Created at

2022-09-03 12:58:15 UTC

Updated at

2022-09-03 12:58:15 UTC

NP-MRD ID

NP0175492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene

Description

Beta-Panasinsene, also known as β-panasinsene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene is found in Dendropanax trifidus and Panax ginseng. (2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene was first documented in 2010 (PMID: 20492218). Based on a literature review a small amount of articles have been published on beta-Panasinsene (PMID: 35747377) (PMID: 35889423) (PMID: 22804575) (PMID: 21259422).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.8632    0.6918   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805    0.6574   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    1.3737   -2.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    1.7878   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    0.4720   -1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093   -0.1745   -0.2454 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7592   -1.6470   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.4765    1.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421    1.0005    1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192    0.5724    0.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3914   -0.7117    1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -1.2663    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.6186    1.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606   -1.2934   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1484   -0.0433   -0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2134    1.2132   -2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878    0.2016   -1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154    2.2945   -2.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.7091   -3.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    2.3073   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061    2.3970   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -0.2129   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1706    0.6104   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649   -1.6423   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -2.1069   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103   -2.1551    0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    1.2939    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1831   -0.2740    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618    0.5780    2.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4641    2.1149    1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    1.3587    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1647   -0.6019    3.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639   -1.4445    2.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -2.2555    2.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500    0.4160    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433   -1.2022    2.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843   -1.1319    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660   -1.5502   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -2.1943    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 10 11  1  0
  6 15  1  0
 15  2  1  6
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 10 31  1  6
  9 29  1  0
  9 30  1  0
  8 27  1  0
  8 28  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  5 22  1  0
  5 23  1  0
  4 20  1  0
  4 21  1  0
  3 18  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652309032214582D          

 15 17  0  0  1  0            999 V2000
    1.5752    2.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    1.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5148    1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817    0.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799    0.1973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9831   -0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759   -0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669    0.4385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8106    1.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0665    0.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9110    0.7948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  6  0  0  0
  2 15  1  0  0  0  0
 10 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@@]23[C@@H]1CC[C@]2(C)CCCC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-5-8-14(4)9-7-12-13(2,3)10-15(11,12)14/h12H,1,5-10H2,2-4H3/t12-,14+,15-/m1/s1

> <INCHI_KEY>
LTMKWDWWHXRNMO-VHDGCEQUSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.48188003056747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8aS,8bR)-2,2,4a-trimethyl-8-methylidene-decahydrocyclobuta[d]indene

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
4.172119880333334

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
64.54839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,8aS,8bR)-2,2,4a-trimethyl-8-methylidene-hexahydro-1H-cyclobuta[d]indene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.940   4.076   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.002   2.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.499   3.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.561   2.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.126   0.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.629   0.368   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.568  -0.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.896  -0.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.382  -0.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.178   0.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.513   2.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.124   1.542   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.848   3.596   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.902   2.873   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.567   1.484   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                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14    2   10    6                                             
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
b-Panasinsene	Generator
Β-panasinsene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(4aS,8aS,8bR)-2,2,4a-trimethyl-8-methylidene-decahydrocyclobuta[d]indene

Traditional Name

(4aS,8aS,8bR)-2,2,4a-trimethyl-8-methylidene-hexahydro-1H-cyclobuta[d]indene

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@@]23[C@@H]1CC[C@]2(C)CCCC3=C

InChI Identifier

InChI=1S/C15H24/c1-11-6-5-8-14(4)9-7-12-13(2,3)10-15(11,12)14/h12H,1,5-10H2,2-4H3/t12-,14+,15-/m1/s1

InChI Key

LTMKWDWWHXRNMO-VHDGCEQUSA-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
Dendropanax trifidus	LOTUS Database	35616633
Panax ginseng	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

Caryophyllane 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	4.6	ALOGPS
logP	4.17	ChemAxon
logS	-5.3	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	64.55 m³·mol⁻¹	ChemAxon
Polarizability	25.48 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

C00021833

Chemspider ID

103883597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101029600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Z, Zeng Z, Hu Y, Sun H, Tang Y, Liu W: Network Pharmacology and Pharmacological Mechanism of CV-3 in Atrial Fibrillation. Evid Based Complement Alternat Med. 2022 Jun 14;2022:5496299. doi: 10.1155/2022/5496299. eCollection 2022. [PubMed:35747377 ]
Lee HY, Lee JH, Shin EC, Cho DY, Jung JG, Kim MJ, Jeong JB, Kang D, Kang SS, Cho KM: Changes in Chemical Compositions and Antioxidant Activities from Fresh to Fermented Red Mountain-Cultivated Ginseng. Molecules. 2022 Jul 17;27(14):4550. doi: 10.3390/molecules27144550. [PubMed:35889423 ]
Cho IH, Lee HJ, Kim YS: Differences in the volatile compositions of ginseng species (Panax sp.). J Agric Food Chem. 2012 Aug 8;60(31):7616-22. doi: 10.1021/jf301835v. Epub 2012 Jul 30. [PubMed:22804575 ]
Maggi F, Nicoletti M, Petitto V, Sagratini G, Papa F, Vittori S: Solid-phase microextraction (SPME) analysis of six Italian populations of Ephedra nebrodensis Tineo ex Guss. subsp. nebrodensis. Chem Biodivers. 2011 Jan;8(1):95-114. doi: 10.1002/cbdv.201000151. [PubMed:21259422 ]
Lee SJ, Moon TW, Lee J: Increases of 2-furanmethanol and maltol in Korean red ginseng during explosive puffing process. J Food Sci. 2010 Mar;75(2):C147-51. doi: 10.1111/j.1750-3841.2009.01461.x. [PubMed:20492218 ]
LOTUS database [Link]

Showing NP-Card for (2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene (NP0175492)

MOL for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

3D MOL for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

3D SDF for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

3D-SDF for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

PDB for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

3D PDB for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

SMILES for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

INCHI for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

Structure for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)

3D Structure for NP0175492 ((2ar,4as,8as)-2,2,4a-trimethyl-8-methylidene-hexahydro-1h-cyclobuta[d]indene)