NP-MRD: Showing NP-Card for alpha-Chamigrene (NP0051788)

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Record Information

Version

2.0

Created at

2022-04-27 23:01:19 UTC

Updated at

2022-04-27 23:01:19 UTC

NP-MRD ID

NP0051788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Chamigrene

Description

Alpha-Chamigrene, also known as α-chamigrene, belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. alpha-Chamigrene is found in Bazzania japonica, Bazzania trilobata, Centella asiatica, Laurencia nipponica, Murraya paniculata , Scapania undulata and Schisandra chinensis . alpha-Chamigrene was first documented in 2002 (PMID: 12381151). Based on a literature review a significant number of articles have been published on alpha-Chamigrene (PMID: 26197495) (PMID: 35389217) (PMID: 34302322) (PMID: 30931617) (PMID: 29976902) (PMID: 29281900).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8583   -1.2752   -0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470   -0.4610   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225   -0.1599   -1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.6841   -1.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    0.2425    0.1620 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8005   -0.3853    1.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    0.1281    0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.3919    0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883    1.9737    2.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8421    1.9034    0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3493    1.3962   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134   -0.0597   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126   -0.6916   -0.2924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6872   -1.9797   -0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -1.1140    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717   -0.8103    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1885   -1.3446   -1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601   -2.2612   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -0.5386   -2.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314    0.7164   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666    1.7563   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -0.2148    2.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605   -1.4921    0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970   -0.1614    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2394    1.2358    0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5229    3.0919    2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319    1.8065    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    1.6867    2.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    2.7537    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561    1.6299   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    2.0346   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1182   -0.5775   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469   -0.2005   -2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -2.4504   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0419   -1.8283   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.7175   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -1.3482    1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6485   -2.0359    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483   -0.3240    1.0604 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
  5  4  1  6
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
  7  2  1  0
 13  5  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
  7 24  1  0
  7 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652304282201012D          

 15 16  0  0  1  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  1  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
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@]2(CC1)C(C)=CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h6-7H,5,8-11H2,1-4H3/t15-/m1/s1

> <INCHI_KEY>
SIBCECUUMHIAAM-OAHLLOKOSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.87716647963127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-1,5,5,9-tetramethylspiro[5.5]undeca-1,8-diene

> <ALOGPS_LOGP>
6.49

> <JCHEM_LOGP>
4.474403745

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.45139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-chamigrene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.103   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.338  -1.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
CONECT    1    2    6    8   12                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
a-Chamigrene	Generator
Α-chamigrene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(6R)-1,5,5,9-tetramethylspiro[5.5]undeca-1,8-diene

Traditional Name

α-chamigrene

CAS Registry Number

Not Available

SMILES

CC1=CC[C@@]2(CC1)C(C)=CCCC2(C)C

InChI Identifier

InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h6-7H,5,8-11H2,1-4H3/t15-/m1/s1

InChI Key

SIBCECUUMHIAAM-OAHLLOKOSA-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
Bazzania japonica	LOTUS Database	35616633
Bazzania trilobata	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Laurencia nipponica	LOTUS Database	35616633
Murraya paniculata	Plant	KNApSAcK
Scapania undulata	LOTUS Database	35616633
Schisandra chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane 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

sesquiterpenoid (CHEBI:10220 )
Sesquiterpenoids (C15) (C09635 )

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	6.49	ALOGPS
logP	4.47	ChemAxon
logS	-4.3	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	68.45 m³·mol⁻¹	ChemAxon
Polarizability	25.88 Å³	ChemAxon
Number of Rings	2	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

C00003115

Chemspider ID

390803

KEGG Compound ID

C09635

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442351

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1561151

References

General References

Kamada T, Vairappan CS: New Laurene-type Sesquiterpene from Bornean Laurencia nangii. Nat Prod Commun. 2015 Jun;10(6):843-4. [PubMed:26197495 ]
Ghosh S, Erchinger JE, Maji R, List B: Catalytic Asymmetric Spirocyclizing Diels-Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of alpha-Chamigrene, beta-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid. J Am Chem Soc. 2022 Apr 20;144(15):6703-6708. doi: 10.1021/jacs.2c01971. Epub 2022 Apr 7. [PubMed:35389217 ]
Sato K, Kaneko K, Kamekawa T, Taba K, Ishigami S, Wada M, Ishii T, Abe T, Kamada T, Suzuki M: Two New Halogenated Compounds from the Marine Red Alga Laurencia nipponica Yamada from the Kunashiri and Etorofu Islands. Chem Biodivers. 2021 Sep;18(9):e2100397. doi: 10.1002/cbdv.202100397. Epub 2021 Aug 4. [PubMed:34302322 ]
Ishii T, Miyagi M, Shinjo Y, Minamida Y, Matsuura H, Abe T, Kikuchi N, Suzuki M: Two new brominated C15-acetogenins from the red alga Laurencia japonensis. Nat Prod Res. 2020 Oct;34(19):2787-2793. doi: 10.1080/14786419.2019.1590712. Epub 2019 Mar 31. [PubMed:30931617 ]
Wang X, Liu Y, Niu Y, Wang N, Gu W: The Chemical Composition and Functional Properties of Essential Oils from Four Species of Schisandra Growing Wild in the Qinling Mountains, China. Molecules. 2018 Jul 5;23(7). pii: molecules23071645. doi: 10.3390/molecules23071645. [PubMed:29976902 ]
Kamada T, Phan CS, Vairappan CS: Nangallenes A and B, halogenated nonterpenoid C15-acetogenins from the Bornean red alga Laurencia nangii. J Asian Nat Prod Res. 2019 Mar;21(3):241-247. doi: 10.1080/10286020.2017.1417265. Epub 2017 Dec 27. [PubMed:29281900 ]
Anderson RR, Girola N, Figueiredo CR, Londero VS, Lago JHG: Circadian variation and in vitro cytotoxic activity evaluation of volatile compounds from leaves of Piper regnellii (Miq) C. DC. var. regnellii (C. DC.) Yunck (Piperaceae). Nat Prod Res. 2018 Apr;32(7):859-862. doi: 10.1080/14786419.2017.1361952. Epub 2017 Aug 3. [PubMed:28774184 ]
Li XD, Ding W, Miao FP, Ji NY: Halogenated chamigrane sesquiterpenes from Laurencia okamurae. Magn Reson Chem. 2012 Feb;50(2):174-7. doi: 10.1002/mrc.2870. Epub 2012 Feb 21. [PubMed:22354806 ]
White DE, Stewart IC, Seashore-Ludlow BA, Grubbs RH, Stoltz BM: A general enantioselective route to the chamigrene natural product family. Tetrahedron. 2010 Mar 26;66(26):4668-4686. doi: 10.1016/j.tet.2010.04.128. [PubMed:20798895 ]
Jelen HH: Volatile sesquiterpene hydrocarbons characteristic for Penicillium roqueforti strains producing PR toxin. J Agric Food Chem. 2002 Oct 23;50(22):6569-74. doi: 10.1021/jf020311o. [PubMed:12381151 ]

Showing NP-Card for alpha-Chamigrene (NP0051788)

MOL for NP0051788 (alpha-Chamigrene)

3D MOL for NP0051788 (alpha-Chamigrene)

3D SDF for NP0051788 (alpha-Chamigrene)

3D-SDF for NP0051788 (alpha-Chamigrene)

PDB for NP0051788 (alpha-Chamigrene)

3D PDB for NP0051788 (alpha-Chamigrene)

SMILES for NP0051788 (alpha-Chamigrene)

INCHI for NP0051788 (alpha-Chamigrene)

Structure for NP0051788 (alpha-Chamigrene)

3D Structure for NP0051788 (alpha-Chamigrene)