NP-MRD: Showing NP-Card for (+-)-carnegine (NP0182318)

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Record Information

Version

2.0

Created at

2022-09-03 20:58:30 UTC

Updated at

2022-09-03 20:58:30 UTC

NP-MRD ID

NP0182318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+-)-carnegine

Description

(-)-Carnegine, also known as carnegine, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. (+-)-carnegine is found in Carnegiea gigantea, Neobuxbaumia multiareolata, Echium humile and Pachycereus weberi. (+-)-carnegine was first documented in 2003 (PMID: 12939030). Based on a literature review a small amount of articles have been published on (-)-Carnegine (PMID: 23677770) (PMID: 20704442) (PMID: 20027474) (PMID: 18671433).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.4856    3.0042    0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404    1.5892    0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207    0.9942    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    1.7116   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811    1.0786   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939   -0.2912   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9079   -1.0334    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856   -0.3836    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119   -1.1149    0.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -2.5421    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236   -0.8499   -0.6301 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5861   -2.3413   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -0.1693    0.2048 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323   -0.8175    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    1.1945   -0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3267    1.8283   -0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7128    3.4397    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    3.2913   -0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4805    3.4107    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1498    2.8106   -0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -2.1212    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872   -2.9712   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -2.8683    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215   -2.9526    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7342   -0.5713   -1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -2.7383    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -2.7511   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -2.6602   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913   -0.0778    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672   -1.3213   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -1.5920    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210    1.7955    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    1.2371   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    2.8410   -0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896    1.9421   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  8  3  1  0
 16  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  7 21  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  6
 12 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
M  END


  Mrv1652309032222582D          

 16 17  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    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
    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
    1.4289   -0.0000    0.0000 C   0  0  2  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
    2.1434   -0.4125    0.0000 N   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   -1.2375    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
  1  2  1  0  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@H](C)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3/t9-/m0/s1

> <INCHI_KEY>
HRSIPKSSEVRSPG-VIFPVBQESA-N

> <FORMULA>
C13H19NO2

> <MOLECULAR_WEIGHT>
221.3

> <EXACT_MASS>
221.141578856

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.460401578414405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline

> <JCHEM_LOGP>
2.0557635826666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.848750766574228

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
65.25550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-carnegine

> <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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    5                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Carnegine	Kegg

Chemical Formula

C₁₃H₁₉NO₂

Average Mass

221.3000 Da

Monoisotopic Mass

221.14158 Da

IUPAC Name

(1S)-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline

Traditional Name

(+-)-carnegine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@H](C)N(C)CC2

InChI Identifier

InChI=1S/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3/t9-/m0/s1

InChI Key

HRSIPKSSEVRSPG-VIFPVBQESA-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
Carnegiea gigantea	LOTUS Database	35616633
Cephalocereus mezcalaensis var. multiareolatus	LOTUS Database	35616633
Echium humile	LOTUS Database	35616633
Pachycereus weberi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:64 )
Isoquinoline alkaloids (C09375 )

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	2.06	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.26 m³·mol⁻¹	ChemAxon
Polarizability	25.46 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

C00001831

Chemspider ID

390694

KEGG Compound ID

C09375

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442186

PDB ID

Not Available

ChEBI ID

Good Scents ID

Not Available

References

General References

Li X, Leonori D, Sheikh NS, Coldham I: Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine. Chemistry. 2013 Jun 10;19(24):7724-30. doi: 10.1002/chem.201301096. Epub 2013 May 15. [PubMed:23677770 ]
Louafi F, Hurvois JP, Chibani A, Roisnel T: Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step. J Org Chem. 2010 Aug 20;75(16):5721-4. doi: 10.1021/jo100714y. [PubMed:20704442 ]
Mezghani-Jarraya R, Hammami H, Ayadi A, Damak M: Molluscicidal activity of Hammada scoparia (Pomel) Iljin leaf extracts and the principal alkaloids isolated from them against Galba truncatula. Mem Inst Oswaldo Cruz. 2009 Nov;104(7):1035-8. doi: 10.1590/s0074-02762009000700017. [PubMed:20027474 ]
Iwasa K, Takahashi T, Nishiyama Y, Moriyasu M, Sugiura M, Takeuchi A, Tode C, Tokuda H, Takeda K: Online structural elucidation of alkaloids and other constituents in crude extracts and cultured cells of Nandina domestica by combination of LC-MS/MS, LC-NMR, and LC-CD analyses. J Nat Prod. 2008 Aug;71(8):1376-85. doi: 10.1021/np8001496. Epub 2008 Aug 1. [PubMed:18671433 ]
El-Shazly A, Wink M: Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). Z Naturforsch C J Biosci. 2003 Jul-Aug;58(7-8):477-80. doi: 10.1515/znc-2003-7-805. [PubMed:12939030 ]
LOTUS database [Link]

Showing NP-Card for (+-)-carnegine (NP0182318)

MOL for NP0182318 ((+-)-carnegine)

3D MOL for NP0182318 ((+-)-carnegine)

3D SDF for NP0182318 ((+-)-carnegine)

3D-SDF for NP0182318 ((+-)-carnegine)

PDB for NP0182318 ((+-)-carnegine)

3D PDB for NP0182318 ((+-)-carnegine)

SMILES for NP0182318 ((+-)-carnegine)

INCHI for NP0182318 ((+-)-carnegine)

Structure for NP0182318 ((+-)-carnegine)

3D Structure for NP0182318 ((+-)-carnegine)