NP-MRD: Showing NP-Card for Gigantine (NP0050982)

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Record Information

Version

2.0

Created at

2022-04-27 22:26:38 UTC

Updated at

2022-04-27 22:26:39 UTC

NP-MRD ID

NP0050982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gigantine

Description

Gigantine belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Gigantine is found in Carnegia gigantea and Carnegiea gigantea. Gigantine was first documented in 1970 (PMID: 5490303). Based on a literature review very few articles have been published on Gigantine (PMID: 957908).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.3647    2.4034    0.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350    1.1412    0.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305    0.5082   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153    1.0815    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617    0.4033    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -0.8479   -0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393   -1.4316   -0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222   -2.6890   -1.4379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.7436   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -1.3191   -0.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735   -2.1083    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.6060   -0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -0.7364   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014    0.1668    0.3649 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    0.0005    1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469    1.0711    0.3785 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8818    2.1313   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634    3.0876    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3012    2.3148    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3683    2.8054    0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    2.0718    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -3.1666   -1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8534   -1.6937    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618   -2.2088    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160   -3.1362   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882   -2.4836   -0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6212   -1.9958   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0475   -0.1628   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7246   -1.3778   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4864    0.8631    2.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708   -0.1576    1.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -0.9103    2.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852    1.5921    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8082    2.6748   -0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8839    1.6271   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204    2.8310   -0.6857 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 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9  3  1  0
 16  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  1
 17 34  1  0
 17 35  1  0
 17 36  1  0
  8 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
M  END


  Mrv1652304282200262D          

 17 18  0  0  1  0            999 V2000
    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
   -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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
    0.0000    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  1  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(CCN(C)[C@H]2C)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1

> <INCHI_KEY>
HRJQUAXWKYISJC-QMMMGPOBSA-N

> <FORMULA>
C13H19NO3

> <MOLECULAR_WEIGHT>
237.299

> <EXACT_MASS>
237.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.00279254885141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-ol

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.752198261

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.090070904169266

> <JCHEM_PKA_STRONGEST_BASIC>
7.239758857187019

> <JCHEM_POLAR_SURFACE_AREA>
41.93

> <JCHEM_REFRACTIVITY>
67.2364

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gigantine

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -4.620   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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
CONECT   11    3                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14    1   16                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₉NO₃

Average Mass

237.2990 Da

Monoisotopic Mass

237.13649 Da

IUPAC Name

(1S)-6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-ol

Traditional Name

gigantine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CCN(C)[C@H]2C)C(O)=C1OC

InChI Identifier

InChI=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1

InChI Key

HRJQUAXWKYISJC-QMMMGPOBSA-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
Carnegia gigantea	-	KNApSAcK
Carnegiea gigantea	Plant	KNApSAcK

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
1-hydroxy-4-unsubstituted benzenoid
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:5351 )
Isoquinoline alkaloids (C09445 )

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	1.75	ALOGPS
logP	1.75	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	7.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.24 m³·mol⁻¹	ChemAxon
Polarizability	26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00001860

Chemspider ID

390724

KEGG Compound ID

C09445

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gigantine

METLIN ID

Not Available

PubChem Compound

442237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bruhn JG, Lundstrom J: Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid. Lloydia. 1976 Jul-Aug;39(4):197-203. [PubMed:957908 ]
Kapadia GJ, Rao GS, Fayez MB, Chowdhury BK, Sethi ML: Total synthesis of (plus or minus)-gigantine. Chem Ind. 1970 Dec 12;50:1593-4. [PubMed:5490303 ]

Showing NP-Card for Gigantine (NP0050982)

MOL for NP0050982 (Gigantine)

3D MOL for NP0050982 (Gigantine)

3D SDF for NP0050982 (Gigantine)

3D-SDF for NP0050982 (Gigantine)

PDB for NP0050982 (Gigantine)

3D PDB for NP0050982 (Gigantine)

SMILES for NP0050982 (Gigantine)

INCHI for NP0050982 (Gigantine)

Structure for NP0050982 (Gigantine)

3D Structure for NP0050982 (Gigantine)