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Showing NP-Card for 1,2-Dihydroisoquinoline (NP0082239)

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Record Information
Version2.0
Created at2022-04-29 03:17:04 UTC
Updated at2022-04-29 03:17:04 UTC
NP-MRD IDNP0082239
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2-Dihydroisoquinoline
Description1,2-Dihydroisoquinoline belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. 1,2-Dihydroisoquinoline is found in Petrosia similis. 1,2-Dihydroisoquinoline was first documented in 2015 (PMID: 26487913). Based on a literature review a significant number of articles have been published on 1,2-Dihydroisoquinoline (PMID: 34432480) (PMID: 33395455) (PMID: 32808795) (PMID: 31880465) (PMID: 31854981) (PMID: 30101274).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0082239 (1,2-Dihydroisoquinoline)


  Mrv1652304292205172D          

 10 11  0  0  0  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    0.0000    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
    2.1434   -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  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
M  END
Download

3D MOL for NP0082239 (1,2-Dihydroisoquinoline)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -1.9188    1.4716    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377    1.7763    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163    0.7032    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647    0.9750   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -0.0172   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1543   -1.3170   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -1.5875   -0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -0.5796   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312   -0.9188    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    0.1616    0.3787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445    2.2278    0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867    2.7696    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9872    2.0103    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324    0.2014   -0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8657   -2.0964   -0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -2.5991   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573   -1.7728    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540   -1.3512   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465   -0.0570    0.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10  1  1  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  8  9  1  0
  4  3  1  0
  9 17  1  0
  9 18  1  0
 10 19  1  0
  1 11  1  0
  2 12  1  0
  7 16  1  0
  6 15  1  0
  5 14  1  0
  4 13  1  0
M  END
Download

3D SDF for NP0082239 (1,2-Dihydroisoquinoline)


  Mrv1652304292205172D          

 10 11  0  0  0  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    0.0000    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
    2.1434   -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  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1NC=CC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-6,10H,7H2

> <INCHI_KEY>
IOEPOEDBBPRAEI-UHFFFAOYSA-N

> <FORMULA>
C9H9N

> <MOLECULAR_WEIGHT>
131.178

> <EXACT_MASS>
131.073499294

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.64236233107338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dihydroisoquinoline

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.6661621970000002

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.528808352119567

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
42.70869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dihydroisoquinoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0082239 (1,2-Dihydroisoquinoline)

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PDB for NP0082239 (1,2-Dihydroisoquinoline)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0082239 (1,2-Dihydroisoquinoline)
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SMILES for NP0082239 (1,2-Dihydroisoquinoline)
C1NC=CC2=C1C=CC=C2
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INCHI for NP0082239 (1,2-Dihydroisoquinoline)
InChI=1S/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-6,10H,7H2
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View in JSmol
Synonyms
ValueSource
DihydroisoquinolineHMDB
Chemical FormulaC9H9N
Average Mass131.1780 Da
Monoisotopic Mass131.07350 Da
IUPAC Name1,2-dihydroisoquinoline
Traditional Name1,2-dihydroisoquinoline
CAS Registry NumberNot Available
SMILES
C1NC=CC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H9N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-6,10H,7H2
InChI KeyIOEPOEDBBPRAEI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Petrosia similis-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct ParentAralkylamines  
Alternative Parents
Substituents
  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Enamine
    • 

  • Secondary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.64ALOGPS
logP1.67ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)7.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.71 m³·mol⁻¹ChemAxon
Polarizability14.64 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0244075  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00049061  
Chemspider ID373983  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound422511  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wu W, Liao N, Wei Q, Huang J, Huang Q, Peng Y: Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds. Org Lett. 2021 Sep 3;23(17):6872-6876. doi: 10.1021/acs.orglett.1c02433. Epub  2021 Aug 25. [PubMed:34432480  ] 
  2. De Abreu M, Tang Y, Brachet E, Selkti M, Michelet V, Belmont P: Silver-catalyzed tandem cycloisomerization/hydroarylation reactions and mechanistic investigations for an efficient access to 1,2-dihydroisoquinolines. Org Biomol Chem. 2021 Feb 7;19(5):1037-1046. doi: 10.1039/d0ob02197k. Epub 2021  Jan 4. [PubMed:33395455  ] 
  3. Zou L, Huang J, Liao N, Liu Y, Guo Q, Peng Y: Catalytic Asymmetric Three-Component Reaction of 2-Alkynylbenzaldehydes, Amines, and Dimethylphosphonate. Org Lett. 2020 Sep 4;22(17):6932-6937. doi: 10.1021/acs.orglett.0c02487. Epub  2020 Aug 18. [PubMed:32808795  ] 
  4. Lee J, Kim HY, Oh K: Tandem Reaction Approaches to Isoquinolones from 2-Vinylbenzaldehydes and Anilines via Imine Formation-6pi-Electrocyclization-Aerobic Oxidation Sequence. Org Lett. 2020 Jan 17;22(2):474-478. doi: 10.1021/acs.orglett.9b04233. Epub 2019  Dec 27. [PubMed:31880465  ] 
  5. Ji X, Huang Z, Lumb JP: Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization. J Org Chem. 2020 Jan 17;85(2):1062-1072. doi: 10.1021/acs.joc.9b02987. Epub 2020  Jan 2. [PubMed:31854981  ] 
  6. Cai Y, Gu Q, You SL: Chemoselective N-H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid. Org Biomol Chem. 2018 Aug 22;16(33):6146-6154. doi: 10.1039/c8ob01863d. [PubMed:30101274  ] 
  7. Huang X, Rao A, Zhou W, Aslanian R, Nargund R, Buevich A, Zhang LK, Qiu H, Yang X, Garlisi CG, Correll C, Palani A: The synthesis of 2,3,6-trisubstituted 1-oxo-1,2-dihydroisoquinolines as potent CRTh(2) antagonists. Bioorg Med Chem Lett. 2017 Dec 1;27(23):5344-5348. doi:  10.1016/j.bmcl.2017.07.064. Epub 2017 Jul 25. [PubMed:29110986  ] 
  8. Ferguson PJ, Vincent MD, Koropatnick J: Synergistic Antiproliferative Activity of the RAD51 Inhibitor IBR2 with Inhibitors of Receptor Tyrosine Kinases and Microtubule Protein. J Pharmacol Exp Ther. 2018 Jan;364(1):46-54. doi: 10.1124/jpet.117.241661. Epub  2017 Oct 23. [PubMed:29061656  ] 
  9. Tiwari VK, Kamal N, Kapur M: One Substrate, Two Modes of C-H Functionalization: A Metal-Controlled Site-Selectivity Switch in C-H Arylation Reactions. Org Lett. 2017 Jan 6;19(1):262-265. doi: 10.1021/acs.orglett.6b03558. Epub 2016  Dec 22. [PubMed:28004937  ] 
  10. Chaudhari TY, Urvashi, Ginotra SK, Yadav P, Kumar G, Tandon V: Regioselective synthesis of functionalized dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction. Org Biomol Chem. 2016 Oct 18;14(41):9896-9906. doi: 10.1039/c6ob01790h. [PubMed:27714285  ] 
  11. Ghorab MM, Alsaid MS, Al-Dosari MS, Ragab FA, Al-Mishari AA, Almoqbil AN: Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents. Acta Pharm. 2016 Jun 1;66(2):155-71. doi: 10.1515/acph-2016-0016. [PubMed:27279061  ] 
  12. Varnas K, Finnema SJ, Stepanov V, Takano A, Toth M, Svedberg M, Moller Nielsen S, Khanzhin NA, Juhl K, Bang-Andersen B, Halldin C, Farde L: Neurokinin-3 Receptor Binding in Guinea Pig, Monkey, and Human Brain: In Vitro and in Vivo Imaging Using the Novel Radioligand, [18F]Lu AF10628. Int J Neuropsychopharmacol. 2016 Aug 12;19(8):pyw023. doi: 10.1093/ijnp/pyw023.  Print 2016 Aug. [PubMed:26993630  ] 
  13. Sun R, Jiang Y, Tang XY, Shi M: Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones. Chemistry. 2016 Apr 11;22(16):5727-33. doi: 10.1002/chem.201504914. Epub 2016 Mar  2. [PubMed:26934455  ] 
  14. Zurro M, Asmus S, Bamberger J, Beckendorf S, Garcia Mancheno O: Chiral Triazoles in Anion-Binding Catalysis: New Entry to Enantioselective Reissert-Type Reactions. Chemistry. 2016 Mar 7;22(11):3785-93. doi: 10.1002/chem.201504094. Epub 2016 Jan  7. [PubMed:26743138  ] 
  15. Tandon V, Urvashi, Yadav P, Sur S, Abbat S, Tiwari V, Hewer R, Papathanasopoulos MA, Raja R, Banerjea AC, Verma AK, Kukreti S, Bharatam PV: Design, Synthesis, and Biological Evaluation of 1,2-Dihydroisoquinolines as HIV-1 Integrase Inhibitors. ACS Med Chem Lett. 2015 Aug 10;6(10):1065-70. doi:  10.1021/acsmedchemlett.5b00230. eCollection 2015 Oct 8. [PubMed:26487913  ]