NP-MRD: Showing NP-Card for 5-Hydroxy-canthin-6-one (NP0140098)

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Record Information

Version

2.0

Created at

2022-06-29 20:45:55 UTC

Updated at

2022-06-29 20:45:55 UTC

NP-MRD ID

NP0140098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Hydroxy-canthin-6-one

Description

3-Hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 5-Hydroxy-canthin-6-one is found in Ailanthus altissima and Simarouba amara. 3-Hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]Hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507122D          

 18 21  0  0  0  0            999 V2000
    0.5010   -0.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
  4 18  1  0  0  0  0
  8 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0140098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=NC=CC3=C2N(C2=C3C=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O2/c17-12-7-10-13-9(5-6-15-10)8-3-1-2-4-11(8)16(13)14(12)18/h1-7,17H

> <INCHI_KEY>
HOTCTNQHGRFRLK-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O2

> <MOLECULAR_WEIGHT>
236.23

> <EXACT_MASS>
236.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.778861668771064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.5660452899999997

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.146342092975932

> <JCHEM_PKA_STRONGEST_BASIC>
3.150023818161574

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
66.4641

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.935  -0.112   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.966   1.032   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.490   2.497   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.520   3.641   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.459   5.479   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.705   6.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.112   5.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.273   4.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.518   3.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.025   3.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.055   2.497   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.579   1.032   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.073   0.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.043   1.857   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.503   1.857   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.472   0.712   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.948  -0.752   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.027   3.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
CONECT   18   15    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₈N₂O₂

Average Mass

236.2300 Da

Monoisotopic Mass

236.05858 Da

IUPAC Name

3-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Traditional Name

3-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=NC=CC3=C2N(C2=C3C=CC=C2)C1=O

InChI Identifier

InChI=1S/C14H8N2O2/c17-12-7-10-13-9(5-6-15-10)8-3-1-2-4-11(8)16(13)14(12)18/h1-7,17H

InChI Key

HOTCTNQHGRFRLK-UHFFFAOYSA-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
Ailanthus altissima	LOTUS Database	35616633
Simarouba amara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Hydroxypyridine
Pyridinone
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Lactam
Organoheterocyclic compound
Azacycle
Organic oxide
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.67	ALOGPS
logP	1.57	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	3.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.46 m³·mol⁻¹	ChemAxon
Polarizability	23.78 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135735549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-Hydroxy-canthin-6-one (NP0140098)

MOL for NP0140098 (5-Hydroxy-canthin-6-one)

3D MOL for NP0140098 (5-Hydroxy-canthin-6-one)

3D SDF for NP0140098 (5-Hydroxy-canthin-6-one)

3D-SDF for NP0140098 (5-Hydroxy-canthin-6-one)

PDB for NP0140098 (5-Hydroxy-canthin-6-one)

3D PDB for NP0140098 (5-Hydroxy-canthin-6-one)

SMILES for NP0140098 (5-Hydroxy-canthin-6-one)

INCHI for NP0140098 (5-Hydroxy-canthin-6-one)

Structure for NP0140098 (5-Hydroxy-canthin-6-one)

3D Structure for NP0140098 (5-Hydroxy-canthin-6-one)