NP-MRD: Showing NP-Card for 1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione (NP0302463)

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Record Information

Version

2.0

Created at

2022-09-10 16:04:25 UTC

Updated at

2022-09-10 16:04:25 UTC

NP-MRD ID

NP0302463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione

Description

9-Hydroxycanthin-6-one, also known as 9-HC-6-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. 1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione is found in Eurycoma longifolia and Simaba orinocensis. 1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione was first documented in 2016 (PMID: 26165243). Based on a literature review a small amount of articles have been published on 9-Hydroxycanthin-6-one (PMID: 29975460) (PMID: 35652145) (PMID: 35600433) (PMID: 29225138).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218042D          

 18 21  0  0  0  0            999 V2000
    3.3384    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2765   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023    2.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3349    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4188    2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862    2.8159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9794    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624    1.0256    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 16 17  2  0  0  0  0
  2 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 18  2  0  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=CC2=C3C=CNC4=C3N(C2=C1)C(=O)C=C4

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

> <INCHI_KEY>
YMNACIYZMIKRMM-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O2

> <MOLECULAR_WEIGHT>
236.23

> <EXACT_MASS>
236.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.728366803754938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione

> <JCHEM_LOGP>
-0.18915076900000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.68140630711465

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1786861208744943

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
72.5584

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       6.232   1.410   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.725   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.249  -0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.743  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.713   0.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.173   0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.858  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.364  -0.374   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.840   1.090   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.810   2.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.871   4.072   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.625   4.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.782   4.351   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.028   5.256   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.943   2.820   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.189   1.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.695   2.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.303   1.914   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15    5   17                                                  
CONECT   17   16    2                                                       
CONECT   18   15   10    6                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
9-HC-6-One	MeSH

Chemical Formula

C₁₄H₈N₂O₂

Average Mass

236.2300 Da

Monoisotopic Mass

236.05858 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O=C1C=CC2=C3C=CNC4=C3N(C2=C1)C(=O)C=C4

InChI Identifier

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

InChI Key

YMNACIYZMIKRMM-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
Eurycoma longifolia	LOTUS Database	35616633
Simaba orinocensis	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
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Pyrrole
Lactam
Cyclic ketone
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036673

Chemspider ID

8438979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10263500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Brauer P, Anielski P, Schwaiger S, Stuppner H, Tran TVA, Vollmer G, Zierau O, Thieme D, Keiler AM: In vitro metabolism of selected bioactive compounds of Eurycoma longifolia root extract to identify suitable markers in doping control. Drug Test Anal. 2019 Jan;11(1):86-94. doi: 10.1002/dta.2449. Epub 2018 Aug 9. [PubMed:29975460 ]
Choonong R, Chaingam J, Chantakul R, Mukda S, Temkitthawon P, Ingkaninan K, Juengwatanatrakul T, Yusakul G, Kanchanapoom T, Putalun W: Phosphodiesterase-5 Inhibitory Activity of Canthin-6-One Alkaloids and the Roots of Eurycoma longifolia and Eurycoma harmandiana. Chem Biodivers. 2022 Jul;19(7):e202200121. doi: 10.1002/cbdv.202200121. Epub 2022 Jun 15. [PubMed:35652145 ]
Mugaranja KP, Kulal A: Investigation of effective natural inhibitors for starch hydrolysing enzymes from Simaroubaceae plants by molecular docking analysis and comparison with in-vitro studies. Heliyon. 2022 May 2;8(5):e09360. doi: 10.1016/j.heliyon.2022.e09360. eCollection 2022 May. [PubMed:35600433 ]
Jeong M, Kim HM, Ahn JH, Lee KT, Jang DS, Choi JH: 9-Hydroxycanthin-6-one isolated from stem bark of Ailanthus altissima induces ovarian cancer cell apoptosis and inhibits the activation of tumor-associated macrophages. Chem Biol Interact. 2018 Jan 25;280:99-108. doi: 10.1016/j.cbi.2017.12.011. Epub 2017 Dec 7. [PubMed:29225138 ]
Ngoc PB, Pham TB, Nguyen HD, Tran TT, Chu HH, Chau VM, Lee JH, Nguyen TD: A new anti-inflammatory beta-carboline alkaloid from the hairy-root cultures of Eurycoma longifolia. Nat Prod Res. 2016 Jun;30(12):1360-5. doi: 10.1080/14786419.2015.1056187. Epub 2015 Jul 13. [PubMed:26165243 ]
LOTUS database [Link]

Showing NP-Card for 1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione (NP0302463)

MOL for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

3D MOL for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

3D SDF for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

3D-SDF for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

PDB for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

3D PDB for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

SMILES for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

INCHI for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

Structure for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)

3D Structure for NP0302463 (1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),7,9,11,14-hexaene-2,13-dione)