NP-MRD: Showing NP-Card for Goniotortiline (NP0341854)

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Record Information

Version

2.0

Created at

2024-09-30 06:45:11 UTC

Updated at

2024-10-08 03:57:15 UTC

NP-MRD ID

NP0341854

Natural Product DOI

https://doi.org/10.57994/3342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Goniotortiline

Description

Goniotortiline belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions. Based on a literature review very few articles have been published on Goniotortiline.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 06142309162D          

 23 26  0  0  0  0            999 V2000
    1.4289    3.3000    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   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   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   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 O   0  0  0  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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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  1  0  0  0  0
  3  6  1  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0341854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)C(=O)NC3=C(C)C4=CC=CC=C4C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO4/c1-8-9-5-3-4-6-10(9)14-13-11(7-12(20)17(14)23-2)16(21)18(22)19-15(8)13/h3-7,20H,1-2H3,(H,19,22)

> <INCHI_KEY>
CFCCNULJQWOLPT-UHFFFAOYSA-N

> <FORMULA>
C18H13NO4

> <MOLECULAR_WEIGHT>
307.305

> <EXACT_MASS>
307.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.342194422450607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-16-methoxy-8-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <JCHEM_LOGP>
2.9826818766666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.523893508253684

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.791611259467969

> <JCHEM_PKA_STRONGEST_BASIC>
-4.694850953687848

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
86.86069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-16-methoxy-8-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-23         0                                  
HETATM    1  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   19                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17                                                            
CONECT   19    6   15   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₃NO₄

Average Mass

307.3050 Da

Monoisotopic Mass

307.08446 Da

IUPAC Name

15-hydroxy-16-methoxy-8-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

Traditional Name

15-hydroxy-16-methoxy-8-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)C(=O)NC3=C(C)C4=CC=CC=C4C1=C23

InChI Identifier

InChI=1S/C18H13NO4/c1-8-9-5-3-4-6-10(9)14-13-11(7-12(20)17(14)23-2)16(21)18(22)19-15(8)13/h3-7,20H,1-2H3,(H,19,22)

InChI Key

CFCCNULJQWOLPT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-09-30	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
tortilipetalus		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

4,5-dioxoaporphines

Direct Parent

4,5-dioxoaporphines

Alternative Parents

Substituents

4,5-dioxoaporphine
Phenanthrol
Phenanthrene
Benzoquinoline
Quinolone
2-naphthol
Isoquinolone
Quinoline
Naphthalene
Aryl ketone
Piperidinedione
Anisole
1-hydroxy-2-unsubstituted benzenoid
Piperidinone
Delta-lactam
Alkyl aryl ether
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Piperidine
N-acyl-amine
Fatty amide
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Lactam
Ketone
Carboxamide group
Azacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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
logP	2.98	ChemAxon
pKa (Strongest Acidic)	8.79	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.86 m³·mol⁻¹	ChemAxon
Polarizability	31.34 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Goniotortiline (NP0341854)

MOL for NP0341854 (Goniotortiline)

3D MOL for NP0341854 (Goniotortiline)

3D SDF for NP0341854 (Goniotortiline)

3D-SDF for NP0341854 (Goniotortiline)

PDB for NP0341854 (Goniotortiline)

3D PDB for NP0341854 (Goniotortiline)

SMILES for NP0341854 (Goniotortiline)

INCHI for NP0341854 (Goniotortiline)

Structure for NP0341854 (Goniotortiline)

3D Structure for NP0341854 (Goniotortiline)