NP-MRD: Showing NP-Card for Arolycoricidine (NP0066737)

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Record Information

Version

2.0

Created at

2022-04-28 10:59:05 UTC

Updated at

2022-04-28 10:59:05 UTC

NP-MRD ID

NP0066737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arolycoricidine

Description

13,15-Dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-1(17),2(7),3,5,8,10,12(16)-heptaene-6,9-diol belongs to the class of organic compounds known as phenanthridine- and phenanthridone-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds based on the phenanthridine or the phenanthridone skeleton. Phenanthridone-type alkaloids have the highest oxygenated C ring in all Amaryllidaceae alkaloids, and they always show an amide group in ring B. On the contrary, alkaloids of the phenanthridine type often show completely aromatic ring system, occasionally with a methylation quaternary nitrogen atom. Arolycoricidine is found in Galanthus trojanus, Lycoris sanguinea and Lycoris sanguinea Maxim. 13,15-Dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-1(17),2(7),3,5,8,10,12(16)-heptaene-6,9-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516012D          

 19 22  0  0  0  0            999 V2000
    1.7942    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4185    0.7268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    1.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.5346    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
  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
  9 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1NC(=O)C1=CC3=C(OCO3)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C14H9NO4/c16-10-3-1-2-7-8-4-11-12(19-6-18-11)5-9(8)14(17)15-13(7)10/h1-5,16H,6H2,(H,15,17)

> <INCHI_KEY>
SCDAZLFIUOBZAZ-UHFFFAOYSA-N

> <FORMULA>
C14H9NO4

> <MOLECULAR_WEIGHT>
255.229

> <EXACT_MASS>
255.053157774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
25.142235601046615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2(7),3,5,10,12(16)-hexaen-9-one

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.058778313666666

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.64826013150741

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.594133221466842

> <JCHEM_PKA_STRONGEST_BASIC>
-4.068600001238954

> <JCHEM_POLAR_SURFACE_AREA>
67.79

> <JCHEM_REFRACTIVITY>
68.4175

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2(7),3,5,10,12(16)-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       3.349   0.815   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.342  -0.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.819  -1.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.811  -2.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.327  -2.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.851  -1.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.858  -0.092   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.381   1.357   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.897   1.628   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.420   3.076   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.890   0.451   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.406   0.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.399  -0.456   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.938  -0.506   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.366  -1.985   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.091  -2.849   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.875  -1.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.359  -2.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.367  -0.998   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₉NO₄

Average Mass

255.2290 Da

Monoisotopic Mass

255.05316 Da

IUPAC Name

6-hydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2(7),3,5,10,12(16)-hexaen-9-one

Traditional Name

6-hydroxy-13,15-dioxa-8-azatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(17),2(7),3,5,10,12(16)-hexaen-9-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1NC(=O)C1=CC3=C(OCO3)C=C21

InChI Identifier

InChI=1S/C14H9NO4/c16-10-3-1-2-7-8-4-11-12(19-6-18-11)5-9(8)14(17)15-13(7)10/h1-5,16H,6H2,(H,15,17)

InChI Key

SCDAZLFIUOBZAZ-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, 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
Galanthus trojanus	LOTUS Database	35616633
Lycoris sanguinea	LOTUS Database	35616633
Lycoris sanguinea Maxim	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridine- and phenanthridone-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds based on the phenanthridine or the phenanthridone skeleton. Phenanthridone-type alkaloids have the highest oxygenated C ring in all Amaryllidaceae alkaloids, and they always show an amide group in ring B. On the contrary, alkaloids of the phenanthridine type often show completely aromatic ring system, occasionally with a methylation quaternary nitrogen atom.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids

Direct Parent

Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Phenanthridone-type amaryllidaceae alkaloid
Benzoquinoline
Phenanthridine
Dihydroquinolone
Isoquinolone
8-hydroxyquinoline
Dihydroquinoline
Isoquinoline
Quinoline
Benzodioxole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Lactam
Azacycle
Acetal
Oxacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen 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	1.84	ALOGPS
logP	2.06	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.42 m³·mol⁻¹	ChemAxon
Polarizability	25.14 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

12305242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Arolycoricidine (NP0066737)

MOL for NP0066737 (Arolycoricidine)

3D MOL for NP0066737 (Arolycoricidine)

3D SDF for NP0066737 (Arolycoricidine)

3D-SDF for NP0066737 (Arolycoricidine)

PDB for NP0066737 (Arolycoricidine)

3D PDB for NP0066737 (Arolycoricidine)

SMILES for NP0066737 (Arolycoricidine)

INCHI for NP0066737 (Arolycoricidine)

Structure for NP0066737 (Arolycoricidine)

3D Structure for NP0066737 (Arolycoricidine)