NP-MRD: Showing NP-Card for (+)-8-O-Demethylhomolycorine (NP0066733)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 10:58:56 UTC

Updated at

2022-04-28 10:58:56 UTC

NP-MRD ID

NP0066733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-8-O-Demethylhomolycorine

Description

9-O-Demethylhomolycorine belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. (+)-8-O-Demethylhomolycorine is found in Crinum defixum, Crinum defixum Ker-Gawl, Galanthus caucasicus , Galanthus elewesii, Galanthus elwesii, Leucojum vernum, Lycoris radiata, Lycoris radiata Herb. , Narcissus bujei, Narcissus poeticus, Narcissus primigenius, Narcissus tazetta L. , Pancratinum maritimum and Pancratium maritimum. Based on a literature review very few articles have been published on 9-O-Demethylhomolycorine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282212582D          

 22 25  0  0  1  0            999 V2000
    4.8217    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892    0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.3465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2815   -1.1707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9764   -1.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7089   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -1.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489   -1.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241    0.0981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4896    0.9121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    0.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690    1.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2492    1.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593    2.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644    2.5054    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
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)O[C@@H]3CC=C4CCN(C)[C@H]4[C@@H]3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO4/c1-18-6-5-9-3-4-13-15(16(9)18)10-8-14(21-2)12(19)7-11(10)17(20)22-13/h3,7-8,13,15-16,19H,4-6H2,1-2H3/t13-,15-,16-/m1/s1

> <INCHI_KEY>
VLDOBKJPRUQEEC-FVQBIDKESA-N

> <FORMULA>
C17H19NO4

> <MOLECULAR_WEIGHT>
301.342

> <EXACT_MASS>
301.131408096

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.517684472041896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,17S)-5-hydroxy-4-methoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.2409792486286737

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.130396655442397

> <JCHEM_PKA_STRONGEST_BASIC>
7.962453018272319

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
82.86070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,17S)-5-hydroxy-4-methoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.001   2.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.298   1.478   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.228  -0.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.860  -0.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.563   0.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.633   1.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.196  -0.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.125  -2.185   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.423  -3.015   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.790  -2.307   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.087  -3.137   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.758  -2.894   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.461  -2.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.531  -0.525   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.898   0.183   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.647   1.703   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.125   1.933   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.435   0.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.729   2.799   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.665   2.187   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.071   3.847   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.774   4.677   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   16                                                            
CONECT   20    2                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉NO₄

Average Mass

301.3420 Da

Monoisotopic Mass

301.13141 Da

IUPAC Name

(1S,10R,17S)-5-hydroxy-4-methoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one

Traditional Name

(1S,10R,17S)-5-hydroxy-4-methoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,12-tetraen-8-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)O[C@@H]3CC=C4CCN(C)[C@H]4[C@@H]3C2=C1

InChI Identifier

InChI=1S/C17H19NO4/c1-18-6-5-9-3-4-13-15(16(9)18)10-8-14(21-2)12(19)7-11(10)17(20)22-13/h3,7-8,13,15-16,19H,4-6H2,1-2H3/t13-,15-,16-/m1/s1

InChI Key

VLDOBKJPRUQEEC-FVQBIDKESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Crinum defixum	LOTUS Database	35616633
Crinum defixum Ker-Gawl	Plant	KNApSAcK
Galanthus caucasicus	Plant	KNApSAcK
Galanthus elewesii	Plant	KNApSAcK
Galanthus elwesii	LOTUS Database	35616633
Leucojum vernum	LOTUS Database	35616633
Lycoris radiata	LOTUS Database	35616633
Lycoris radiata Herb.	Plant	KNApSAcK
Narcissus bujei	Plant	KNApSAcK
Narcissus poeticus	LOTUS Database	35616633
Narcissus primigenius	Plant	KNApSAcK
Narcissus tazetta	Plant	KNApSAcK
Pancratinum maritimum	-	KNApSAcK
Pancratium maritimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
Benzopyran
Isochromane
2-benzopyran
Indole or derivatives
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:31154 )

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	1.73	ALOGPS
logP	1.24	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.86 m³·mol⁻¹	ChemAxon
Polarizability	31.52 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

C00024361

Chemspider ID

344597

KEGG Compound ID

C12190

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

388787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-8-O-Demethylhomolycorine (NP0066733)

MOL for NP0066733 ((+)-8-O-Demethylhomolycorine)

3D MOL for NP0066733 ((+)-8-O-Demethylhomolycorine)

3D SDF for NP0066733 ((+)-8-O-Demethylhomolycorine)

3D-SDF for NP0066733 ((+)-8-O-Demethylhomolycorine)

PDB for NP0066733 ((+)-8-O-Demethylhomolycorine)

3D PDB for NP0066733 ((+)-8-O-Demethylhomolycorine)

SMILES for NP0066733 ((+)-8-O-Demethylhomolycorine)

INCHI for NP0066733 ((+)-8-O-Demethylhomolycorine)

Structure for NP0066733 ((+)-8-O-Demethylhomolycorine)

3D Structure for NP0066733 ((+)-8-O-Demethylhomolycorine)