NP-MRD: Showing NP-Card for 4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one (NP0294982)

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Record Information

Version

2.0

Created at

2022-09-10 03:45:40 UTC

Updated at

2022-09-10 03:45:41 UTC

NP-MRD ID

NP0294982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one

Description

AC1NLDYA belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety. 4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one is found in Colchicum kesselringii. AC1NLDYA is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161513502D          

 24 28  0  0  0  0            999 V2000
    6.1531    0.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3444    0.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    0.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2962   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957   -0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5035   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274   -1.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481   -0.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.5583    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0931   -2.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -0.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7471    0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    0.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7465    1.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    1.8748    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3416    0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    0.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411   -0.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  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
 13 15  1  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 24  1  0  0  0  0
 17 24  1  0  0  0  0
M  CHG  2  13   1  20  -1
M  END


  Mrv1533004161513502D          

 24 28  0  0  0  0            999 V2000
    6.1531    0.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3444    0.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    0.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2962   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957   -0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5035   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3274   -1.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2481   -0.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -1.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.5583    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0931   -2.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -0.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7471    0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    0.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7465    1.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    1.8748    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3416    0.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    0.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411   -0.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  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
 13 15  1  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 24  1  0  0  0  0
 17 24  1  0  0  0  0
M  CHG  2  13   1  20  -1
M  END
> <DATABASE_ID>
NP0294982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12CC3(CCC1O)CCC1=[N+](C)CCC4=CC([O-])=C(O2)C3=C14

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-20-8-5-11-9-13(21)17-16-15(11)12(20)3-6-18(16)7-4-14(22)19(10-18,23-2)24-17/h9,14,22H,3-8,10H2,1-2H3

> <INCHI_KEY>
YAPXMAINSYHBRI-UHFFFAOYSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.396

> <EXACT_MASS>
329.162708225

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.49820612653147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7,9,13,17-tetraen-13-ium-8-olate

> <ALOGPS_LOGP>
-1.48

> <JCHEM_LOGP>
-1.6816098361384129

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.234774135194417

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.331801467747457

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5710432383590076

> <JCHEM_POLAR_SURFACE_AREA>
64.76

> <JCHEM_REFRACTIVITY>
111.81919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7,9,13,17-tetraen-13-ium-8-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      11.486   1.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.976   1.378   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.957   0.224   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.020  -0.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.085  -1.834   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.406  -2.880   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.944  -2.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.219  -0.815   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.663  -0.280   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.499  -3.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.014  -3.683   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.958  -2.542   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.454  -2.909   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0       2.040  -4.392   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.358  -1.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.770  -0.327   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.261   0.087   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.648   1.591   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.127   2.008   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.509   3.500   0.000  0.00  0.00           O-1
HETATM   21  C   UNK     0       6.238   0.917   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.774   1.342   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.891  -0.666   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.370  -1.033   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   22                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   10   23                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21    3                                                       
CONECT   23   21    5   24                                                  
CONECT   24   23   12   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₄

Average Mass

329.3960 Da

Monoisotopic Mass

329.16271 Da

IUPAC Name

4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7,9,13,17-tetraen-13-ium-8-olate

Traditional Name

4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7,9,13,17-tetraen-13-ium-8-olate

CAS Registry Number

Not Available

SMILES

COC12CC3(CCC1O)CCC1=[N+](C)CCC4=CC([O-])=C(O2)C3=C14

InChI Identifier

InChI=1S/C19H23NO4/c1-20-8-5-11-9-13(21)17-16-15(11)12(20)3-6-18(16)7-4-14(22)19(10-18,23-2)24-17/h9,14,22H,3-8,10H2,1-2H3

InChI Key

YAPXMAINSYHBRI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Colchicum kesselringii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinolones and derivatives

Direct Parent

Isoquinolones and derivatives

Alternative Parents

Substituents

Isoquinolone
Tetrahydropyridine
Ketal
Cyclic alcohol
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Acetal
Enamine
Azacycle
Oxacycle
Amine
Organopnictogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-1.5	ALOGPS
logP	-1.7	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	111.82 m³·mol⁻¹	ChemAxon
Polarizability	35.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

4979409

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one (NP0294982)

MOL for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

3D MOL for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

3D SDF for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

3D-SDF for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

PDB for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

3D PDB for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

SMILES for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

INCHI for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

Structure for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)

3D Structure for NP0294982 (4-hydroxy-5-methoxy-13-methyl-6-oxa-13-azapentacyclo[8.6.2.1¹,⁵.0⁷,¹⁷.0¹⁴,¹⁸]nonadeca-7(17),9,14(18)-trien-8-one)