NP-MRD: Showing NP-Card for 5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol (NP0283075)

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Record Information

Version

2.0

Created at

2022-09-09 10:10:50 UTC

Updated at

2022-09-09 10:10:50 UTC

NP-MRD ID

NP0283075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol

Description

5,7-Dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]Octadeca-2,4(8),9,14-tetraene-16,17-diol belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol is found in Lycoris incarnata. 5,7-Dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]Octadeca-2,4(8),9,14-tetraene-16,17-diol is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506332D          

 20 24  0  0  0  0            999 V2000
   -1.6801    1.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    1.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5352    0.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0524   -0.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -1.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3797   -0.8104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063    0.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765    1.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    1.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    0.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413    0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409    1.1102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522    0.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -0.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4941   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0955   -0.4002    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  2  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
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  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
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 20  1  0  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C=C2CCN3C2C(C1O)C1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO4/c17-10-3-7-1-2-16-9-5-12-11(19-6-20-12)4-8(9)13(14(7)16)15(10)18/h3-5,10,13-15,17-18H,1-2,6H2

> <INCHI_KEY>
KQAOMBGKIWRWNA-UHFFFAOYSA-N

> <FORMULA>
C15H15NO4

> <MOLECULAR_WEIGHT>
273.288

> <EXACT_MASS>
273.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.013658308006065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.32898090200000013

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.906970360066502

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.466989662639936

> <JCHEM_PKA_STRONGEST_BASIC>
1.065651055675872

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
72.0675

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -3.136   3.267   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.235   2.019   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.866   0.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.965  -0.635   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.453  -2.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.078  -2.918   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.709  -1.513   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.432  -0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.198   0.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.703   2.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.072   3.580   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.729   0.760   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.877   1.787   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.340   1.307   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.676   2.072   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.818   1.038   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.187  -0.367   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.656  -0.201   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.508  -1.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.045  -0.747   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₅NO₄

Average Mass

273.2880 Da

Monoisotopic Mass

273.10011 Da

IUPAC Name

5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol

Traditional Name

5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol

CAS Registry Number

Not Available

SMILES

OC1C=C2CCN3C2C(C1O)C1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C15H15NO4/c17-10-3-7-1-2-16-9-5-12-11(19-6-20-12)4-8(9)13(14(7)16)15(10)18/h3-5,10,13-15,17-18H,1-2,6H2

InChI Key

KQAOMBGKIWRWNA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lycoris incarnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Benzodioxole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
Benzenoid
Pyrrolidine
Tertiary amine
1,2-diol
Secondary alcohol
Azacycle
Oxacycle
Acetal
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Hydrocarbon derivative
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	0.45	ALOGPS
logP	0.33	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	1.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.07 m³·mol⁻¹	ChemAxon
Polarizability	28.01 Å³	ChemAxon
Number of Rings	5	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

LOTUS database [Link]

Showing NP-Card for 5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol (NP0283075)

MOL for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

3D MOL for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

3D SDF for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

3D-SDF for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

PDB for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

3D PDB for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

SMILES for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

INCHI for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

Structure for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)

3D Structure for NP0283075 (5,7-dioxa-11-azapentacyclo[9.6.1.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]octadeca-2,4(8),9,14-tetraene-16,17-diol)