NP-MRD: Showing NP-Card for ossian (NP0306580)

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Record Information

Version

2.0

Created at

2022-09-10 23:08:36 UTC

Updated at

2022-09-10 23:08:37 UTC

NP-MRD ID

NP0306580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ossian

Description

ossian is found in Apis cerana. ossian was first documented in 1976 (PMID: 1245092).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.9842   -2.7061    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -2.0649   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474   -0.6791   -0.6292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.2862   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205    1.6273   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    2.6494   -1.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9792    2.3357   -1.4491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286    3.9994   -0.9885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636    2.0079   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    3.2323   -0.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.0316   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    1.4678    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    0.5671    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422   -0.7726    0.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0786   -1.2230    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0760   -0.3251   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -1.4598    0.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5710   -0.5263    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639    0.7292    0.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678   -3.7620    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277   -2.2408    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -2.6724    0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340   -2.6335   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3029   -2.1563   -1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472   -0.0469   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670    4.3984   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    2.5267    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977   -2.2873   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509   -0.6236   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876   -0.6794    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 14 15  1  0
 15 16  2  0
 16  3  1  0
 16 11  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  4 25  1  0
  8 26  1  0
 12 27  1  0
 18 29  1  0
 18 30  1  0
 15 28  1  0
M  END


  Mrv0541 05041409062D          

 19 21  0  0  0  0            999 V2000
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18  6  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

> <INCHI_KEY>
KYGZCKSPAKDVKC-UHFFFAOYSA-N

> <FORMULA>
C13H11NO5

> <MOLECULAR_WEIGHT>
261.2301

> <EXACT_MASS>
261.063722467

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.521229530139497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
1.3531468610000004

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.579866110343406

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282722549478013

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
65.84330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ossian

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    7   10                                                       
CONECT    4    9   11                                                       
CONECT    5    8   14                                                       
CONECT    6   18   19                                                       
CONECT    7    3    9   12                                                  
CONECT    8    5   12   13                                                  
CONECT    9    4    7   14                                                  
CONECT   10    3   11   18                                                  
CONECT   11    4   10   19                                                  
CONECT   12    7    8   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14    2    5    9                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18    6   10                                                       
CONECT   19    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid	ChEBI
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid	ChEBI
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid	ChEBI
Acide oxolinique	ChEBI
Acido oxolinico	ChEBI
Acidum oxolinicum	ChEBI
OA	ChEBI
Aqualinic	Kegg
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylate	Generator
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylate	Generator
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylate	Generator
Oxolinate	Generator
Acid, oxolinic	MeSH
Gramurin	MeSH
Oxolinate, sodium	MeSH
Sodium oxolinate	MeSH

Chemical Formula

C₁₃H₁₁NO₅

Average Mass

261.2301 Da

Monoisotopic Mass

261.06372 Da

IUPAC Name

5-ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

Traditional Name

ossian

CAS Registry Number

Not Available

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

InChI Key

KYGZCKSPAKDVKC-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-3-carboxylic acid
Dihydroquinolone
Dihydroquinoline
Benzodioxole
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:138856 )
oxacycle (CHEBI:138856 )
quinolone antibiotic (CHEBI:138856 )
quinolinemonocarboxylic acid (CHEBI:138856 )
aromatic carboxylic acid (CHEBI:138856 )
Quinone fungicides (C11342 )

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	0.86	ALOGPS
logP	1.35	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	5.58	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.84 m³·mol⁻¹	ChemAxon
Polarizability	25.52 Å³	ChemAxon
Number of Rings	3	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

DB13627

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11342

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxolinic_acid

METLIN ID

Not Available

PubChem Compound

4628

PDB ID

Not Available

ChEBI ID

138856

Good Scents ID

Not Available

References

General References

Mannisto PT: Pharmacokinetics of nalidixinic acid and oxolinic acid in healthy women. Clin Pharmacol Ther. 1976 Jan;19(1):37-46. doi: 10.1002/cpt197619137. [PubMed:1245092 ]
Caipang CM, Lazado CC, Brinchmann MF, Berg I, Kiron V: In vivo modulation of immune response and antioxidant defense in Atlantic cod, Gadus morhua following oral administration of oxolinic acid and florfenicol. Comp Biochem Physiol C Toxicol Pharmacol. 2009 Nov;150(4):459-64. doi: 10.1016/j.cbpc.2009.07.001. Epub 2009 Jul 19. [PubMed:19596082 ]
Kwon HR, Choi GJ, Choi YH, Jang KS, Sung ND, Kang MS, Moon Y, Lee SK, Kim JC: Suppression of pine wilt disease by an antibacterial agent, oxolinic acid. Pest Manag Sci. 2010 Jun;66(6):634-9. doi: 10.1002/ps.1920. [PubMed:20151406 ]
Touraki M, Niopas I, Karagiannis V: Treatment of vibriosis in European sea bass larvae, Dicentrarchus labrax L., with oxolinic acid administered by bath or through medicated nauplii of Artemia franciscana (Kellogg): efficacy and residual kinetics. J Fish Dis. 2012 Jul;35(7):513-22. doi: 10.1111/j.1365-2761.2012.01387.x. Epub 2012 Jun 6. [PubMed:22670590 ]
LOTUS database [Link]

Showing NP-Card for ossian (NP0306580)

MOL for NP0306580 (ossian)

3D MOL for NP0306580 (ossian)

3D SDF for NP0306580 (ossian)

3D-SDF for NP0306580 (ossian)

PDB for NP0306580 (ossian)

3D PDB for NP0306580 (ossian)

SMILES for NP0306580 (ossian)

INCHI for NP0306580 (ossian)

Structure for NP0306580 (ossian)

3D Structure for NP0306580 (ossian)