NP-MRD: Showing NP-Card for 4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid (NP0204198)

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Record Information

Version

2.0

Created at

2022-09-04 23:49:57 UTC

Updated at

2022-09-04 23:49:58 UTC

NP-MRD ID

NP0204198

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid

Description

4-Hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]Undeca-5,9-diene-10-carboximidic acid belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. 4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid is found in Streptomyces albogriseolus. 4-Hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]Undeca-5,9-diene-10-carboximidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151514172D          

 16 18  0  0  0  0            999 V2000
    3.2075    1.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822    2.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    0.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9493   -0.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992    1.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227    1.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584   -0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453   -0.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0523    0.2645    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CC2C3C=CC2(O)C(=O)OC3O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)

> <INCHI_KEY>
OXSZHYWOGQJUST-UHFFFAOYSA-N

> <FORMULA>
C10H9NO5

> <MOLECULAR_WEIGHT>
223.184

> <EXACT_MASS>
223.048072394

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.625758527300263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboxamide

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-1.3120722376666665

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.004341110566195

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.692498526827766

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0967647246048848

> <JCHEM_POLAR_SURFACE_AREA>
98.85000000000002

> <JCHEM_REFRACTIVITY>
52.46650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  N   UNK     0       5.987   2.920   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.494   3.297   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.073   4.778   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.421   2.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.953   2.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.144   1.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.772  -0.525   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.340  -0.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.224   0.762   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.185   1.330   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.425   2.851   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.031   1.392   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.896   2.666   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.589  -0.162   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.258  -0.902   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.831   0.494   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0,]undeca-5,9-diene-10-carboximidate	Generator

Chemical Formula

C₁₀H₉NO₅

Average Mass

223.1840 Da

Monoisotopic Mass

223.04807 Da

IUPAC Name

4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboxamide

Traditional Name

4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CC2C3C=CC2(O)C(=O)OC3O1

InChI Identifier

InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)

InChI Key

OXSZHYWOGQJUST-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
Streptomyces albogriseolus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Delta_valerolactone
Oxane
Tertiary alcohol
Carboxamide group
Carboxylic acid ester
Primary carboxylic acid amide
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	-0.95	ALOGPS
logP	-1.3	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.47 m³·mol⁻¹	ChemAxon
Polarizability	19.63 Å³	ChemAxon
Number of Rings	3	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

434786

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-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid (NP0204198)

MOL for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D MOL for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D SDF for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D-SDF for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

PDB for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D PDB for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

SMILES for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

INCHI for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

Structure for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D Structure for NP0204198 (4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)