NP-MRD: Showing NP-Card for 4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid (NP0193074)

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Record Information

Version

2.0

Created at

2022-09-04 10:25:40 UTC

Updated at

2022-09-04 10:25:40 UTC

NP-MRD ID

NP0193074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid

Description

Porric acid C, also known as porrate C, belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. Porric acid C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, porric acid C has been detected, but not quantified in, onion-family vegetables. 4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid is found in Allium obliquum. This could make porric acid C a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217122D          

 19 21  0  0  0  0            999 V2000
   -2.1407    0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -0.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    1.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272    1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -1.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435   -1.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(OC3=C2C=C(O)C=C3C(O)=O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(14(17)18)13(9)19-11/h2-5,15-16H,1H3,(H,17,18)

> <INCHI_KEY>
XERKTCDLFDGUHP-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.736093690178286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2(7),3,5,9,11-hexaene-6-carboxylic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.7151207509999997

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.841174216442061

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1468285255381065

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5937550973124446

> <JCHEM_POLAR_SURFACE_AREA>
90.90000000000002

> <JCHEM_REFRACTIVITY>
67.486

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2(7),3,5,9,11-hexaene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.996   1.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.996  -0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.664  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.335  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.335   1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.664   1.924   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.003  -1.156   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.335  -0.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.335   1.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.996  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.996   1.156   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.924   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.331   1.926   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.664   3.464   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.331  -1.154   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -2.694   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.332  -3.464   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -3.464   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5   15                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    5    8   13                                                  
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13    9   12                                                       
CONECT   14   12                                                            
CONECT   15    6                                                            
CONECT   16    2                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Porrate C	Generator
4,11-Dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylate	Generator

Chemical Formula

C₁₄H₁₀O₅

Average Mass

258.2262 Da

Monoisotopic Mass

258.05282 Da

IUPAC Name

4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2(7),3,5,9,11-hexaene-6-carboxylic acid

Traditional Name

4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2(7),3,5,9,11-hexaene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C2C(OC3=C2C=C(O)C=C3C(O)=O)=CC(O)=C1

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(14(17)18)13(9)19-11/h2-5,15-16H,1H3,(H,17,18)

InChI Key

XERKTCDLFDGUHP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium obliquum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Dibenzofurans

Direct Parent

Dibenzofurans

Alternative Parents

Substituents

Dibenzofuran
Hydroxybenzoic acid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.39	ALOGPS
logP	2.72	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.49 m³·mol⁻¹	ChemAxon
Polarizability	25.74 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

HMDB0031898

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008584

KNApSAcK ID

Not Available

Chemspider ID

420252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

478956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid (NP0193074)

MOL for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

3D MOL for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

3D SDF for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

3D-SDF for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

PDB for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

3D PDB for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

SMILES for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

INCHI for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

Structure for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)

3D Structure for NP0193074 (4,11-dihydroxy-13-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene-6-carboxylic acid)