NP-MRD: Showing NP-Card for (+)-Megacerotonic acid (NP0050429)

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Record Information

Version

2.0

Created at

2022-04-27 21:36:28 UTC

Updated at

2022-04-27 21:36:28 UTC

NP-MRD ID

NP0050429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Megacerotonic acid

Description

(2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. (+)-Megacerotonic acid is found in Megaceros flagellaris, Notothylas temperata and Phaeoceros laevis. Based on a literature review very few articles have been published on (2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223362D          

 25 27  0  0  1  0            999 V2000
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  8 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  3 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1OC(=O)\C(=C\C2=CC=C(O)C=C2)[C@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O7/c19-11-4-1-9(2-5-11)7-12-15(16(17(22)23)25-18(12)24)10-3-6-13(20)14(21)8-10/h1-8,15-16,19-21H,(H,22,23)/b12-7+/t15-,16-/m1/s1

> <INCHI_KEY>
ARPWMKRUUOTSGU-PWEFJHHISA-N

> <FORMULA>
C18H14O7

> <MOLECULAR_WEIGHT>
342.303

> <EXACT_MASS>
342.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.077562039672024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.7153516856666666

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.011428665481363

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1639241308377013

> <JCHEM_PKA_STRONGEST_BASIC>
-5.957138752491905

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
86.7937

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.572  -4.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.127  -6.041   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.657  -3.885   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.833  -1.348   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.134   2.195   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.802   3.735   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    3                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4E)-3-(3,4-Dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylate	Generator

Chemical Formula

C₁₈H₁₄O₇

Average Mass

342.3030 Da

Monoisotopic Mass

342.07395 Da

IUPAC Name

(2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

Traditional Name

(2R,3R,4E)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H]1OC(=O)\C(=C\C2=CC=C(O)C=C2)[C@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C18H14O7/c19-11-4-1-9(2-5-11)7-12-15(16(17(22)23)25-18(12)24)10-3-6-13(20)14(21)8-10/h1-8,15-16,19-21H,(H,22,23)/b12-7+/t15-,16-/m1/s1

InChI Key

ARPWMKRUUOTSGU-PWEFJHHISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Megaceros flagellaris	Plant	KNApSAcK
Notothylas temperata	Plant	KNApSAcK
Phaeoceros laevis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.16	ALOGPS
logP	2.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.79 m³·mol⁻¹	ChemAxon
Polarizability	32.08 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9306784

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11131665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Megacerotonic acid (NP0050429)

MOL for NP0050429 ((+)-Megacerotonic acid)

3D MOL for NP0050429 ((+)-Megacerotonic acid)

3D SDF for NP0050429 ((+)-Megacerotonic acid)

3D-SDF for NP0050429 ((+)-Megacerotonic acid)

PDB for NP0050429 ((+)-Megacerotonic acid)

3D PDB for NP0050429 ((+)-Megacerotonic acid)

SMILES for NP0050429 ((+)-Megacerotonic acid)

INCHI for NP0050429 ((+)-Megacerotonic acid)

Structure for NP0050429 ((+)-Megacerotonic acid)

3D Structure for NP0050429 ((+)-Megacerotonic acid)