NP-MRD: Showing NP-Card for 7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate (NP0226259)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 05:14:22 UTC

Updated at

2022-09-06 05:14:23 UTC

NP-MRD ID

NP0226259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate

Description

7-Hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]Undec-8-en-6-yl but-2-enoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate is found in Xylaria multiplex. 7-Hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]Undec-8-en-6-yl but-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121517012D          

 20 21  0  0  0  0            999 V2000
    6.6525   -0.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001    0.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7699    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4175    2.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8874    2.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5953    2.1869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4779    0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604   -0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636    0.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    1.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6589    1.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    2.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9509    2.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3033    1.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246    1.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC(=O)OC1CC(C)OC(=O)C2OC2C=CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O6/c1-3-4-12(16)19-11-7-8(2)18-14(17)13-10(20-13)6-5-9(11)15/h3-6,8-11,13,15H,7H2,1-2H3

> <INCHI_KEY>
MKNCRDRXKFGNDG-UHFFFAOYSA-N

> <FORMULA>
C14H18O6

> <MOLECULAR_WEIGHT>
282.292

> <EXACT_MASS>
282.1103383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.028496160802526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.2375675686666667

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.79028368521137

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3279299160885465

> <JCHEM_POLAR_SURFACE_AREA>
85.36

> <JCHEM_REFRACTIVITY>
70.34420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      12.418  -0.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.760   1.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.637   2.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.979   3.956   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.856   5.222   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      10.445   4.082   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.568   2.816   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.225   1.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.348   0.158   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.006  -1.234   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.814   0.285   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.156   1.677   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.279   0.411   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.621   1.804   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.086   1.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.963   3.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.840   4.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.375   4.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.033   2.943   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.579   2.434   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoic acid	Generator

Chemical Formula

C₁₄H₁₈O₆

Average Mass

282.2920 Da

Monoisotopic Mass

282.11034 Da

IUPAC Name

7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate

Traditional Name

7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate

CAS Registry Number

Not Available

SMILES

CC=CC(=O)OC1CC(C)OC(=O)C2OC2C=CC1O

InChI Identifier

InChI=1S/C14H18O6/c1-3-4-12(16)19-11-7-8(2)18-14(17)13-10(20-13)6-5-9(11)15/h3-6,8-11,13,15H,7H2,1-2H3

InChI Key

MKNCRDRXKFGNDG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylaria multiplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	0.84	ALOGPS
logP	1.24	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.79	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.34 m³·mol⁻¹	ChemAxon
Polarizability	28.03 Å³	ChemAxon
Number of Rings	2	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

73097538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate (NP0226259)

MOL for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

3D MOL for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

3D SDF for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

3D-SDF for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

PDB for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

3D PDB for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

SMILES for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

INCHI for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

Structure for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)

3D Structure for NP0226259 (7-hydroxy-4-methyl-2-oxo-3,11-dioxabicyclo[8.1.0]undec-8-en-6-yl but-2-enoate)