NP-MRD: Showing NP-Card for 4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate (NP0191350)

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Record Information

Version

2.0

Created at

2022-09-04 08:16:50 UTC

Updated at

2022-09-04 08:16:50 UTC

NP-MRD ID

NP0191350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate

Description

4-Hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate is found in Centaurea scoparia. Based on a literature review very few articles have been published on 4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042210162D          

 26 28  0  0  0  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -0.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -2.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  4  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  END


  Mrv1652309042210162D          

 26 28  0  0  0  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -0.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -1.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -2.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  4  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=CCO)C(=O)OC1CC2C(C3OC(=O)C(=C)C3C(O)CC2=C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-9(5-6-21)19(23)25-15-8-13-10(2)7-14(22)17-12(4)20(24)26-18(17)16(13)11(15)3/h5,13-18,21-22H,2-4,6-8H2,1H3

> <INCHI_KEY>
WWSYEWWKDKWTKC-UHFFFAOYSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.81580595566746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.4314484283333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.621039670337627

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.655712046535282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.552215751920948

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
94.66209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.333  -1.598   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.103  -0.075   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.871  -2.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.642  -4.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.305  -1.995   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.509  -2.956   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.279  -4.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   16   26                                                       
CONECT   26   25    2   13                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

4-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate

Traditional Name

4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=CCO)C(=O)OC1CC2C(C3OC(=O)C(=C)C3C(O)CC2=C)C1=C

InChI Identifier

InChI=1S/C20H24O6/c1-9(5-6-21)19(23)25-15-8-13-10(2)7-14(22)17-12(4)20(24)26-18(17)16(13)11(15)3/h5,13-18,21-22H,2-4,6-8H2,1H3

InChI Key

WWSYEWWKDKWTKC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea scoparia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.43	ChemAxon
pKa (Strongest Acidic)	14.66	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.66 m³·mol⁻¹	ChemAxon
Polarizability	37.82 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

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

163049985

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-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate (NP0191350)

MOL for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

3D MOL for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

3D SDF for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

3D-SDF for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

PDB for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

3D PDB for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

SMILES for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

INCHI for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

Structure for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)

3D Structure for NP0191350 (4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl 4-hydroxy-2-methylbut-2-enoate)