NP-MRD: Showing NP-Card for 4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one (NP0272771)

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Record Information

Version

2.0

Created at

2022-09-08 19:32:49 UTC

Updated at

2022-09-08 19:32:49 UTC

NP-MRD ID

NP0272771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one

Description

4,6-Dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one 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. 4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one is found in Tanacetum argenteum. Based on a literature review very few articles have been published on 4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082221322D          

 20 22  0  0  0  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -1.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1523    1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  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  1  0  0  0  0
 17 20  1  0  0  0  0
  6 20  1  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CC(O)C2C(OC(=O)C2=C)C2C1CC=C2CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-7-11-10(17)5-15(2,19)9-4-3-8(6-16)12(9)13(11)20-14(7)18/h3,9-13,16-17,19H,1,4-6H2,2H3

> <INCHI_KEY>
MAOPOOUQNGEQGA-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.81795375150151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_LOGP>
-0.6489668296666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.881465731421187

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.310785925661722

> <JCHEM_PKA_STRONGEST_BASIC>
-2.733686201945856

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
72.2503

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.665  -4.108   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343  -4.649   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.146  -3.148   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.018   3.474   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    6   14                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1(O)CC(O)C2C(OC(=O)C2=C)C2C1CC=C2CO

InChI Identifier

InChI=1S/C15H20O5/c1-7-11-10(17)5-15(2,19)9-4-3-8(6-16)12(9)13(11)20-14(7)18/h3,9-13,16-17,19H,1,4-6H2,2H3

InChI Key

MAOPOOUQNGEQGA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tanacetum argenteum	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
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
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	-0.65	ChemAxon
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.25 m³·mol⁻¹	ChemAxon
Polarizability	28.82 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

85289028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one (NP0272771)

MOL for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

3D MOL for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

3D SDF for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

3D-SDF for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

PDB for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

3D PDB for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

SMILES for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

INCHI for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

Structure for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)

3D Structure for NP0272771 (4,6-dihydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-2-one)