NP-MRD: Showing NP-Card for 6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0330145)

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Record Information

Version

2.0

Created at

2022-09-12 15:12:54 UTC

Updated at

2022-09-12 15:12:54 UTC

NP-MRD ID

NP0330145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate

Description

6A-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate 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. 6A-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241508342D          

 24 26  0  0  0  0            999 V2000
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   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 C   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
    4.8016    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5823    0.7472    0.0000 O   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
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218   -1.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.2426    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 O   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
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    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  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(=C)C2(OO)C=CC(C)(O)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O7/c1-8-7-11(22-10(3)18)12-9(2)15(19)23-13(12)14-16(4,20)5-6-17(8,14)24-21/h5-6,11-14,20-21H,1-2,7H2,3-4H3

> <INCHI_KEY>
YQEIZFUUAYCBQU-UHFFFAOYSA-N

> <FORMULA>
C17H20O7

> <MOLECULAR_WEIGHT>
336.34

> <EXACT_MASS>
336.120902984

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.48753867525694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.6682684373333341

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.273585848993122

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.67473141217103

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1493614186022088

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
81.90249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.963   1.892   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.420   1.395   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.254  -3.044   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.325  -2.319   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12   17                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    9   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   18                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
6a-Hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,9H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₇

Average Mass

336.3400 Da

Monoisotopic Mass

336.12090 Da

IUPAC Name

6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(=C)C2(OO)C=CC(C)(O)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C17H20O7/c1-8-7-11(22-10(3)18)12-9(2)15(19)23-13(12)14-16(4,20)5-6-17(8,14)24-21/h5-6,11-14,20-21H,1-2,7H2,3-4H3

InChI Key

YQEIZFUUAYCBQU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Oxacycle
Organoheterocyclic compound
Peroxol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
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	0.77	ALOGPS
logP	0.67	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.9 m³·mol⁻¹	ChemAxon
Polarizability	32.49 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0330145)

MOL for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D MOL for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D SDF for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D-SDF for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

PDB for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D PDB for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

SMILES for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

INCHI for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

Structure for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D Structure for NP0330145 (6a-hydroperoxy-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl acetate)