NP-MRD: Showing NP-Card for (3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0325922)

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Record Information

Version

2.0

Created at

2022-09-12 07:03:13 UTC

Updated at

2022-09-12 07:03:14 UTC

NP-MRD ID

NP0325922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate

Description

(3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review very few articles have been published on (3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122209032D          

 24 26  0  0  1  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  1  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  1  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  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  1  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
    6.3287   -0.8560    0.0000 O   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
    3.8305   -1.6349    0.0000 C   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  1  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  1  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  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  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  1  1  0  0  0
 24 22  1  1  0  0  0
  5 24  1  0  0  0  0
 18 24  1  0  0  0  0
M  END


  Mrv1652309122209032D          

 24 26  0  0  1  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  1  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  1  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  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  1  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
    6.3287   -0.8560    0.0000 O   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
    3.8305   -1.6349    0.0000 C   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  1  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  1  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  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  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  1  1  0  0  0
 24 22  1  1  0  0  0
  5 24  1  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@H](OC1=O)C1=C(C)[C@@H](C[C@H]1[C@](C)(O)C[C@@H]2OC(C)=O)OO

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O7/c1-7-11(24-21)5-10-13(7)15-14(8(2)16(19)23-15)12(22-9(3)18)6-17(10,4)20/h8,10-12,14-15,20-21H,5-6H2,1-4H3/t8-,10+,11+,12-,14-,15+,17+/m0/s1

> <INCHI_KEY>
RRKXQZYCHYEZHU-JCXGAQQHSA-N

> <FORMULA>
C17H24O7

> <MOLECULAR_WEIGHT>
340.372

> <EXACT_MASS>
340.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.4093538306283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_LOGP>
0.18409524866666688

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.627797961591103

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.71065211459558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9635707735944443

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
82.3458

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         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       7.803   3.882   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.001   2.381   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      11.813  -1.598   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+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   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   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
(3S,3AS,4S,6R,6ar,8R,9BS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,8H,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₇

Average Mass

340.3720 Da

Monoisotopic Mass

340.15220 Da

IUPAC Name

(3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

(3S,3aS,4S,6R,6aR,8R,9bS)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@H](OC1=O)C1=C(C)[C@@H](C[C@H]1[C@](C)(O)C[C@@H]2OC(C)=O)OO

InChI Identifier

InChI=1S/C17H24O7/c1-7-11(24-21)5-10-13(7)15-14(8(2)16(19)23-15)12(22-9(3)18)6-17(10,4)20/h8,10-12,14-15,20-21H,5-6H2,1-4H3/t8-,10+,11+,12-,14-,15+,17+/m0/s1

InChI Key

RRKXQZYCHYEZHU-JCXGAQQHSA-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 gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Oxacycle
Peroxol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
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	0.18	ChemAxon
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3	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	82.35 m³·mol⁻¹	ChemAxon
Polarizability	34.41 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

162998315

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate (NP0325922)

MOL for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D MOL for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D SDF for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D-SDF for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

PDB for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D PDB for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

SMILES for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

INCHI for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

Structure for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)

3D Structure for NP0325922 ((3s,3as,4s,6r,6ar,8r,9bs)-8-hydroperoxy-6-hydroxy-3,6,9-trimethyl-2-oxo-3h,3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-4-yl acetate)