NP-MRD: Showing NP-Card for (3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one (NP0245440)

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Record Information

Version

2.0

Created at

2022-09-07 06:31:20 UTC

Updated at

2022-09-07 06:31:20 UTC

NP-MRD ID

NP0245440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one

Description

(3AS)-3a,4,5,6,6abeta,7,8,9balpha-Octahydro-6,9-dimethyl-3-methylene-5beta,6beta,8beta-trihydroxyazuleno[4,5-b]furan-2(3H)-one 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. (3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one is found in Ajania achilleoides. Based on a literature review very few articles have been published on (3aS)-3a,4,5,6,6abeta,7,8,9balpha-Octahydro-6,9-dimethyl-3-methylene-5beta,6beta,8beta-trihydroxyazuleno[4,5-b]furan-2(3H)-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072208312D          

 20 22  0  0  1  0            999 V2000
   -0.1007   -1.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -1.0076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996   -1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.5386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5944   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -1.6526    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0304   -2.4569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8554   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -3.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -2.8149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2871   -3.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -1.6526    0.0000 C   0  0  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  2  1  1  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@H]3OC(=O)C(=C)[C@@H]3C[C@@H](O)[C@@](C)(O)[C@@H]2C[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-6-8-4-11(17)15(3,19)9-5-10(16)7(2)12(9)13(8)20-14(6)18/h8-11,13,16-17,19H,1,4-5H2,2-3H3/t8-,9+,10+,11+,13-,15-/m0/s1

> <INCHI_KEY>
DPYNIKWDGAULLI-JNMKMZOPSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.038350146769517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5R,6S,6aR,8R,9bS)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_LOGP>
-0.22165863566666644

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.467449574185867

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.51111126601382

> <JCHEM_PKA_STRONGEST_BASIC>
-2.985413707531719

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.4819

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5R,6S,6aR,8R,9bS)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.188  -3.392   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.097  -2.544   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.166  -1.005   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.038  -0.045   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.651  -0.596   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.499  -1.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.039  -1.881   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.888  -0.596   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.346   0.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.372  -1.005   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.576  -0.045   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.441  -2.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.999  -3.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.657  -4.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.197  -4.586   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.999  -6.088   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.269  -5.254   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.269  -6.794   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.882  -4.586   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.539  -3.085   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(3AS)-3a,4,5,6,6abeta,7,8,9balpha-octahydro-6,9-dimethyl-3-methylene-5b,6b,8b-trihydroxyazuleno[4,5-b]furan-2(3H)-one	Generator
(3AS)-3a,4,5,6,6abeta,7,8,9balpha-octahydro-6,9-dimethyl-3-methylene-5β,6β,8β-trihydroxyazuleno[4,5-b]furan-2(3H)-one	Generator

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

(3aS,5R,6S,6aR,8R,9bS)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

(3aS,5R,6S,6aR,8R,9bS)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1=C2[C@H]3OC(=O)C(=C)[C@@H]3C[C@@H](O)[C@@](C)(O)[C@@H]2C[C@H]1O

InChI Identifier

InChI=1S/C15H20O5/c1-6-8-4-11(17)15(3,19)9-5-10(16)7(2)12(9)13(8)20-14(6)18/h8-11,13,16-17,19H,1,4-5H2,2-3H3/t8-,9+,10+,11+,13-,15-/m0/s1

InChI Key

DPYNIKWDGAULLI-JNMKMZOPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajania achilleoides	LOTUS Database	35616633

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

Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	-0.22	ChemAxon
pKa (Strongest Acidic)	13.51	ChemAxon
pKa (Strongest Basic)	-3	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	0	ChemAxon
Refractivity	71.48 m³·mol⁻¹	ChemAxon
Polarizability	29.04 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

102437443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one (NP0245440)

MOL for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

3D MOL for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

3D SDF for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

3D-SDF for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

PDB for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

3D PDB for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

SMILES for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

INCHI for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

Structure for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)

3D Structure for NP0245440 ((3as,5r,6s,6ar,8r,9bs)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-3ah,4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-2-one)