NP-MRD: Showing NP-Card for 6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0283467)

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Record Information

Version

2.0

Created at

2022-09-09 10:44:09 UTC

Updated at

2022-09-09 10:44:09 UTC

NP-MRD ID

NP0283467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione

Description

6,9-Dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 6,9-Dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241505532D          

 28 31  0  0  0  0            999 V2000
    1.7100   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -0.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    1.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    2.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4305    2.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    3.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4305    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    0.8627    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
 11 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
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 18  1  0  0  0  0
  2 18  1  0  0  0  0
  6 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1533004241505532D          

 28 31  0  0  0  0            999 V2000
    1.7100   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -0.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    1.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016    2.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    3.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4305    2.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    3.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4305    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    1.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160    0.8627    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
 11 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
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 18  1  0  0  0  0
  2 18  1  0  0  0  0
  6 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(C)C(CC3C(OC(=O)C3=C)C12)OC1OCC(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-7-4-11(21)15-9(3)13(27-20-17(24)16(23)12(22)6-26-20)5-10-8(2)19(25)28-18(10)14(7)15/h4,10,12-14,16-18,20,22-24H,2,5-6H2,1,3H3

> <INCHI_KEY>
ZWNSWJQXKACWNW-UHFFFAOYSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.508147738440954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
0.2368800663333341

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.384127461126578

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.244323694094884

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265808768929308

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000002

> <JCHEM_REFRACTIVITY>
96.48600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <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       3.192  -4.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.651  -3.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.166  -2.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.097  -1.100   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.188  -0.252   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.539  -0.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.882   0.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.678   1.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.269   1.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.657   0.942   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.999  -0.559   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.039  -1.763   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.888  -3.049   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.372  -2.639   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.576  -3.599   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.441  -1.100   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.726  -0.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.499  -1.763   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.269   3.150   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.603   3.920   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.603   5.460   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.937   6.230   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.270   5.460   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.604   6.230   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.270   3.920   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.604   3.150   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.937   3.150   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.937   1.610   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17                                                  
CONECT   17   16                                                            
CONECT   18   12    2    6                                                  
CONECT   19    9   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(C)C(CC3C(OC(=O)C3=C)C12)OC1OCC(O)C(O)C1O

InChI Identifier

InChI=1S/C20H24O8/c1-7-4-11(21)15-9(3)13(27-20-17(24)16(23)12(22)6-26-20)5-10-8(2)19(25)28-18(10)14(7)15/h4,10,12-14,16-18,20,22-24H,2,5-6H2,1,3H3

InChI Key

ZWNSWJQXKACWNW-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 o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	-0.62	ALOGPS
logP	0.24	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.49 m³·mol⁻¹	ChemAxon
Polarizability	39.51 Å³	ChemAxon
Number of Rings	4	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 6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione (NP0283467)

MOL for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D MOL for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D SDF for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D-SDF for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

PDB for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D PDB for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

SMILES for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

INCHI for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

Structure for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)

3D Structure for NP0283467 (6,9-dimethyl-3-methylidene-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-2,7-dione)