NP-MRD: Showing NP-Card for (3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate (NP0224281)

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Record Information

Version

2.0

Created at

2022-09-06 02:36:13 UTC

Updated at

2022-09-06 02:36:13 UTC

NP-MRD ID

NP0224281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate

Description

(3AS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on (3aS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204362D          

 28 30  0  0  1  0            999 V2000
   -0.5218   -4.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -4.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336   -4.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -5.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -4.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535   -3.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1652   -3.6938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5165   -3.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781   -2.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -1.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -1.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -0.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424   -1.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945   -1.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -1.6906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8626   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -2.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -2.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619   -2.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.6826    0.0000 C   0  0  2  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  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  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
 13 15  2  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  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  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  6  0  0  0
 16 28  1  0  0  0  0
  6 28  1  0  0  0  0
M  END


  Mrv1652309062204362D          

 28 30  0  0  1  0            999 V2000
   -0.5218   -4.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -4.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336   -4.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -5.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -4.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535   -3.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1652   -3.6938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5165   -3.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781   -2.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -1.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -1.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -0.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424   -1.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3945   -1.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -1.6906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8626   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5771   -2.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -2.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619   -2.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.6826    0.0000 C   0  0  2  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  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  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
 13 15  2  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  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  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  6  0  0  0
 16 28  1  0  0  0  0
  6 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1CC2=C(COC(C)=O)CC[C@@H]3[C@H](OC(=O)C3=C)[C@H]2C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O6/c1-11(2)8-19(24)27-18-9-17-15(10-26-14(5)23)6-7-16-12(3)22(25)28-21(16)20(17)13(18)4/h11,16,18,20-21H,3-4,6-10H2,1-2,5H3/t16-,18-,20-,21-/m0/s1

> <INCHI_KEY>
VMZPMJZNNBIDDN-GIUOSPMZSA-N

> <FORMULA>
C22H28O6

> <MOLECULAR_WEIGHT>
388.46

> <EXACT_MASS>
388.188588622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.394183254453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate

> <JCHEM_LOGP>
2.7764559276666656

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.491261591877489

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
102.14699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.974  -9.321   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.285  -8.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.743  -8.933   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.197 -10.404   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.666  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.780  -6.441   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.308  -6.895   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.964  -6.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.079  -4.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.050  -3.444   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.404  -1.973   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.906  -1.630   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.360  -0.159   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.861   0.184   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.312   0.970   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.573  -3.674   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.603  -2.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.010  -3.156   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.344  -2.386   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.677  -3.156   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.677  -4.696   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.011  -2.386   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.345  -3.156   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.678  -2.386   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.345  -4.696   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.849  -4.687   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.993  -5.718   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.343  -5.008   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   28                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   16    6                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(3AS,8S,9ar,9BS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,7H,8H,9H,9ah,9BH-azuleno[4,5-b]furan-8-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₂H₂₈O₆

Average Mass

388.4600 Da

Monoisotopic Mass

388.18859 Da

IUPAC Name

(3aS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate

Traditional Name

(3aS,8S,9aR,9bS)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-8-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1CC2=C(COC(C)=O)CC[C@@H]3[C@H](OC(=O)C3=C)[C@H]2C1=C

InChI Identifier

InChI=1S/C22H28O6/c1-11(2)8-19(24)27-18-9-17-15(10-26-14(5)23)6-7-16-12(3)22(25)28-21(16)20(17)13(18)4/h11,16,18,20-21H,3-4,6-10H2,1-2,5H3/t16-,18-,20-,21-/m0/s1

InChI Key

VMZPMJZNNBIDDN-GIUOSPMZSA-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 tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
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	2.78	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.15 m³·mol⁻¹	ChemAxon
Polarizability	41.39 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	Yes	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

163025171

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate (NP0224281)

MOL for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

3D MOL for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

3D SDF for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

3D-SDF for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

PDB for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

3D PDB for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

SMILES for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

INCHI for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

Structure for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)

3D Structure for NP0224281 ((3as,8s,9ar,9bs)-6-[(acetyloxy)methyl]-3,9-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9ah,9bh-azuleno[4,5-b]furan-8-yl 3-methylbutanoate)