NP-MRD: Showing NP-Card for 1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate (NP0262170)

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Record Information

Version

2.0

Created at

2022-09-08 04:49:47 UTC

Updated at

2022-09-08 04:49:47 UTC

NP-MRD ID

NP0262170

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate

Description

Dihydroxanthinin belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. 1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate is found in Xanthium strumarium. Dihydroxanthinin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191523342D          

 22 23  0  0  0  0            999 V2000
    5.3967   -3.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516   -3.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9352   -4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208   -5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6758   -6.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -6.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -7.4622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -6.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563   -6.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815   -4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2650   -3.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -2.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939   -2.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -1.0854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -1.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228   -2.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3873   -0.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4373   -1.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 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
M  END
> <DATABASE_ID>
NP0262170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC=C(C(CC(C)=O)OC(C)=O)C(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O5/c1-9-7-15-14(11(3)17(20)22-15)6-5-13(9)16(8-10(2)18)21-12(4)19/h5,9,11,14-16H,6-8H2,1-4H3

> <INCHI_KEY>
XXKCCBFCBFYRGB-UHFFFAOYSA-N

> <FORMULA>
C17H24O5

> <MOLECULAR_WEIGHT>
308.374

> <EXACT_MASS>
308.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.26620081162217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3,7-dimethyl-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.855220859666666

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.759534600390474

> <JCHEM_PKA_STRONGEST_BASIC>
-6.647051963445222

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
80.5755

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{3,7-dimethyl-2-oxo-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      10.074  -6.354   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.870  -7.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.212  -8.816   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.252 -10.020   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.728 -11.484   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.482 -12.389   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.482 -13.929   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.236 -11.484   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.772 -11.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.712 -10.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.752  -8.816   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.095  -7.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.482  -6.646   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.482  -5.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.149  -4.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.149  -2.796   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.482  -2.026   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.815  -2.026   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.816  -4.336   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.816  -2.796   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.190  -1.389   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.150  -2.026   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₅

Average Mass

308.3740 Da

Monoisotopic Mass

308.16237 Da

IUPAC Name

1-{3,7-dimethyl-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate

Traditional Name

1-{3,7-dimethyl-2-oxo-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate

CAS Registry Number

Not Available

SMILES

CC1C2CC=C(C(CC(C)=O)OC(C)=O)C(C)CC2OC1=O

InChI Identifier

InChI=1S/C17H24O5/c1-9-7-15-14(11(3)17(20)22-15)6-5-13(9)16(8-10(2)18)21-12(4)19/h5,9,11,14-16H,6-8H2,1-4H3

InChI Key

XXKCCBFCBFYRGB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Xanthanolides

Alternative Parents

Substituents

Xanthanolide-skeleton
Sesquiterpenoid
Xanthane sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	2.23	ALOGPS
logP	1.86	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	18.76	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.58 m³·mol⁻¹	ChemAxon
Polarizability	33.27 Å³	ChemAxon
Number of Rings	2	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

282782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate (NP0262170)

MOL for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

3D MOL for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

3D SDF for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

3D-SDF for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

PDB for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

3D PDB for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

SMILES for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

INCHI for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

Structure for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)

3D Structure for NP0262170 (1-{3,7-dimethyl-2-oxo-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-6-yl}-3-oxobutyl acetate)