NP-MRD: Showing NP-Card for (3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one (NP0226482)

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Record Information

Version

2.0

Created at

2022-09-06 05:32:02 UTC

Updated at

2022-09-06 05:32:02 UTC

NP-MRD ID

NP0226482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one

Description

Dihydroxanthatin 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. (3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one is found in Xanthium sibiricum and Xanthium strumarium. (3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one was first documented in 2005 (PMID: 16018663). Based on a literature review very few articles have been published on Dihydroxanthatin (PMID: 19873782).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207322D          

 18 19  0  0  1  0            999 V2000
    6.0235    0.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0235    1.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533    1.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7017    0.3491    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
 10 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0226482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2CC=C(\C=C\C(C)=O)[C@@H](C)C[C@@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,11,13-14H,7-8H2,1-3H3/b5-4+/t9-,11-,13+,14-/m0/s1

> <INCHI_KEY>
OJOBWKNNIJPJRN-FXSQWFEKSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.91401297312396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,7S,8aS)-3,7-dimethyl-6-[(1E)-3-oxobut-1-en-1-yl]-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

> <JCHEM_LOGP>
2.4868225459999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.70887985254123

> <JCHEM_PKA_STRONGEST_BASIC>
-4.62373662192975

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
71.1558

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,7S,8aS)-3,7-dimethyl-6-[(1E)-3-oxobut-1-en-1-yl]-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

> <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      11.244   0.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.474   2.028   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.244   3.362   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.934   2.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.164   3.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.786   4.608   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.659   3.362   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.310   0.652   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                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3S,3aR,7S,8aS)-3,7-dimethyl-6-[(1E)-3-oxobut-1-en-1-yl]-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

Traditional Name

(3S,3aR,7S,8aS)-3,7-dimethyl-6-[(1E)-3-oxobut-1-en-1-yl]-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2CC=C(\C=C\C(C)=O)[C@@H](C)C[C@@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,11,13-14H,7-8H2,1-3H3/b5-4+/t9-,11-,13+,14-/m0/s1

InChI Key

OJOBWKNNIJPJRN-FXSQWFEKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xanthium sibiricum	LOTUS Database	35616633
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
Gamma butyrolactone
Acryloyl-group
Enone
Oxolane
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	2.49	ChemAxon
pKa (Strongest Acidic)	19.71	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.16 m³·mol⁻¹	ChemAxon
Polarizability	27.91 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

9554566

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11379652

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang W, Han W, Li Y, Zhang S, Zhao D: [Chemical constituents from Xanthium mongolicum]. Zhongguo Zhong Yao Za Zhi. 2009 Jul;34(13):1687-9. [PubMed:19873782 ]
Evans MA, Morken JP: Asymmetric synthesis of (-)-dihydroxanthatin by the stereoselective Oshima-Utimoto reaction. Org Lett. 2005 Jul 21;7(15):3371-3. doi: 10.1021/ol051276k. [PubMed:16018663 ]
LOTUS database [Link]

Showing NP-Card for (3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one (NP0226482)

MOL for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

3D MOL for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

3D SDF for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

3D-SDF for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

PDB for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

3D PDB for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

SMILES for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

INCHI for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

Structure for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)

3D Structure for NP0226482 ((3s,3ar,7s,8as)-3,7-dimethyl-6-[(1e)-3-oxobut-1-en-1-yl]-3h,3ah,4h,7h,8h,8ah-cyclohepta[b]furan-2-one)