NP-MRD: Showing NP-Card for 6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate (NP0283407)

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Record Information

Version

2.0

Created at

2022-09-09 10:39:31 UTC

Updated at

2022-09-09 10:39:31 UTC

NP-MRD ID

NP0283407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

Description

6,9A-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate is found in Tithonia pedunculata. 6,9A-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241515262D          

 27 30  0  0  0  0            999 V2000
    1.4073    2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0680    2.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931    3.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6948    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218    1.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    2.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402    0.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.5778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  END


  Mrv1533004241515262D          

 27 30  0  0  0  0            999 V2000
    1.4073    2.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0680    2.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931    3.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6948    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218    1.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    2.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402    0.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8457   -1.5778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC1(C)C(=O)OC1CC2(C)C(O)CCC(=C)C2(O)C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-9-6-7-13(21)18(4)8-12(25-17(23)19(5)11(3)27-19)14-10(2)16(22)26-15(14)20(9,18)24/h11-15,21,24H,1-2,6-8H2,3-5H3

> <INCHI_KEY>
IXJLFSPGJWNXAL-UHFFFAOYSA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.421

> <EXACT_MASS>
378.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.29328062024594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.2472011930000002

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.696774941327117

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.850547537727866

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9765501840654105

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
92.86299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3aH-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

> <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       2.627   3.901   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.860   4.823   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.467   6.238   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.389   5.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.897   5.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.201   3.696   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.740   3.744   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.473   2.339   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.363   1.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.902   1.174   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.990  -4.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.179  -2.945   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.638  -3.041   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.060  -0.694   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.884   0.300   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    4                                                       
CONECT    4    3    2    5    6                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   19                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    9   21                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
6,9a-Dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₆O₇

Average Mass

378.4210 Da

Monoisotopic Mass

378.16785 Da

IUPAC Name

6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3aH-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1OC1(C)C(=O)OC1CC2(C)C(O)CCC(=C)C2(O)C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H26O7/c1-9-6-7-13(21)18(4)8-12(25-17(23)19(5)11(3)27-19)14-10(2)16(22)26-15(14)20(9,18)24/h11-15,21,24H,1-2,6-8H2,3-5H3

InChI Key

IXJLFSPGJWNXAL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tithonia pedunculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Lactone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.05	ALOGPS
logP	1.25	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.86 m³·mol⁻¹	ChemAxon
Polarizability	39.29 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 6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate (NP0283407)

MOL for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0283407 (6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-2-oxo-hexahydro-3ah-naphtho[1,2-b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)