NP-MRD: Showing NP-Card for 6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate (NP0217485)

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Record Information

Version

2.0

Created at

2022-09-05 17:51:09 UTC

Updated at

2022-09-05 17:51:09 UTC

NP-MRD ID

NP0217485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

Description

6,9-Dihydroxy-3,5a,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate 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. 6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate is found in Daucus decipiens. 6,9-Dihydroxy-3,5a,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241503352D          

 26 28  0  0  0  0            999 V2000
    1.7280    2.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398    2.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4240    1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996    0.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    0.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    0.4455    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
    1.3506   -0.3977    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
    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
    4.8388   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -1.8582    0.0000 O   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
    3.4111   -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  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1533004241503352D          

 26 28  0  0  0  0            999 V2000
    1.7280    2.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398    2.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4240    1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996    0.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    0.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    0.4455    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
    1.3506   -0.3977    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
    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
    4.8388   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -1.8582    0.0000 O   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
    3.4111   -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  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1(C)C2CCC3(C)C(O)C=CC(C)(O)C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-6-11(2)16(22)26-20(5)12-7-9-18(3)13(21)8-10-19(4,24)15(18)14(12)25-17(20)23/h6,8,10,12-15,21,24H,7,9H2,1-5H3

> <INCHI_KEY>
KDPHCSNHVZVWJT-UHFFFAOYSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.200107730612714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.2826057756666653

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.627732107872578

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.004041593730925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1010096610810676

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
95.88589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3aH,4H,5H,6H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

> <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       3.226   5.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.434   3.883   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.217   2.939   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.792   3.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.426   1.414   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.209   0.470   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.852   0.832   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.060  -0.694   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.521  -0.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.363   1.126   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.902   1.174   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.032  -4.405   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.288  -3.469   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.638  -3.041   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   25                                             
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   13   23                                                  
CONECT   23   22   10   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    8   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
6,9-Dihydroxy-3,5a,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,5ah,6H,9H,9ah,9BH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

Traditional Name

6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3aH,4H,5H,6H,9aH,9bH-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1(C)C2CCC3(C)C(O)C=CC(C)(O)C3C2OC1=O

InChI Identifier

InChI=1S/C20H28O6/c1-6-11(2)16(22)26-20(5)12-7-9-18(3)13(21)8-10-19(4,24)15(18)14(12)25-17(20)23/h6,8,10,12-15,21,24H,7,9H2,1-5H3

InChI Key

KDPHCSNHVZVWJT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melanoselinum decipiens	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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Oxolane
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.16	ALOGPS
logP	2.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.89 m³·mol⁻¹	ChemAxon
Polarizability	38.2 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	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-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate (NP0217485)

MOL for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

3D MOL for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

3D SDF for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

3D-SDF for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

PDB for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

3D PDB for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

SMILES for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

INCHI for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

Structure for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)

3D Structure for NP0217485 (6,9-dihydroxy-3,5a,9-trimethyl-2-oxo-3ah,4h,5h,6h,9ah,9bh-naphtho[1,2-b]furan-3-yl 2-methylbut-2-enoate)