NP-MRD: Showing NP-Card for 4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid (NP0316655)

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Record Information

Version

2.0

Created at

2022-09-11 15:59:21 UTC

Updated at

2022-09-11 15:59:21 UTC

NP-MRD ID

NP0316655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid

Description

4,9-Dihydroxy-3,4a-dimethyl-4H,4aH,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid is found in Ligularia intermedia. Based on a literature review very few articles have been published on 4,9-dihydroxy-3,4a-dimethyl-4H,4aH,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112217592D          

 20 22  0  0  0  0            999 V2000
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(O)C1(C)C(CCCC1=C2O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-7-6-20-12-10(7)13(17)15(2)8(11(12)16)4-3-5-9(15)14(18)19/h6,9,13,16-17H,3-5H2,1-2H3,(H,18,19)

> <INCHI_KEY>
MRZYPKDTXGJJEW-UHFFFAOYSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.32678180429614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dihydroxy-3,4a-dimethyl-4H,4aH,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid

> <JCHEM_LOGP>
1.3700793213333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.000866803632094

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.410614026221044

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8510080547669103

> <JCHEM_POLAR_SURFACE_AREA>
90.90000000000002

> <JCHEM_REFRACTIVITY>
72.28809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,9-dihydroxy-3,4a-dimethyl-4H,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
4,9-Dihydroxy-3,4a-dimethyl-4H,4ah,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylate	Generator

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

4,9-dihydroxy-3,4a-dimethyl-4H,4aH,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid

Traditional Name

4,9-dihydroxy-3,4a-dimethyl-4H,5H,6H,7H,8H-naphtho[2,3-b]furan-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(O)C1(C)C(CCCC1=C2O)C(O)=O

InChI Identifier

InChI=1S/C15H18O5/c1-7-6-20-12-10(7)13(17)15(2)8(11(12)16)4-3-5-9(15)14(18)19/h6,9,13,16-17H,3-5H2,1-2H3,(H,18,19)

InChI Key

MRZYPKDTXGJJEW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia intermedia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Furan
Heteroaromatic compound
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Enol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.37	ChemAxon
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.29 m³·mol⁻¹	ChemAxon
Polarizability	28.33 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

162955018

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid (NP0316655)

MOL for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

3D MOL for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

3D SDF for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

3D-SDF for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

PDB for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

3D PDB for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

SMILES for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

INCHI for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

Structure for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)

3D Structure for NP0316655 (4,9-dihydroxy-3,4a-dimethyl-4h,5h,6h,7h,8h-naphtho[2,3-b]furan-5-carboxylic acid)