NP-MRD: Showing NP-Card for 8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate (NP0206474)

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Record Information

Version

2.0

Created at

2022-09-05 02:44:09 UTC

Updated at

2022-09-05 02:44:09 UTC

NP-MRD ID

NP0206474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate

Description

8-Hydroxy-3,5-dimethyl-4-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 8-Hydroxy-3,5-dimethyl-4-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241503422D          

 25 27  0  0  0  0            999 V2000
    2.5130   -1.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -1.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963   -1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    0.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731    1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0606    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909   -0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814   -1.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -2.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662   -3.0031    0.0000 O   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  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
 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
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1533004241503422D          

 25 27  0  0  0  0            999 V2000
    2.5130   -1.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -1.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963   -1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    0.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731    1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0606    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909   -0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814   -1.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -2.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662   -3.0031    0.0000 O   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  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
 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
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0206474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C(O)CCC(C)(OC(=O)C(=C)CO)C3C2=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-9(8-20)17(22)25-19(4)6-5-13(21)12-7-14-15(10(2)16(12)19)11(3)18(23)24-14/h11-16,20-21H,1-2,5-8H2,3-4H3

> <INCHI_KEY>
ABAXGHGZDPNOET-UHFFFAOYSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.80759926418729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.124851655333333

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.207706194568694

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.605399181040628

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8351432160750143

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
89.67309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3H-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-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       4.691  -3.196   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.166  -2.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.443  -1.622   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.926  -1.889   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.064  -0.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.463   0.738   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.527   1.917   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.043   1.650   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000   3.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.517   3.632   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.506   2.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.496   3.632   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.840   1.682   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.174   2.452   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.174   3.992   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.508   1.682   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.508   0.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.841   2.452   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.175   1.682   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.980   1.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.970  -0.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.486   0.093   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.712  -3.414   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.096  -4.089   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.364  -5.606   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   11    6   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
CONECT   23    4   24                                                       
CONECT   24   23    2   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-3,5-dimethyl-4-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-dodecahydronaphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3H-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C(O)CCC(C)(OC(=O)C(=C)CO)C3C2=C)OC1=O

InChI Identifier

InChI=1S/C19H26O6/c1-9(8-20)17(22)25-19(4)6-5-13(21)12-7-14-15(10(2)16(12)19)11(3)18(23)24-14/h11-16,20-21H,1-2,5-8H2,3-4H3

InChI Key

ABAXGHGZDPNOET-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
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	1.38	ALOGPS
logP	1.12	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-2.8	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	4	ChemAxon
Refractivity	89.67 m³·mol⁻¹	ChemAxon
Polarizability	36.81 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 8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate (NP0206474)

MOL for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

3D MOL for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

3D SDF for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

3D-SDF for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

PDB for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

3D PDB for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

SMILES for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

INCHI for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

Structure for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)

3D Structure for NP0206474 (8-hydroxy-3,5-dimethyl-4-methylidene-2-oxo-octahydro-3h-naphtho[2,3-b]furan-5-yl 2-(hydroxymethyl)prop-2-enoate)