NP-MRD: Showing NP-Card for 3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one (NP0165016)

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Record Information

Version

2.0

Created at

2022-09-03 00:01:11 UTC

Updated at

2022-09-03 00:01:11 UTC

NP-MRD ID

NP0165016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one

Description

3-(2-{9-Hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one is found in Salvia melissodora. 3-(2-{9-Hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191521452D          

 25 28  0  0  0  0            999 V2000
    0.0595   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708   -0.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.8725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7627    0.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189    1.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403   -0.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -1.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -1.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707   -2.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -2.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285   -3.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -3.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927   -4.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954   -5.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -4.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184   -3.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -3.3336    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
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1533004191521452D          

 25 28  0  0  0  0            999 V2000
    0.0595   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708   -0.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.8725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7627    0.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189    1.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403   -0.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346   -1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -1.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -1.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707   -2.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -2.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285   -3.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -3.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927   -4.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8954   -5.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -4.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184   -3.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -3.3336    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
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)CC23COC(=O)C2=CCCC3C1(C)CCC1=CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-12-15(21)10-20-11-25-18(23)14(20)4-3-5-16(20)19(12,2)8-6-13-7-9-24-17(13)22/h4,7,12,15-16,21H,3,5-6,8-11H2,1-2H3

> <INCHI_KEY>
GMKZQTXTISTVFH-UHFFFAOYSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.73216233090708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.690834936333334

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.920776917530187

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.380988976265158

> <JCHEM_PKA_STRONGEST_BASIC>
-2.839187079199191

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
92.9435

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.111  -3.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.450  -2.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.461  -0.794   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.132  -0.015   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.378  -0.143   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.128  -0.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.991   0.226   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.627   1.629   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.157   1.457   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.195   2.594   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.467  -0.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.795  -0.831   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.785  -2.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.446  -3.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.117  -2.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.778  -3.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.492  -4.478   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.046  -4.468   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.853  -5.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.121  -7.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.786  -8.523   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.671  -9.585   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.317  -8.853   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.594  -7.338   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.468  -6.223   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11   15                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-2,5-dihydrofuran-2-one

Traditional Name

3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-7-yl}ethyl)-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CC1C(O)CC23COC(=O)C2=CCCC3C1(C)CCC1=CCOC1=O

InChI Identifier

InChI=1S/C20H26O5/c1-12-15(21)10-20-11-25-18(23)14(20)4-3-5-16(20)19(12,2)8-6-13-7-9-24-17(13)22/h4,7,12,15-16,21H,3,5-6,8-11H2,1-2H3

InChI Key

GMKZQTXTISTVFH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia melissodora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthofuran
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen 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	2.63	ALOGPS
logP	2.69	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.94 m³·mol⁻¹	ChemAxon
Polarizability	36.73 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

14262810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one (NP0165016)

MOL for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

3D MOL for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

3D SDF for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

3D-SDF for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

PDB for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

3D PDB for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

SMILES for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

INCHI for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

Structure for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)

3D Structure for NP0165016 (3-(2-{9-hydroxy-7,8-dimethyl-3-oxo-1h,5h,6h,6ah,8h,9h,10h-naphtho[4,4a-c]furan-7-yl}ethyl)-5h-furan-2-one)