NP-MRD: Showing NP-Card for 3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione (NP0325077)

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Record Information

Version

2.0

Created at

2022-09-12 05:33:27 UTC

Updated at

2022-09-12 05:33:27 UTC

NP-MRD ID

NP0325077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione

Description

3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)-1,4-dihydronaphthalene-1,4-dione belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione is found in Eleutherine bulbosa. Based on a literature review very few articles have been published on 3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)-1,4-dihydronaphthalene-1,4-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122207332D          

 21 22  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
   -0.7145   -0.4125    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
    0.0000   -1.6500    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   -0.4125    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
    1.4289    0.8250    0.0000 O   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
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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   -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  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  6  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1C(=O)C([C@@H](C)O)=C(CC(C)=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-8(17)7-11-13(9(2)18)16(20)14-10(15(11)19)5-4-6-12(14)21-3/h4-6,9,18H,7H2,1-3H3/t9-/m1/s1

> <INCHI_KEY>
QBHNGFXJGYIVTI-SECBINFHSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.299

> <EXACT_MASS>
288.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.440589569843738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)-1,4-dihydronaphthalene-1,4-dione

> <JCHEM_LOGP>
0.7175039543333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.769237218034576

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.80589088773014

> <JCHEM_PKA_STRONGEST_BASIC>
-2.940969854953803

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
77.37159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15    7   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₅

Average Mass

288.2990 Da

Monoisotopic Mass

288.09977 Da

IUPAC Name

3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

3-[(1R)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(=O)C([C@@H](C)O)=C(CC(C)=O)C2=O

InChI Identifier

InChI=1S/C16H16O5/c1-8(17)7-11-13(9(2)18)16(20)14-10(15(11)19)5-4-6-12(14)21-3/h4-6,9,18H,7H2,1-3H3/t9-/m1/s1

InChI Key

QBHNGFXJGYIVTI-SECBINFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eleutherine bulbosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Anisole
Alkyl aryl ether
Secondary alcohol
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	0.72	ChemAxon
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.37 m³·mol⁻¹	ChemAxon
Polarizability	29.44 Å³	ChemAxon
Number of Rings	2	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

163021581

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione (NP0325077)

MOL for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

3D MOL for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

3D SDF for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

3D-SDF for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

PDB for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

3D PDB for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

SMILES for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

INCHI for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

Structure for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)

3D Structure for NP0325077 (3-[(1r)-1-hydroxyethyl]-5-methoxy-2-(2-oxopropyl)naphthalene-1,4-dione)