NP-MRD: Showing NP-Card for 4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one (NP0144759)

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Record Information

Version

1.0

Created at

2022-09-01 23:48:31 UTC

Updated at

2022-09-01 23:48:31 UTC

NP-MRD ID

NP0144759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one

Description

4,5,8-Trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Based on a literature review very few articles have been published on 4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.2291    1.5139   -1.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    0.8820   -1.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1254    0.2422   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2810   -1.0673   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297   -1.7907    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767   -3.0734    0.7280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -1.2341    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299    0.0318   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    0.7567   -0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    2.0213   -1.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5868    0.6608   -0.3442 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7426    1.1945   -1.6480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -0.1590    0.0064 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5311    0.5237    1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641    1.9655    0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887    2.3672   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0580    2.8714    1.3084 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -1.6042    0.2924 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4353   -2.1145    1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153   -3.5134    1.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -1.9896    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467   -2.9869    1.4053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906    1.5342   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2698    2.6415   -1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2480    1.0964   -1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2787   -1.5097   -0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -3.5582    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301    2.5647   -1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5045    1.5759    0.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    2.1611   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -0.1371   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -0.0030    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834    0.5069    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614    2.1093    0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    3.4672   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8113    1.8836   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -2.2338   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -1.7334    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -2.0063    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055   -3.8573    0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7 21  1  0
 21 22  2  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 11  1  0
 11 12  1  0
 11  8  1  0
  8  9  2  0
  9 10  1  0
  9  3  1  0
  8  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 18 37  1  6
 19 38  1  0
 19 39  1  0
 20 40  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 11 29  1  1
 12 30  1  0
 10 28  1  0
M  END


  Mrv1652309022201482D          

 22 23  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
   -0.7145   -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
    0.0000   -2.4750    0.0000 O   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
    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 O   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  0  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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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 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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0144759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C(CO)C(CC(C)=O)C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O7/c1-6(17)3-7-8(5-16)14(20)11-9(18)4-10(22-2)15(21)12(11)13(7)19/h4,7-8,13,16,18-19,21H,3,5H2,1-2H3

> <INCHI_KEY>
WUEWJCUSVRCGFI-UHFFFAOYSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.345667679815392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
0.016652063000000467

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.524346835782143

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.968255299247039

> <JCHEM_PKA_STRONGEST_BASIC>
-2.672847467296693

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
76.90549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  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    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18    7   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₇

Average Mass

310.3020 Da

Monoisotopic Mass

310.10525 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C(CO)C(CC(C)=O)C(O)C2=C1O

InChI Identifier

InChI=1S/C15H18O7/c1-6(17)3-7-8(5-16)14(20)11-9(18)4-10(22-2)15(21)12(11)13(7)19/h4,7-8,13,16,18-19,21H,3,5H2,1-2H3

InChI Key

WUEWJCUSVRCGFI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Secondary alcohol
Ketone
Ether
Polyol
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
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	-0.03	ALOGPS
logP	0.017	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	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

75244347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one (NP0144759)

MOL for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D MOL for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D SDF for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D-SDF for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

PDB for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D PDB for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

SMILES for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

INCHI for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

Structure for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D Structure for NP0144759 (4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)