NP-MRD: Showing NP-Card for (4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one (NP0245134)

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Record Information

Version

2.0

Created at

2022-09-07 06:06:12 UTC

Updated at

2022-09-07 06:06:12 UTC

NP-MRD ID

NP0245134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one

Description

Isosclerone 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. (4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one is found in Cytospora eucalypti, Diplogelasinospora grovesii, Engelhardia roxburghiana, Garcinia atroviridis, Juglans mandshurica, Juglans regia, Mycosphaerella recutita, Talaromyces diversus, Pyricularia oryzae, Sclerotinia sclerotiorum, Trichocladium griseum and Tubakia dryina. (4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one was first documented in 2018 (PMID: 29677644). Based on a literature review a small amount of articles have been published on Isosclerone (PMID: 33636028) (PMID: 35850839) (PMID: 36079659) (PMID: 35049995).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208062D          

 13 14  0  0  1  0            999 V2000
    1.4289   -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
    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  2  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
    3.5724   -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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCC(=O)C2=C(O)C=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2/t7-/m0/s1

> <INCHI_KEY>
ZXYYTDCENDYKBR-ZETCQYMHSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.187

> <EXACT_MASS>
178.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.883572261894287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

> <JCHEM_LOGP>
1.3967482796666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.32542600289596

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.596665938135132

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144565390501521

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
47.82310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7    2                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₀O₃

Average Mass

178.1870 Da

Monoisotopic Mass

178.06299 Da

IUPAC Name

(4S)-4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

(4S)-4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CCC(=O)C2=C(O)C=CC=C12

InChI Identifier

InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2/t7-/m0/s1

InChI Key

ZXYYTDCENDYKBR-ZETCQYMHSA-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

Species Name	Source	Reference
Cytospora eucalypti	LOTUS Database	35616633
Diplogelasinospora grovesii	LOTUS Database	35616633
Engelhardia roxburghiana	LOTUS Database	35616633
Garcinia atroviridis	LOTUS Database	35616633
Juglans mandshurica	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Mycosphaerella recutita	LOTUS Database	35616633
Penicillium diversum	LOTUS Database	35616633
Pyricularia oryzae	LOTUS Database	35616633
Sclerotinia sclerotiorum	LOTUS Database	35616633
Trichocladium griseum	LOTUS Database	35616633
Tubakia dryina	LOTUS Database	35616633

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
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.4	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.82 m³·mol⁻¹	ChemAxon
Polarizability	17.88 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

34543012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13369486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sadorn K, Saepua S, Boonyuen N, Boonruangprapa T, Rachtawee P, Pittayakhajonwut P: Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696. Phytochemistry. 2018 Jul;151:99-109. doi: 10.1016/j.phytochem.2018.04.001. Epub 2018 Apr 24. [PubMed:29677644 ]
Zhu C, Lew CI, Neuhaus GF, Adpressa DA, Zakharov LN, Kaweesa EN, Plitzko B, Loesgen S: Biodiversity, Bioactivity, and Metabolites of High Desert Derived Oregonian Soil Bacteria. Chem Biodivers. 2021 Apr;18(4):e2100046. doi: 10.1002/cbdv.202100046. Epub 2021 Mar 24. [PubMed:33636028 ]
Yu YH, Chen JY, Yi WT, Li MM, Li X, Zeng HT, Yuan T: [Secondary metabolites of endophyte Hypoxylon sp. HD-2014 from Uncaria rhynchophylla]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3816-3821. doi: 10.19540/j.cnki.cjcmm.20220225.201. [PubMed:35850839 ]
Scarano L, Mazzone F, Mannerucci F, D'Amico M, Bruno GL, Marsico AD: Preliminary Studies on the In Vitro Interactions Between the Secondary Metabolites Produced by Esca-Associated Fungi and Enological Saccharomyces cerevisiae Strains. Plants (Basel). 2022 Aug 31;11(17):2277. doi: 10.3390/plants11172277. [PubMed:36079659 ]
Reveglia P, Raimondo ML, Masi M, Cimmino A, Nuzzo G, Corso G, Fontana A, Carlucci A, Evidente A: Untargeted and Targeted LC-MS/MS Based Metabolomics Study on In Vitro Culture of Phaeoacremonium Species. J Fungi (Basel). 2022 Jan 6;8(1):55. doi: 10.3390/jof8010055. [PubMed:35049995 ]
LOTUS database [Link]

Showing NP-Card for (4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one (NP0245134)

MOL for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

3D MOL for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

3D SDF for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

3D-SDF for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

PDB for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

3D PDB for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

SMILES for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

INCHI for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

Structure for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

3D Structure for NP0245134 ((4s)-4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)