NP-MRD: Showing NP-Card for (3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one (NP0180059)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 18:21:36 UTC

Updated at

2022-09-03 18:21:36 UTC

NP-MRD ID

NP0180059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one

Description

Botryosphaerone D 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. (3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one is found in Neofusicoccum australe. (3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one was first documented in 2012 (PMID: 23046443). Based on a literature review a small amount of articles have been published on Botryosphaerone D (PMID: 29374570) (PMID: 23877026).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.7262   -1.1122   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9332   -1.3001    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -0.7151    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571    0.6392    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172    1.4139    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3325    2.8101    0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120    1.2192    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    0.4437    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8100   -0.9317    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -1.5252    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6289   -2.8624    0.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -1.7331    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0505   -2.8858    0.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -1.1823   -0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493    0.2967   -0.9645 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3239    0.8353   -1.1077 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3754    0.9590    0.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4293    2.3367    0.1338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243   -1.7752   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2084   -1.3869   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500   -0.0710   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106   -2.3739    0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980   -0.7807    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    3.3332    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801    3.0629    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988    3.2259    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0223    2.2795    0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246   -3.5769   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -1.3412   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6866   -1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818    0.4557   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.5666   -0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9887    0.6775    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896    2.6855   -0.6216 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
  4  7  1  0
  7  8  2  0
  8 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 12  9  1  0
  9 10  2  0
 10 11  1  0
 10  3  1  0
  9  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
 17 33  1  1
 18 34  1  0
 15 31  1  6
 16 32  1  0
 14 29  1  0
 14 30  1  0
 11 28  1  0
M  END


  Mrv1652309032220212D          

 18 19  0  0  1  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 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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
    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
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  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
  4  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
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0180059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(OC)C=C2[C@H](O)[C@@H](O)CC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-3-6-10(18-2)4-7-11(13(6)17)8(14)5-9(15)12(7)16/h4,9,12,15-17H,3,5H2,1-2H3/t9-,12-/m0/s1

> <INCHI_KEY>
CALZOMFTGJDTHS-CABZTGNLSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.266

> <EXACT_MASS>
252.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.649681157209884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-7-ethyl-3,4,8-trihydroxy-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one

> <JCHEM_LOGP>
1.2780709213333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.043879381366455

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.864190290227661

> <JCHEM_PKA_STRONGEST_BASIC>
-3.306639108297457

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
65.13600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+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  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  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   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆O₅

Average Mass

252.2660 Da

Monoisotopic Mass

252.09977 Da

IUPAC Name

(3S,4S)-7-ethyl-3,4,8-trihydroxy-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

(3S,4S)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

CAS Registry Number

Not Available

SMILES

CCC1=C(OC)C=C2[C@H](O)[C@@H](O)CC(=O)C2=C1O

InChI Identifier

InChI=1S/C13H16O5/c1-3-6-10(18-2)4-7-11(13(6)17)8(14)5-9(15)12(7)16/h4,9,12,15-17H,3,5H2,1-2H3/t9-,12-/m0/s1

InChI Key

CALZOMFTGJDTHS-CABZTGNLSA-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
Neofusicoccum australe	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
Anisole
Aryl alkyl ketone
Aryl ketone
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous acid
1,2-diol
Secondary alcohol
Ketone
Ether
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen 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	1.28	ChemAxon
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.14 m³·mol⁻¹	ChemAxon
Polarizability	25.65 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

30797230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53360466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Andolfi A, Maddau L, Cimmino A, Linaldeddu BT, Franceschini A, Serra S, Basso S, Melck D, Evidente A: Cyclobotryoxide, a phytotoxic metabolite produced by the plurivorous pathogen Neofusicoccum australe. J Nat Prod. 2012 Oct 26;75(10):1785-91. doi: 10.1021/np300512m. Epub 2012 Oct 9. [PubMed:23046443 ]
Cui H, Zhang H, Liu Y, Gu Q, Xu J, Huang X, She Z: Ethylnaphthoquinone derivatives as inhibitors of indoleamine-2, 3-dioxygenase from the mangrove endophytic fungus Neofusicoccum austral SYSU-SKS024. Fitoterapia. 2018 Mar;125:281-285. doi: 10.1016/j.fitote.2018.01.014. Epub 2018 Jan 31. [PubMed:29374570 ]
Deng CM, Liu SX, Huang CH, Pang JY, Lin YC: Secondary metabolites of a mangrove endophytic fungus Aspergillus terreus (No. GX7-3B) from the South China Sea. Mar Drugs. 2013 Jul 19;11(7):2616-24. doi: 10.3390/md11072616. [PubMed:23877026 ]
LOTUS database [Link]

Showing NP-Card for (3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one (NP0180059)

MOL for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

3D MOL for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

3D SDF for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

3D-SDF for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

PDB for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

3D PDB for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

SMILES for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

INCHI for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

Structure for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)

3D Structure for NP0180059 ((3s,4s)-7-ethyl-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one)