NP-MRD: Showing NP-Card for 6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol (NP0169246)

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Record Information

Version

2.0

Created at

2022-09-03 05:10:01 UTC

Updated at

2022-09-03 05:10:01 UTC

NP-MRD ID

NP0169246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol

Description

6,7-Dihydroxy-2-aminotetralin, also known as 2-amino-6,7-dihydroxytetralin or 6,7-adtn, 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. 6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol is found in Apis mellifera. 6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol was first documented in 1982 (PMID: 7119802). Based on a literature review a small amount of articles have been published on 6,7-Dihydroxy-2-aminotetralin (PMID: 7876148) (PMID: 2863760) (PMID: 3969068) (PMID: 6090664).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207102D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 N   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
    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 O   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
    4.2868   -1.6500    0.0000 O   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
    2.1434   -1.2375    0.0000 C   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  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1CCC2=CC(O)=C(O)C=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO2/c11-8-2-1-6-4-9(12)10(13)5-7(6)3-8/h4-5,8,12-13H,1-3,11H2

> <INCHI_KEY>
ASXGAOFCKGHGMF-UHFFFAOYSA-N

> <FORMULA>
C10H13NO2

> <MOLECULAR_WEIGHT>
179.219

> <EXACT_MASS>
179.094628663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.213353832111114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.6047680422237239

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.070838218918293

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.228885189855324

> <JCHEM_PKA_STRONGEST_BASIC>
9.475279849972438

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
50.82899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol

> <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  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   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   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene	HMDB
2-Amino-6,7-dihydroxytetralin	HMDB
6,7-ADTN	HMDB
ADTN hydrobromide	HMDB
ADTN hydrochloride	HMDB
ADTN, (R)-isomer	HMDB
ADTN, (S)-isomer	HMDB

Chemical Formula

C₁₀H₁₃NO₂

Average Mass

179.2190 Da

Monoisotopic Mass

179.09463 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

NC1CCC2=CC(O)=C(O)C=C2C1

InChI Identifier

InChI=1S/C10H13NO2/c11-8-2-1-6-4-9(12)10(13)5-7(6)3-8/h4-5,8,12-13H,1-3,11H2

InChI Key

ASXGAOFCKGHGMF-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

Species Name	Source	Reference
Apis mellifera	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
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
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

External Links

HMDB ID

HMDB0248032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3041

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Demchyshyn LL, Sugamori KS, Lee FJ, Hamadanizadeh SA, Niznik HB: The dopamine D1D receptor. Cloning and characterization of three pharmacologically distinct D1-like receptors from Gallus domesticus. J Biol Chem. 1995 Feb 24;270(8):4005-12. doi: 10.1074/jbc.270.8.4005. [PubMed:7876148 ]
Niznik HB, Grigoriadis DE, Pri-Bar I, Buchman O, Seeman P: Dopamine D2 receptors selectively labeled by a benzamide neuroleptic: [3H]-YM-09151-2. Naunyn Schmiedebergs Arch Pharmacol. 1985 Jun;329(4):333-43. doi: 10.1007/BF00496365. [PubMed:2863760 ]
Niznik HB, Guan JH, Neumeyer JL, Seeman P: A photoaffinity ligand for dopamine D2 receptors: azidoclebopride. Mol Pharmacol. 1985 Feb;27(2):193-9. [PubMed:3969068 ]
Horn AS, Kaptein B, Mulder TB, de Vries JB, Wynberg H: 6,7-Dihydroxy-3-chromanamine: synthesis and pharmacological activity of an oxygen isostere of the dopamine agonist 6,7-dihydroxy-2-aminotetralin. J Med Chem. 1984 Oct;27(10):1340-3. doi: 10.1021/jm00376a020. [PubMed:6090664 ]
List SJ, Seeman P: [3H]dopamine labeling of D3 dopaminergic sites in human, rat, and calf brain. J Neurochem. 1982 Nov;39(5):1363-73. doi: 10.1111/j.1471-4159.1982.tb12579.x. [PubMed:7119802 ]
LOTUS database [Link]

Showing NP-Card for 6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol (NP0169246)

MOL for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

3D MOL for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

3D SDF for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

3D-SDF for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

PDB for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

3D PDB for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

SMILES for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

INCHI for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

Structure for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)

3D Structure for NP0169246 (6-amino-5,6,7,8-tetrahydronaphthalene-2,3-diol)