6-(Benzylamino)-5,6,7,8-tetrahydro-4H-[7]annuleno-[b]thiophen-4-ol

Names and Identifiers

Canonical SMILES: OC1CC(NCc2ccccc2)CCc2sccc21

Standard InChI: InChI=1S/C16H19NOS/c18-15-10-13(6-7-16-14(15)8-9-19-16)17-11-12-4-2-1-3-5-12/h1-5,8-9,13,15,17-18H,6-7,10-11H2

Standard InChI Key: GSSRNSHXCDBXPR-UHFFFAOYSA-N

Molfile:

 
     RDKit          2D

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   18.3650  -10.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3664  -12.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1703  -10.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1727  -11.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5275  -11.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3447  -11.0718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7518  -10.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3416   -9.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7525   -8.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3430   -8.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5250   -8.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1181   -8.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5299   -9.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1797   -9.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7167  -11.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7190  -10.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9376  -10.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4522  -11.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9338  -11.7436    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  0
 15  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
M  END

Alternative Forms

Parent:

ALA4513837
---

Associated Targets(Human)

GRIN2B Tclin Glutamate [NMDA] receptor subunit epsilon 2 (467 Activities)

Discover Target: GRIN2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

SIGMAR1 Sigma-1 receptor (3326 Activities)

Discover Target: SIGMAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Tmem97 Sigma intracellular receptor 2 (922 Activities)

Discover Target: Tmem97

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Molecule Features

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Unknown	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 273.40	Molecular Weight (Monoisotopic): 273.1187	AlogP: 3.28	#Rotatable Bonds: 3
Polar Surface Area: 32.26	Molecular Species: BASE	HBA: 3	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 2	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: 9.32	CX LogP: 3.14	CX LogD: 1.24
Aromatic Rings: 2	Heavy Atoms: 19	QED Weighted: 0.84	Np Likeness Score: -0.80

References

1. Baumeister S, Schepmann D, Wünsch B.. (2019) Synthesis and receptor binding of thiophene bioisosteres of potent GluN2B ligands with a benzo[7]annulene-scaffold., 10 (2): [PMID:30881618] [10.1039/C8MD00545A]

Source

Source(1):

Scientific Literature