(7R)-spiro[1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene-2,2'-naphtho[1,8-de][1,3]dioxine]-6,7-diol

ID: ALA153990

Chembl Id: CHEMBL153990

PubChem CID: 9884095

Max Phase: Preclinical

Molecular Formula: C20H14O5

Molecular Weight: 334.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SCH-53823 | CHEMBL153990|SCH-53823

Canonical SMILES:  Oc1cccc2c1[C@@H](O)[C@H]1O[C@H]1C21Oc2cccc3cccc(c23)O1

Standard InChI:  InChI=1S/C20H14O5/c21-12-7-3-6-11-16(12)17(22)18-19(23-18)20(11)24-13-8-1-4-10-5-2-9-14(25-20)15(10)13/h1-9,17-19,21-22H/t17-,18-,19-/m1/s1

Standard InChI Key:  HDSAIJZBOBVWLA-GUDVDZBRSA-N

Alternative Forms

1. Parent:

   

   ALA153990

   (1'aR,2'R,7'aR)-spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,7'-2,7a-dihydro-1aH-naphtho[2,3-b]oxirene]-2',3'-diol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 334.33

Molecular Weight (Monoisotopic): 334.0841

AlogP: 2.98

#Rotatable Bonds: 0

Polar Surface Area: 71.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.57

CX Basic pKa:

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: 1.96

References

1. Chu M, Patel MG, Pai J, Das PR, Puar MS.  (1996)  Sch 53823 and Sch 53825, novel fungal metabolites with phospholipase D inhibitory activity,  6  (5): [10.1016/0960-894X(96)00074-1]

2. Shan T, Tian J, Wang X, Mou Y, Mao Z, Lai D, Dai J, Peng Y, Zhou L, Wang M..  (2014)  Bioactive spirobisnaphthalenes from the endophytic fungus Berkleasmium sp.,  77  (10): [PMID:25237727] [10.1021/np400988a]

3. Jiang H, Ma SG, Li Y, Liu YB, Li L, Qu J, Yu SS..  (2016)  Spirobisnaphthalenes and lactones from the seeds of Strychnos angustiflora with potential anti-inflammatory activity.,  26  (19): [PMID:27592135] [10.1016/j.bmcl.2016.08.019]

Source

Source(1):

• Scientific Literature