8'-hydroxy-4,4,4',4',8',13'-hexamethylspiro[9,10-dihydro-4H,8H-[1,4]dioxepino[2,3-g]indole-8,3'-(11',13'-diazatetracyclo[5.5.2.01,5.07,11]tetradecane)]-9,14'-dione

ID: ALA462728

Chembl Id: CHEMBL462728

PubChem CID: 44584122

Max Phase: Preclinical

Molecular Formula: C28H35N3O5

Molecular Weight: 493.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paraherquamide | CHEMBL462728

Canonical SMILES:  CN1C(=O)[C@]23C[C@H]4C(C)(C)[C@@]5(C[C@@]41CN2CC[C@@]3(C)O)C(=O)Nc1cc2c(cc15)OC(C)(C)C=CO2

Standard InChI:  InChI=1S/C28H35N3O5/c1-23(2)8-10-35-18-12-17-16(11-19(18)36-23)27(21(32)29-17)14-26-15-31-9-7-25(5,34)28(31,22(33)30(26)6)13-20(26)24(27,3)4/h8,10-12,20,34H,7,9,13-15H2,1-6H3,(H,29,32)/t20-,25+,26+,27+,28-/m0/s1

Standard InChI Key:  NERDPEDPLXOGNU-MAWBUHMLSA-N

Alternative Forms

1. Parent:

   

   ALA462728

   PARAHERQUAMIDE

Molecule Features

Natural Product: No

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: 493.60

Molecular Weight (Monoisotopic): 493.2577

AlogP: 2.80

#Rotatable Bonds: ┄

Polar Surface Area: 91.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 8.21

CX LogP: 1.61

CX LogD: 0.74

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.58

Np Likeness Score: 2.22

References

1. Sinclair PJ, Schaeffer JM, Shoop W, Mrozik H.  (1992)  The preparation and utilization of paraherquamide-2-O-methyl imidate in the synthesis of 14-O-substituted paraherquamide derivatives,  2  (12): [10.1016/S0960-894X(00)80438-2]

2. Ondeyka JG, Byrne K, Vesey D, Zink DL, Shoop WL, Goetz MA, Singh SB..  (2003)  Nodulisporic acids C, C1, and C2: a series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.,  66  (1): [PMID:12542359] [10.1021/np020339u]

Source

Source(1):

• Scientific Literature