lyngbyastatin 7

ID: ALA398726

Chembl Id: CHEMBL398726

PubChem CID: 23657291

Max Phase: Preclinical

Molecular Formula: C48H66N8O12

Molecular Weight: 947.10

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lyngbyastatin 7 | lyngbyastatin 7|(2S)-N-[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-(hexanoylamino)pentanediamide|CHEMBL398726|CHEBI:198536|DTXSID501047264|BDBM50429202

Canonical SMILES:  C/C=C1\NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)CCCCC)[C@@H](C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2ccc(O)cc2)N(C)C(=O)[C@H](Cc2ccccc2)N2C(=O)[C@H](CC[C@H]2O)NC1=O

Standard InChI:  InChI=1S/C48H66N8O12/c1-7-9-11-16-38(59)50-33(21-23-37(49)58)43(62)54-41-28(5)68-48(67)40(27(3)4)53-44(63)35(25-30-17-19-31(57)20-18-30)55(6)47(66)36(26-29-14-12-10-13-15-29)56-39(60)24-22-34(46(56)65)52-42(61)32(8-2)51-45(41)64/h8,10,12-15,17-20,27-28,33-36,39-41,57,60H,7,9,11,16,21-26H2,1-6H3,(H2,49,58)(H,50,59)(H,51,64)(H,52,61)(H,53,63)(H,54,62)/b32-8-/t28-,33+,34+,35+,36+,39-,40+,41+/m1/s1

Standard InChI Key:  DZIGKKCSWPSVIO-SWEGFNRNSA-N

Alternative Forms

1. Parent:

   

   ALA398726

   LYNGBYASTATIN 7

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: 947.10

Molecular Weight (Monoisotopic): 946.4800

AlogP: 0.72

#Rotatable Bonds: 15

Polar Surface Area: 295.97

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 2

Heavy Atoms: 68

QED Weighted: 0.07

Np Likeness Score: 1.00

References

1. Taori K, Matthew S, Rocca JR, Paul VJ, Luesch H..  (2007)  Lyngbyastatins 5-7, potent elastase inhibitors from Floridian marine cyanobacteria, Lyngbya spp.,  70  (10): [PMID:17910513] [10.1021/np0702436]

2. Taori K, Paul VJ, Luesch H..  (2008)  Kempopeptins A and B, serine protease inhibitors with different selectivity profiles from a marine cyanobacterium, Lyngbya sp.,  71  (9): [PMID:18693761] [10.1021/np8002172]

3. Salvador LA, Taori K, Biggs JS, Jakoncic J, Ostrov DA, Paul VJ, Luesch H..  (2013)  Potent elastase inhibitors from cyanobacteria: structural basis and mechanisms mediating cytoprotective and anti-inflammatory effects in bronchial epithelial cells.,  56  (3): [PMID:23350733] [10.1021/jm3017305]

4. Luo D, Luesch H..  (2020)  Ahp-Cyclodepsipeptide Inhibitors of Elastase: Lyngbyastatin 7 Stability, Scalable Synthesis, and Focused Library Analysis.,  11  (4): [PMID:32292544] [10.1021/acsmedchemlett.9b00473]

5. Chen QY, Luo D, Seabra GM, Luesch H..  (2020)  Ahp-Cyclodepsipeptides as tunable inhibitors of human neutrophil elastase and kallikrein 7: Total synthesis of tutuilamide A, serine protease selectivity profile and comparison with lyngbyastatin 7.,  28  (23.0): [PMID:33002682] [10.1016/j.bmc.2020.115756]

Source

Source(1):

• Scientific Literature