cyanopeptolin S

ID: ALA1076838

Chembl Id: CHEMBL1076838

PubChem CID: 46881045

Max Phase: Preclinical

Molecular Formula: C40H63N9O14S

Molecular Weight: 926.06

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cyanopeptolin S | Cyanopeptolin S|CHEMBL1076838

Canonical SMILES:  CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H]([C@@H](C)CC)N2C(=O)[C@H](CC[C@H]2O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](O)COS(=O)(=O)O)[C@@H](C)OC1=O

Standard InChI:  InChI=1S/C40H63N9O14S/c1-7-21(3)30-39(58)63-23(5)31(47-35(54)28(50)20-62-64(59,60)61)36(55)44-25(15-12-18-43-40(41)42)33(52)45-26-16-17-29(51)49(37(26)56)32(22(4)8-2)38(57)48(6)27(34(53)46-30)19-24-13-10-9-11-14-24/h9-11,13-14,21-23,25-32,50-51H,7-8,12,15-20H2,1-6H3,(H,44,55)(H,45,52)(H,46,53)(H,47,54)(H4,41,42,43)(H,59,60,61)/t21-,22-,23+,25-,26-,27-,28+,29+,30-,31-,32-/m0/s1

Standard InChI Key:  LQLBUPVHKUILGJ-LKAQEJCWSA-N

Alternative Forms

1. Parent:

   

   ALA1076838

   CYANOPEPTOLIN S

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: 926.06

Molecular Weight (Monoisotopic): 925.4215

AlogP: -2.21

#Rotatable Bonds: 15

Polar Surface Area: 349.28

Molecular Species: ZWITTERION

HBA: 14

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -2.16

CX Basic pKa: 11.40

CX LogP: -1.73

CX LogD: -1.73

Aromatic Rings: 1

Heavy Atoms: 64

QED Weighted: 0.03

Np Likeness Score: 1.36

References

1. Linington RG, Edwards DJ, Shuman CF, McPhail KL, Matainaho T, Gerwick WH..  (2008)  Symplocamide A, a potent cytotoxin and chymotrypsin inhibitor from the marine Cyanobacterium Symploca sp.,  71  (1): [PMID:18163584] [10.1021/np070280x]

2. Zafrir E, Carmeli S..  (2010)  Micropeptins from an Israeli fishpond water bloom of the cyanobacterium Microcystis sp.,  73  (3): [PMID:20028081] [10.1021/np900546u]

3. Adiv S, Carmeli S..  (2013)  Protease inhibitors from Microcystis aeruginosa bloom material collected from the Dalton Reservoir, Israel.,  76  (12): [PMID:24261937] [10.1021/np4006844]

Source

Source(1):

• Scientific Literature