ID: ALA604166

Max Phase: Preclinical

Molecular Formula: C111H182N34O41S6

Molecular Weight: 2841.28

Molecule Type: Protein

Representations

Synonyms (1): Kalata B1
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)C[C@@H]1NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)CNC(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C111H182N34O41S6/c1-45(2)30-59-109(185)144-28-17-21-69(144)100(176)137-80(47(5)6)102(178)130-61(39-187)88(164)119-35-73(155)122-55(22-24-77(159)160)90(166)139-84(51(11)149)106(182)134-65(43-191)96(172)136-79(46(3)4)101(177)121-33-72(154)117-34-76(158)135-82(49(9)147)104(180)132-63(41-189)93(169)128-58(32-71(113)153)91(167)142-86(53(13)151)110(186)145-29-15-19-67(145)98(174)120-37-75(157)124-62(40-188)95(171)140-85(52(12)150)107(183)133-64(42-190)94(170)129-60(38-146)92(168)126-56(23-25-78(161)162)108(184)143-27-16-20-68(143)99(175)138-81(48(7)8)103(179)131-66(44-192)97(173)141-83(50(10)148)105(181)125-54(18-14-26-116-111(114)115)89(165)127-57(31-70(112)152)87(163)118-36-74(156)123-59/h45-69,79-86,146-151,187-192H,14-44H2,1-13H3,(H2,112,152)(H2,113,153)(H,117,154)(H,118,163)(H,119,164)(H,120,174)(H,121,177)(H,122,155)(H,123,156)(H,124,157)(H,125,181)(H,126,168)(H,127,165)(H,128,169)(H,129,170)(H,130,178)(H,131,179)(H,132,180)(H,133,183)(H,134,182)(H,135,158)(H,136,172)(H,137,176)(H,138,175)(H,139,166)(H,140,171)(H,141,173)(H,142,167)(H,159,160)(H,161,162)(H4,114,115,116)/t49-,50-,51-,52-,53-,54+,55+,56+,57+,58+,59+,60+,61+,62+,63+,64+,65+,66+,67+,68+,69+,79+,80+,81+,82+,83+,84+,85+,86+/m1/s1

Standard InChI Key:  GQMIKDMGMMDPCG-JBVIHKKMSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 2841.28

Molecular Weight (Monoisotopic): 2839.1526

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Gunasekera S, Foley FM, Clark RJ, Sando L, Fabri LJ, Craik DJ, Daly NL..  (2008)  Engineering stabilized vascular endothelial growth factor-A antagonists: synthesis, structural characterization, and bioactivity of grafted analogues of cyclotides.,  51  (24): [PMID:19053834] [10.1021/jm800704e]

2. Chen B, Colgrave ML, Wang C, Craik DJ..  (2006)  Cycloviolacin H4, a hydrophobic cyclotide from Viola hederaceae.,  69  (1): [PMID:16441062] [10.1021/np050317i]

3. Gao Y, Cui T, Lam Y..  (2010)  Synthesis and disulfide bond connectivity-activity studies of a kalata B1-inspired cyclopeptide against dengue NS2B-NS3 protease.,  18  (3): [PMID:20042339] [10.1016/j.bmc.2009.12.026]

4. Ireland DC, Clark RJ, Daly NL, Craik DJ..  (2010)  Isolation, sequencing, and structure-activity relationships of cyclotides.,  73  (9): [PMID:20718473] [10.1021/np1000413]

5. Gründemann C, Koehbach J, Huber R, Gruber CW..  (2012)  Do plant cyclotides have potential as immunosuppressant peptides?,  75  (2): [PMID:22272797] [10.1021/np200722w]

6. Hellinger R, Koehbach J, Puigpinós A, Clark RJ, Tarragó T, Giralt E, Gruber CW..  (2015)  Inhibition of Human Prolyl Oligopeptidase Activity by the Cyclotide Psysol 2 Isolated from Psychotria solitudinum.,  78  (5): [PMID:25894999] [10.1021/np501061t]

Source

Source(1):

• Scientific Literature