ID: ALA442494

Max Phase: Preclinical

Molecular Formula: C137H207N41O39S3

Molecular Weight: 3148.61

Molecule Type: Protein

Representations

Synonyms (1): SRIF-28
Synonyms from Alternative Forms(1):

Canonical SMILES:  CSCC[C@H](NC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H]1CSSC[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CCCCN)NC1=O

Standard InChI:  InChI=1S/C137H207N41O39S3/c1-69(154-113(194)82(37-19-22-47-138)159-115(196)85(40-25-50-149-136(145)146)160-118(199)87(44-45-106(188)189)163-116(197)86(41-26-51-150-137(147)148)164-130(211)101-43-27-52-177(101)133(214)72(4)156-114(195)88(46-54-218-7)158-110(191)71(3)155-129(210)100-42-28-53-178(100)134(215)95(61-104(144)186)171-126(207)96(65-180)172-124(205)93(59-102(142)184)165-111(192)70(2)153-112(193)80(141)64-179)109(190)152-63-105(187)157-98-67-219-220-68-99(135(216)217)174-127(208)97(66-181)173-132(213)108(74(6)183)176-125(206)91(57-77-33-15-10-16-34-77)170-131(212)107(73(5)182)175-119(200)84(39-21-24-49-140)161-122(203)92(58-78-62-151-81-36-18-17-35-79(78)81)168-121(202)90(56-76-31-13-9-14-32-76)166-120(201)89(55-75-29-11-8-12-30-75)167-123(204)94(60-103(143)185)169-117(198)83(162-128(98)209)38-20-23-48-139/h8-18,29-36,62,69-74,80,82-101,107-108,151,179-183H,19-28,37-61,63-68,138-141H2,1-7H3,(H2,142,184)(H2,143,185)(H2,144,186)(H,152,190)(H,153,193)(H,154,194)(H,155,210)(H,156,195)(H,157,187)(H,158,191)(H,159,196)(H,160,199)(H,161,203)(H,162,209)(H,163,197)(H,164,211)(H,165,192)(H,166,201)(H,167,204)(H,168,202)(H,169,198)(H,170,212)(H,171,207)(H,172,205)(H,173,213)(H,174,208)(H,175,200)(H,176,206)(H,188,189)(H,216,217)(H4,145,146,149)(H4,147,148,150)/t69-,70-,71-,72-,73+,74+,80-,82-,83+,84-,85-,86-,87-,88-,89+,90-,91-,92+,93-,94-,95-,96-,97-,98+,99-,100-,101-,107+,108+/m0/s1

Standard InChI Key:  GGYTXJNZMFRSLX-OKOIUDDXSA-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: 3148.61

Molecular Weight (Monoisotopic): 3146.4637

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. Rajeswaran WG, Hocart SJ, Murphy WA, Taylor JE, Coy DH..  (2001)  Highly potent and subtype selective ligands derived by N-methyl scan of a somatostatin antagonist.,  44  (8): [PMID:11312929] [10.1021/jm0005048]

2. Choi KI, Cha JH, Cho YS, Pae AN, Jin C, Yook J, Cheon HG, Jeong D, Kong JY, Koh HY..  (1999)  Binding affinities of 3-(3-phenylisoxazol-5-yl)methylidene-1-azabicycles to acetylcholine receptors.,  9  (19): [PMID:10522693] [10.1016/s0960-894x(99)00477-1]

3. Erchegyi J, Hoeger CA, Low W, Hoyer D, Waser B, Eltschinger V, Schaer JC, Cescato R, Reubi JC, Rivier JE..  (2005)  Somatostatin receptor 1 selective analogues: 2. N(alpha)-Methylated scan.,  48  (2): [PMID:15658864] [10.1021/jm049520l]

4. D'Addona D, Carotenuto A, Novellino E, Piccand V, Reubi JC, Di Cianni A, Gori F, Papini AM, Ginanneschi M..  (2008)  Novel sst5-selective somatostatin dicarba-analogues: synthesis and conformation-affinity relationships.,  51  (3): [PMID:18210999] [10.1021/jm070886i]

5. Cescato R, Erchegyi J, Waser B, Piccand V, Maecke HR, Rivier JE, Reubi JC..  (2008)  Design and in vitro characterization of highly sst2-selective somatostatin antagonists suitable for radiotargeting.,  51  (13): [PMID:18543899] [10.1021/jm701618q]

6. Feytens D, De Vlaeminck M, Cescato R, Tourwé D, Reubi JC..  (2009)  Highly potent 4-amino-indolo[2,3-c]azepin-3-one-containing somatostatin mimetics with a range of sst receptor selectivities.,  52  (1): [PMID:19067538] [10.1021/jm801205x]

7. Grace CR, Erchegyi J, Samant M, Cescato R, Piccand V, Riek R, Reubi JC, Rivier JE..  (2008)  Ring size in octreotide amide modulates differently agonist versus antagonist binding affinity and selectivity.,  51  (9): [PMID:18410083] [10.1021/jm701445q]

8. Erchegyi J, Grace CR, Samant M, Cescato R, Piccand V, Riek R, Reubi JC, Rivier JE..  (2008)  Ring size of somatostatin analogues (ODT-8) modulates receptor selectivity and binding affinity.,  51  (9): [PMID:18410084] [10.1021/jm701444y]

9. Erchegyi J, Cescato R, Grace CR, Waser B, Piccand V, Hoyer D, Riek R, Rivier JE, Reubi JC..  (2009)  Novel, potent, and radio-iodinatable somatostatin receptor 1 (sst1) selective analogues.,  52  (9): [PMID:19351180] [10.1021/jm801314f]

10. Di Cianni A, Carotenuto A, Brancaccio D, Novellino E, Reubi JC, Beetschen K, Papini AM, Ginanneschi M..  (2010)  Novel octreotide dicarba-analogues with high affinity and different selectivity for somatostatin receptors.,  53  (16): [PMID:20666484] [10.1021/jm1005868]

11. Chatterjee J, Laufer B, Beck JG, Helyes Z, Pintér E, Szolcsányi J, Horvath A, Mandl J, Reubi JC, Kéri G, Kessler H..  (2011)  N-Methylated sst2 Selective Somatostatin Cyclic Peptide Analogue as a Potent Candidate for Treating Neurogenic Inflammation.,  2  (7): [PMID:24900340] [10.1021/ml200032v]

Source

Source(1):

• Scientific Literature