KBP-042

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C149H244N44O48S2
Molecular Weight	3483.9357
Optical Activity	UNSPECIFIED
Defined Stereocenters	33 / 33
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)C[C@H](NC(=O)[C@@H](NC(=O)[C@@H]1CSSC[C@H](NC(C)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1)C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC=N2)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC3=CC=C(O)C=C3)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N5CCC[C@H]5C(N)=O

InChI

InChIKey=KRSXWFQIZOXHPX-XTWYBNIISA-N

InChI=1S/C149H244N44O48S2/c1-67(2)48-89(180-143(236)115(73(13)14)188-140(233)103-65-243-242-64-102(166-79(20)200)139(232)185-100(62-195)137(230)179-96(56-109(155)205)134(227)177-93(52-71(9)10)132(225)184-101(63-196)138(231)191-118(78(19)199)146(239)186-103)121(214)161-60-111(207)167-83(28-21-23-43-150)122(215)174-92(51-70(7)8)131(224)183-99(61-194)136(229)171-86(37-40-106(152)202)124(217)169-88(39-42-112(208)209)125(218)176-91(50-69(5)6)130(223)178-94(54-81-58-159-66-163-81)133(226)168-84(29-22-24-44-151)123(216)175-90(49-68(3)4)129(222)170-87(38-41-107(153)203)127(220)190-117(77(18)198)145(238)182-98(53-80-33-35-82(201)36-34-80)148(241)193-47-27-32-105(193)141(234)172-85(30-25-45-160-149(157)158)126(219)189-116(76(17)197)144(237)181-97(57-113(210)211)135(228)187-114(72(11)12)142(235)162-59-110(206)164-74(15)120(213)173-95(55-108(154)204)128(221)165-75(16)147(240)192-46-26-31-104(192)119(156)212/h33-36,58,66-78,83-105,114-118,194-199,201H,21-32,37-57,59-65,150-151H2,1-20H3,(H2,152,202)(H2,153,203)(H2,154,204)(H2,155,205)(H2,156,212)(H,159,163)(H,161,214)(H,162,235)(H,164,206)(H,165,221)(H,166,200)(H,167,207)(H,168,226)(H,169,217)(H,170,222)(H,171,229)(H,172,234)(H,173,213)(H,174,215)(H,175,216)(H,176,218)(H,177,227)(H,178,223)(H,179,230)(H,180,236)(H,181,237)(H,182,238)(H,183,224)(H,184,225)(H,185,232)(H,186,239)(H,187,228)(H,188,233)(H,189,219)(H,190,220)(H,191,231)(H,208,209)(H,210,211)(H4,157,158,160)/t74-,75-,76+,77+,78+,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,114-,115-,116-,117-,118-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C149H244N44O48S2
Molecular Weight	3483.9357
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	33 / 33
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical
Record UNII	Q91PJI8O7T
Record Status	`FAILED`
Record Version

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Name

Type

Language

KBP 042

Preferred Name

English

KBP-042

Common Name

English

UGP 302

Code

English

UGP-302

Code

English

L-PROLINAMIDE, N-ACETYL-L-CYSTEINYL-L-SERYL-L-ASPARAGINYL-L-LEUCYL-L-SERYL-L-THREONYL-L-CYSTEINYL-L-VALYL-L-LEUCYLGLYCYL-L-LYSYL-L-LEUCYL-L-SERYL-L-GLUTAMINYL-L-.ALPHA.-GLUTAMYL-L-LEUCYL-L-HISTIDYL-L-LYSYL-L-LEUCYL-L-GLUTAMINYL-L-THREONYL-L-TYROSYL-L-PRO

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

138454980

PRIMARY

SMS_ID

300000041432

PRIMARY

CAS

1432581-36-6

PRIMARY

FDA UNII

Q91PJI8O7T

PRIMARY

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Related Record

Type

Details


					KH8JT676IM

CALCITONIN RECEPTOR

TARGET -> AGONIST

Amount:

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Type

Details


					Q91PJI8O7T

KBP-042

ACTIVE MOIETY

Comments:

In vitro, KBP-042 demonstrated superior binding affinity and activation of amylin and calcitonin receptors, and ex vivo, KBP-042 exerted inhibitory action on stimulated insulin and glucagon release from isolated islets. In vivo, KBP-042 induced a superior and pronounced reduction in food intake in conjunction with a sustained pair-fed corrected weight loss in DIO rats. Concomitantly, KBP-042 improved glucose homeostasis and reduced hyperinsulinemia and hyperleptinemia in conjunction with enhanced insulin sensitivity. In ZDF rats, KBP-042 induced a superior attenuation of diabetic hyperglycemia and alleviated impaired glucose and insulin tolerance. These results could provide the basis for oral KBP-042 as a novel therapeutic agent in type 2 diabetes.


					Q91PJI8O7T

KBP-042

ACTIVE MOIETY

Comments:

At the same time, s.c. KBP-042 suppressed the inappropriate glucagon response better than the oral formulation. Furthermore, KBP-042 was found to reduce incretins GLP-1 and GIP and considerably, improve gastric emptying, and to alleviate leptin resistance, as well as insulin resistance. In conclusion, the subcutaneous route of administration was found to have the same beneficial effects on blood glucose homeostasis and weight loss as well as resistance towards important insulin and leptin, albeit with a markedly lower variation in both exposure and biological responses. These data support the application of subcutaneously delivered peptide for mechanistic studies, and highlight the potential of developing s.c. KBP-042 as a therapy for T2D.

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