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V4380

Sigma-Aldrich

[D-p-Cl-Phe6, Leu17]-Vasoactive Intestinal Peptide human, porcine, rat

≥97% (HPLC)

Synonym(s):

[D-p-Cl-Phe6, Leu17]-VIP

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About This Item

Empirical Formula (Hill Notation):
C148H239ClN44O42
CAS Number:
102805-45-8
Molecular Weight:
3342.20
MDL number:
MFCD00133956
UNSPSC Code:
12352202
PubChem Substance ID:
24900747
NACRES:
NA.32

Quality Level

100

Assay

≥97% (HPLC)

UniProt accession no.

P01282

storage temp.

−20°C

SMILES string

CCC(C)C(NC(=O)C(CO)NC(=O)C(CC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCC(N)=O)NC(=O)C(CCCCN)NC(=O)C(CCCNC(N)=N)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CC(N)=O)NC(=O)C(CC(O)=O)NC(=O)C(NC(=O)C(Cc3ccc(Cl)cc3)NC(=O)C(NC(=O)C(C)NC(=O)C(CC(O)=O)NC(=O)C(CO)NC(=O)C(N)Cc4cnc[nH]4)C(C)C)C(C)O)C(C)O)C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(N)=O)C(N)=O

InChI

1S/C148H239ClN44O42/c1-19-75(14)116(144(233)184-98(55-72(8)9)132(221)175-94(119(158)208)60-109(155)201)191-141(230)107(67-195)188-136(225)103(62-111(157)203)181-133(222)97(54-71(6)7)178-134(223)99(57-81-35-41-85(198)42-36-81)179-126(215)89(29-21-24-48-151)170-124(213)90(30-22-25-49-152)173-142(231)114(73(10)11)189-120(209)76(15)167-129(218)95(52-69(2)3)176-128(217)93(45-46-108(154)200)172-123(212)88(28-20-23-47-150)169-125(214)91(31-26-50-164-147(159)160)171-131(220)96(53-70(4)5)177-127(216)92(32-27-51-165-148(161)162)174-145(234)117(78(17)196)192-138(227)100(58-82-37-43-86(199)44-38-82)180-135(224)102(61-110(156)202)182-137(226)105(64-113(206)207)186-146(235)118(79(18)197)193-139(228)101(56-80-33-39-83(149)40-34-80)185-143(232)115(74(12)13)190-121(210)77(16)168-130(219)104(63-112(204)205)183-140(229)106(66-194)187-122(211)87(153)59-84-65-163-68-166-84/h33-44,65,68-79,87-107,114-118,194-199H,19-32,45-64,66-67,150-153H2,1-18H3,(H2,154,200)(H2,155,201)(H2,156,202)(H2,157,203)(H2,158,208)(H,163,166)(H,167,218)(H,168,219)(H,169,214)(H,170,213)(H,171,220)(H,172,212)(H,173,231)(H,174,234)(H,175,221)(H,176,217)(H,177,216)(H,178,223)(H,179,215)(H,180,224)(H,181,222)(H,182,226)(H,183,229)(H,184,233)(H,185,232)(H,186,235)(H,187,211)(H,188,225)(H,189,209)(H,190,210)(H,191,230)(H,192,227)(H,193,228)(H,204,205)(H,206,207)(H4,159,160,164)(H4,161,162,165)

InChI key

BUTRVBZATBJGPP-UHFFFAOYSA-N

Gene Information

human ... VIP(7432)

Amino Acid Sequence

His-Ser-Asp-Ala-Val-Cl-Phe-Thr-Asp-Asn-Tyr-Thr-Arg-Leu-Arg-Lys-Gln-Leu-Ala-Val-Lys-Lys-Tyr-Leu-Asn-Ser-Ile-Leu-Asn-NH2

Biochem/physiol Actions

VIP receptor antagonist

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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M Rekik et al.
The Journal of pharmacology and experimental therapeutics, 287(3), 832-838 (1998-12-24)
Distension of the small intestine can play a role in the pathogenesis of various functional intestinal disorders. This study determined the role of vasoactive intestinal polypeptide (VIP) in the adaptative response of intestinal smooth muscle to acute and chronic distension
S J Pandol et al.
The American journal of physiology, 250(4 Pt 1), G553-G557 (1986-04-01)
From structure-activity relationship studies of rat growth hormone-releasing factor (rGFR) on the vasoactive intestinal peptide (VIP) receptor in an in vitro preparation of exocrine pancreas, we predicted that [4Cl-D-Phe6, Leu17]VIP would be a competitive antagonist for the action of VIP.
F Chang et al.
Circulation research, 74(1), 157-162 (1994-01-01)
We have investigated the actions of vasoactive intestinal peptide (VIP) and neuropeptide Y (NPY) on the pacemaker current (I(f)) in canine Purkinje fibers. On voltage pulses to the middle of the I(f) activation range, VIP reversibly increases I(f), whereas NPY
L Feliciano et al.
Journal of the autonomic nervous system, 68(1-2), 78-88 (1998-04-08)
Vasoactive intestinal peptide (VIP) is present in post-ganglionic vagal nerve fibers in the coronary arteries and right ventricle but no significant amounts are found in the left ventricle. We determined the effects of VIP, released endogenously from cardiac vagal nerves
Interaction of a sulfhydryl analogue of vasoactive intestinal peptide (VIP) with murine lymphocytes.
C A Ottaway
Advances in experimental medicine and biology, 371A, 553-558 (1995-01-01)
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