Details of the Drug

General Information of Drug (ID: DMSFLTK)

Drug Name
astressin
Synonyms
Astressin; 170809-51-5; GTPL925; CHEBI:76649; MFCD00798715; AKOS024456701; fHLLREVLE-Nle-ARAEQLAQ-cyclo-(EAHK)NRKL-Nle-EII-NH2; [D-Phe(12), Nle(21,38), Glu(30), Lys(33)]-CRF (12-41); [D-Phe12, Nle21,38, Glu30, Lys33]-Corticotropin Releasing Factor fragment 12-41; D-Phe-His-Leu-Leu-Arg-Glu-Val-Leu-Glu-Nle-Ala-Arg-Ala-Glu-Gln-Leu-Ala-Gln-cyclo-(Glu-Ala-His-Lys)-Asn-Arg-Lys-Leu-Nle-Glu-Ile-Ile-NH2; [D-Phe(12), Nle(21,38), Glu(30), Lys(33)]-corticotropin releasing factor fragment 12-41
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 3563.2
Logarithm of the Partition Coefficient (xlogp) -8
Rotatable Bond Count (rotbonds) 119
Hydrogen Bond Donor Count (hbonddonor) 51
Hydrogen Bond Acceptor Count (hbondacc) 49
Chemical Identifiers
Formula
C161H269N49O42
IUPAC Name
(4S)-5-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(3S,6S,9S,18S)-18-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S,3S)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]carbamoyl]-3-(1H-imidazol-4-ylmethyl)-6-methyl-2,5,8,12-tetraoxo-1,4,7,13-tetrazacyclooctadec-9-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]-5-oxopentanoic acid
Canonical SMILES
CCCC[C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@H]1CCC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C)CC2=CNC=N2)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3=CNC=N3)NC(=O)[C@@H](CC4=CC=CC=C4)N
InChI
InChI=1S/C161H269N49O42/c1-23-27-41-96(189-145(239)107(52-59-123(217)218)199-152(246)114(71-84(13)14)207-157(251)126(85(15)16)208-147(241)108(53-60-124(219)220)197-140(234)102(47-38-66-179-161(172)173)193-151(245)112(69-82(9)10)204-153(247)113(70-83(11)12)205-155(249)116(74-94-77-175-79-181-94)201-134(228)95(163)72-92-39-30-29-31-40-92)135(229)182-88(19)130(224)186-100(45-36-64-177-159(168)169)136(230)183-89(20)131(225)188-106(51-58-122(215)216)144(238)195-104(49-56-119(165)212)146(240)202-110(67-80(5)6)149(243)185-90(21)132(226)187-103(48-55-118(164)211)143(237)196-105-50-57-121(214)176-63-35-33-44-99(192-154(248)115(73-93-76-174-78-180-93)200-133(227)91(22)184-137(105)231)142(236)206-117(75-120(166)213)156(250)194-101(46-37-65-178-160(170)171)139(233)190-98(43-32-34-62-162)141(235)203-111(68-81(7)8)150(244)191-97(42-28-24-2)138(232)198-109(54-61-125(221)222)148(242)210-128(87(18)26-4)158(252)209-127(129(167)223)86(17)25-3/h29-31,39-40,76-91,95-117,126-128H,23-28,32-38,41-75,162-163H2,1-22H3,(H2,164,211)(H2,165,212)(H2,166,213)(H2,167,223)(H,174,180)(H,175,181)(H,176,214)(H,182,229)(H,183,230)(H,184,231)(H,185,243)(H,186,224)(H,187,226)(H,188,225)(H,189,239)(H,190,233)(H,191,244)(H,192,248)(H,193,245)(H,194,250)(H,195,238)(H,196,237)(H,197,234)(H,198,232)(H,199,246)(H,200,227)(H,201,228)(H,202,240)(H,203,235)(H,204,247)(H,205,249)(H,206,236)(H,207,251)(H,208,241)(H,209,252)(H,210,242)(H,215,216)(H,217,218)(H,219,220)(H,221,222)(H4,168,169,177)(H4,170,171,178)(H4,172,173,179)/t86-,87-,88-,89-,90-,91-,95+,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,126-,127-,128-/m0/s1
InChIKey
HPYIIXJJVYSMCV-MGDXKYBTSA-N
Cross-matching ID
PubChem CID
16133798
ChEBI ID
CHEBI:76649
TTD ID
D0L5RY

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Corticotropin-releasing factor receptor 2 (CRHR2) TTIY658 CRFR2_HUMAN Antagonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cholesterol side-chain cleavage enzyme, mitochondrial (CYP11A1) OT2NV3AN CP11A_HUMAN Gene/Protein Processing [3]
Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1) OTZKVLVJ CP17A_HUMAN Gene/Protein Processing [3]
Steroidogenic acute regulatory protein, mitochondrial (STAR) OTFEZ5AI STAR_HUMAN Gene/Protein Processing [3]
Sulfotransferase 2A1 (SULT2A1) OT0ISKQ4 ST2A1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 925).
2 Comparison of an agonist, urocortin, and an antagonist, astressin, as radioligands for characterization of corticotropin-releasing factor receptors. J Pharmacol Exp Ther. 1999 Feb;288(2):729-34.
3 Corticotropin-releasing hormone (CRH) and urocortin act through type 1 CRH receptors to stimulate dehydroepiandrosterone sulfate production in human fetal adrenal cells. J Clin Endocrinol Metab. 2005 Sep;90(9):5393-400.