Details of the Drug

General Information of Drug (ID: DM9GRTK)

Drug Name
ACYLINE
Synonyms
Acyline; UNII-S3439D3B35; CHEMBL262747; S3439D3B35; BDBM50102456; DB11906; D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-(acetylamino)-L-phenylalanyl-4-(acetylamino)-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-; Z-3146; Ac-D-Nal-[D-(pCl)Phe]-D-Pal-Ser-[Aph(Ac)]-D-[Aph(Ac)]-Leu-ILys-Pro-DAla-NH2
Indication
Disease Entry ICD 11 Status REF
Prostate cancer 2C82.0 Phase 2 [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1533.2
Logarithm of the Partition Coefficient (xlogp) 5.4
Rotatable Bond Count (rotbonds) 40
Hydrogen Bond Donor Count (hbonddonor) 14
Hydrogen Bond Acceptor Count (hbondacc) 16
Chemical Identifiers
Formula
C80H102ClN15O14
IUPAC Name
(2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-acetamidophenyl)propanoyl]amino]-3-(4-acetamidophenyl)propanoyl]amino]-4-methylpentanoyl]amino]-6-(propan-2-ylamino)hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
Canonical SMILES
C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=C(C=C2)NC(=O)C)NC(=O)[C@H](CC3=CC=C(C=C3)NC(=O)C)NC(=O)[C@H](CO)NC(=O)[C@@H](CC4=CN=CC=C4)NC(=O)[C@@H](CC5=CC=C(C=C5)Cl)NC(=O)[C@@H](CC6=CC7=CC=CC=C7C=C6)NC(=O)C
InChI
InChI=1S/C80H102ClN15O14/c1-46(2)37-63(72(102)89-62(18-11-12-35-84-47(3)4)80(110)96-36-14-19-70(96)79(109)85-48(5)71(82)101)90-74(104)66(40-53-23-30-60(31-24-53)86-49(6)98)92-76(106)67(41-54-25-32-61(33-26-54)87-50(7)99)94-78(108)69(45-97)95-77(107)68(43-56-15-13-34-83-44-56)93-75(105)65(39-52-21-28-59(81)29-22-52)91-73(103)64(88-51(8)100)42-55-20-27-57-16-9-10-17-58(57)38-55/h9-10,13,15-17,20-34,38,44,46-48,62-70,84,97H,11-12,14,18-19,35-37,39-43,45H2,1-8H3,(H2,82,101)(H,85,109)(H,86,98)(H,87,99)(H,88,100)(H,89,102)(H,90,104)(H,91,103)(H,92,106)(H,93,105)(H,94,108)(H,95,107)/t48-,62+,63+,64-,65-,66-,67+,68-,69+,70+/m1/s1
InChIKey
ZWNUQDJANZGVFO-YHSALVGYSA-N
Cross-matching ID
PubChem CID
16137348
ChEBI ID
CHEMBL262747
CAS Number
170157-13-8
UNII
S3439D3B35
DrugBank ID
DB11906
TTD ID
D0F0UT
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gonadotropin-releasing hormone receptor (GNRHR) TT8R70G GNRHR_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein sigma (SFN) OTLJCZ1U 1433S_HUMAN Gene/Protein Processing [3]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [3]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [3]
Alpha-1-acid glycoprotein 2 (ORM2) OTRJGZP8 A1AG2_HUMAN Gene/Protein Processing [3]
AN1-type zinc finger protein 5 OT4F47U6 ZFAN5_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 1 (CCL1) OT23NON8 CCL1_HUMAN Gene/Protein Processing [3]
CCN family member 2 (CCN2) OTC39NSU CCN2_HUMAN Gene/Protein Processing [3]
Conserved oligomeric Golgi complex subunit 4 (COG4) OT6U94UE COG4_HUMAN Gene/Protein Processing [3]
Cysteine-rich secretory protein LCCL domain-containing 1 (CRISPLD1) OT38HXJP CRLD1_HUMAN Gene/Protein Processing [3]
DmX-like protein 1 (DMXL1) OTWVL31L DMXL1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02147964) ITT-5 Mechanisms of Spermatogenesis. U.S. National Institutes of Health.
2 Structure-activity relationship studies of gonadotropin-releasing hormone antagonists containing S-aryl/alkyl norcysteines and their oxidized deriv... J Med Chem. 2007 May 3;50(9):2067-77.
3 Intraprostatic androgens and androgen-regulated gene expression persist after testosterone suppression: therapeutic implications for castration-resistant prostate cancer. Cancer Res. 2007 May 15;67(10):5033-41.