BU08028   Click here for help

GtoPdb Ligand ID: 9294

Synonyms: compound 1b [PMID: 21866885]
Compound class: Synthetic organic
Comment: BU08028 is a novel research compound that provides the pain relief of opiates, without their addictive effects in mouse models of acute pain and cocaine-induced reward [1-2]. Structurally it is a derivative of buprenorphine, with only the addition of an additional methylene group at the C20 substituent. Increasing affinity for the NOP receptor is predicted to reduce the behavioural side-effects associated with buprenorphine.
Note that the compound referred to as 1b in [1] has a marginally different stereo compared to the same compound (named as BUB8028) in [2], with identical data provided for 1b and BUB8028 in both articles. Compound 1b resolves to PubChem CID 56664973. We have chosen to link to CID 50922685 as the specified stereochemistry of this is identical to that of buprenorphine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 62.16
Molecular weight 481.32
XLogP 4.13
No. Lipinski's rules broken 0
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Canonical SMILES COC12CCC3(CC1C(C(CC)(C)C)(O)C)C14C2Oc2c4c(CC3N(CC1)CC1CC1)ccc2O
Isomeric SMILES CO[C@]12CC[C@]3(C[C@@H]1[C@@](C(CC)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@H]3N(CC1)CC1CC1)ccc2O
InChI InChI=1S/C30H43NO4/c1-6-26(2,3)27(4,33)21-16-28-11-12-30(21,34-5)25-29(28)13-14-31(17-18-7-8-18)22(28)15-19-9-10-20(32)24(35-25)23(19)29/h9-10,18,21-22,25,32-33H,6-8,11-17H2,1-5H3/t21-,22-,25-,27+,28-,29+,30-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Synonyms Click here for help
compound 1b [PMID: 21866885]
Database Links Click here for help
GtoPdb PubChem SID 318164813
PubChem CID 50922685
Search Google for chemical match using the InChIKey HBENZIXOGRCSQN-VQWWACLZSA-N
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Search UniChem for chemical match using the InChIKey HBENZIXOGRCSQN-VQWWACLZSA-N
Search UniChem for chemicals with the same backbone HBENZIXOGRCSQN