SMTP-7   Click here for help

GtoPdb Ligand ID: 12300

Synonyms: Stachybotrys microspora triprenyl phenol 7 | BIIB131 | orniplabin | SMTP7 | TMS-007
Compound class: Synthetic organic
Comment: SMTP-7 is a natural triprenyl phenol that's produced by Stachybotrys microspora (a fungus) [2]. It is a complex molecule with 5 chiral centers whose absolute stereochemical configuration has been determined using microcrystal electron diffraction (MicroED) [6]. SMTP-7 produces thrombolytic [4], anti-inflammatory, and antioxidant effects. It is being considered as a clinical anti-thrombotic agent for use in stroke patients [5]. The compound has activity as a plasminogen modulator and soluble epoxide hydrolase inhibitor that may offer a novel therapeutic intervention for cardiometabolic diseases [1].
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 18
Topological polar surface area 177.3
Molecular weight 868.49
XLogP 8.7
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES C/C(=C\CC[C@]1(C)Oc2c3CN(C(=O)c3cc(c2C[C@@H]1O)O)CCC[C@H](N1Cc2c(C1=O)cc(c1c2O[C@@](C)(CC/C=C(/CCC=C(C)C)\C)[C@H](C1)O)O)C(=O)O)/CCC=C(C)C
Isomeric SMILES CC(=CCC/C(=C/CC[C@]1([C@H](Cc2c(cc3c(c2O1)CN(C3=O)CCC[C@@H](C(=O)O)N1Cc2c3c(c(cc2C1=O)O)C[C@@H]([C@](O3)(C)CC/C=C(\C)/CCC=C(C)C)O)O)O)C)/C)C
InChI InChI=1S/C51H68N2O10/c1-30(2)14-9-16-32(5)18-11-21-50(7)43(56)26-36-41(54)24-34-38(45(36)62-50)28-52(47(34)58)23-13-20-40(49(60)61)53-29-39-35(48(53)59)25-42(55)37-27-44(57)51(8,63-46(37)39)22-12-19-33(6)17-10-15-31(3)4/h14-15,18-19,24-25,40,43-44,54-57H,9-13,16-17,20-23,26-29H2,1-8H3,(H,60,61)/b32-18+,33-19+/t40-,43-,44-,50-,51-/m0/s1
InChI Key CRNDCHORWGDFGR-PXTWCNKMSA-N
No information available.
Summary of Clinical Use Click here for help
SMTP-7 (BIIB131, TMS-007) is being evaluated as a novel thrombolytic agent for the treatment of acute ischemic stroke. Results from a first-in-human study in healthy volunteers were published in late 2022 [3]. SMTP-7 was well tolerated and no serious adverse events were reported.