Orniplabin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563730

CAS#: 733805-92-0

Description: Orniplabin, also known as SMTP-7 is a dual inhibitor of thrombolysis and soluble epoxide hydrolase. SMTP-7 promotes thrombolysis and inhibits soluble epoxide hydrolase.


Chemical Structure

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Orniplabin
CAS# 733805-92-0

Theoretical Analysis

MedKoo Cat#: 563730
Name: Orniplabin
CAS#: 733805-92-0
Chemical Formula: C51H68N2O10
Exact Mass: 868.4874
Molecular Weight: 869.1
Elemental Analysis: C, 70.48; H, 7.89; N, 3.22; O, 18.41

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 733805-92-0    

Synonym: SMTP-7; SMTP 7; SMTP7; SMTP-7L; SMTP 7L; SMTP7L; Orniplabin;

IUPAC/Chemical Name: (S)-2,5-bis((2S,3S)-2-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-2-methyl-7-oxo-3,4,7,9-tetrahydropyrano[2,3-e]isoindol-8(2H)-yl)pentanoic acid

InChi Key: CRNDCHORWGDFGR-PXTWCNKMSA-N

InChi Code: 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

SMILES Code: O=C(O)[C@@H](N(CC1=C2C=C(O)C3=C1O[C@@](C)(CC/C=C(C)/CC/C=C(C)/C)[C@@H](O)C3)C2=O)CCCN(CC4=C5C=C(O)C6=C4O[C@@](C)(CC/C=C(C)/CC/C=C(C)/C)[C@@H](O)C6)C5=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 869.1 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Huang Y, Ohta Y, Shang J, Morihara R, Nakano Y, Fukui Y, Liu X, Shi X, Feng T, Yamashita T, Sato K, Takemoto M, Hishikawa N, Suzuki E, Hasumi K, Abe K. Antineuroinflammatory Effect of SMTP-7 in Ischemic Mice. J Stroke Cerebrovasc Dis. 2018 Aug 2. pii: S1052-3057(18)30364-1. doi: 10.1016/j.jstrokecerebrovasdis.2018.06.039. [Epub ahead of print] PubMed PMID: 30078758.

2: Shibata K, Hashimoto T, Hasumi K, Honda K, Nobe K. Evaluation of the effects of a new series of SMTPs in the acetic acid-induced embolic cerebral infarct mouse model. Eur J Pharmacol. 2018 Jan 5;818:221-227. doi: 10.1016/j.ejphar.2017.10.055. Epub 2017 Oct 28. PubMed PMID: 29107671.

3: Matsumoto N, Suzuki E, Tsujihara K, Nishimura Y, Hasumi K. Structure-activity relationships of the plasminogen modulator SMTP with respect to the inhibition of soluble epoxide hydrolase. J Antibiot (Tokyo). 2015 Nov;68(11):685-90. doi: 10.1038/ja.2015.58. Epub 2015 May 13. PubMed PMID: 25966853.

4: Matsumoto N, Suzuki E, Ishikawa M, Shirafuji T, Hasumi K. Soluble epoxide hydrolase as an anti-inflammatory target of the thrombolytic stroke drug SMTP-7. J Biol Chem. 2014 Dec 26;289(52):35826-38. doi: 10.1074/jbc.M114.588087. Epub 2014 Oct 31. PubMed PMID: 25361765; PubMed Central PMCID: PMC4276851.

5: Ito A, Niizuma K, Shimizu H, Fujimura M, Hasumi K, Tominaga T. SMTP-7, a new thrombolytic agent, decreases hemorrhagic transformation after transient middle cerebral artery occlusion under warfarin anticoagulation in mice. Brain Res. 2014 Aug 26;1578:38-48. doi: 10.1016/j.brainres.2014.07.004. Epub 2014 Jul 9. PubMed PMID: 25016287.

6: Hashimoto T, Shibata K, Ohata H, Hasumi K, Honda K. Altered gene expression in an embolic stroke model after thrombolysis with tissue plasminogen activator and Stachybotrys microspora triprenyl phenol-7. J Pharmacol Sci. 2014;125(1):99-106. Epub 2014 May 1. PubMed PMID: 24784876.

7: Koyanagi K, Narasaki R, Yamamichi S, Suzuki E, Hasumi K. Mechanism of the action of SMTP-7, a novel small-molecule modulator of plasminogen activation. Blood Coagul Fibrinolysis. 2014 Jun;25(4):316-21. doi: 10.1097/MBC.0000000000000032. PubMed PMID: 24784315.

8: Sawada H, Nishimura N, Suzuki E, Zhuang J, Hasegawa K, Takamatsu H, Honda K, Hasumi K. SMTP-7, a novel small-molecule thrombolytic for ischemic stroke: a study in rodents and primates. J Cereb Blood Flow Metab. 2014 Feb;34(2):235-41. doi: 10.1038/jcbfm.2013.191. Epub 2013 Nov 6. PubMed PMID: 24192639; PubMed Central PMCID: PMC3915202.

9: Kemmochi S, Hayashi H, Taniai E, Hasumi K, Sugita-Konishi Y, Kumagai S, Mitsumori K, Shibutani M. Protective Effect of Stachybotrys microspora Triprenyl Phenol-7on the Deposition of IgA to the Glomerular Mesangium in Nivalenol-induced IgA Nephropathy Using BALB/c Mice. J Toxicol Pathol. 2012 Jun;25(2):149-54. doi: 10.1293/tox.25.149. PubMed PMID: 22907981; PubMed Central PMCID: PMC3392907.

10: Koide H, Hasegawa K, Nishimura N, Narasaki R, Hasumi K. A new series of the SMTP plasminogen modulators with a phenylamine-based side chain. J Antibiot (Tokyo). 2012 Jul;65(7):361-7. doi: 10.1038/ja.2012.29. Epub 2012 Apr 18. PubMed PMID: 22511228.

11: Hu W, Narasaki R, Nishimura N, Hasumi K. SMTP (Stachybotrys microspora triprenyl phenol) enhances clot clearance in a pulmonary embolism model in rats. Thromb J. 2012 Jan 9;10(1):2. doi: 10.1186/1477-9560-10-2. PubMed PMID: 22230042; PubMed Central PMCID: PMC3310738.

12: Akamatsu Y, Saito A, Fujimura M, Shimizu H, Mekawy M, Hasumi K, Tominaga T. Stachybotrys microspora triprenyl phenol-7, a novel fibrinolytic agent, suppresses superoxide production, matrix metalloproteinase-9 expression, and thereby attenuates ischemia/reperfusion injury in rat brain. Neurosci Lett. 2011 Oct 3;503(2):110-4. doi: 10.1016/j.neulet.2011.08.018. Epub 2011 Aug 17. PubMed PMID: 21871536.

13: Shibata K, Hashimoto T, Nobe K, Hasumi K, Honda K. Neuroprotective mechanisms of SMTP-7 in cerebral infarction model in mice. Naunyn Schmiedebergs Arch Pharmacol. 2011 Jul;384(1):103-8. doi: 10.1007/s00210-011-0642-x. Epub 2011 May 2. PubMed PMID: 21533990.

14: Miyazaki T, Kimura Y, Ohata H, Hashimoto T, Shibata K, Hasumi K, Honda K. Distinct effects of tissue-type plasminogen activator and SMTP-7 on cerebrovascular inflammation following thrombolytic reperfusion. Stroke. 2011 Apr;42(4):1097-104. doi: 10.1161/STROKEAHA.110.598359. Epub 2011 Feb 24. PubMed PMID: 21350203.

15: Hashimoto T, Shibata K, Nobe K, Hasumi K, Honda K. A novel embolic model of cerebral infarction and evaluation of Stachybotrys microspora triprenyl phenol-7 (SMTP-7), a novel fungal triprenyl phenol metabolite. J Pharmacol Sci. 2010;114(1):41-9. Epub 2010 Aug 10. PubMed PMID: 20703011.

16: Shibata K, Hashimoto T, Nobe K, Hasumi K, Honda K. A novel finding of a low-molecular-weight compound, SMTP-7, having thrombolytic and anti-inflammatory effects in cerebral infarction of mice. Naunyn Schmiedebergs Arch Pharmacol. 2010 Sep;382(3):245-53. doi: 10.1007/s00210-010-0542-5. Epub 2010 Aug 3. PubMed PMID: 20680247; PubMed Central PMCID: PMC2926440.

17: Huttunen K, Pelkonen J, Nielsen KF, Nuutinen U, Jussila J, Hirvonen MR. Synergistic interaction in simultaneous exposure to Streptomyces californicus and Stachybotrys chartarum. Environ Health Perspect. 2004 May;112(6):659-65. PubMed PMID: 15121507; PubMed Central PMCID: PMC1241958.

18: Hu W, Ohyama S, Hasumi K. Activation of fibrinolysis by SMTP-7 and -8, novel staplabin analogs with a pseudosymmetric structure. J Antibiot (Tokyo). 2000 Mar;53(3):241-7. PubMed PMID: 10819294.