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Incyclinide

CAS No.:
15866-90-7
Catalog Number:
AG00ANSL
Molecular Formula:
C19H17NO7
Molecular Weight:
371.3408
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Product Description
Catalog Number:
AG00ANSL
Chemical Name:
Incyclinide
CAS Number:
15866-90-7
Molecular Formula:
C19H17NO7
Molecular Weight:
371.3408
MDL Number:
MFCD09970644
IUPAC Name:
(4aS,5aR,12aR)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
InChI:
InChI=1S/C19H17NO7/c20-18(26)14-11(22)6-9-5-8-4-7-2-1-3-10(21)12(7)15(23)13(8)16(24)19(9,27)17(14)25/h1-3,8-9,21,23,25,27H,4-6H2,(H2,20,26)/t8-,9-,19-/m0/s1
InChI Key:
NBRQRXRBIHVLGI-OWXODZSWSA-N
SMILES:
NC(=O)C1=C(O)C[C@H]2[C@](C1=O)(O)C(=C1[C@H](C2)Cc2c(C1=O)c(O)ccc2)O
UNII:
21G64WZQ4I
Properties
Complexity:
813  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
371.101g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
371.345g/mol
Monoisotopic Mass:
371.101g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
158A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1  
Literature
Title Journal
Chemically modified tetracycline 3 prevents acute respiratory distress syndrome in a porcine model of sepsis + ischemia/reperfusion-induced lung injury. Shock (Augusta, Ga.) 20120401
Chemically modified tetracycline-3 (CMT-3): a novel inhibitor of the serine proteinase, elastase. Pharmacological research 20111201
Jack of all trades: pleiotropy and the application of chemically modified tetracycline-3 in sepsis and the acute respiratory distress syndrome (ARDS). Pharmacological research 20111201
Non-antibacterial tetracyclines modulate mediators of periodontitis and atherosclerotic cardiovascular disease: a mechanistic link between local and systemic inflammation. Pharmacological research 20111201
Phase I and pharmacokinetic study of COL-3 in patients with recurrent high-grade gliomas. Journal of neuro-oncology 20111101
A tetracycline analog improves acute respiratory distress syndrome survival in an ovine model. The Annals of thoracic surgery 20100801
Matrix metalloproteinase inhibitors reduce collagen gel contraction and alpha-smooth muscle actin expression by periodontal ligament cells. Journal of periodontal research 20090401
Tetracyclines and chemically modified tetracycline-3 (CMT-3) modulate cytokine secretion by lipopolysaccharide-stimulated whole blood. Inflammation 20090401
Human laminin-332 degradation by Candida proteinases. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology 20080701
A phase II and pharmacological study of the matrix metalloproteinase inhibitor (MMPI) COL-3 in patients with advanced soft tissue sarcomas. Investigational new drugs 20070801
Chemically modified tetracycline (COL-3) improves survival if given 12 but not 24 hours after cecal ligation and puncture. Shock (Augusta, Ga.) 20061201
Differentiated thyroid cancer cell invasion is regulated through epidermal growth factor receptor-dependent activation of matrix metalloproteinase (MMP)-2/gelatinase A. Endocrine-related cancer 20061201
The immunoglobulin A1 proteinase from Streptococcus pneumoniae is inhibited by tetracycline compounds. FEMS immunology and medical microbiology 20061101
In vitro inhibition of matrix metalloproteinase activity in tracheal epithelial lining fluid from horses with recurrent airway obstruction. American journal of veterinary research 20060701
Tetracycline analogues (doxycycline and COL-3) induce caspase-dependent and -independent apoptosis in human colon cancer cells. International journal of cancer 20060301
Rob Ashley of AmpliMed discusses the discovery and development of Imexon. Interview by Steve Carney. Drug discovery today 20051015
Chemically modified tetracyclines induce apoptosis in cultured mast cells. International immunopharmacology 20051001
Chemically modified tetracycline prevents the development of septic shock and acute respiratory distress syndrome in a clinically applicable porcine model. Shock (Augusta, Ga.) 20051001
[Role of extracellular matrix degradation enzyme for glioma invasion]. Nihon rinsho. Japanese journal of clinical medicine 20050901
Effect of chemically modified tetracycline on transforming growth factor-beta1 and caspase-3 activation in liver of septic rats. Critical care medicine 20050701
Tetracycline: from antibiotic to antisepsis. Critical care medicine 20050701
Chemically modified tetracycline (CMT)-3 inhibits histamine release and cytokine production in mast cells: possible involvement of protein kinase C. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20050701
Cyclooxygenase-2 inhibitor celecoxib augments chemotherapeutic drug-induced apoptosis by enhancing activation of caspase-3 and -9 in prostate cancer cells. International journal of cancer 20050620
A sensitive method for determination of COL-3, a chemically modified tetracycline, in human plasma using high-performance liquid chromatography and ultraviolet detection. Journal of pharmaceutical and biomedical analysis 20050401
Significant intestinal excretion, one source of variability in pharmacokinetics of COL-3, a chemically modified tetracycline. Pharmaceutical research 20050301
Role of chemically modified tetracycline on TNF-alpha and mitogen-activated protein kinases in sepsis. Shock (Augusta, Ga.) 20041101
A phase I and pharmacokinetic study of Col-3 (Metastat), an oral tetracycline derivative with potent matrix metalloproteinase and antitumor properties. Clinical cancer research : an official journal of the American Association for Cancer Research 20041001
Transactivator mutants with altered effector specificity allow selective regulation of two genes by tetracycline variants. Gene 20040428
Levels and molecular forms of MMP-7 (matrilysin-1) and MMP-8 (collagenase-2) in diseased human peri-implant sulcular fluid. Journal of periodontal research 20031201
A nonantibiotic chemically modified tetracycline (CMT-3) inhibits intimal thickening. The American journal of pathology 20031001
Factors involved in the pharmacokinetics of COL-3, a matrix metalloproteinase inhibitor, in patients with refractory metastatic cancer: clinical and experimental studies. Journal of clinical pharmacology 20031001
Inhibition of matrix metalloproteinases by chemically modified tetracyclines in sepsis. Shock (Augusta, Ga.) 20030901
Quantification of 6-deoxy-6-demethyl-4-dedimethylaminotetracycline (COL-3) in human plasma using liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030825
Metalloproteinase inhibition reduces lung injury and improves survival after cecal ligation and puncture in rats. The Journal of surgical research 20030515
Cleaning up the environment. Drug discovery today 20030201
Targeting the tumor microenvironment with chemically modified tetracyclines: inhibition of laminin 5 gamma2 chain promigratory fragments and vasculogenic mimicry. Molecular cancer therapeutics 20021101
A chemically modified tetracycline (CMT-3) is a new antifungal agent. Antimicrobial agents and chemotherapy 20020501
Inhibition of cell proliferation, invasion, tumor growth and metastasis by an oral non-antimicrobial tetracycline analog (COL-3) in a metastatic prostate cancer model. International journal of cancer 20020310
Matrix metalloproteinase inhibitor COL-3 in the treatment of AIDS-related Kaposi's sarcoma: a phase I AIDS malignancy consortium study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020101
Inhibition of proteolytic, serpinolytic, and progelatinase-b activation activities of periodontopathogens by doxycycline and the non-antimicrobial chemically modified tetracycline derivatives. Journal of periodontology 20020101
Metalloproteinase inhibition prevents acute respiratory distress syndrome. The Journal of surgical research 20010801
Reversible sideroblastic anemia associated with the tetracycline analogue COL-3. American journal of hematology 20010501
Drug-induced lupus associated with COL-3: report of 3 cases. Archives of dermatology 20010401
Development of matrix metalloproteinase inhibitors in cancer therapy. Journal of the National Cancer Institute 20010207
Biodistribution of radiolabeled [(3)H] CMT-3 in rats. Current medicinal chemistry 20010201
CMT-3, a non-antimicrobial tetracycline (TC), inhibits MT1-MMP activity: relevance to cancer. Current medicinal chemistry 20010201
Cytotoxic activity and inhibition of tumor cell invasion by derivatives of a chemically modified tetracycline CMT-3 (COL-3). Current medicinal chemistry 20010201
Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity. Current medicinal chemistry 20010201
Properties