Seocalcitol

HCID 5288149CAS 134404-52-7
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Grundinformationen

Standard-SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/C=C/C(O)(CC)CC)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChIKey
LVLLALCJVJNGQQ-SEODYNFXSA-N
Summenformel
C30H46O3
Durchschnittliche Molmasse
454,7 g/mol
Monoisotopische Masse
454,34469533

Überblick

Seocalcitol is a vitamin D3 analogue with potential antineoplastic activity. Seocalcitol binds to and activates the vitamin D receptor, a cytoplasmic polypeptide expressed in normal vitamin D responsive tissues, but also overexpressed in certain cancers including hepatocellular carcinoma and pancreatic cancer. Mediated through vitamin D receptor, this agent induces cancer cell differentiation, inhibits cancer cell growth and induces apoptosis. In addition, seocalcitol may also induce growth arrest and apoptosis independent of vitamin D receptor activation through mechanisms that are not fully elucidated.

Namen und Bezeichner

Bevorzugter Name
Seocalcitol
IUPAC
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,3E,5E)-7-ethyl-7-hydroxynona-3,5-dien-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
Englischer Name
Seocalcitol
Summenformel
C30H46O3
Molmasse
454.68

Namen und Synonyme

Seocalcitol134404-52-7EB-1089CB-1089DTXSID601025740Q0OZ0D9223(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,3E,5E)-7-ethyl-7-hydroxynona-3,5-dien-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol(5Z,7E,22E,24E)-(1S,3R)-26,27-dimethyl-24a-homo-9,10-seco-5,7,10(19),22,24-cholestapentaene-1,3,25-triol1(S),3(R)-Dihydroxy-20(R)-(5'-ethyl-5'-hydroxyhepta-1'(E),3'(E)-dien-1'-yl)-9,10-secopregna-5(Z),7(E),10(19)-trieneseocalcitolum(1R,3S,5Z)-5-((2E)-2-((1R,3aS,7aR)-1-((2R,3E,5E)-7-ethyl-7-hydroxynona-3,5-dien-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene)ethylidene)-4-methylidenecyclohexane-1,3-diolRefChem:884890
Weitere Namen anzeigen
Theocalcitriol(1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R,3E,5E)-7-Ethyl-7-hydroxynona-3,5-dien-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol(1R,3S,5Z)-5-((2E)-((1R,3aS,7aR)-1-((1R,2E,4E)-6-Ethyl-6-hydroxy-1-methyl-2,4-octadienyl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylene-1,3-cyclohexanediol(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4E)-6-Ethyl-6-hydroxy-1-methyl-2,4-octadien-1-yl]-octahydro-7α-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol1,3-Cyclohexanediol, 5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4E)-6-ethyl-6-hydroxy-1-methyl-2,4-octadien-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-, (1R,3S,5Z)-EB 1089,(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4E)-6-Ethyl-6-hydroxy-1-methyl-2,4-octadien-1-yl]-octahydro-7α-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol
DTXCID501510003(1R-(1alpha(1R*,2E,4E),3abeta,4E(1R*,3S*,5Z),7aalpha))-5-((1-(6-Ethyl-6-hydroxy-1-methyl-2,4-octadienyl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylene-1,3-cyclohexanediolUNII-Q0OZ0D9223EB1089EB 1089MFCD00871599AKOS024457918MS-28286

Datenbank-Bezeichner

CAS
134404-52-7
PubChem CID
5288149
DTXSID
DTXSID601025740
ChEMBL
CHEMBL1908376
UNII
Q0OZ0D9223
EC Number
110-826-4
Nikkaji
J532.199I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,8
Polarare Oberfläche (TPSA)
60,7 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
7
Schwere Atome
33

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt
123 · 123-125°
Siedepunkt
608.5 · 608.5±55.0 °C(Predicted)
Dichte
1.06 · 1.06±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
Soluble in DMSO
Aggregatzustand
solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAquatic Chronic 4 (100%)

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Aquatic Chronic 4

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Anwendungen · 2 Einträge

BeschreibungEB 1089 is a synthetic vitamin D analog that is 50-200 times more potent than calcitriol at inhibiting cell proliferation and differentiation, yet displays reduced calcemic activity compared to that of calcitriol. It has been shown to promote tumor regression in vitro by inducing apoptosis.

VerwendenEB 1089 is an analogue of Calcitriol (C144500), which is a biologically active form of Vitamin D3 (1). It can be used in androgen receptor-targeted therapy research for breast cancer (2). EB 1089 exhibits anti-cancer properties.

Anbieter50 Anbieter

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海策嵘生物科技有限公司[email protected]
Henan Rane Chemical Co., Ltd.+86-18738066252 · [email protected]
湖北研科时代科技有限公司15780669880 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]

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