CAS 113558-15-9 | 4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)- | CAS Number 113558-15-9

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113558-15-9 | 4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-

CAS No: 113558-15-9 Catalog No: AG0008Z1 MDL No:MFCD15071140

Product Description

Catalog Number:

AG0008Z1

Chemical Name:

4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-

CAS Number:

113558-15-9

Molecular Formula:

C27H30O10

Molecular Weight:

514.5211

MDL Number:

MFCD15071140

IUPAC Name:

5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

InChI:

InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1

InChI Key:

NGMYNFJANBHLKA-LVKFHIPRSA-N

SMILES:

COc1ccc(cc1)c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O

Properties

Complexity:

874

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

514.184g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

514.527g/mol

Monoisotopic Mass:

514.184g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

155A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

3.5

Literature

Title	Journal
Blockade of epidermal growth factor receptor/mammalian target of rapamycin pathway by Icariside II results in reduced cell proliferation of osteosarcoma cells.	Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20141101
Herba epimedii flavonoids suppress osteoclastic differentiation and bone resorption by inducing G2/M arrest and apoptosis.	Biochimie 20121201
Icariside II potentiates paclitaxel-induced apoptosis in human melanoma A375 cells by inhibiting TLR4 signaling pathway.	Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120901
Reactive oxygen species-mediated mitochondrial pathway is involved in Baohuoside I-induced apoptosis in human non-small cell lung cancer.	Chemico-biological interactions 20120730
Icarisid II, a PDE5 inhibitor from Epimedium wanshanense, increases cellular cGMP by enhancing NOS in diabetic ED rats corpus cavernosum tissue.	Andrologia 20120501
[Comparative study on chemical quality of main species of epimedium].	Yao xue xue bao = Acta pharmaceutica Sinica 20120401
Influence of vitamin E tocopherol polyethylene glycol succinate 1000 on intestinal absorption of icariside II.	Die Pharmazie 20120101
Effects of icariside II on improving erectile function in rats with streptozotocin-induced diabetes.	Journal of andrology 20120101
Icariside II induces apoptosis in U937 acute myeloid leukemia cells: role of inactivation of STAT3-related signaling.	PloS one 20120101
Icariside II enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression coupled with the ERK, Akt and JNK signaling pathways.	Molecules (Basel, Switzerland) 20111103
[Effects of icariin and icariside II on eNOS expression and NOS activity in porcine aorta endothelial cells].	Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20110818
Janus activated kinase 2/signal transducer and activator of transcription 3 pathway mediates icariside II-induced apoptosis in U266 multiple myeloma cells.	European journal of pharmacology 20110301
Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans.	PloS one 20110101
[Comparative study on the osteogenic differentiation of rat bone marrow stromal cells effected by icariin and icariside II].	Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20101201
Preparation of icariside II from icariin by enzymatic hydrolysis method.	Fitoterapia 20100701
[Quality research on Epimedium cut crude drug processed with oil].	Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601
Synthesis and antimultidrug resistance evaluation of icariin and its derivatives.	Bioorganic & medicinal chemistry letters 20090801
Cyclooxygenase-2/prostaglandin E2 pathway mediates icariside II induced apoptosis in human PC-3 prostate cancer cells.	Cancer letters 20090718
[Sampling in quality control of medicinal materials-A case of Epimedium].	Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090401
Intestinal absorption mechanisms of prenylated flavonoids present in the heat-processed Epimedium koreanum Nakai (Yin Yanghuo).	Pharmaceutical research 20080901
Icariside II from Epimedium koreanum inhibits hypoxia-inducible factor-1alpha in human osteosarcoma cells.	European journal of pharmacology 20080128
Statistically designed enzymatic hydrolysis for optimized production of icariside II as a novel melanogenesis inhibitor.	Journal of microbiology and biotechnology 20080101
Simultaneous determination of icariin, icariside II and osthole in rat plasma after oral administration of the extract of Gushudan (a Chinese compound formulation) by LC-MS/MS.	Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071201
LC-MS/MS method for the simultaneous determination of icariin and its major metabolites in rat plasma.	Journal of pharmaceutical and biomedical analysis 20071130
Simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and high-performance liquid chromatography.	Journal of chromatography. A 20070907
Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro.	Life sciences 20070816
Effect of Baohuoside-1 aglycone and tacrolimus monotherapy and combination therapy on prevention of acute heart allograft rejection in the rat.	Microsurgery 20070101
Multiple conformations of phosphodiesterase-5: implications for enzyme function and drug development.	The Journal of biological chemistry 20060728
Baohuoside-1 inhibits activated T cell proliferation at G(1)-S phase transition.	Transplant immunology 20051001
Baohuoside-1, a novel immunosuppressive molecule, inhibits lymphocyte activation in vitro and in vivo.	Transplantation 20040927