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470-17-7 | (3aR,4aS,8aR,9aR)-Decahydro-8a-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one
CAS No: 470-17-7 Catalog No: AG003AQ8 MDL No:MFCD08689940
Product Description
Catalog Number:
AG003AQ8
Chemical Name:
(3aR,4aS,8aR,9aR)-Decahydro-8a-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one
CAS Number:
470-17-7
Molecular Formula:
C15H20O2
Molecular Weight:
232.3181
MDL Number:
MFCD08689940
IUPAC Name:
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
InChI:
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1
InChI Key:
CVUANYCQTOGILD-QVHKTLOISA-N
SMILES:
O=C1O[C@H]2[C@@H](C1=C)C[C@@H]1[C@](C2)(C)CCCC1=C
UNII:
BYH07P620U
NSC Number:
241036
Properties
Complexity:
409
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
232.146g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
232.323g/mol
Monoisotopic Mass:
232.146g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.4
Literature
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|---|---|
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| Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage. | European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20120601 |
| Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs. | Natural product communications 20120501 |
| Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells. | International journal of biological sciences 20120101 |
| Ultrasound-assisted extraction of total flavonoids from Inula helenium. | Pharmacognosy magazine 20120101 |
| Antitumour activities of sesquiterpene lactones from Inula helenium and Inula japonica. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20120101 |
| Isoalantolactone protects against Staphylococcus aureus pneumonia. | FEMS microbiology letters 20111101 |
| Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa. | Toxicology in vitro : an international journal published in association with BIBRA 20100901 |
| Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults. | Chemistry & biodiversity 20100701 |
| HPLC determination and NMR structural elucidation of sesquiterpene lactones in Inula helenium. | Journal of pharmaceutical and biomedical analysis 20100311 |
| Ultrasound-assisted extraction of alantolactone and isoalantolactone from Inula helenium roots. | Pharmacognosy magazine 20100101 |
| Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes. | Journal of medicinal food 20091001 |
| Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium. | Phytotherapy research : PTR 20081101 |
| Neural networks as valuable tools to differentiate between sesquiterpene lactones' inhibitory activity on serotonin release and on NF-kappaB. | Journal of medicinal chemistry 20080313 |
| Induction of detoxifying enzyme by sesquiterpenes present in Inula helenium. | Journal of medicinal food 20070901 |
| Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography. | Phytochemical analysis : PCA 20060101 |
| Separation and determination of two sesquiterpene lactones in Radix inulae and Liuwei Anxian San by microemulsion electrokinetic chromatography. | Biomedical chromatography : BMC 20041201 |
| Constituents of two Flourensia species. | Phytochemistry 20040701 |
| Antiproliferative sesquiterpene lactones from the roots of Inula helenium. | Biological & pharmaceutical bulletin 20021001 |
| Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones. | Planta medica 20020801 |
| Antimycobacterial plant terpenoids. | Planta medica 20011101 |
| Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone. | Bioorganic & medicinal chemistry letters 20010212 |
| Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa. | Planta medica 19990501 |
| A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones. | Archives of dermatological research 19920101 |
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