Ailanthone

CAT: 0957-S6885-1mgSize: 1 mgDry Ice: NoHazardous: No

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CAT#:0957-S6885-1mgSize:1 mg

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CAS Number

981-15-7

Synonyms

AIL, Δ13-Dehydrochaparrinone

Target

Androgen Receptor

Applications

Endocrinology & Hormones

Smiles

CC1=CC (=O) C (C2 (C1CC3C45C2C (C (C (=C) C4CC (=O) O3) O) (OC5) O) C) O

Molecular Formula

C20H24O7

Additionnal Information

Ailanthone (AIL, Δ13-Dehydrochaparrinone), a natural anti-hepatocellular carcinoma (HCC) component in Ailanthus altissima, induces G0/G1-phase cell cycle arrest by decreasing expression of cyclins and CDKs and increases expression of p21 and p27. Ailanthone triggers DNA damage characterized by activation of the ATM/ATR pathway. Ailanthone induces apoptosis which is mitochondrion-mediated and involves the PI3K/AKT signaling pathway in Huh7 cells. Ailanthone is also a potent inhibitor of both full-length Androgen Receptor (AR-FL) and constitutively active truncated AR splice variants (AR-Vs, AR1-651) with IC50 of 69 nM and 309 nM, respectively.

Storage Conditions

3 years -20°C powder

Chemical Information

Ailanthone

Ailanthone is a triterpenoid.

CAS Number	981-15-7
PubChem CID	72965
IUPAC Name	(1S,4R,5R,7S,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
Molecular Formula	C20H24O7
Molecular Weight	376.4
XLogP	-1.1
Topological Polar Surface Area	113
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	0
Heavy Atom Count	27
Formal Charge	0
Complexity	817

SMILES

CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@]([C@@H](C(=C)[C@@H]4CC(=O)O3)O)(OC5)O)C)O

InChI

InChI=1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1

InChIKey

WBBVXGHSWZIJST-RLQYZCPESA-N

Chemical Structure

2D Structure

CAS: 981-15-7

CID: 72965

Formula: C20H24O7

MW: 376.4

Interactive 3D Structure

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Computed Properties

Property	Value
Molecular Weight	376.4
XLogP3	-1.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	0
Exact Mass	376.15220310
Monoisotopic Mass	376.15220310
Topological Polar Surface Area	113 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	817
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
HY-N1943-01	Ailanthone

Ailanthone

Chemical Information

Alternative Products

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