M1390
3,3′- 亚甲基-双(4-羟基香豆素)
别名:
双羟香豆素
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关于此项目
经验公式（希尔记法）:
C19H12O6
化学文摘社编号:
分子量:
336.29
NACRES:
NA.47
PubChem Substance ID:
UNSPSC Code:
12352103
EC Number:
200-632-9
MDL number:
InChI key
DOBMPNYZJYQDGZ-UHFFFAOYSA-N
InChI
1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
SMILES string
OC1=C(CC2=C(O)c3ccccc3OC2=O)C(=O)Oc4ccccc14
biological source
synthetic (organic)
assay
≥98% (TLC)
form
powder
mp
290-292 °C (lit.)
solubility
pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow
Quality Level
Gene Information
human ... CYP2C9(1559), VKORC1(79001)
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Biochem/physiol Actions
4-羟基香豆素类抗凝血剂的原型，它是维生素K拮抗剂，可防止凝血酶原形成。有许多报道称，双香豆素还能够抑制NADPH:醌氧化还原酶（NQO(1)）。在一项研究中，它抑制胰腺癌细胞系中的NQO(1)，导致超氧化物形成增加并抑制细胞生长。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
法规信息
农药列管产品
此项目有
Karen Ann Nolan et al.
Biochemical pharmacology, 80(7), 977-981 (2010-07-06)
NAD(P)H quinone oxidoreductase (NQO1) has multiple functions in the cell including an ability to act as a detoxifying enzyme and as a protein chaperone. The latter property is particularly important in oncology as one of the client proteins of NQO1
C O Lemley et al.
Journal of dairy science, 93(10), 4613-4624 (2010-09-22)
Progesterone is required for maintenance of pregnancy, and peripheral concentrations of progesterone are affected by both production and inactivation. Hepatic cytochrome P450 (EC 1.14.14.1) and aldo-keto reductase (EC 1.1.1.145-151) enzymes play a pivotal role in the first step of steroid
Katherine Ann Scott et al.
Biochemical pharmacology, 81(3), 355-363 (2010-10-26)
The enzyme NAD(P)H quinone oxidoreductase (NQO1) can function both as a detoxifying enzyme as well as chaperone protein. The latter property has been extensively characterized by the use of dicoumarol which inhibits the chaperone properties of NQO1 in cells. However
Alexandra Reichstein et al.
Journal of medicinal chemistry, 55(16), 7273-7284 (2012-08-01)
A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in
Yi-Ting Wu et al.
Journal of biomedical science, 18, 70-70 (2011-09-23)
β-Lapachone has antitumor and wound healing-promoting activities. To address the potential influences of various chemicals on heart development of zebrafish embryos, we previously treated zebrafish embryos with chemicals from a Sigma LOPAC1280™ library and found several chemicals including β-lapachone that
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