6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

• ChemBase编号: 105191
• 分子式: C17H11NO7
• 平均质量: 341.27174
• 单一同位素质量: 341.0535517
• SMILES: COc1cccc2c3c4c(OCO4)cc(C(=O)O)c3c(cc12)[N+](=O)[O-]
• Canonical SMILES: COc1cccc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)O
• InChI: InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)
• InChIKey: BBFQZRXNYIEMAW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid; 6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid
• IUPAC传统名: birthwort
• 别名: 8-Methoxy-6-nitro-phenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid; Aristolochia A; Aristolochic Acid; Aristolochic Acid 1; Aristolochic Acid I; NSC 11926; NSC 50413; Tardolyt; Aristolochic Acid A; Aristolochine; Birthwort; 8-Methoxy-6-Nitrophenanthol-(3,4-d)-1,3-Dioxole-5-Carboxylic Acid; ARISTOLOCHIC ACID; Aristinic acid; Aristolochia yellod; Aristolochic acid d; Aristolochid; Aristolochind; Descresepd; Tardolyd; TR 1736; Aristolochic acid I

登记号

• CAS号: 313-67-7
• EC号: 206-238-3
• MDL号: MFCD00004996
• PubChem SID: 24890982; 162092000
• PubChem CID: 2236
• CHEMBL: 93353
• Chemspider ID: 2149
• KEGG ID: C08469
• 维基百科标题: Aristolochic_acid

理论计算性质

• Acid pKa: 3.3240964
• 质子受体: 7
• 质子供体: 1
• LogD (pH = 5.5): 0.85536474
• LogD (pH = 7.4): -0.40555608
• Log P: 3.0153286
• 摩尔折射率: 85.7694 cm^3
• 极化性: 34.543518 Å^3
• 极化表面积: 110.81 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble; ethanol: soluble
• 外观: yellow powder; Yellow Solid
• 熔点: 260 - 265 °C; 274-276°C (dec.); 280-286°C
• 沸点: 615.5°C @760mmHg
• 闪点: 326°C
• 密度: 1.571g/cm^3

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: CF3325000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544; 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 25; R:25
• 安全公开号: 7-35-45; S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS06
• GHS警示词: Danger
• NFPA704:
  

  1

  2

  0
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: 97%
• Empirical Formula (Hill Notation): C17H11NO7

详细说明

MP Biomedicals - 02159019

From Aristolochiaceae
Purity: 97%
1:1 mixture of aristolochic acids I and II. A phenanthrene carboxylic acid derivative which irreversibly blocks phospholipase A₂ from various sources.

Sigma Aldrich - A5512

Biochem/physiol Actions
Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model.1
Application
Aristolochic acid I is a potent phospholipase A2 inhibitor. Aristolochic acid I induces tumor formation in rat kidneys and apoptosis in human renal proximal tubular epithelial cells.

Toronto Research Chemicals - A771300

Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids.

参考文献

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• Coutts, et al.: J. Pharm. Pharmacol., 11, 607 (1959)
• Kupchan, D., et al.: J. Med. Pharm. Chem., 5, 657 (1959)
• Mix, D.B., et al.: J. Nat. Prod., 45, 657 (1959)
• Mengs, U., et al.: Arch. Toxixol., 59, 328 (1959)