基本情報
- CAS
38966-21-1- 標準SMILES
C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1C[C@@H]3C[C@@]12CC[C@]3(O)CO- InChIKey
NOFOAYPPHIUXJR-APNQCZIXSA-N- 分子式
- C20H34O4
- 平均分子量
- 338.5 g/mol
- 単同位体質量
- 338.24570956
概要
Aphidicolin is a tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It has a role as an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor, an antimicrobial agent, an antineoplastic agent, an antiviral drug, a DNA synthesis inhibitor, an antimitotic, an apoptosis inducer, a fungal metabolite and an Aspergillus metabolite.
名称と識別子
- 優先名称
- Aphidicolin
- IUPAC
- (1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
- 現地名
- (+)-アフィディコリン
- 英語名
- APHIDICOLIN
- 分子式
- C20H34O4
- 分子量
- 338.48
名称と別名
aphidicolin38966-21-1(+)-AphidicolinNSC-234714ICI 69653DTXSID5036711(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diolNSC 234714ICI-69653NSC234714192TJ6PP19CHEBI:2766
名称をさらに表示
(+)-アフィディコリンアフィディコリンアフィジコリンアフィディコリン NIGROSPORA SPHAERICA由来(3R,4aβ,6aα)-テトラデカヒドロ-3β,9α-ジヒドロキシ-4,11bα-ジメチル-8α,11aα-メタノ-11aH-シクロヘプタ[a]ナフタレン-4β,9β-ジメタノール(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-ビス(ヒドロキシメチル)-2,6-ジメチルテトラシクロ[10.3.1.01,10.02,7]ヘキサデカン-5,13-ジオール3α,17α-ジヒドロキシ-4-メチル-9,15-シクロ-C,18-ジノル-14,15-セコ-5α-アンドロスタン-4α,17-ジメタノールAPC,11a-beta,11b-beta))-APHIDICOLIN USP/EP/BPAphidicolin, Ready Made Solution(+)-APHIDICOLIN, NIGROSPORA ORYZAEAphidicolin, froM Nigrospora oryzae
9,15-Cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol, 3,17-dihydroxy-4-methyl-, (3alpha,4alpha,5alpha,17alpha)-(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diolNSC3511408,11A-METHANO-11AH-CYCLOHEPTA(A)NAPHTHALENE-4,9-DIMETHANOL, TETRADECAHYDRO-3,9-DIHYDROXY-4,11B-DIMETHYL-, (3R,4R,4AR,6AS,8R,9R,11AS,11BS)-(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo(10.3.1.01,10.02,7)hexadecane-5,13-diol(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta(a)naphthalene-3,9-diolICI69653NSC 351140
物性
構造計算による物性
- XLogP
- 2.5
- 極性表面積
- 80.9 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 4
- 回転可能結合数
- 2
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 524
実験および物理化学的性質
DrugsPharmaceuticals -> Antibiotics
物理化学的性質
- 融点
- 218 · 218-220°C
- 比旋光度
- 27 · D27 +12° (c = 1 in methanol)
- 沸点
- 394.61 °C · 394.61°C (rough estimate)
- 比重(密度)
- 1.0057 · 1.0057 (rough estimate)
- 蒸気圧
- 0.55 hPa · 0.55 hPa ( 20 °C)
- 屈折率
- 1.4434 · 1.4434 (estimate)
- 闪点
- 87 ℃ · 87℃
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 1 mg/mL · エタノール：可溶1mg/mL（4℃で1週間以上安定）
- 酸解離定数(Pka)
- 14.24 · 14.24±0.70(Predicted)
- 外見
- 白い固体
- 色
- 無色
- 由来生物
- Nigrospora sphaerica
- 水溶解度
- -20 °で溶液を保管してください · DMSOまたはメタノールに可溶。水に不溶。 -20°で溶液を保管してください
- Merck
- 13 · 13,734
- BRN
- 4689958 · 4689958
- 安定性
- 2 · 購入日から2年間安定です。この DMSO またはエタノール溶液は、-20°C で 1 か月間保存できます。
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Regulatory InformationAphidicoline: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全データ
- F
- 10-21
- wgk
- 3
- rtecs
- PB9185000
- ridadr
- NA 1993 / PGIII
- hs_code
- 29419090
- safety_code
- 22-24
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
応用分野
用途1.DNAポリメラーゼαおよびDNA合成に関する研究。2.同調培養試薬
説明(+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex. In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels. Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.
使用(+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties.
一般的な説明A cell-permeable tetracyclic diterpene antibiotic. Cell synchronization agent. Blocks the cell cycle at the early S-phase. Specific inhibitor of DNA polymerase α and δ in eukaryotic cells and in some viruses of animal origin. Potentiates apoptosis induced by arabinosyl nucleosides in leukemia cell lines. Also induces apoptosis in HeLaS3 cells, but inhibits vincristine-induced apoptosis in the p53-negative human prostate cancer cell line PC-3.
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