莽草素 | 54952-43-1
中文名称:
莽草素
英文名称:
Shikonin (mixture of optical isomers, about 1:1)
CAS No.:
54952-43-1
分子式:
C1 6 H1 6 O5
分子量:
288.30
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:莽草素结构式
名称和标识符
MDL
MFCD00016668
InChIKey
NEZONWMXZKDMKF-UHFFFAOYSA-N
Inchi
1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
SMILES
OC1=CC=C(O)C2=C1C(=O)C=C(C(O)C/C=C(\C)/C)C2=O
别名信息
- 中文别名 -
莽草素
紫草宁
右旋紫草素
5,8-二羟基-2-[(1R)-1-羟基-4-甲基戊-3-烯基]萘-1,4-二酮
莽草素(光学异构体混合物1:1)
紫草素
紫草素Shikonin
WAKO198-13601紫草醌(旋光异构体混合物,约1:1)
欧根草
紫草宁,Shikalkin,植物提取物,标准品,对照品
紫草素,紫草醌
紫根色素
- 英文别名 -
Shikalkin
5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9ci)
Arnebin-4
Nsc 291845
(±)-Alkannin
(±)-Shikalkin
(±)-Shikonin
(±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
Shikonin (mixture of optical isomers, about 1:1)
Anchusin
natural red 20
NEZONWMXZKDMKF-UHFFFAOYSA-
54952-43-1
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
NSC-407295
3-(2,2-Dimethylpropionylamino)isonicotinicacid
shikonin
BCP34282
5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
KBio3_001080
LS-14485
CHEMBL29285
(+)-Shikonin
ALKANNIN, 1-
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
FT-0746742
C.I. Natural Red 20
C.I. 75535
Isoarnebin 4
1, 5,8-dihydroxy-6-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
CS-0032051
NSC-94524
H1780
NS00018361
NSC 291845
NSC-291845
(Rac)-Shikonin
23444-65-7
ARNEBIN-4
SCHEMBL14305203
Bio2_000475
(-)-Shikonin
C.I. 75535
Isoarnebin 4
5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione
MFCD00016668
SMP2_000188
NSC407295
Bio2_000955
5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYLPENT-3-EN-1-YL)NAPHTHALENE-1,4-DIONE
KBio3_001079
DTXSID00862100
FT-0651798
NSC94524
(+/-)-Alkannin
SCHEMBL3182028
(+/-)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
FT-0774471
5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
SHIKALKIN
Shikonine
Shikonin (7b)
5,8-Dihydroxy-6-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
KBio2_005746
NSC-252844
Shikonin, >=98% (HPLC)
Q-100621
KBio2_003178
(+-)-Alkannin
KBioGR_000610
NCI60_002031
KBioSS_000610
IDI1_002230
(+-)-Shikonin
CHEBI:174748
11019-15-1
( inverted exclamation markA)-Shikonin
85251-58-7
NSC252844
QTL1_000075
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)
AKOS016034343
C.I. 75530
BCP29329
(+-)-Shikalkin
NS00123717
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
C.I. Natural Red 20 (VAN)
KBio2_000610
HY-N6004
NSC291845
1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)-
HMS1362P11
InChI=1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
(+/-)-Shikonin
BDBM178090
物化性质
实验特性
LogP
2.12040
PSA
94.83
沸点
567.4±50.0 °C at 760 mmHg
熔点
Not available
蒸气压
0.0±1.6 mmHg at 25°C
闪点
311.0±26.6 °C
溶解度
methanol: soluble1mg/mL
密度
1.4±0.1 g/cm3
计算特性
精确分子量
288.09978
氢键供体数量
3
氢键受体数量
5
可旋转化学键数量
3
同位素质量
288.099774
重原子数量
21
复杂度
501
同位素原子数量
0
确定原子立构中心数量
0
不确定原子立构中心数量
1
确定化学键立构中心数量
0
不确定化学键立构中心数量
0
共价键单元数量
1
疏水参数计算参考值(XlogP)
3
互变异构体数量
15
表面电荷
0
拓扑分子极性表面积
94.8
相关文献
1.
Metabolic profiling study of shikonin's cytotoxic activity in the Huh7 human hepatoma cell line
E. D. Spyrelli,A. V. Kyriazou,C. Virgiliou,A. Nakas,O. Deda,V. P. Papageorgiou,A. N. Assimopoulou,H. G. Gika Mol. BioSyst. 2017 13 841
2.
Total synthesis of shikalkin [(±)-shikonin]
Akira Terada,Yasuhiro Tanoue,Akira Hatada,Hiroshi Sakamoto J. Chem. Soc. Chem. Commun. 1983 987
3.
Design, synthesis and biological evaluation of shikonin thio-glycoside derivatives: new anti-tubulin agents
Hong-Yan Lin,Hong-Wei Han,Li-Fei Bai,Han-Yue Qiu,De-Zheng Yin,Jin-Liang Qi,Xiao-Ming Wang,Hong-Wei Gu,Yong-Hua Yang RSC Adv. 2014 4 49796
4.
Modeling of hyperbranched polyesters as hosts for the multifunctional bioactive agent shikonin
I. Tanis,K. Karatasos,A. N. Assimopoulou,V. P. Papageorgiou Phys. Chem. Chem. Phys. 2011 13 10808
5.
Box–Behnken designed adsorption based elution – unique separation process for commercially important acetyl shikonin from Arnebia nobilis
Shankar Subramaniam,Anbumathi Palanisamy,Aravind Sivasubramanian RSC Adv. 2015 5 6265
6.
Excited state deactivation mechanisms in Shikonin rationalized from its naphthoquinone parent structures
Catarina M. Pinto,Jo?o Pina,Estefanía Delgado-Pinar,J. Sérgio Seixas de Melo Phys. Chem. Chem. Phys. 2022 24 20348
7.
Electrochemical and theoretical analysis of the reactivity of shikonin derivatives: dissociative electron transfer in esterified compounds
Georgina Armendáriz-Vidales,Carlos Frontana Org. Biomol. Chem. 2014 12 6393
8.
Design, synthesis and mechanism of novel shikonin derivatives as potent anticancer agents
Shahla Karim Baloch,Lin Ma,Xue-Liang Wang,Jing Shi,Yu Zhu,Feng-Yao Wu,Yan-Jun Pang,Gui-Hua Lu,Jin-Liang Qi,Xiao-Ming Wang,Hong-Wei Gu,Yong-Hua Yang RSC Adv. 2015 5 31759
9.
Acetyl shikonin induces IL-12, nitric oxide and ROS to kill intracellular parasite Leishmania donovani in infected hosts
Mamilla R. Charan Raja,Sujatha Srinivasan,Shankar Subramaniam,Narendran Rajendran,Aravind Sivasubramanian,Santanu Kar Mahapatra RSC Adv. 2016 6 61777
10.
Jacalin-capped silver nanoparticles minimize the dosage use of the anticancer drug, shikonin derivatives, against human chronic myeloid leukemia
Khan Behlol Ayaz Ahmed,Santanu Kar Mahapatra,Mamilla R. Charan Raja,Shankar Subramaniam,Megarajan Sengan,Narendran Rajendran,Sandeep Kumar Das,Kuntal Haldar,Somenath Roy,Aravind Sivasubramanian,Veerappan Anbazhagan RSC Adv. 2016 6 18980
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