| ImmunCR Id : | ICR76 |
| Chemical Name : | Β-Hydroxyisovalerylshikonin |
| Plant Source : | Lithospermum erythrorhizon |
| Nutraceutical information : | --- |
| Mode of administration : | --- |
| Immunomodulatory mechanism : | Anti-cancer (inhibits PTK (protein tyrosine kinase) and v-Src, downregulates TRAP1 (Tumor necrosis factor receptor-associated protein 1) gene expression; Anti-inflammatory (supressess IL-6, tnfα, NO, PEG2, COX-2, inos, inhibits PI3K/AKT/NF-κb signaling pathways, IL-1β, activates Nrf2/HO-1 pathway); Anti-arthritic (upregulates collagen II, aggrecan expression, downregulates MMP-13 (matrix metalloproteinase), ADAMTS5 (thrombospondin protein motifs)); Anti-apoptotic (ROS generation, upregulates cytosolic cytochrome c, caspase 8,9,3, bad, G2/M cell cycle arrest, downregulates Bcl2, Bid); Anti-antigiogenesis (inhibits expression and phosphorylation of VEGFR2 (Vascular endothelial growth factor receptor)and Tie2, suppresses (MAPK)-Sp1 pathway) |
| Description : | It is a 1,4 naphtoquinone derivative of shikonin extracted from the Boraginaceae family, possessing strongest anti-apoptotic property among the shikonin and its derivatives. |
| IUPAC Name | [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate |
| SMILES | CC(C)(O)CC(=O)OC(C\C=C(/C)C)C1=CC(O)c2c(O)ccc(O)c2C1O |
| Formula | C21H28O7 |
| InchiKey | BVRYLTBIGIAADD-MRXNPFEDSA-N |
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Naphthoquinones |
| LogP | 2.189 |
| Molecular weight | 392.443 |
| Hydrogen Bond Acceptor | 7 |
| Hydrogen Bond Donor | 5 |
| Polar surface area | --- |
| No. of rotatable bonds | 7 |
| Number of Aromatic Rings | 1 |
| Number of rings | 2 |
| Absorption level | --- |
| Solubility level | --- |
| Blood Brain Barrier | --- |
| Plasma protein binding | Binder |
| CYP2D6 inhibition | Non-Inhibitor |
