ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR72
Chemical Name : Deoxyshikonin H
Plant Source : Triptrtygium Wilford II
Nutraceutical information : ---
Mode of administration : ---
Immunomodulatory mechanism : Anti-cancer (Acute myeloid leukemia (increases CYT C, caspase 3,7, suppresses PKM2 enzyme, glycolysis, inhibit phosphorylation of mtor, Akt, GSK3β, P70S6K, 4EBP1 in a dose dependent manner, inactivates Akt/mtor pathway), Colorectal cancer (cell cycle arrest in G0/G1 phase, inhibits P13K/Akt/mtor pathway), Tounge cancer (cleaves caspase 3, upregulates HO-1 (heme oxygenase-1) expression, Nrf2/Ho-1, caspase 3,8,9, PARP (poly (ADP-ribose) polymerase 1), downregulates XIAP (X linked inhibitor of apoptosis protein), ciap-1 (cellular inhibitor of apoptosis protein-1), phosphorylates ERK1/2, p38, JNK)); inhibit CYP1A2, 2E1, 2B6, 3A4, 2D6, 2C9; Antioxidant (suppresses ROS, MDA (malondialdehyde), upregulates expression of NQO1, HO-1, CAT); Wound healing (activates erk and p38 to form tubes and cell proliferation in HUVEC (Human umbilical vein endothelial cells)); Anti-bacterial (inhibited biofilm formation, effective against PEN resistant microbes, can prolong life after infection with Streptococcus pneumoniae)
Description : Deoxyshikonin or 5,8-dihydroxy-2-(4-methylpent-3-enyl) naphthalene-1,4-dione is a natural napthoquinone extracted from a Chinese medical plant Lithospermaum erythrorhizon.

Chemical Structure Information

IUPAC Name 5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
SMILES CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)C
Formula C16H16O4
InchiKey VOMDIEGPEURZJO-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Benzenoids
Class Naphthalenes
Subclass Naphthoquinones

Physicochemical properties

LogP 3.546
Molecular weight 272.296
Hydrogen Bond Acceptor 4
Hydrogen Bond Donor 2
Polar surface area 76.232
No. of rotatable bonds 3
Number of Aromatic Rings 1
Number of rings 2

ADMET Properties

Absorption level Good
Solubility level Very Soluble
Blood Brain Barrier Medium
Plasma protein binding Binder
CYP2D6 inhibition Non-Inhibitor

Other Biological Properties

  • ---

References

    1. https://doi: 10.1016/B978-0-12-394591-4.00004-0
    2. https://doi.org/10.3389/fonc.2020.01253
    3. https://doi.org/10.1080/13880209.2019.1626447


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