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THUNBERGINOL A
ID: ALA68810
Max Phase: Preclinical
Molecular Formula: C15H10O5
Molecular Weight: 270.24
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=c1oc(-c2ccc(O)c(O)c2)cc2cccc(O)c12
Standard InChI: InChI=1S/C15H10O5/c16-10-5-4-8(6-12(10)18)13-7-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,16-18H
Standard InChI Key: WHZXJVJVGGWZQI-UHFFFAOYSA-N
Associated Targets(Human)
Lysine-specific demethylase 4A 52245 Activities
ATPase family AAA domain-containing protein 5 122566 Activities
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Importin subunit beta-1/Snurportin-1 25097 Activities
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|---|
GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 21853 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DNA polymerase iota 116820 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Flap endonuclease 1 12055 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DNA polymerase eta 21678 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DNA polymerase kappa 8653 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SN12C 47755 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
NCI-H23 49055 Activities
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|---|
UO-31 46270 Activities
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|---|
ACHN 49357 Activities
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|---|
HL-60 67320 Activities
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|---|
HOP-92 41141 Activities
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|---|
DU-145 51482 Activities
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|---|
SF-539 44845 Activities
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|---|
SK-MEL-5 47095 Activities
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|---|
Malme-3M 44254 Activities
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|---|
A498 42825 Activities
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|---|
K562 73714 Activities
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|---|
OVCAR-3 48710 Activities
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|---|
MOLT-4 49676 Activities
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|---|
HOP-62 47048 Activities
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|---|
NCI/ADR-RES 33767 Activities
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|---|
OVCAR-5 45555 Activities
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|---|
OVCAR-8 47708 Activities
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SNB-19 46794 Activities
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|---|
SW-620 52400 Activities
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|---|
TK-10 45540 Activities
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|---|
NCI-H522 44358 Activities
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|---|
KM12 47707 Activities
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|---|
M14 47487 Activities
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|---|
RPMI-8226 44974 Activities
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|---|
NCI-H322M 45589 Activities
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|---|
OVCAR-4 44535 Activities
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|---|
BT-549 31254 Activities
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|---|
SK-MEL-2 46422 Activities
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|---|
A549 127892 Activities
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|---|
HCC 2998 41480 Activities
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|---|
SNB-75 44215 Activities
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|---|
HCT-15 51914 Activities
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|---|
SF-268 49410 Activities
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HCT-116 91556 Activities
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EKVX 44102 Activities
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MCF7 126967 Activities
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|---|
PC-3 62116 Activities
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|---|
SK-OV-3 52876 Activities
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|---|
T47D 39041 Activities
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|---|
NCI-H460 60772 Activities
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|---|
MDA-MB-435 38290 Activities
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CAKI-1 44928 Activities
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IGROV-1 47897 Activities
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SF-295 48000 Activities
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Hs-578T 29457 Activities
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UACC-257 46019 Activities
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786-0 47912 Activities
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CCRF-CEM 65223 Activities
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|---|
RXF 393 41971 Activities
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|---|
COLO 205 50209 Activities
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|---|
Geminin 128009 Activities
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|---|
Rac GTPase-activating protein 1 2057 Activities
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|---|
Glutaminase kidney isoform, mitochondrial 16997 Activities
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|---|
Sphingomyelin phosphodiesterase 13561 Activities
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|---|
Glucagon-like peptide 1 receptor 111429 Activities
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|---|
Werner syndrome ATP-dependent helicase 8824 Activities
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|---|
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 36611 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Nuclear factor erythroid 2-related factor 2 95332 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Tyrosyl-DNA phosphodiesterase 1 345557 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Arachidonate 5-lipoxygenase 6568 Activities
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|---|
Prostaglandin E synthase 3082 Activities
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|---|
Prostaglandin E synthase/G/H synthase 2 7 Activities
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|---|
HeLa 62764 Activities
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|---|
Associated Targets(non-human)
Rattus norvegicus 775804 Activities
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|---|
Mus musculus 284745 Activities
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|---|
Ovis aries 854 Activities
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|---|
3T3-L1 3664 Activities
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|---|
ATP-dependent Clp protease proteolytic subunit 20705 Activities
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|---|
Molecule Features
| Natural Product: Yes | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 270.24 | Molecular Weight (Monoisotopic): 270.0528 | AlogP: 2.58 | #Rotatable Bonds: 1 |
| Polar Surface Area: 90.90 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.35 | CX Basic pKa: | CX LogP: 3.09 | CX LogD: 3.04 |
| Aromatic Rings: 3 | Heavy Atoms: 20 | QED Weighted: 0.59 | Np Likeness Score: 1.07 |
References
| 1. Matsuda H, Shimoda H, Yamahara J, Yoshikawa M.. (1998) Immunomodulatory activity of thunberginol A and related compounds isolated from Hydrangeae Dulcis Folium on splenocyte proliferation activated by mitogens., 8 (3): [PMID:9871657] [10.1016/s0960-894x(97)10221-9] |
| 2. Zhang H, Matsuda H, Kumahara A, Ito Y, Nakamura S, Yoshikawa M.. (2007) New type of anti-diabetic compounds from the processed leaves of Hydrangea macrophylla var. thunbergii (Hydrangeae Dulcis Folium)., 17 (17): [PMID:17609121] [10.1016/j.bmcl.2007.06.027] |
| 3. PubChem BioAssay data set, |
| 4. PubChem BioAssay data set, |
| 5. Ramanan M, Sinha S, Sudarshan K, Aidhen IS, Doble M.. (2016) Inhibition of the enzymes in the leukotriene and prostaglandin pathways in inflammation by 3-aryl isocoumarins., 124 [PMID:27597418] [10.1016/j.ejmech.2016.08.066] |
| 6. Zima V,Radilová K,Kožíšek M,Albiñana CB,Karlukova E,Brynda J,Fanfrlík J,Flieger M,Hodek J,Weber J,Majer P,Konvalinka J,Machara A. (2020) Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors., 208 [PMID:32883638] [10.1016/j.ejmech.2020.112754] |
Source
Source(2):