5-Desgalloylstachyurin

Details

• Internal ID: 590f27c1-fe1c-406d-9b24-ee4a6b2e5efb
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: (14R,15S,19S)-14-[(10R,11R)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.02,7]nonadeca-1(19),2,4,6,15,17-hexaen-10-yl]-2,3,4,7,8,9,19-heptahydroxy-13,16-dioxatetracyclo[13.3.1.05,18.06,11]nonadeca-1,3,5(18),6,8,10-hexaene-12,17-dione
• SMILES (Canonical): C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)O)C4C5C(C6=C(C(=C(C(=C6C(=O)O5)C7=C(C(=C(C=C7C(=O)O4)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H](OC(=O)C2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)O)[C@H]4[C@@H]5[C@H](C6=C(C(=C(C(=C6C(=O)O5)C7=C(C(=C(C=C7C(=O)O4)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C34H24O22/c35-8-1-5-12(21(42)18(8)39)13-6(2-9(36)19(40)22(13)43)32(50)54-28(11(38)4-53-31(5)49)30-29-26(47)17-16(34(52)55-29)15(24(45)27(48)25(17)46)14-7(33(51)56-30)3-10(37)20(41)23(14)44/h1-3,11,26,28-30,35-48H,4H2/t11-,26+,28-,29+,30+/m1/s1
• InChI Key: CHBITXAMNKHJCR-VGYCLGPVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₂₄O₂₂
• Molecular Weight: 784.50 g/mol
• Exact Mass: 784.07592239 g/mol
• Topological Polar Surface Area (TPSA): 388.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 1

Synonyms

• CHEMBL488110
• D07HWB
• BDBM50269547
• PD182561

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7620	76.20%
Caco-2	-	0.8990	89.90%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5827	58.27%
OATP2B1 inhibitior	+	0.5787	57.87%
OATP1B1 inhibitior	+	0.7872	78.72%
OATP1B3 inhibitior	+	0.9202	92.02%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8168	81.68%
P-glycoprotein inhibitior	+	0.6811	68.11%
P-glycoprotein substrate	-	0.7642	76.42%
CYP3A4 substrate	+	0.5590	55.90%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8227	82.27%
CYP3A4 inhibition	-	0.8678	86.78%
CYP2C9 inhibition	-	0.9278	92.78%
CYP2C19 inhibition	-	0.9666	96.66%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	-	0.9406	94.06%
CYP2C8 inhibition	-	0.7902	79.02%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7217	72.17%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8524	85.24%
Skin irritation	-	0.7421	74.21%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	+	0.6046	60.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7821	78.21%
Micronuclear	+	0.8133	81.33%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.8672	86.72%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6509	65.09%
Acute Oral Toxicity (c)	III	0.3775	37.75%
Estrogen receptor binding	+	0.7882	78.82%
Androgen receptor binding	+	0.7032	70.32%
Thyroid receptor binding	-	0.5186	51.86%
Glucocorticoid receptor binding	+	0.5445	54.45%
Aromatase binding	-	0.6110	61.10%
PPAR gamma	+	0.6762	67.62%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8604	86.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL244	P00742	Coagulation factor X	280 nM; 450 nM; 280 nM	IC50; Ki; IC50	via Super-PRED; via Super-PRED; PMID: 9834152

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.67%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.34%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.67%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.54%	85.14%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.06%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.96%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.91%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.13%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.31%	100.00%
CHEMBL4530	P00488	Coagulation factor XIII	83.66%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.55%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.57%	90.00%

Plants that contains it

• Aglaia elaeagnoidea
• Allocasuarina verticillata
• Aristolochia littoralis
• Astragalus gummifer
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Combretum indicum
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Elaeagnus umbellata
• Erigeron canadensis
• Euphorbia segetalis
• Euphorbia thymifolia
• Euphorbia tirucalli
• Garcinia celebica
• Liquidambar formosana
• Osbeckia chinensis
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phytolacca acinosa
• Piper arboreum
• Platycarya strobilacea
• Pouzolzia occidentalis
• Punica granatum
• Quercus salicina
• Quercus suber
• Ruta microcarpa
• Selinum carvifolium
• Sidastrum multiflorum
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 10417809
• NPASS: NPC166851
• ChEMBL: CHEMBL488110
• LOTUS: LTS0042847
• wikiData: Q104958588