Palstatin

Details

• Internal ID: c7a5de0b-2be6-4223-8d8b-343e55464768
• Taxonomy: Lignans, neolignans and related compounds > Flavonolignans
• IUPAC Name: 5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydro-1,4-benzodioxin-7-yl]chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C(OC3=C(O2)C=C(C=C3OC)C4=CC(=O)C5=C(C=C(C=C5O4)O)O)CO
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3OC)C4=CC(=O)C5=C(C=C(C=C5O4)O)O)CO
• InChI: InChI=1S/C27H24O11/c1-33-19-6-13(7-20(34-2)25(19)32)26-23(11-28)38-27-21(35-3)4-12(5-22(27)37-26)17-10-16(31)24-15(30)8-14(29)9-18(24)36-17/h4-10,23,26,28-30,32H,11H2,1-3H3/t23-,26-/m1/s1
• InChI Key: KIEFQALNZCXSHH-ZEQKJWHPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₁
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.13186158 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.48
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• CHEMBL523569
• SCHEMBL14829819
• 5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydro-1,4-benzodioxin-7-yl]chromen-4-one
• 4H-1-benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-8-methoxy-1,4-benzodioxin-6-yl]-5,7-dihydroxy-
• 5,7-Dihydroxy-2-[3-(4-hydroxy-3,5-dimethoxy-phenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chromen-4-one
• InChI=1/C27H24O11/c1-33-19-6-13(7-20(34-2)25(19)32)26-23(11-28)38-27-21(35-3)4-12(5-22(27)37-26)17-10-16(31)24-15(30)8-14(29)9-18(24)36-17/h4-10,23,26,28-30,32H,11H2,1-3H3/t23-,26-/m1/s
• rel-5,7-dihydroxy-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-8-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl]-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8893	88.93%
Caco-2	-	0.7648	76.48%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6699	66.99%
OATP2B1 inhibitior	-	0.7097	70.97%
OATP1B1 inhibitior	+	0.8567	85.67%
OATP1B3 inhibitior	-	0.3164	31.64%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9341	93.41%
P-glycoprotein inhibitior	+	0.9331	93.31%
P-glycoprotein substrate	-	0.5545	55.45%
CYP3A4 substrate	+	0.6306	63.06%
CYP2C9 substrate	-	0.6235	62.35%
CYP2D6 substrate	-	0.8293	82.93%
CYP3A4 inhibition	-	0.5928	59.28%
CYP2C9 inhibition	-	0.6736	67.36%
CYP2C19 inhibition	-	0.7375	73.75%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	-	0.8181	81.81%
CYP2C8 inhibition	+	0.7305	73.05%
CYP inhibitory promiscuity	+	0.6513	65.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7217	72.17%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8525	85.25%
Skin irritation	-	0.8350	83.50%
Skin corrosion	-	0.9670	96.70%
Ames mutagenesis	-	0.5928	59.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6986	69.86%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8982	89.82%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6774	67.74%
Acute Oral Toxicity (c)	III	0.6807	68.07%
Estrogen receptor binding	+	0.8922	89.22%
Androgen receptor binding	+	0.7585	75.85%
Thyroid receptor binding	+	0.6592	65.92%
Glucocorticoid receptor binding	+	0.8663	86.63%
Aromatase binding	+	0.5898	58.98%
PPAR gamma	+	0.7465	74.65%
Honey bee toxicity	-	0.6908	69.08%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.4517	45.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.37%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.76%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.96%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.28%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.70%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL3194	P02766	Transthyretin	89.72%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.18%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.71%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.28%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.11%	99.23%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	83.58%	95.55%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.44%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.36%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	83.19%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.64%	95.50%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium sagittatum
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Stipa robusta
• Succisa pratensis

Cross-Links

• PubChem: 5323578
• NPASS: NPC101731
• LOTUS: LTS0105069
• wikiData: Q105141468