beta-Peltatin A

Details

• Internal ID: 08aadf5d-0923-474c-bd94-e09fb8bb8b68
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: 4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=C(C5=C(C=C24)OCO5)O)COC3=O
• InChI: InChI=1S/C22H22O8/c1-25-14-5-10(6-15(26-2)20(14)27-3)17-12-7-16-21(30-9-29-16)19(23)13(12)4-11-8-28-22(24)18(11)17/h5-7,11,17-18,23H,4,8-9H2,1-3H3
• InChI Key: HLBPOYVRLSXWJJ-UHFFFAOYSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.40 g/mol
• Exact Mass: 414.13146766 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 299431-00-8
• MLS002702982
• NSC659372
• SCHEMBL516628
• CHEMBL1435754
• DTXSID00871732
• HLBPOYVRLSXWJJ-UHFFFAOYSA-N
• AKOS024322664
• NCGC00095966-01
• NCGC00095966-02
• 10-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• SMR001566792
• 10-HO-5-(3,4,5-TRI-MEO-PH)-4H-5AH-FURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-6-ONE
• 10-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one #
• 4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
• 5,8,8a,9-Tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
• Naphtho(2,3-d)-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-9-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-, .gamma.-lactone
• NCGC00095966-03!4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9748	97.48%
Caco-2	+	0.7319	73.19%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7677	76.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9633	96.33%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8404	84.04%
P-glycoprotein inhibitior	-	0.5055	50.55%
P-glycoprotein substrate	-	0.8111	81.11%
CYP3A4 substrate	+	0.6261	62.61%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.7535	75.35%
CYP3A4 inhibition	+	0.7775	77.75%
CYP2C9 inhibition	+	0.9063	90.63%
CYP2C19 inhibition	+	0.8951	89.51%
CYP2D6 inhibition	-	0.9057	90.57%
CYP1A2 inhibition	-	0.8748	87.48%
CYP2C8 inhibition	+	0.5641	56.41%
CYP inhibitory promiscuity	+	0.8027	80.27%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4266	42.66%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.8067	80.67%
Skin corrosion	-	0.9660	96.60%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5559	55.59%
Micronuclear	+	0.8474	84.74%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8186	81.86%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7055	70.55%
Acute Oral Toxicity (c)	III	0.4135	41.35%
Estrogen receptor binding	+	0.8811	88.11%
Androgen receptor binding	+	0.6778	67.78%
Thyroid receptor binding	+	0.8026	80.26%
Glucocorticoid receptor binding	+	0.8529	85.29%
Aromatase binding	-	0.7266	72.66%
PPAR gamma	+	0.7113	71.13%
Honey bee toxicity	-	0.7277	72.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9596	95.96%

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	99.21%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.90%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.35%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.30%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.51%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	88.09%	83.82%
CHEMBL2535	P11166	Glucose transporter	87.19%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.30%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.73%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.51%	97.09%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.01%	82.67%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.23%	96.77%
CHEMBL2581	P07339	Cathepsin D	82.71%	98.95%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	82.12%	96.86%

Plants that contains it

• Condea verticillata
• Eriope latifolia
• Linum capitatum
• Linum cariense
• Podophyllum peltatum
• Podophyllum versipelle
• Pulsatilla chinensis
• Thujopsis dolabrata var. hondae

Cross-Links

• PubChem: 2363
• LOTUS: LTS0013861
• wikiData: Q105030066