sinolignan B

Details

• Internal ID: 3f54b981-e427-4b77-afd2-70230aac2a19
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aS,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@H]2[C@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O18/c1-43-17-3-11(4-18(44-2)23(17)35)21-12-5-15-16(48-10-47-15)6-13(12)30(14-8-45-31(42)22(14)21)51-33-29(41)27(39)25(37)20(50-33)9-46-32-28(40)26(38)24(36)19(7-34)49-32/h3-6,14,19-22,24-30,32-41H,7-10H2,1-2H3/t14-,19+,20+,21+,22+,24+,25+,26-,27-,28+,29+,30-,32+,33-/m0/s1
• InChI Key: PDLSJRZSXQFCFE-APVDPNJASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₈
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.22146442 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.25
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• CHEMBL1778159

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5958	59.58%
Caco-2	-	0.8899	88.99%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6367	63.67%
OATP2B1 inhibitior	-	0.8689	86.89%
OATP1B1 inhibitior	-	0.3715	37.15%
OATP1B3 inhibitior	+	0.9648	96.48%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6802	68.02%
P-glycoprotein inhibitior	-	0.5431	54.31%
P-glycoprotein substrate	+	0.6668	66.68%
CYP3A4 substrate	+	0.7072	70.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.5237	52.37%
CYP2C9 inhibition	-	0.8011	80.11%
CYP2C19 inhibition	-	0.7261	72.61%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.9203	92.03%
CYP2C8 inhibition	+	0.5599	55.99%
CYP inhibitory promiscuity	+	0.6363	63.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6053	60.53%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9235	92.35%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.7078	70.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6556	65.56%
Micronuclear	+	0.7133	71.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8827	88.27%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7666	76.66%
Acute Oral Toxicity (c)	III	0.7719	77.19%
Estrogen receptor binding	+	0.8647	86.47%
Androgen receptor binding	+	0.7827	78.27%
Thyroid receptor binding	-	0.4902	49.02%
Glucocorticoid receptor binding	+	0.6570	65.70%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6581	65.81%
Honey bee toxicity	-	0.6628	66.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.7675	76.75%

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	99.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.21%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.86%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.55%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.26%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.06%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.91%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.78%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.97%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.10%	89.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.98%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.81%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.78%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.32%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.02%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.83%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.92%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.83%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.43%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.02%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.71%	92.50%

Plants that contains it

• Dimorphotheca sinuata
• Dodecadenia grandiflora
• Heptapleurum capitatum
• Podophyllum hexandrum
• Roldana mexicana

Cross-Links

• PubChem: 54581699
• NPASS: NPC179240
• LOTUS: LTS0173412
• wikiData: Q105279642