Podorhizol beta-D-glucoside

Details

• Internal ID: bd1b8afd-dec5-436a-baf8-d50b899b1bbc
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(S)-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C(C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]([C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H34O13/c1-34-18-8-14(9-19(35-2)26(18)36-3)25(41-28-24(32)23(31)22(30)20(10-29)40-28)21-15(11-37-27(21)33)6-13-4-5-16-17(7-13)39-12-38-16/h4-5,7-9,15,20-25,28-32H,6,10-12H2,1-3H3/t15-,20+,21-,22+,23-,24+,25+,28-/m0/s1
• InChI Key: IETDTZKBVWFSKR-XYEVPOBGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₃
• Molecular Weight: 578.60 g/mol
• Exact Mass: 578.19994113 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.33
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 17187-73-4
• (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(S)-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• (S)-[(3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-2-oxotetrahydrofuran-3-yl](3,4,5-trimethoxyphenyl)methyl beta-D-glucopyranoside
• CHEBI:27901
• DTXSID90938060
• Q27103398
• (3S)-3alpha-[(alphaS)-alpha-(beta-D-Glucopyranosyloxy)-3,4,5-trimethoxybenzyl]-4beta-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
• {4-[(2H-1,3-Benzodioxol-5-yl)methyl]-2-oxooxolan-3-yl}(3,4,5-trimethoxyphenyl)methyl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4809	48.09%
Caco-2	-	0.8192	81.92%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5415	54.15%
OATP2B1 inhibitior	-	0.7325	73.25%
OATP1B1 inhibitior	+	0.8776	87.76%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9246	92.46%
P-glycoprotein inhibitior	+	0.6174	61.74%
P-glycoprotein substrate	-	0.6283	62.83%
CYP3A4 substrate	+	0.6431	64.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8419	84.19%
CYP3A4 inhibition	-	0.7410	74.10%
CYP2C9 inhibition	-	0.8577	85.77%
CYP2C19 inhibition	-	0.7633	76.33%
CYP2D6 inhibition	-	0.8845	88.45%
CYP1A2 inhibition	-	0.9108	91.08%
CYP2C8 inhibition	-	0.6003	60.03%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5882	58.82%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.8287	82.87%
Skin corrosion	-	0.9540	95.40%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7394	73.94%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8643	86.43%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7824	78.24%
Acute Oral Toxicity (c)	III	0.7464	74.64%
Estrogen receptor binding	+	0.8146	81.46%
Androgen receptor binding	+	0.6477	64.77%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6675	66.75%
Aromatase binding	-	0.5991	59.91%
PPAR gamma	+	0.6611	66.11%
Honey bee toxicity	-	0.7094	70.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	+	0.7235	72.35%

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	98.76%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.66%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.62%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	96.88%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.12%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.62%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.80%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.62%	92.62%
CHEMBL261	P00915	Carbonic anhydrase I	93.45%	96.76%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.48%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.04%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.09%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.94%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.75%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.38%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.10%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.63%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.27%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.89%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.86%	95.89%
CHEMBL4208	P20618	Proteasome component C5	85.04%	90.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.19%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.23%	97.14%

Plants that contains it

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

Cross-Links

• PubChem: 443015
• NPASS: NPC270048
• LOTUS: LTS0042938
• wikiData: Q27103398