Podophyllinic acid

Details

• Internal ID: aef09bed-3e95-45a9-a158-ed036446a94a
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans > 9,9p-dihydroxyaryltetralin lignans
• IUPAC Name: (5R,6R,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C(C(C(C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]([C@@H]([C@H](C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O
• InChI: InChI=1S/C22H24O9/c1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26/h4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26)/t13-,18+,19-,20-/m0/s1
• InChI Key: XRBSKUSTLXISAB-XVVDYKMHSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₉
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.14203234 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 1853-37-8
• Podophyllic acid
• UNII-16FK9L3306
• 16FK9L3306
• Diaethyl-(2-chlor-1-(2,4-dichlorphenyl))-vinyl-phosphat
• Naphtho(2,3-d)-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-, (5R,6R,7R,8R)-
• Diaethyl-(2-chlor-1-(2,4-dichlorphenyl))-vinyl-phosphat [German]
• SCHEMBL8016
• CHEMBL32955
• Naphtho[2,3-d]-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,6.alpha.,7.beta.,8.alpha.)]-
• (5R,6R,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid
• Q27251810

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8716	87.16%
Caco-2	+	0.5900	59.00%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5943	59.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8489	84.89%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7488	74.88%
P-glycoprotein inhibitior	-	0.5216	52.16%
P-glycoprotein substrate	-	0.9259	92.59%
CYP3A4 substrate	+	0.5440	54.40%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8083	80.83%
CYP3A4 inhibition	+	0.6846	68.46%
CYP2C9 inhibition	+	0.6549	65.49%
CYP2C19 inhibition	+	0.5767	57.67%
CYP2D6 inhibition	-	0.8915	89.15%
CYP1A2 inhibition	-	0.8763	87.63%
CYP2C8 inhibition	+	0.4732	47.32%
CYP inhibitory promiscuity	+	0.8787	87.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4674	46.74%
Micronuclear	+	0.7674	76.74%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8575	85.75%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7171	71.71%
Acute Oral Toxicity (c)	III	0.6479	64.79%
Estrogen receptor binding	+	0.8448	84.48%
Androgen receptor binding	+	0.8120	81.20%
Thyroid receptor binding	+	0.7673	76.73%
Glucocorticoid receptor binding	+	0.7924	79.24%
Aromatase binding	-	0.7634	76.34%
PPAR gamma	+	0.5632	56.32%
Honey bee toxicity	-	0.8433	84.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9150	91.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.15%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.42%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.48%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.92%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.80%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.76%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.33%	89.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	89.79%	89.44%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.41%	96.77%
CHEMBL2581	P07339	Cathepsin D	87.84%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.90%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.80%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.64%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.15%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.89%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.90%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.10%	91.19%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 134632
• NPASS: NPC245948
• ChEMBL: CHEMBL32955
• LOTUS: LTS0017301
• wikiData: Q27251810