4'-Demethyldeoxypodophyllotoxin

Details

• Internal ID: e3ceec7b-f390-48dd-8779-add2a1f63519
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: (5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@@H](CC4=CC5=C(C=C24)OCO5)COC3=O
• InChI: InChI=1S/C21H20O7/c1-24-16-5-11(6-17(25-2)20(16)22)18-13-7-15-14(27-9-28-15)4-10(13)3-12-8-26-21(23)19(12)18/h4-7,12,18-19,22H,3,8-9H2,1-2H3/t12-,18+,19-/m0/s1
• InChI Key: RFDMNXDDRXVJTM-RQUSPXKASA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.12090297 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 3590-93-0
• 4'-Demethyldesoxypodophyllotoxin
• 4-Demethyldeoxypodophyllotoxin
• A 80198
• CHEBI:1729
• (5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
• (-)-4'-demethyldeoxypodophyllotoxin
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R-(5-alpha,5a-beta,8a-alpha))-
• NSC267714
• 4'-demethyl-
• Podophyllotoxin, 4'-O-demethyl-4-deoxy- (7CI,8CI)
• CHEMBL89905
• 4-Demethyl-Deoxypodophyllotoxin
• 4'-desmethyldesoxypodophyllotoxin
• 4/'-Demethyldeoxypodophyllotoxin
• SCHEMBL15892698
• DTXSID50189475
• HY-N10829
• (-)-4'-demethyl-deoxypodophyllotoxin
• 7-Dehydroxy-4-demethylpodophyllotoxin
• (-)-4'-desmethyl-deoxypodophyllotoxin
• AKOS004120062
• NCGC00161920-01
• LS-70851
• Podophyllotoxin, 4'-O-demethyl-4-deoxy-
• CS-0637021
• Q27105498
• (10R,11R,15R)-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one
• (5r,5ar,8ar)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5ah-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one, AldrichCPR
• (5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• (5R,5aR,8aR)-5-(4-Hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.6747	67.47%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	0.8659	86.59%
OATP1B1 inhibitior	+	0.7323	73.23%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8828	88.28%
P-glycoprotein inhibitior	-	0.5266	52.66%
P-glycoprotein substrate	-	0.7573	75.73%
CYP3A4 substrate	+	0.6093	60.93%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.7535	75.35%
CYP3A4 inhibition	+	0.8608	86.08%
CYP2C9 inhibition	+	0.9479	94.79%
CYP2C19 inhibition	+	0.9331	93.31%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	-	0.8380	83.80%
CYP2C8 inhibition	-	0.6633	66.33%
CYP inhibitory promiscuity	+	0.8569	85.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4107	41.07%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8374	83.74%
Skin irritation	-	0.7831	78.31%
Skin corrosion	-	0.9685	96.85%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6617	66.17%
Micronuclear	+	0.8874	88.74%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.6947	69.47%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7664	76.64%
Acute Oral Toxicity (c)	III	0.6221	62.21%
Estrogen receptor binding	+	0.9098	90.98%
Androgen receptor binding	+	0.7029	70.29%
Thyroid receptor binding	+	0.7690	76.90%
Glucocorticoid receptor binding	+	0.8791	87.91%
Aromatase binding	-	0.7188	71.88%
PPAR gamma	+	0.7644	76.44%
Honey bee toxicity	-	0.7850	78.50%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9535	95.35%

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	99.29%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.83%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.69%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.45%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.21%	92.62%
CHEMBL4040	P28482	MAP kinase ERK2	90.50%	83.82%
CHEMBL2581	P07339	Cathepsin D	90.47%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.72%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.54%	96.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.91%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.88%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.26%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.07%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.88%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.83%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.69%	89.62%

Plants that contains it

• Condea verticillata
• Hebecarpa macradenia
• Podophyllum delavayi
• Podophyllum hexandrum
• Podophyllum peltatum
• Podophyllum pleianthum
• Podophyllum sinense
• Podophyllum versipelle
• Polygala tenuifolia
• Protium tonkinense

Cross-Links

• PubChem: 160705
• NPASS: NPC30009
• ChEMBL: CHEMBL89905
• LOTUS: LTS0228469
• wikiData: Q27105498