Picropodophyllin

Details

• Internal ID: ac062bd2-8dbe-424f-9941-6b53a7d581ee
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aS,9R)-5-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(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O
• InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
• InChI Key: YJGVMLPVUAXIQN-HAEOHBJNSA-N
• Popularity: 297 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: 2.00
• Atomic LogP (AlogP): 2.41
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• Picropodophyllotoxin
• 477-47-4
• AXL1717
• Picropodophyllin (PPP)
• IGF-1R Inhibitor, PPP
• AXL-1717
• NSC 36407
• AXL 1717
• NSC36407
• NSC-36407
• BRN 0099161
• 17434-18-3
• UNII-0F35AOI227
• Podophyllotoxin picropodophyllin
• (-)PPP
• (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CHEBI:75251
• 0F35AOI227
• cyclolignan PPP
• picro-podophyllin
• (5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• (5R,5aS,8aR,9R)-9-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
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5-alpha,5a-alpha,8a-alpha,9-alpha))-
• AXL1717 (Picropodophyllotoxin)
• AXL1717;Picropodophyllin;PPP
• C22-H22-O8
• (5R,5AS,8AR,9R)-9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,5A,8A,9-TETRAHYDROFURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-6(8H)-ONE
• Spectrum_001636
• Spectrum2_000520
• Spectrum3_001671
• Spectrum4_001836
• Spectrum5_000631
• BSPBio_003481
• KBioGR_002538
• KBioSS_002116
• SCHEMBL159598
• SPECTRUM1504410
• SPBio_000479
• CHEMBL283120
• GTPL7873
• KBio2_002116
• KBio2_004684
• KBio2_007252
• KBio3_002701
• DTXSID80197245
• PICROPODOPHYLLIN [WHO-DD]
• YJGVMLPVUAXIQN-HAEOHBJNSA-N
• HMS1923O05
• BCP18482
• EX-A4921
• CCG-39920
• MFCD01742647
• NSC799342
• s7668
• AKOS015965529
• CS-1184
• DB12802
• NSC-799342
• SDCCGMLS-0066757.P001
• NCGC00161923-01
• NCGC00161923-02
• NCGC00161923-04
• NCGC00161923-29
• Picropodophyllotoxin;Picropodophyllin;PPP
• AC-20289
• AC-36894
• BS-16874
• HY-15494
• LS-70860
• PODOPHYLLOTOXIN PICROPODOPHYLLIN [MI]
• Picropodophyllotoxin, >=96% (HPLC), powder
• PODOPHYLLOTOXIN IMPURITY A [EP IMPURITY]
• EN300-24434020
• BRD-K81829253-001-02-9
• BRD-K81829253-001-03-7
• Q27088385
• Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-Isomer
• WLN: T E5 C665 FVO NO PO OHTT&&J DR CO1 DO1 EO1& JQ
• (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one
• (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
• (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
• (5R,5aS,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
• 118627-04-6
• 5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, [5R-(.alpha.-5a.alpha.,8a.alpha.,9.alpha.)]
• Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.alpha.,8a.alpha.,9.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	+	0.6986	69.86%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7743	77.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7428	74.28%
OATP1B3 inhibitior	+	0.9603	96.03%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8646	86.46%
P-glycoprotein inhibitior	-	0.4318	43.18%
P-glycoprotein substrate	-	0.9449	94.49%
CYP3A4 substrate	+	0.5939	59.39%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.7886	78.86%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.6856	68.56%
CYP inhibitory promiscuity	+	0.7468	74.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4302	43.02%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8127	81.27%
Skin corrosion	-	0.9705	97.05%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5567	55.67%
Micronuclear	+	0.8674	86.74%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7800	78.00%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.5663	56.63%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8462	84.62%
Glucocorticoid receptor binding	+	0.8610	86.10%
Aromatase binding	-	0.7966	79.66%
PPAR gamma	+	0.5637	56.37%
Honey bee toxicity	-	0.7128	71.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9578	95.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	15.8 nM	Potency	via Super-PRED
CHEMBL1806	P11388	DNA topoisomerase II alpha	486 nM	Kd	via Super-PRED
CHEMBL1293278	O75496	Geminin	35.5 nM	Potency	via Super-PRED
CHEMBL2034	P04150	Glucocorticoid receptor	14 nM	IC50	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	2 nM; 15.8 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	25.1 nM; 79.4 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	125.9 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	501.2 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	3.2 nM; 14.1 nM; 89.1 nM; 28.2 nM	Potency; Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	112.2 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	14.7 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	446.7 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	39.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.92%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.61%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.60%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.72%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.28%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.11%	82.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.84%	94.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.80%	96.86%
CHEMBL2535	P11166	Glucose transporter	81.69%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.57%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.67%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.41%	97.14%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Anthriscus sylvestris
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Croton nitens
• Dimorphotheca sinuata
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Heptapleurum capitatum
• Hernandia sonora
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus sabina
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Panax notoginseng
• Plectranthus amboinicus
• Plumbago europaea
• Podophyllum grayi
• Podophyllum hexandrum
• Podophyllum peltatum
• Podophyllum sinense
• Reissantia indica
• Rhodanthe stricta
• Roldana mexicana
• Simmondsia chinensis
• Swertia paniculata
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 72435
• NPASS: NPC32373
• ChEMBL: CHEMBL283120
• LOTUS: LTS0147106
• wikiData: Q27088385