Natural Product: ENC000361

NPs Basic Information

Download MOL File
Name
Podofilox
Molecular Formula C22H22O8
IUPAC Name*
(5R,5aR,8aR,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
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
InChIKey
YJGVMLPVUAXIQN-XVVDYKMHSA-N
Synonyms
podophyllotoxin; Podofilox; 518-28-5; Condylox; Condyline; (-)-Podophyllotoxin; Wartec; Podophyllinic acid lactone; Podophyllotoxin 7; Warticon; Podofilox [USAN]; Podophyllum; NSC24818; CHEMBL61; MFCD00075290; NSC-24818; (10R,11R,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,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one; MLS000069495; (5R,5aR,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; CHEBI:50305; Podofilox (USAN); L36H50F353; (5R,5aR,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; NCGC00022001-05; Podofilm; SMR000059121; NSC 24818; DSSTox_CID_25645; DSSTox_RID_81023; DSSTox_GSID_45645; (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one; (5R,5aR,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; Podocon-25; Podophilox; (5R,5aR,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; CCRIS 565; HSDB 7238; SR-05000001749; MLS002702981; EINECS 208-250-4; Podofillina; Podophylotoxin; AI3-50456; Mayapple isolate; UNII-L36H50F353; Condylox (TN); CAS-518-28-5; Podophyllotoxin,(S); Prestwick_1018; 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-(5alpha,5abeta,8aalpha,9alpha))-; Podofillina [Italian]; Podophyllotoxin (BAN); Podophyllotoxin, 95%; Spectrum_000199; PODOFILOX [HSDB]; Opera_ID_1397; Prestwick0_000782; Prestwick1_000782; Prestwick2_000782; Prestwick3_000782; Spectrum2_000878; Spectrum4_000592; Spectrum5_001368; PODOFILOX [VANDF]; UPCMLD-DP035; PODOPHYLLOTOXIN [MI]; SCHEMBL42243; BSPBio_000884; BSPBio_002352; KBioGR_001084; KBioSS_000679; MLS001148204; MLS002172467; MLS006010754; MLS006011412; BIDD:GT0123; DivK1c_000292; UNII-16902YVY2B; SPBio_000955; SPBio_002823; BPBio1_000974; CCRIS 4391; PODOFILOX [ORANGE BOOK]; PODOPHYLLOTOXIN [MART.]; DTXSID3045645; PODOPHYLLOTOXIN [WHO-DD]; UPCMLD-DP035:001; UPCMLD-DP035:002; BCBcMAP01_000165; HMS500O14; KBio1_000292; KBio2_000679; KBio2_003247; KBio2_005815; AMY2648; NINDS_000292; 16902YVY2B; HMS1570M06; HMS2093P16; HMS2097M06; HMS2235A23; HMS3259J19; HMS3714M06; Pharmakon1600-02300332; (5R,5aR,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; 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; ALBB-020906; BCP24085; 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.BETA.,8A.ALPHA.,9.ALPHA.))-; Podophyllotoxin, analytical standard; ZINC3861806; EINECS 232-546-2; Tox21_110874; Tox21_202922; B18-5C; BBL033695; BDBM50035218; CCG-39894; NSC759591; STK801918; PODOPHYLLOTOXIN [EP MONOGRAPH]; AKOS000265559; Tox21_110874_1; AC-1656; CS-1185; DB01179; KS-1281; NC00675; ND-1185; NSC-759591; SDCCGMLS-0066888.P001; IDI1_000292; SMP1_000243; NCGC00022001-03; NCGC00022001-07; NCGC00022001-08; NCGC00022001-09; NCGC00022001-10; NCGC00022001-11; NCGC00022001-13; NCGC00022001-14; NCGC00260468-01; (5R,9R,5aR,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2H -isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one; 1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one; HY-15552; NCI60_001981; RD4-6269; P1771; EN300-52746; D05529; P-6980; 518P285; A828801; Q421193; SR-01000003030; SR-01000003030-3; SR-05000001749-1; SR-05000001749-2; BRD-K47869605-001-05-6; BRD-K47869605-001-18-9; Z759291658; (10R,11R,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,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one; (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one; (5R,5aR,8aR,9R)-5-oxidanyl-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one; 11016-28-7; 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-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]; 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,5aR,8aR,9R)-; 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.beta.,8a.alpha.,9.alpha.)]-; Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone
CAS 518-28-5
PubChem CID 10607
ChEMBL ID CHEMBL61
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lignans, neolignans and r
      • Class: Lignan lactones
        • Subclass: Podophyllotoxins
          • Direct Parent: Podophyllotoxins

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 414.4 ALogp: 2.0
HBD: 1 HBA: 8
Rotatable Bonds: 4 Lipinski's rule of five: Accepted
Polar Surface Area: 92.7 Aromatic Rings: 5
Heavy Atoms: 30 QED Weighted: 0.763

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.879 MDCK Permeability: 0.00003820
Pgp-inhibitor: 0.949 Pgp-substrate: 0.001
Human Intestinal Absorption (HIA): 0.002 20% Bioavailability (F20%): 0.003
30% Bioavailability (F30%): 0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.236 Plasma Protein Binding (PPB): 93.22%
Volume Distribution (VD): 1.275 Fu: 5.26%

ADMET: Metabolism

CYP1A2-inhibitor: 0.059 CYP1A2-substrate: 0.973
CYP2C19-inhibitor: 0.733 CYP2C19-substrate: 0.912
CYP2C9-inhibitor: 0.39 CYP2C9-substrate: 0.796
CYP2D6-inhibitor: 0.13 CYP2D6-substrate: 0.44
CYP3A4-inhibitor: 0.939 CYP3A4-substrate: 0.922

ADMET: Excretion

Clearance (CL): 5.732 Half-life (T1/2): 0.277

ADMET: Toxicity

hERG Blockers: 0.107 Human Hepatotoxicity (H-HT): 0.164
Drug-inuced Liver Injury (DILI): 0.69 AMES Toxicity: 0.033
Rat Oral Acute Toxicity: 0.097 Maximum Recommended Daily Dose: 0.938
Skin Sensitization: 0.089 Carcinogencity: 0.089
Eye Corrosion: 0.003 Eye Irritation: 0.023
Respiratory Toxicity: 0.8
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC004644 0.357 D0D4HN 1.000
ENC001376 0.356 D09NIB 0.569
ENC001892 0.323 D01DBQ 0.507
ENC001423 0.319 D0L1JW 0.435
ENC001396 0.319 D0W8WB 0.362
ENC001403 0.318 D04TDQ 0.360
ENC002388 0.314 D0F7CS 0.358
ENC005931 0.308 D02LZB 0.333
ENC001085 0.307 D06GCK 0.328
ENC000523 0.306 D09DHY 0.320
*Note: the compound similarity was calculated by RDKIT.