Structure

Physi-Chem Properties

Molecular Weight:  444.14
Volume:  424.239
LogP:  1.437
LogD:  1.811
LogS:  -3.394
# Rotatable Bonds:  5
TPSA:  101.91
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.697
Synthetic Accessibility Score:  3.936
Fsp3:  0.435
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.825
MDCK Permeability:  3.071806349908002e-05
Pgp-inhibitor:  0.989
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.165
Plasma Protein Binding (PPB):  91.6719741821289%
Volume Distribution (VD):  1.249
Pgp-substrate:  7.6865458488464355%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.976
CYP2C19-inhibitor:  0.544
CYP2C19-substrate:  0.924
CYP2C9-inhibitor:  0.265
CYP2C9-substrate:  0.816
CYP2D6-inhibitor:  0.091
CYP2D6-substrate:  0.349
CYP3A4-inhibitor:  0.928
CYP3A4-substrate:  0.924

ADMET: Excretion

Clearance (CL):  3.8
Half-life (T1/2):  0.25

ADMET: Toxicity

hERG Blockers:  0.238
Human Hepatotoxicity (H-HT):  0.125
Drug-inuced Liver Injury (DILI):  0.438
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.097
Maximum Recommended Daily Dose:  0.938
Skin Sensitization:  0.078
Carcinogencity:  0.042
Eye Corrosion:  0.003
Eye Irritation:  0.056
Respiratory Toxicity:  0.644

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC207584

Natural Product ID:  NPC207584
Common Name*:   5-Methoxypodophyllotoxin
IUPAC Name:   (5R,5aR,8aR,9R)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Synonyms:   5-Methoxy Podophyllotoxin; 5-Methoxypodophyllotoxin
Standard InCHIKey:  PDQAOYGENRRPQO-UXDKQJBESA-N
Standard InCHI:  InChI=1S/C23H24O9/c1-26-13-5-10(6-14(27-2)20(13)28-3)16-11-7-15-21(32-9-31-15)22(29-4)18(11)19(24)12-8-30-23(25)17(12)16/h5-7,12,16-17,19,24H,8-9H2,1-4H3/t12-,16+,17-,19+/m0/s1
SMILES:  COc1cc(cc(c1OC)OC)[C@@H]1c2cc3c(c(c2[C@@H]([C@H]2COC(=O)[C@H]12)O)OC)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL292945
PubChem CID:   3035544
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001510] Lignan lactones
        • [CHEMONTID:0000047] Podophyllotoxins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO5212 Ascophyllum nodosum Species Fucaceae Eukaryota n.a. n.a. n.a. PMID[11121113]
NPO3003 Linum flavum Species Linaceae Eukaryota root n.a. n.a. PMID[1602298]
NPO23703 Libocedrus chevalieri Species Cupressaceae Eukaryota bark n.a. n.a. PMID[17676899]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[24417583]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. n.a. PMID[26923696]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO549 Musa X paradisiaca Strain Musaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO549 Musa X paradisiaca Strain Musaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6192 Phanera variegata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO549 Musa X paradisiaca Strain Musaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12821 Geigeria ornativa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11148 Antigonon leptopus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9556 Annona atemoya Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9432 Galium fagetorum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26353 Thuridilla hopei Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3929 Linum cariense Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6063 Collariella virescens Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12515 Xeromphis nilotica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5042 Salpichroa diffusa Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3003 Linum flavum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23703 Libocedrus chevalieri Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6192 Phanera variegata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO207 Tephrosia maxima Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7816 Cystoseira adriatica Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO549 Musa X paradisiaca Strain Musaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5212 Ascophyllum nodosum Species Fucaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11337 Machilus pseudolongifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT3950 Cell Line GLC4 cell line IC50 = 60.0 nM PMID[503826]
NPT3950 Cell Line GLC4 cell line IC50 = 250.0 nM PMID[503826]
NPT91 Cell Line KB Homo sapiens IC50 = 11.0 nM PMID[503827]
NPT165 Cell Line HeLa Homo sapiens ED50 = 22.0 ug ml-1 PMID[503828]
NPT2 Others Unspecified IC50 = 5000.0 nM PMID[503827]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 32.0 ug ml-1 PMID[503828]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC207584 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC19947
0.9933 High Similarity NPC32373
0.9933 High Similarity NPC237946
0.9803 High Similarity NPC288149
0.9737 High Similarity NPC91634
0.9737 High Similarity NPC268718
0.9737 High Similarity NPC150943
0.9737 High Similarity NPC96593
0.9737 High Similarity NPC119910
0.9732 High Similarity NPC245948
0.9605 High Similarity NPC163527
0.9605 High Similarity NPC115281
0.9605 High Similarity NPC181168
0.9597 High Similarity NPC210642
0.9597 High Similarity NPC13985
0.9548 High Similarity NPC14294
0.9548 High Similarity NPC116759
0.9545 High Similarity NPC152424
0.9545 High Similarity NPC100465
0.9536 High Similarity NPC273578
0.953 High Similarity NPC149505
0.9487 High Similarity NPC222531
0.9419 High Similarity NPC115624
0.9408 High Similarity NPC103197
0.9408 High Similarity NPC30009
0.9367 High Similarity NPC185498
0.9342 High Similarity NPC178574
0.9342 High Similarity NPC65591
0.9329 High Similarity NPC304687
0.9329 High Similarity NPC65574
0.9329 High Similarity NPC80230
0.9329 High Similarity NPC101755
0.9329 High Similarity NPC104024
0.9304 High Similarity NPC306475
0.9276 High Similarity NPC56184
0.925 High Similarity NPC179240
0.9211 High Similarity NPC303519
0.9205 High Similarity NPC477698
0.9205 High Similarity NPC177476
0.9205 High Similarity NPC262455
0.9182 High Similarity NPC474042
0.9182 High Similarity NPC174734
0.9156 High Similarity NPC136757
0.9145 High Similarity NPC473989
0.9145 High Similarity NPC24425
0.9139 High Similarity NPC304821
0.9085 High Similarity NPC164082
0.9079 High Similarity NPC474965
0.9079 High Similarity NPC668
0.9079 High Similarity NPC293757
0.9079 High Similarity NPC174512
0.9079 High Similarity NPC477695
0.9068 High Similarity NPC117911
0.9032 High Similarity NPC178195
0.9032 High Similarity NPC312763
0.9032 High Similarity NPC348849
0.9026 High Similarity NPC477699
0.9013 High Similarity NPC325720
0.9013 High Similarity NPC316676
0.8993 High Similarity NPC40237
0.8993 High Similarity NPC287124
0.8993 High Similarity NPC151423
0.8987 High Similarity NPC474770
0.8974 High Similarity NPC238834
0.8961 High Similarity NPC477700
0.8954 High Similarity NPC216223
0.8954 High Similarity NPC145569
0.8924 High Similarity NPC474043
0.891 High Similarity NPC473425
0.8889 High Similarity NPC79322
0.8889 High Similarity NPC40654
0.8889 High Similarity NPC262804
0.8882 High Similarity NPC3982
0.8882 High Similarity NPC212890
0.8875 High Similarity NPC22130
0.8875 High Similarity NPC116838
0.8874 High Similarity NPC477701
0.8874 High Similarity NPC218841
0.8874 High Similarity NPC141569
0.8874 High Similarity NPC166884
0.8874 High Similarity NPC475000
0.8874 High Similarity NPC92693
0.8868 High Similarity NPC470637
0.8867 High Similarity NPC176586
0.8867 High Similarity NPC210354
0.8846 High Similarity NPC474606
0.8846 High Similarity NPC24562
0.8839 High Similarity NPC475756
0.8839 High Similarity NPC32079
0.8831 High Similarity NPC125570
0.882 High Similarity NPC475865
0.8816 High Similarity NPC475868
0.8816 High Similarity NPC477702
0.8812 High Similarity NPC258322
0.8812 High Similarity NPC191352
0.8808 High Similarity NPC474288
0.8795 High Similarity NPC196771
0.879 High Similarity NPC198461
0.8782 High Similarity NPC471154
0.8773 High Similarity NPC471180
0.8773 High Similarity NPC311912
0.8758 High Similarity NPC33832
0.8758 High Similarity NPC321696
0.8758 High Similarity NPC321958
0.8758 High Similarity NPC193779
0.875 High Similarity NPC191158
0.875 High Similarity NPC177644
0.875 High Similarity NPC172171
0.875 High Similarity NPC239254
0.8734 High Similarity NPC234730
0.8727 High Similarity NPC471920
0.8727 High Similarity NPC292712
0.8727 High Similarity NPC312006
0.8727 High Similarity NPC20114
0.8727 High Similarity NPC129930
0.8727 High Similarity NPC474075
0.8727 High Similarity NPC114550
0.8727 High Similarity NPC471921
0.8727 High Similarity NPC471922
0.8726 High Similarity NPC473236
0.872 High Similarity NPC88557
0.8712 High Similarity NPC118162
0.8712 High Similarity NPC83049
0.8712 High Similarity NPC320471
0.871 High Similarity NPC85141
0.8701 High Similarity NPC116019
0.8696 High Similarity NPC239890
0.8696 High Similarity NPC209411
0.8693 High Similarity NPC318286
0.8693 High Similarity NPC327651
0.8688 High Similarity NPC173726
0.8688 High Similarity NPC241600
0.8684 High Similarity NPC324962
0.8684 High Similarity NPC218510
0.8684 High Similarity NPC477696
0.8684 High Similarity NPC76415
0.8684 High Similarity NPC477697
0.8684 High Similarity NPC470811
0.8683 High Similarity NPC23593
0.8679 High Similarity NPC115123
0.8679 High Similarity NPC473323
0.8679 High Similarity NPC239113
0.8679 High Similarity NPC478055
0.8679 High Similarity NPC29727
0.8675 High Similarity NPC184624
0.8662 High Similarity NPC476434
0.8662 High Similarity NPC302610
0.8658 High Similarity NPC11453
0.8654 High Similarity NPC260781
0.8654 High Similarity NPC182368
0.8654 High Similarity NPC229882
0.8654 High Similarity NPC218041
0.8654 High Similarity NPC469706
0.8654 High Similarity NPC145979
0.8654 High Similarity NPC9933
0.8654 High Similarity NPC185955
0.8654 High Similarity NPC214326
0.8654 High Similarity NPC225815
0.8654 High Similarity NPC158635
0.8654 High Similarity NPC469707
0.8642 High Similarity NPC198796
0.8636 High Similarity NPC87295
0.8634 High Similarity NPC63061
0.8627 High Similarity NPC326144
0.8623 High Similarity NPC107739
0.8618 High Similarity NPC230538
0.8618 High Similarity NPC103637
0.8618 High Similarity NPC229172
0.8618 High Similarity NPC191231
0.8618 High Similarity NPC36531
0.8616 High Similarity NPC476065
0.8616 High Similarity NPC186316
0.8614 High Similarity NPC471181
0.8609 High Similarity NPC46591
0.8608 High Similarity NPC297271
0.8608 High Similarity NPC16791
0.8608 High Similarity NPC61604
0.8608 High Similarity NPC308739
0.8608 High Similarity NPC126405
0.8608 High Similarity NPC245615
0.8608 High Similarity NPC299706
0.8608 High Similarity NPC217708
0.8608 High Similarity NPC115466
0.8608 High Similarity NPC474514
0.8608 High Similarity NPC77237
0.8608 High Similarity NPC53669
0.86 High Similarity NPC283949
0.86 High Similarity NPC196420
0.8599 High Similarity NPC224472
0.8591 High Similarity NPC44245
0.8591 High Similarity NPC150534
0.8591 High Similarity NPC72796
0.858 High Similarity NPC319749
0.858 High Similarity NPC236089
0.8571 High Similarity NPC263955
0.8571 High Similarity NPC230531
0.8571 High Similarity NPC474158
0.8571 High Similarity NPC325122
0.8571 High Similarity NPC215400
0.8571 High Similarity NPC180953

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC207584 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9933 High Similarity NPD4965 Approved
0.9933 High Similarity NPD4966 Approved
0.9933 High Similarity NPD4967 Phase 2
0.9732 High Similarity NPD37 Approved
0.9671 High Similarity NPD6234 Discontinued
0.9367 High Similarity NPD7228 Approved
0.9018 High Similarity NPD7240 Approved
0.8931 High Similarity NPD7199 Phase 2
0.8704 High Similarity NPD7184 Clinical (unspecified phase)
0.8412 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.8362 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6232 Discontinued
0.8177 Intermediate Similarity NPD7680 Approved
0.8166 Intermediate Similarity NPD5844 Phase 1
0.8155 Intermediate Similarity NPD7473 Discontinued
0.815 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8107 Intermediate Similarity NPD3818 Discontinued
0.8063 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD6674 Discontinued
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7803 Intermediate Similarity NPD7074 Phase 3
0.7771 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7229 Phase 3
0.7746 Intermediate Similarity NPD7054 Approved
0.7716 Intermediate Similarity NPD2533 Approved
0.7716 Intermediate Similarity NPD2534 Approved
0.7716 Intermediate Similarity NPD2532 Approved
0.7712 Intermediate Similarity NPD3027 Phase 3
0.7706 Intermediate Similarity NPD8127 Discontinued
0.7701 Intermediate Similarity NPD7472 Approved
0.7683 Intermediate Similarity NPD1653 Approved
0.7665 Intermediate Similarity NPD8455 Phase 2
0.7665 Intermediate Similarity NPD1465 Phase 2
0.7651 Intermediate Similarity NPD3705 Approved
0.7647 Intermediate Similarity NPD5494 Approved
0.7619 Intermediate Similarity NPD3817 Phase 2
0.7611 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD1934 Approved
0.7572 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD6166 Phase 2
0.7571 Intermediate Similarity NPD7808 Phase 3
0.7564 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD1613 Approved
0.756 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7819 Suspended
0.7558 Intermediate Similarity NPD3787 Discontinued
0.7557 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD6797 Phase 2
0.7548 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD8313 Approved
0.7528 Intermediate Similarity NPD8312 Approved
0.7527 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7251 Discontinued
0.7514 Intermediate Similarity NPD7685 Pre-registration
0.7485 Intermediate Similarity NPD7028 Phase 2
0.7471 Intermediate Similarity NPD3882 Suspended
0.7469 Intermediate Similarity NPD4110 Phase 3
0.7469 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD7827 Phase 1
0.7456 Intermediate Similarity NPD2801 Approved
0.7453 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD2438 Suspended
0.7423 Intermediate Similarity NPD6190 Approved
0.7405 Intermediate Similarity NPD6355 Discontinued
0.7399 Intermediate Similarity NPD6959 Discontinued
0.7391 Intermediate Similarity NPD6005 Phase 3
0.7391 Intermediate Similarity NPD7266 Discontinued
0.7391 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6004 Phase 3
0.7391 Intermediate Similarity NPD6002 Phase 3
0.7391 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3751 Discontinued
0.7381 Intermediate Similarity NPD4380 Phase 2
0.7362 Intermediate Similarity NPD3750 Approved
0.7355 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD5006 Approved
0.7354 Intermediate Similarity NPD5005 Approved
0.7345 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD4060 Phase 1
0.7342 Intermediate Similarity NPD3620 Phase 2
0.7329 Intermediate Similarity NPD6100 Approved
0.7329 Intermediate Similarity NPD6099 Approved
0.7326 Intermediate Similarity NPD7075 Discontinued
0.7325 Intermediate Similarity NPD6798 Discontinued
0.7325 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7458 Discontinued
0.7312 Intermediate Similarity NPD7097 Phase 1
0.731 Intermediate Similarity NPD5402 Approved
0.7308 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4908 Phase 1
0.7306 Intermediate Similarity NPD8151 Discontinued
0.7294 Intermediate Similarity NPD6801 Discontinued
0.7284 Intermediate Similarity NPD5763 Approved
0.7284 Intermediate Similarity NPD5762 Approved
0.7273 Intermediate Similarity NPD1283 Approved
0.7256 Intermediate Similarity NPD4628 Phase 3
0.7251 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6273 Approved
0.7243 Intermediate Similarity NPD7296 Approved
0.7235 Intermediate Similarity NPD7411 Suspended
0.7234 Intermediate Similarity NPD4420 Approved
0.7233 Intermediate Similarity NPD2979 Phase 3
0.7233 Intermediate Similarity NPD4140 Approved
0.7219 Intermediate Similarity NPD3226 Approved
0.7215 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD230 Phase 1
0.7179 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6663 Approved
0.717 Intermediate Similarity NPD6233 Phase 2
0.7168 Intermediate Similarity NPD7768 Phase 2
0.716 Intermediate Similarity NPD7033 Discontinued
0.716 Intermediate Similarity NPD3748 Approved
0.7159 Intermediate Similarity NPD5710 Approved
0.7159 Intermediate Similarity NPD5711 Approved
0.7152 Intermediate Similarity NPD4625 Phase 3
0.7152 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6746 Phase 2
0.7135 Intermediate Similarity NPD7435 Discontinued
0.7134 Intermediate Similarity NPD3018 Phase 2
0.7126 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD3749 Approved
0.7126 Intermediate Similarity NPD1511 Approved
0.712 Intermediate Similarity NPD8434 Phase 2
0.7117 Intermediate Similarity NPD2935 Discontinued
0.7115 Intermediate Similarity NPD2797 Approved
0.7108 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD3764 Approved
0.7105 Intermediate Similarity NPD1357 Approved
0.7101 Intermediate Similarity NPD5403 Approved
0.7091 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD919 Approved
0.7083 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5124 Phase 1
0.7078 Intermediate Similarity NPD1610 Phase 2
0.7078 Intermediate Similarity NPD1281 Approved
0.7076 Intermediate Similarity NPD6599 Discontinued
0.7068 Intermediate Similarity NPD6780 Approved
0.7068 Intermediate Similarity NPD6778 Approved
0.7068 Intermediate Similarity NPD6781 Approved
0.7068 Intermediate Similarity NPD6777 Approved
0.7068 Intermediate Similarity NPD6776 Approved
0.7068 Intermediate Similarity NPD6782 Approved
0.7068 Intermediate Similarity NPD6779 Approved
0.7063 Intermediate Similarity NPD8032 Phase 2
0.7048 Intermediate Similarity NPD7003 Approved
0.7048 Intermediate Similarity NPD8166 Discontinued
0.7041 Intermediate Similarity NPD1512 Approved
0.7041 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1608 Approved
0.7025 Intermediate Similarity NPD5736 Approved
0.7025 Intermediate Similarity NPD2861 Phase 2
0.7024 Intermediate Similarity NPD6799 Approved
0.7022 Intermediate Similarity NPD5242 Approved
0.7022 Intermediate Similarity NPD3926 Phase 2
0.7011 Intermediate Similarity NPD5353 Approved
0.7 Intermediate Similarity NPD3268 Approved
0.6995 Remote Similarity NPD7549 Discontinued
0.6995 Remote Similarity NPD6823 Phase 2
0.6987 Remote Similarity NPD2982 Phase 2
0.6987 Remote Similarity NPD2983 Phase 2
0.6987 Remote Similarity NPD4749 Approved
0.6983 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6982 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5401 Approved
0.6975 Remote Similarity NPD5735 Approved
0.6975 Remote Similarity NPD447 Suspended
0.6975 Remote Similarity NPD1933 Approved
0.697 Remote Similarity NPD1552 Clinical (unspecified phase)
0.697 Remote Similarity NPD7783 Phase 2
0.697 Remote Similarity NPD2346 Discontinued
0.697 Remote Similarity NPD7782 Clinical (unspecified phase)
0.697 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1091 Approved
0.6959 Remote Similarity NPD7696 Phase 3
0.6959 Remote Similarity NPD7698 Approved
0.6959 Remote Similarity NPD7697 Approved
0.6951 Remote Similarity NPD1510 Phase 2
0.6948 Remote Similarity NPD5126 Approved
0.6948 Remote Similarity NPD4626 Approved
0.6948 Remote Similarity NPD5125 Phase 3
0.6937 Remote Similarity NPD7095 Approved
0.6937 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6935 Remote Similarity NPD8150 Discontinued
0.6933 Remote Similarity NPD6653 Approved
0.6933 Remote Similarity NPD5283 Phase 1
0.6928 Remote Similarity NPD1549 Phase 2
0.6923 Remote Similarity NPD4357 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data