Structure

Physi-Chem Properties

Molecular Weight:  340.13
Volume:  339.826
LogP:  5.132
LogD:  4.26
LogS:  -6.532
# Rotatable Bonds:  2
TPSA:  46.15
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.819
Synthetic Accessibility Score:  3.524
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.886
MDCK Permeability:  3.4232311008963734e-05
Pgp-inhibitor:  0.959
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.107
Plasma Protein Binding (PPB):  97.38642120361328%
Volume Distribution (VD):  1.628
Pgp-substrate:  1.0732005834579468%

ADMET: Metabolism

CYP1A2-inhibitor:  0.693
CYP1A2-substrate:  0.201
CYP2C19-inhibitor:  0.978
CYP2C19-substrate:  0.394
CYP2C9-inhibitor:  0.857
CYP2C9-substrate:  0.896
CYP2D6-inhibitor:  0.968
CYP2D6-substrate:  0.899
CYP3A4-inhibitor:  0.977
CYP3A4-substrate:  0.484

ADMET: Excretion

Clearance (CL):  16.576
Half-life (T1/2):  0.121

ADMET: Toxicity

hERG Blockers:  0.151
Human Hepatotoxicity (H-HT):  0.138
Drug-inuced Liver Injury (DILI):  0.865
AMES Toxicity:  0.265
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.097
Skin Sensitization:  0.086
Carcinogencity:  0.869
Eye Corrosion:  0.003
Eye Irritation:  0.123
Respiratory Toxicity:  0.287

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC233224

Natural Product ID:  NPC233224
Common Name*:   5-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-Yl)-3,4-Dimethyloxolan-2-Yl]-1,3-Benzodioxole
IUPAC Name:   5-[(2R,3S,4R,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-1,3-benzodioxole
Synonyms:   (+)-zuonin A
Standard InCHIKey:  QFUXQRHAJWXPGP-BINDOVRGSA-N
Standard InCHI:  InChI=1S/C20H20O5/c1-11-12(2)20(14-4-6-16-18(8-14)24-10-22-16)25-19(11)13-3-5-15-17(7-13)23-9-21-15/h3-8,11-12,19-20H,9-10H2,1-2H3/t11-,12+,19-,20-/m1/s1
SMILES:  C[C@@H]1[C@H](C)[C@H](c2ccc3c(c2)OCO3)O[C@H]1c1ccc2c(c1)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1980140
PubChem CID:   338287
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[11040054]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16724856]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. leaf n.a. PMID[17999353]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota Roots; Tubers n.a. n.a. PMID[19639966]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[19900811]
NPO9925 Rhododendron latoucheae Species Ericaceae Eukaryota Twigs; Leaves n.a. n.a. PMID[30106288]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[8237383]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8237383]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8368081]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6475 Gymnosporia trigyna Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7522 Streptomyces amakusaensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO313 Castilleja sulphurea Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9571 Pseudobrickellia brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9301 Dioscorea sativa Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9925 Rhododendron latoucheae Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19174 Anoplophora chinensis Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1155 Forsythia japonica Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4682 Lindera aggregata 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 59566.21 nM PMID[530567]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 36224.3 nM PMID[530567]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 55590.43 nM PMID[530567]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 2792.54 nM PMID[530567]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 66527.32 nM PMID[530567]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 23120.65 nM PMID[530567]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 49203.95 nM PMID[530567]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 82794.22 nM PMID[530567]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 84139.51 nM PMID[530567]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 29716.66 nM PMID[530567]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 85113.8 nM PMID[530567]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 46665.94 nM PMID[530567]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 60813.5 nM PMID[530567]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 7780.37 nM PMID[530567]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 43551.19 nM PMID[530567]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 21577.44 nM PMID[530567]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 68391.16 nM PMID[530567]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 60117.37 nM PMID[530567]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 40644.33 nM PMID[530567]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 38370.72 nM PMID[530567]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 53333.49 nM PMID[530567]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16218.1 nM PMID[530567]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 87096.36 nM PMID[530567]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 66069.34 nM PMID[530567]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 38282.47 nM PMID[530567]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 66374.31 nM PMID[530567]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 29174.27 nM PMID[530567]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 50118.72 nM PMID[530567]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 77446.18 nM PMID[530567]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 89949.76 nM PMID[530567]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 91833.26 nM PMID[530567]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 50234.26 nM PMID[530567]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 74301.91 nM PMID[530567]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 36643.76 nM PMID[530567]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 34355.79 nM PMID[530567]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[530567]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 40271.7 nM PMID[530567]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 19275.25 nM PMID[530567]
NPT1427 Individual Protein c-Jun N-terminal kinase 2 Homo sapiens IC50 = 2500.0 nM PMID[530568]
NPT1427 Individual Protein c-Jun N-terminal kinase 2 Homo sapiens Inhibition = 15.0 % PMID[530568]

☑ 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 NPC233224 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 NPC271208
0.9919 High Similarity NPC227160
0.9919 High Similarity NPC82111
0.9837 High Similarity NPC226862
0.9837 High Similarity NPC165128
0.9837 High Similarity NPC158471
0.9837 High Similarity NPC57119
0.9683 High Similarity NPC100223
0.9683 High Similarity NPC158526
0.9683 High Similarity NPC16830
0.9683 High Similarity NPC171928
0.9683 High Similarity NPC33611
0.9683 High Similarity NPC129687
0.9609 High Similarity NPC474139
0.9609 High Similarity NPC189474
0.9597 High Similarity NPC158737
0.9531 High Similarity NPC31530
0.9531 High Similarity NPC47181
0.9528 High Similarity NPC7744
0.9457 High Similarity NPC25333
0.9457 High Similarity NPC49235
0.9457 High Similarity NPC148893
0.9457 High Similarity NPC18576
0.9453 High Similarity NPC266848
0.9453 High Similarity NPC136750
0.9389 High Similarity NPC123526
0.9389 High Similarity NPC193666
0.9389 High Similarity NPC88640
0.938 High Similarity NPC170779
0.938 High Similarity NPC90083
0.9375 High Similarity NPC65183
0.9375 High Similarity NPC261812
0.9375 High Similarity NPC104077
0.9375 High Similarity NPC259742
0.9375 High Similarity NPC72046
0.9375 High Similarity NPC147616
0.9375 High Similarity NPC219671
0.9355 High Similarity NPC18449
0.9355 High Similarity NPC121783
0.9355 High Similarity NPC34902
0.9313 High Similarity NPC101807
0.9313 High Similarity NPC469981
0.9308 High Similarity NPC135777
0.9308 High Similarity NPC142547
0.9297 High Similarity NPC192255
0.9268 High Similarity NPC126935
0.9268 High Similarity NPC57268
0.9268 High Similarity NPC172676
0.9268 High Similarity NPC301641
0.9268 High Similarity NPC80241
0.9268 High Similarity NPC216929
0.9268 High Similarity NPC65933
0.9268 High Similarity NPC312713
0.9248 High Similarity NPC312199
0.9242 High Similarity NPC113550
0.9219 High Similarity NPC171550
0.9219 High Similarity NPC134764
0.9173 High Similarity NPC46591
0.9141 High Similarity NPC476748
0.9111 High Similarity NPC298317
0.9111 High Similarity NPC255566
0.9111 High Similarity NPC265154
0.9106 High Similarity NPC344161
0.9104 High Similarity NPC471908
0.9091 High Similarity NPC121651
0.9077 High Similarity NPC471505
0.9062 High Similarity NPC222127
0.9062 High Similarity NPC82862
0.9055 High Similarity NPC213711
0.9055 High Similarity NPC40352
0.9044 High Similarity NPC179521
0.9037 High Similarity NPC311057
0.9037 High Similarity NPC474295
0.903 High Similarity NPC56091
0.9023 High Similarity NPC185908
0.9015 High Similarity NPC174191
0.8984 High Similarity NPC8050
0.8984 High Similarity NPC473093
0.8984 High Similarity NPC473092
0.8971 High Similarity NPC185071
0.8971 High Similarity NPC12728
0.8955 High Similarity NPC156376
0.8947 High Similarity NPC11453
0.8931 High Similarity NPC106739
0.8915 High Similarity NPC281864
0.8915 High Similarity NPC54321
0.8915 High Similarity NPC328682
0.8906 High Similarity NPC285725
0.8906 High Similarity NPC50683
0.8906 High Similarity NPC206882
0.8906 High Similarity NPC112571
0.8905 High Similarity NPC141569
0.8905 High Similarity NPC477701
0.8905 High Similarity NPC166884
0.8897 High Similarity NPC80326
0.8897 High Similarity NPC302506
0.8897 High Similarity NPC246947
0.8897 High Similarity NPC472562
0.8889 High Similarity NPC177868
0.8889 High Similarity NPC216434
0.8889 High Similarity NPC103448
0.8881 High Similarity NPC166184
0.8881 High Similarity NPC283949
0.8872 High Similarity NPC184938
0.8872 High Similarity NPC150534
0.8872 High Similarity NPC101624
0.8864 High Similarity NPC169973
0.8864 High Similarity NPC196937
0.8864 High Similarity NPC1474
0.8855 High Similarity NPC40432
0.8855 High Similarity NPC161557
0.8855 High Similarity NPC27843
0.8855 High Similarity NPC115207
0.8855 High Similarity NPC228346
0.8855 High Similarity NPC158079
0.8855 High Similarity NPC7171
0.8841 High Similarity NPC205316
0.8837 High Similarity NPC177167
0.8837 High Similarity NPC98745
0.8832 High Similarity NPC477898
0.8824 High Similarity NPC58137
0.8824 High Similarity NPC300798
0.8806 High Similarity NPC143895
0.8797 High Similarity NPC110958
0.8797 High Similarity NPC19890
0.8788 High Similarity NPC181049
0.8788 High Similarity NPC207400
0.8779 High Similarity NPC275950
0.8777 High Similarity NPC3982
0.8769 High Similarity NPC21867
0.8769 High Similarity NPC129570
0.8769 High Similarity NPC45774
0.8769 High Similarity NPC470084
0.8769 High Similarity NPC11258
0.8769 High Similarity NPC184733
0.8769 High Similarity NPC128208
0.8769 High Similarity NPC282703
0.8768 High Similarity NPC84181
0.8768 High Similarity NPC191158
0.8768 High Similarity NPC177644
0.876 High Similarity NPC9891
0.876 High Similarity NPC186845
0.876 High Similarity NPC88297
0.8759 High Similarity NPC287124
0.8759 High Similarity NPC174522
0.875 High Similarity NPC226547
0.875 High Similarity NPC278076
0.8722 High Similarity NPC205915
0.8712 High Similarity NPC476345
0.8705 High Similarity NPC38041
0.8705 High Similarity NPC469586
0.8705 High Similarity NPC279298
0.8705 High Similarity NPC22150
0.8705 High Similarity NPC180953
0.8696 High Similarity NPC474808
0.8686 High Similarity NPC472711
0.8682 High Similarity NPC17348
0.8672 High Similarity NPC249788
0.8667 High Similarity NPC32189
0.8647 High Similarity NPC97316
0.8647 High Similarity NPC4940
0.8643 High Similarity NPC205796
0.8643 High Similarity NPC276753
0.8643 High Similarity NPC241846
0.8643 High Similarity NPC112861
0.8643 High Similarity NPC93610
0.8636 High Similarity NPC145305
0.8636 High Similarity NPC242807
0.8636 High Similarity NPC187998
0.8636 High Similarity NPC153739
0.8636 High Similarity NPC42300
0.8636 High Similarity NPC92164
0.8636 High Similarity NPC64201
0.8636 High Similarity NPC77040
0.8636 High Similarity NPC257582
0.8636 High Similarity NPC181079
0.8636 High Similarity NPC241522
0.8636 High Similarity NPC173308
0.8636 High Similarity NPC174495
0.8633 High Similarity NPC92693
0.8633 High Similarity NPC218841
0.8629 High Similarity NPC81067
0.8629 High Similarity NPC9341
0.8623 High Similarity NPC210354
0.8623 High Similarity NPC176586
0.8615 High Similarity NPC274356
0.8603 High Similarity NPC14022
0.8603 High Similarity NPC474039
0.8603 High Similarity NPC196420
0.8593 High Similarity NPC99572
0.8593 High Similarity NPC236522
0.8593 High Similarity NPC126409
0.8571 High Similarity NPC18979
0.8571 High Similarity NPC277804
0.8571 High Similarity NPC477702
0.8561 High Similarity NPC470950
0.8561 High Similarity NPC475875
0.8561 High Similarity NPC185307
0.854 High Similarity NPC9068
0.8537 High Similarity NPC165106

  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 NPC233224 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
0.896 High Similarity NPD3705 Approved
0.8537 High Similarity NPD5283 Phase 1
0.8015 Intermediate Similarity NPD3027 Phase 3
0.8 Intermediate Similarity NPD1357 Approved
0.7947 Intermediate Similarity NPD4967 Phase 2
0.7947 Intermediate Similarity NPD4965 Approved
0.7947 Intermediate Similarity NPD4966 Approved
0.7931 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD6234 Discontinued
0.7748 Intermediate Similarity NPD37 Approved
0.7671 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD6674 Discontinued
0.7639 Intermediate Similarity NPD1375 Discontinued
0.763 Intermediate Similarity NPD2981 Phase 2
0.7609 Intermediate Similarity NPD2861 Phase 2
0.7576 Intermediate Similarity NPD5536 Phase 2
0.7574 Intermediate Similarity NPD2982 Phase 2
0.7574 Intermediate Similarity NPD2983 Phase 2
0.7533 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7228 Approved
0.7482 Intermediate Similarity NPD3018 Phase 2
0.7465 Intermediate Similarity NPD1613 Approved
0.7465 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5111 Phase 2
0.7447 Intermediate Similarity NPD5110 Phase 2
0.7447 Intermediate Similarity NPD5109 Approved
0.7432 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD4237 Approved
0.7415 Intermediate Similarity NPD4236 Phase 3
0.7413 Intermediate Similarity NPD3657 Discovery
0.7397 Intermediate Similarity NPD7266 Discontinued
0.7385 Intermediate Similarity NPD228 Approved
0.7383 Intermediate Similarity NPD5058 Phase 3
0.7368 Intermediate Similarity NPD4210 Discontinued
0.7365 Intermediate Similarity NPD4110 Phase 3
0.7365 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2978 Approved
0.7355 Intermediate Similarity NPD2977 Approved
0.7343 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD3620 Phase 2
0.7319 Intermediate Similarity NPD5327 Phase 3
0.7317 Intermediate Similarity NPD7240 Approved
0.7305 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1091 Approved
0.7293 Intermediate Similarity NPD7157 Approved
0.7287 Intermediate Similarity NPD2684 Approved
0.7273 Intermediate Similarity NPD7028 Phase 2
0.726 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4108 Discontinued
0.726 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6331 Phase 2
0.7244 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD3022 Approved
0.7231 Intermediate Similarity NPD3021 Approved
0.7222 Intermediate Similarity NPD4060 Phase 1
0.7211 Intermediate Similarity NPD2161 Phase 2
0.7208 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD5585 Approved
0.7197 Intermediate Similarity NPD7843 Approved
0.7197 Intermediate Similarity NPD5535 Approved
0.7194 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD6895 Approved
0.7192 Intermediate Similarity NPD6896 Approved
0.7183 Intermediate Similarity NPD4908 Phase 1
0.7172 Intermediate Similarity NPD6355 Discontinued
0.7172 Intermediate Similarity NPD5735 Approved
0.7153 Intermediate Similarity NPD5125 Phase 3
0.7153 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD5126 Approved
0.7153 Intermediate Similarity NPD17 Approved
0.7152 Intermediate Similarity NPD7124 Phase 2
0.7133 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD5494 Approved
0.7107 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD2979 Phase 3
0.7099 Intermediate Similarity NPD5451 Approved
0.7095 Intermediate Similarity NPD2438 Suspended
0.7083 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD5691 Approved
0.7077 Intermediate Similarity NPD1358 Approved
0.7073 Intermediate Similarity NPD3818 Discontinued
0.7071 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3382 Approved
0.707 Intermediate Similarity NPD3383 Approved
0.707 Intermediate Similarity NPD3384 Approved
0.7067 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD3060 Approved
0.7059 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD1610 Phase 2
0.7047 Intermediate Similarity NPD5762 Approved
0.7047 Intermediate Similarity NPD5763 Approved
0.7041 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6387 Discontinued
0.7032 Intermediate Similarity NPD1653 Approved
0.7027 Intermediate Similarity NPD5588 Approved
0.7021 Intermediate Similarity NPD8651 Approved
0.7021 Intermediate Similarity NPD2922 Phase 1
0.7014 Intermediate Similarity NPD7095 Approved
0.7013 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2492 Phase 1
0.7007 Intermediate Similarity NPD1182 Approved
0.7 Intermediate Similarity NPD1608 Approved
0.7 Intermediate Similarity NPD1840 Phase 2
0.7 Intermediate Similarity NPD3134 Approved
0.6992 Remote Similarity NPD1139 Approved
0.6992 Remote Similarity NPD1137 Approved
0.6986 Remote Similarity NPD4140 Approved
0.6986 Remote Similarity NPD1558 Phase 1
0.6982 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6374 Clinical (unspecified phase)
0.698 Remote Similarity NPD3539 Phase 1
0.6968 Remote Similarity NPD5976 Discontinued
0.6966 Remote Similarity NPD5718 Phase 2
0.6962 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6111 Discontinued
0.6959 Remote Similarity NPD4536 Approved
0.6959 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7097 Phase 1
0.6959 Remote Similarity NPD4538 Approved
0.6957 Remote Similarity NPD1651 Approved
0.6954 Remote Similarity NPD4162 Approved
0.695 Remote Similarity NPD4359 Approved
0.695 Remote Similarity NPD3685 Discontinued
0.6948 Remote Similarity NPD4123 Phase 3
0.694 Remote Similarity NPD1138 Approved
0.6933 Remote Similarity NPD3540 Phase 1
0.6929 Remote Similarity NPD1281 Approved
0.6912 Remote Similarity NPD709 Approved
0.6908 Remote Similarity NPD4628 Phase 3
0.6906 Remote Similarity NPD6516 Phase 2
0.6906 Remote Similarity NPD5846 Approved
0.6905 Remote Similarity NPD7685 Pre-registration
0.6903 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6385 Approved
0.6899 Remote Similarity NPD6386 Approved
0.6894 Remote Similarity NPD5604 Discontinued
0.6892 Remote Similarity NPD6353 Approved
0.6887 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6887 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7074 Phase 3
0.6871 Remote Similarity NPD8127 Discontinued
0.6871 Remote Similarity NPD2238 Phase 2
0.6863 Remote Similarity NPD2677 Approved
0.6861 Remote Similarity NPD3596 Phase 2
0.6855 Remote Similarity NPD1934 Approved
0.6849 Remote Similarity NPD6798 Discontinued
0.6848 Remote Similarity NPD4481 Phase 3
0.6846 Remote Similarity NPD7119 Phase 2
0.6842 Remote Similarity NPD5177 Phase 3
0.6833 Remote Similarity NPD7680 Approved
0.6826 Remote Similarity NPD7054 Approved
0.6821 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6815 Remote Similarity NPD3686 Approved
0.6815 Remote Similarity NPD3687 Approved
0.6813 Remote Similarity NPD5772 Approved
0.6813 Remote Similarity NPD8455 Phase 2
0.6813 Remote Similarity NPD5773 Approved
0.6809 Remote Similarity NPD1611 Approved
0.6806 Remote Similarity NPD4624 Approved
0.6806 Remote Similarity NPD6584 Phase 3
0.6803 Remote Similarity NPD4870 Approved
0.6803 Remote Similarity NPD6233 Phase 2
0.68 Remote Similarity NPD5960 Phase 3
0.6797 Remote Similarity NPD3020 Approved
0.6795 Remote Similarity NPD7526 Approved
0.6795 Remote Similarity NPD52 Approved
0.6795 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6671 Approved
0.6786 Remote Similarity NPD2668 Approved
0.6786 Remote Similarity NPD4626 Approved
0.6786 Remote Similarity NPD2667 Approved
0.6786 Remote Similarity NPD7472 Approved
0.6783 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6783 Remote Similarity NPD1283 Approved
0.6781 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6779 Remote Similarity NPD2653 Approved
0.6779 Remote Similarity NPD6653 Approved
0.6776 Remote Similarity NPD2808 Discontinued
0.6772 Remote Similarity NPD4005 Discontinued
0.677 Remote Similarity NPD2358 Clinical (unspecified phase)
0.677 Remote Similarity NPD2560 Approved
0.677 Remote Similarity NPD3817 Phase 2
0.677 Remote Similarity NPD2563 Approved
0.6763 Remote Similarity NPD6580 Approved
0.6763 Remote Similarity NPD6581 Approved
0.6763 Remote Similarity NPD1548 Phase 1
0.6761 Remote Similarity NPD2231 Phase 2
0.6761 Remote Similarity NPD2232 Approved
0.6761 Remote Similarity NPD2230 Approved
0.6761 Remote Similarity NPD2235 Phase 2
0.6761 Remote Similarity NPD2233 Approved
0.6757 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6755 Remote Similarity NPD6032 Approved

  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