Structure

Physi-Chem Properties

Molecular Weight:  304.06
Volume:  285.403
LogP:  0.291
LogD:  -0.231
LogS:  -2.355
# Rotatable Bonds:  1
TPSA:  127.45
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.501
Synthetic Accessibility Score:  3.594
Fsp3:  0.133
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.125
MDCK Permeability:  4.0755176087259315e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.925
30% Bioavailability (F30%):  0.63

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  89.9701919555664%
Volume Distribution (VD):  0.605
Pgp-substrate:  12.492057800292969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.296
CYP2C9-substrate:  0.672
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.229
CYP3A4-inhibitor:  0.128
CYP3A4-substrate:  0.245

ADMET: Excretion

Clearance (CL):  9.372
Half-life (T1/2):  0.862

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.931
AMES Toxicity:  0.323
Rat Oral Acute Toxicity:  0.231
Maximum Recommended Daily Dose:  0.595
Skin Sensitization:  0.95
Carcinogencity:  0.043
Eye Corrosion:  0.003
Eye Irritation:  0.887
Respiratory Toxicity:  0.306

Download Data

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

  Natural Product: NPC325028

Natural Product ID:  NPC325028
Common Name*:   Dihydrobinetin
IUPAC Name:   3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:   NSC-59266
Standard InCHIKey:  VSJCDPYIMBSOKN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,14-18,20-21H
SMILES:  C1=CC2=C(C=C1O)OC(C(C2=O)O)C3=CC(=C(C(=C3)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444171
PubChem CID:   20399
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0001632] Flavanones
            • [CHEMONTID:0001362] Flavanonols

*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
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 23.0 ug ml-1 PMID[481459]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 18365.38 nM PMID[481461]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 20417.38 nM PMID[481461]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 34514.37 nM PMID[481461]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 25822.6 nM PMID[481461]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 67764.15 nM PMID[481461]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 47315.13 nM PMID[481461]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 19860.95 nM PMID[481461]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 21527.82 nM PMID[481461]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 33036.95 nM PMID[481461]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 28119.01 nM PMID[481461]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 47863.01 nM PMID[481461]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 19054.61 nM PMID[481461]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 35481.34 nM PMID[481461]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 25061.09 nM PMID[481461]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 22490.55 nM PMID[481461]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 21978.6 nM PMID[481461]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 58210.32 nM PMID[481461]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 21134.89 nM PMID[481461]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 41399.97 nM PMID[481461]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 20464.45 nM PMID[481461]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 23550.49 nM PMID[481461]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 25003.45 nM PMID[481461]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 24831.33 nM PMID[481461]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 26668.59 nM PMID[481461]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 17782.79 nM PMID[481461]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 37931.5 nM PMID[481461]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 19142.56 nM PMID[481461]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 20511.62 nM PMID[481461]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 33113.11 nM PMID[481461]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 31550.05 nM PMID[481461]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 33728.73 nM PMID[481461]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 21978.6 nM PMID[481461]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 34119.29 nM PMID[481461]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 19010.78 nM PMID[481461]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 25703.96 nM PMID[481461]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 37844.26 nM PMID[481461]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 19815.27 nM PMID[481461]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 53826.98 nM PMID[481461]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 30130.06 nM PMID[481461]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 19769.7 nM PMID[481461]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 21827.3 nM PMID[481461]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 18030.18 nM PMID[481461]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 70145.53 nM PMID[481461]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 23823.19 nM PMID[481461]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 34753.62 nM PMID[481461]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 24099.05 nM PMID[481461]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 39084.09 nM PMID[481461]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 23442.29 nM PMID[481461]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 46773.51 nM PMID[481461]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[481461]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 32359.37 nM PMID[481461]
NPT2 Others Unspecified Activity = 7.94 10'6/M PMID[481460]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 256.0 ug.mL-1 PMID[481460]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC > 512.0 ug.mL-1 PMID[481460]

☑ 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 NPC325028 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 NPC27532
1.0 High Similarity NPC256346
1.0 High Similarity NPC246328
0.9932 High Similarity NPC240476
0.9932 High Similarity NPC9743
0.9932 High Similarity NPC36835
0.9932 High Similarity NPC260491
0.9932 High Similarity NPC246162
0.9932 High Similarity NPC61506
0.9799 High Similarity NPC52530
0.9796 High Similarity NPC19721
0.9732 High Similarity NPC320825
0.9732 High Similarity NPC326037
0.9732 High Similarity NPC201837
0.9732 High Similarity NPC13858
0.973 High Similarity NPC141212
0.9726 High Similarity NPC183959
0.9726 High Similarity NPC1612
0.9658 High Similarity NPC294852
0.9658 High Similarity NPC321011
0.9658 High Similarity NPC188679
0.9658 High Similarity NPC218569
0.9605 High Similarity NPC308992
0.9603 High Similarity NPC22192
0.96 High Similarity NPC250922
0.96 High Similarity NPC474638
0.96 High Similarity NPC471500
0.9589 High Similarity NPC21835
0.9539 High Similarity NPC282009
0.9539 High Similarity NPC263449
0.9539 High Similarity NPC287328
0.9539 High Similarity NPC470183
0.9536 High Similarity NPC471479
0.9536 High Similarity NPC67876
0.9536 High Similarity NPC471515
0.953 High Similarity NPC219582
0.953 High Similarity NPC302950
0.953 High Similarity NPC236637
0.9521 High Similarity NPC1940
0.9521 High Similarity NPC148011
0.9477 High Similarity NPC471499
0.9477 High Similarity NPC289771
0.9474 High Similarity NPC55738
0.9467 High Similarity NPC18727
0.9463 High Similarity NPC204515
0.9459 High Similarity NPC105512
0.9456 High Similarity NPC74881
0.9456 High Similarity NPC95864
0.9456 High Similarity NPC51443
0.9452 High Similarity NPC62290
0.9452 High Similarity NPC279417
0.9452 High Similarity NPC142731
0.9452 High Similarity NPC326506
0.9452 High Similarity NPC306607
0.9452 High Similarity NPC4152
0.9452 High Similarity NPC208176
0.9452 High Similarity NPC49130
0.9412 High Similarity NPC471744
0.9412 High Similarity NPC470326
0.9408 High Similarity NPC210084
0.9408 High Similarity NPC99597
0.9408 High Similarity NPC474055
0.9408 High Similarity NPC472598
0.9408 High Similarity NPC291508
0.9404 High Similarity NPC321779
0.94 High Similarity NPC55205
0.9396 High Similarity NPC29231
0.9392 High Similarity NPC43669
0.9392 High Similarity NPC272721
0.9392 High Similarity NPC3036
0.9392 High Similarity NPC119059
0.9392 High Similarity NPC196277
0.9388 High Similarity NPC20791
0.9388 High Similarity NPC179271
0.9355 High Similarity NPC472625
0.9351 High Similarity NPC112418
0.9351 High Similarity NPC173137
0.9346 High Similarity NPC117418
0.9346 High Similarity NPC53545
0.9342 High Similarity NPC195796
0.9342 High Similarity NPC235165
0.9342 High Similarity NPC35038
0.9342 High Similarity NPC278778
0.9342 High Similarity NPC291878
0.9342 High Similarity NPC255106
0.9338 High Similarity NPC88645
0.9338 High Similarity NPC167091
0.9338 High Similarity NPC469550
0.9338 High Similarity NPC192083
0.9338 High Similarity NPC206238
0.9338 High Similarity NPC292214
0.9338 High Similarity NPC213896
0.9338 High Similarity NPC271779
0.9333 High Similarity NPC251110
0.9333 High Similarity NPC31363
0.9333 High Similarity NPC125062
0.9333 High Similarity NPC54394
0.9333 High Similarity NPC252933
0.9333 High Similarity NPC260895
0.9333 High Similarity NPC200740
0.9329 High Similarity NPC87125
0.9329 High Similarity NPC270465
0.9324 High Similarity NPC211466
0.9324 High Similarity NPC44721
0.9324 High Similarity NPC122828
0.9324 High Similarity NPC77378
0.9324 High Similarity NPC3779
0.9324 High Similarity NPC476182
0.9324 High Similarity NPC176869
0.9324 High Similarity NPC40086
0.932 High Similarity NPC70136
0.9299 High Similarity NPC260266
0.9295 High Similarity NPC58223
0.9295 High Similarity NPC72787
0.9295 High Similarity NPC7154
0.9295 High Similarity NPC36916
0.9295 High Similarity NPC7688
0.9295 High Similarity NPC125039
0.9295 High Similarity NPC36
0.929 High Similarity NPC211107
0.929 High Similarity NPC474034
0.929 High Similarity NPC472964
0.929 High Similarity NPC471745
0.929 High Similarity NPC476247
0.929 High Similarity NPC474033
0.9286 High Similarity NPC472902
0.9281 High Similarity NPC129684
0.9281 High Similarity NPC27337
0.9281 High Similarity NPC156057
0.9281 High Similarity NPC162869
0.9281 High Similarity NPC475267
0.9281 High Similarity NPC48208
0.9281 High Similarity NPC299520
0.9281 High Similarity NPC474836
0.9281 High Similarity NPC474208
0.9276 High Similarity NPC45849
0.9276 High Similarity NPC200761
0.9276 High Similarity NPC2928
0.9276 High Similarity NPC67396
0.9276 High Similarity NPC470327
0.9276 High Similarity NPC477503
0.9272 High Similarity NPC82325
0.9272 High Similarity NPC180234
0.9272 High Similarity NPC477231
0.9272 High Similarity NPC120537
0.9272 High Similarity NPC260979
0.9272 High Similarity NPC39007
0.9272 High Similarity NPC106976
0.9272 High Similarity NPC472912
0.9272 High Similarity NPC171651
0.9272 High Similarity NPC161277
0.9272 High Similarity NPC279989
0.9272 High Similarity NPC35567
0.9272 High Similarity NPC257648
0.9272 High Similarity NPC243171
0.9272 High Similarity NPC101996
0.9272 High Similarity NPC199100
0.9267 High Similarity NPC248102
0.9267 High Similarity NPC62042
0.9267 High Similarity NPC188871
0.9267 High Similarity NPC149127
0.9267 High Similarity NPC286342
0.9267 High Similarity NPC61620
0.9267 High Similarity NPC338131
0.9262 High Similarity NPC194856
0.9262 High Similarity NPC276930
0.9262 High Similarity NPC19545
0.9257 High Similarity NPC229190
0.9257 High Similarity NPC169749
0.9252 High Similarity NPC38065
0.9252 High Similarity NPC242893
0.9252 High Similarity NPC279121
0.9247 High Similarity NPC150023
0.9236 High Similarity NPC477517
0.9236 High Similarity NPC471213
0.9231 High Similarity NPC124038
0.9226 High Similarity NPC472634
0.9226 High Similarity NPC26326
0.9226 High Similarity NPC474038
0.9226 High Similarity NPC472632
0.9226 High Similarity NPC158188
0.9226 High Similarity NPC142252
0.9221 High Similarity NPC152904
0.9216 High Similarity NPC472916
0.9216 High Similarity NPC470328
0.9216 High Similarity NPC265511
0.9216 High Similarity NPC472626
0.9216 High Similarity NPC209614
0.9216 High Similarity NPC24640
0.9211 High Similarity NPC179126
0.9211 High Similarity NPC270620
0.9211 High Similarity NPC298692
0.9211 High Similarity NPC78326
0.9211 High Similarity NPC74924
0.9211 High Similarity NPC236223
0.9211 High Similarity NPC293286
0.9205 High Similarity NPC319910
0.9205 High Similarity NPC262039
0.9205 High Similarity NPC262038
0.9205 High Similarity NPC254412

  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 NPC325028 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
0.953 High Similarity NPD1934 Approved
0.9388 High Similarity NPD1512 Approved
0.9338 High Similarity NPD2393 Clinical (unspecified phase)
0.9295 High Similarity NPD6167 Clinical (unspecified phase)
0.9295 High Similarity NPD6168 Clinical (unspecified phase)
0.9295 High Similarity NPD6166 Phase 2
0.9252 High Similarity NPD1511 Approved
0.9091 High Similarity NPD3882 Suspended
0.9041 High Similarity NPD1549 Phase 2
0.8973 High Similarity NPD1552 Clinical (unspecified phase)
0.8973 High Similarity NPD1550 Clinical (unspecified phase)
0.8961 High Similarity NPD2801 Approved
0.8938 High Similarity NPD3818 Discontinued
0.8889 High Similarity NPD6797 Phase 2
0.8889 High Similarity NPD4380 Phase 2
0.8846 High Similarity NPD4868 Clinical (unspecified phase)
0.8834 High Similarity NPD7251 Discontinued
0.8827 High Similarity NPD7074 Phase 3
0.879 High Similarity NPD7075 Discontinued
0.879 High Similarity NPD4381 Clinical (unspecified phase)
0.8782 High Similarity NPD3817 Phase 2
0.878 High Similarity NPD4338 Clinical (unspecified phase)
0.8765 High Similarity NPD7054 Approved
0.8718 High Similarity NPD7096 Clinical (unspecified phase)
0.8712 High Similarity NPD7472 Approved
0.8707 High Similarity NPD1510 Phase 2
0.8684 High Similarity NPD4378 Clinical (unspecified phase)
0.8667 High Similarity NPD7808 Phase 3
0.8659 High Similarity NPD7993 Clinical (unspecified phase)
0.8562 High Similarity NPD1613 Approved
0.8562 High Similarity NPD1612 Clinical (unspecified phase)
0.8535 High Similarity NPD6801 Discontinued
0.8497 Intermediate Similarity NPD6799 Approved
0.8447 Intermediate Similarity NPD5494 Approved
0.8435 Intermediate Similarity NPD943 Approved
0.8435 Intermediate Similarity NPD1240 Approved
0.8428 Intermediate Similarity NPD5402 Approved
0.8424 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD2796 Approved
0.8365 Intermediate Similarity NPD1465 Phase 2
0.8333 Intermediate Similarity NPD5403 Approved
0.8323 Intermediate Similarity NPD5401 Approved
0.8322 Intermediate Similarity NPD1607 Approved
0.8291 Intermediate Similarity NPD6599 Discontinued
0.8288 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD7819 Suspended
0.8219 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD5844 Phase 1
0.8199 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD1247 Approved
0.8166 Intermediate Similarity NPD6559 Discontinued
0.816 Intermediate Similarity NPD919 Approved
0.8125 Intermediate Similarity NPD7411 Suspended
0.8092 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD6959 Discontinued
0.8039 Intermediate Similarity NPD1551 Phase 2
0.8036 Intermediate Similarity NPD3751 Discontinued
0.8013 Intermediate Similarity NPD230 Phase 1
0.8012 Intermediate Similarity NPD6232 Discontinued
0.7976 Intermediate Similarity NPD7473 Discontinued
0.7964 Intermediate Similarity NPD3926 Phase 2
0.7949 Intermediate Similarity NPD3750 Approved
0.7935 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD6190 Approved
0.7879 Intermediate Similarity NPD3749 Approved
0.7867 Intermediate Similarity NPD3027 Phase 3
0.7834 Intermediate Similarity NPD4628 Phase 3
0.7826 Intermediate Similarity NPD1653 Approved
0.7811 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD3787 Discontinued
0.7778 Intermediate Similarity NPD447 Suspended
0.7711 Intermediate Similarity NPD7768 Phase 2
0.7692 Intermediate Similarity NPD2935 Discontinued
0.7658 Intermediate Similarity NPD2800 Approved
0.7658 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD920 Approved
0.764 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD3748 Approved
0.7625 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD9494 Approved
0.761 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD1203 Approved
0.7582 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD1610 Phase 2
0.7548 Intermediate Similarity NPD1933 Approved
0.7547 Intermediate Similarity NPD1243 Approved
0.7544 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD2344 Approved
0.7531 Intermediate Similarity NPD2534 Approved
0.7531 Intermediate Similarity NPD2533 Approved
0.7531 Intermediate Similarity NPD2532 Approved
0.7529 Intermediate Similarity NPD7199 Phase 2
0.7516 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD2313 Discontinued
0.7468 Intermediate Similarity NPD6100 Approved
0.7468 Intermediate Similarity NPD6099 Approved
0.7459 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD8312 Approved
0.7458 Intermediate Similarity NPD8313 Approved
0.7455 Intermediate Similarity NPD3226 Approved
0.7444 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD8434 Phase 2
0.7423 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD2346 Discontinued
0.7415 Intermediate Similarity NPD1548 Phase 1
0.7412 Intermediate Similarity NPD6234 Discontinued
0.7401 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD9269 Phase 2
0.7386 Intermediate Similarity NPD5953 Discontinued
0.7371 Intermediate Similarity NPD7286 Phase 2
0.7366 Intermediate Similarity NPD6780 Approved
0.7366 Intermediate Similarity NPD6776 Approved
0.7366 Intermediate Similarity NPD6778 Approved
0.7366 Intermediate Similarity NPD6781 Approved
0.7366 Intermediate Similarity NPD6782 Approved
0.7366 Intermediate Similarity NPD6777 Approved
0.7366 Intermediate Similarity NPD6779 Approved
0.7362 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6798 Discontinued
0.7351 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2309 Approved
0.7345 Intermediate Similarity NPD7685 Pre-registration
0.7338 Intermediate Similarity NPD4908 Phase 1
0.7333 Intermediate Similarity NPD8150 Discontinued
0.7325 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD37 Approved
0.7314 Intermediate Similarity NPD7228 Approved
0.7296 Intermediate Similarity NPD2799 Discontinued
0.7296 Intermediate Similarity NPD7033 Discontinued
0.7294 Intermediate Similarity NPD4967 Phase 2
0.7294 Intermediate Similarity NPD4965 Approved
0.7294 Intermediate Similarity NPD4966 Approved
0.7285 Intermediate Similarity NPD9717 Approved
0.7284 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4363 Phase 3
0.7283 Intermediate Similarity NPD4360 Phase 2
0.7278 Intermediate Similarity NPD6651 Approved
0.7249 Intermediate Similarity NPD7435 Discontinued
0.7246 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6832 Phase 2
0.7225 Intermediate Similarity NPD7584 Approved
0.7222 Intermediate Similarity NPD1652 Phase 2
0.7219 Intermediate Similarity NPD6844 Discontinued
0.7215 Intermediate Similarity NPD6355 Discontinued
0.7205 Intermediate Similarity NPD7266 Discontinued
0.7197 Intermediate Similarity NPD6233 Phase 2
0.7171 Intermediate Similarity NPD1608 Approved
0.7161 Intermediate Similarity NPD2861 Phase 2
0.7158 Intermediate Similarity NPD7698 Approved
0.7158 Intermediate Similarity NPD7696 Phase 3
0.7158 Intermediate Similarity NPD7697 Approved
0.7152 Intermediate Similarity NPD7390 Discontinued
0.715 Intermediate Similarity NPD8151 Discontinued
0.7143 Intermediate Similarity NPD1470 Approved
0.7143 Intermediate Similarity NPD5242 Approved
0.7135 Intermediate Similarity NPD5353 Approved
0.7134 Intermediate Similarity NPD2354 Approved
0.7134 Intermediate Similarity NPD411 Approved
0.7133 Intermediate Similarity NPD9268 Approved
0.712 Intermediate Similarity NPD7871 Phase 2
0.712 Intermediate Similarity NPD7870 Phase 2
0.7119 Intermediate Similarity NPD2163 Approved
0.7108 Intermediate Similarity NPD4662 Approved
0.7108 Intermediate Similarity NPD4661 Approved
0.7105 Intermediate Similarity NPD422 Phase 1
0.7105 Intermediate Similarity NPD1201 Approved
0.7102 Intermediate Similarity NPD2403 Approved
0.7102 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1471 Phase 3
0.7098 Intermediate Similarity NPD7701 Phase 2
0.7097 Intermediate Similarity NPD6534 Approved
0.7097 Intermediate Similarity NPD6535 Approved
0.7097 Intermediate Similarity NPD2798 Approved
0.7086 Intermediate Similarity NPD5711 Approved
0.7086 Intermediate Similarity NPD5710 Approved
0.7081 Intermediate Similarity NPD4308 Phase 3
0.7076 Intermediate Similarity NPD8455 Phase 2
0.7067 Intermediate Similarity NPD9545 Approved
0.7059 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2424 Discontinued
0.7044 Intermediate Similarity NPD4060 Phase 1
0.7035 Intermediate Similarity NPD4288 Approved
0.703 Intermediate Similarity NPD3887 Approved
0.7026 Intermediate Similarity NPD7874 Approved
0.7026 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD3268 Approved
0.7006 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5124 Phase 1
0.7 Intermediate Similarity NPD4665 Approved
0.7 Intermediate Similarity NPD3823 Discontinued
0.7 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4111 Phase 1

  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