Structure

Physi-Chem Properties

Molecular Weight:  367.11
Volume:  348.42
LogP:  2.756
LogD:  2.356
LogS:  -4.606
# Rotatable Bonds:  1
TPSA:  66.46
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.718
Synthetic Accessibility Score:  3.599
Fsp3:  0.35
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.994
MDCK Permeability:  5.0195743824588135e-05
Pgp-inhibitor:  0.041
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.08
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.956
Plasma Protein Binding (PPB):  93.5989761352539%
Volume Distribution (VD):  2.203
Pgp-substrate:  2.7684361934661865%

ADMET: Metabolism

CYP1A2-inhibitor:  0.911
CYP1A2-substrate:  0.623
CYP2C19-inhibitor:  0.971
CYP2C19-substrate:  0.807
CYP2C9-inhibitor:  0.724
CYP2C9-substrate:  0.845
CYP2D6-inhibitor:  0.977
CYP2D6-substrate:  0.906
CYP3A4-inhibitor:  0.965
CYP3A4-substrate:  0.732

ADMET: Excretion

Clearance (CL):  15.106
Half-life (T1/2):  0.105

ADMET: Toxicity

hERG Blockers:  0.152
Human Hepatotoxicity (H-HT):  0.213
Drug-inuced Liver Injury (DILI):  0.493
AMES Toxicity:  0.669
Rat Oral Acute Toxicity:  0.418
Maximum Recommended Daily Dose:  0.915
Skin Sensitization:  0.067
Carcinogencity:  0.914
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.645

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

  Natural Product: NPC226652

Natural Product ID:  NPC226652
Common Name*:   Bicuculline
IUPAC Name:   (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
Synonyms:   (+)-Bicuculline; Bicuculline
Standard InCHIKey:  IYGYMKDQCDOMRE-ZWKOTPCHSA-N
Standard InCHI:  InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
SMILES:  CN1CCc2cc3c(cc2[C@H]1[C@H]1c2ccc4c(c2C(=O)O1)OCO4)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL417990
PubChem CID:   10237
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002188] Phthalide isoquinolines

*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
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO5305 Corydalis mucronifera Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[29400966]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[31599578]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5305 Corydalis mucronifera Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4033 Corydalis gigantea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5305 Corydalis mucronifera Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4033 Corydalis gigantea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4033 Corydalis gigantea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5305 Corydalis mucronifera Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14045 Corydalis decumbens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4033 Corydalis gigantea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5305 Corydalis mucronifera Species Papaveraceae 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
NPT1404 Individual Protein GABA receptor gamma-1 subunit Rattus norvegicus IC50 = 3800.0 nM PMID[548422]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 25118.9 nM PMID[548426]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 79432.8 nM PMID[548426]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2310.9 nM PMID[548426]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 20.68 % PMID[548427]
NPT996 Protein Complex GABA-A receptor; anion channel Homo sapiens IC50 = 15000.0 nM PMID[548418]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Displacement = 7.0 % PMID[548419]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Displacement = -1.0 % PMID[548419]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Displacement = 45.0 % PMID[548419]
NPT899 Protein Complex GABA-A receptor; alpha-1/beta-2/gamma-2 Rattus norvegicus GABA current = -100.0 % PMID[548419]
NPT1774 Protein Family Sodium channel alpha subunits; brain (Types I, II, III) Homo sapiens Inhibition = 1.8 % PMID[548420]
NPT996 Protein Complex GABA-A receptor; anion channel Homo sapiens IC50 = 44000.0 nM PMID[548421]
NPT996 Protein Complex GABA-A receptor; anion channel Homo sapiens IC50 = 6200.0 nM PMID[548421]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Relative affinity = 0.0056 n.a. PMID[548422]
NPT32 Organism Mus musculus Mus musculus ED50 = 14.6 mg.kg-1 PMID[548424]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 70794.6 nM PMID[548426]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 70794.6 nM PMID[548426]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 0.63 % PMID[548427]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 3.43 % PMID[548428]
NPT20 Organism Candida albicans Candida albicans Inhibition = -1.4 % PMID[548428]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -11.52 % PMID[548428]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 11.14 % PMID[548428]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = -4.97 % PMID[548428]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 17.91 % PMID[548428]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 11.38 % PMID[548428]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 21.67 % PMID[548430]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.05 % PMID[548431]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[548432]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[548432]

☑ 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 NPC226652 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 NPC314100
1.0 High Similarity NPC120671
1.0 High Similarity NPC72788
0.9887 High Similarity NPC124302
0.9887 High Similarity NPC46744
0.9887 High Similarity NPC14622
0.9887 High Similarity NPC73020
0.9887 High Similarity NPC70290
0.9887 High Similarity NPC215098
0.9669 High Similarity NPC202771
0.9669 High Similarity NPC119818
0.9669 High Similarity NPC328700
0.9669 High Similarity NPC2173
0.9171 High Similarity NPC226708
0.8939 High Similarity NPC27887
0.8817 High Similarity NPC125924
0.8763 High Similarity NPC469815
0.8763 High Similarity NPC469816
0.8649 High Similarity NPC141440
0.8617 High Similarity NPC477258
0.8595 High Similarity NPC477259
0.8595 High Similarity NPC169387
0.8505 High Similarity NPC80472
0.8449 Intermediate Similarity NPC166979
0.8351 Intermediate Similarity NPC208890
0.8351 Intermediate Similarity NPC286135
0.8281 Intermediate Similarity NPC24228
0.8229 Intermediate Similarity NPC33256
0.8216 Intermediate Similarity NPC222524
0.8197 Intermediate Similarity NPC474708
0.8196 Intermediate Similarity NPC207239
0.8191 Intermediate Similarity NPC116007
0.8191 Intermediate Similarity NPC83511
0.8168 Intermediate Similarity NPC63152
0.8162 Intermediate Similarity NPC308267
0.8142 Intermediate Similarity NPC475845
0.8135 Intermediate Similarity NPC470646
0.8125 Intermediate Similarity NPC94499
0.8118 Intermediate Similarity NPC474470
0.8118 Intermediate Similarity NPC35680
0.81 Intermediate Similarity NPC46990
0.8095 Intermediate Similarity NPC475981
0.8095 Intermediate Similarity NPC474746
0.8087 Intermediate Similarity NPC474324
0.8087 Intermediate Similarity NPC57812
0.8063 Intermediate Similarity NPC237579
0.8054 Intermediate Similarity NPC67978
0.8054 Intermediate Similarity NPC303581
0.8053 Intermediate Similarity NPC18306
0.8043 Intermediate Similarity NPC86469
0.8011 Intermediate Similarity NPC2314
0.801 Intermediate Similarity NPC230098
0.8 Intermediate Similarity NPC75958
0.7937 Intermediate Similarity NPC244554
0.7937 Intermediate Similarity NPC474745
0.7935 Intermediate Similarity NPC474858
0.7914 Intermediate Similarity NPC329992
0.7884 Intermediate Similarity NPC474325
0.788 Intermediate Similarity NPC15212
0.788 Intermediate Similarity NPC247972
0.7879 Intermediate Similarity NPC474427
0.7872 Intermediate Similarity NPC304675
0.7868 Intermediate Similarity NPC83019
0.7861 Intermediate Similarity NPC65403
0.7861 Intermediate Similarity NPC477640
0.7861 Intermediate Similarity NPC470739
0.7861 Intermediate Similarity NPC225597
0.7857 Intermediate Similarity NPC301897
0.7853 Intermediate Similarity NPC475959
0.785 Intermediate Similarity NPC207971
0.7849 Intermediate Similarity NPC82533
0.7849 Intermediate Similarity NPC158148
0.7849 Intermediate Similarity NPC266176
0.7849 Intermediate Similarity NPC290759
0.7845 Intermediate Similarity NPC31311
0.7845 Intermediate Similarity NPC234392
0.7831 Intermediate Similarity NPC237044
0.7826 Intermediate Similarity NPC78944
0.7824 Intermediate Similarity NPC162694
0.7817 Intermediate Similarity NPC475713
0.7817 Intermediate Similarity NPC204580
0.7817 Intermediate Similarity NPC474432
0.7812 Intermediate Similarity NPC156576
0.7811 Intermediate Similarity NPC268077
0.7807 Intermediate Similarity NPC474475
0.7796 Intermediate Similarity NPC210918
0.7796 Intermediate Similarity NPC247389
0.779 Intermediate Similarity NPC216459
0.779 Intermediate Similarity NPC138487
0.779 Intermediate Similarity NPC41178
0.7789 Intermediate Similarity NPC118633
0.7789 Intermediate Similarity NPC148693
0.7789 Intermediate Similarity NPC121400
0.7789 Intermediate Similarity NPC294790
0.7778 Intermediate Similarity NPC476220
0.7778 Intermediate Similarity NPC233029
0.7778 Intermediate Similarity NPC160113
0.7778 Intermediate Similarity NPC210148
0.7766 Intermediate Similarity NPC227683
0.776 Intermediate Similarity NPC248642
0.7754 Intermediate Similarity NPC475686
0.7754 Intermediate Similarity NPC58766
0.7749 Intermediate Similarity NPC220961
0.7747 Intermediate Similarity NPC146288
0.7742 Intermediate Similarity NPC476432
0.7742 Intermediate Similarity NPC219341
0.7742 Intermediate Similarity NPC24264
0.7742 Intermediate Similarity NPC154922
0.774 Intermediate Similarity NPC478047
0.774 Intermediate Similarity NPC180210
0.774 Intermediate Similarity NPC321226
0.774 Intermediate Similarity NPC314914
0.774 Intermediate Similarity NPC328856
0.774 Intermediate Similarity NPC478046
0.7737 Intermediate Similarity NPC241704
0.773 Intermediate Similarity NPC218614
0.7717 Intermediate Similarity NPC304837
0.7717 Intermediate Similarity NPC476258
0.7717 Intermediate Similarity NPC19600
0.7708 Intermediate Similarity NPC473562
0.7704 Intermediate Similarity NPC319549
0.7703 Intermediate Similarity NPC316368
0.7703 Intermediate Similarity NPC284236
0.7701 Intermediate Similarity NPC284842
0.7692 Intermediate Similarity NPC478048
0.7692 Intermediate Similarity NPC78733
0.7688 Intermediate Similarity NPC302527
0.7688 Intermediate Similarity NPC167546
0.7688 Intermediate Similarity NPC16805
0.7688 Intermediate Similarity NPC225774
0.7688 Intermediate Similarity NPC231198
0.768 Intermediate Similarity NPC9867
0.7676 Intermediate Similarity NPC153631
0.7672 Intermediate Similarity NPC149090
0.7672 Intermediate Similarity NPC19520
0.7668 Intermediate Similarity NPC102760
0.7667 Intermediate Similarity NPC223125
0.7663 Intermediate Similarity NPC477080
0.7663 Intermediate Similarity NPC239113
0.7663 Intermediate Similarity NPC115123
0.7656 Intermediate Similarity NPC32154
0.7656 Intermediate Similarity NPC126284
0.7656 Intermediate Similarity NPC267408
0.765 Intermediate Similarity NPC267414
0.7647 Intermediate Similarity NPC113455
0.7641 Intermediate Similarity NPC214116
0.763 Intermediate Similarity NPC170101
0.7622 Intermediate Similarity NPC26353
0.7619 Intermediate Similarity NPC311991
0.7609 Intermediate Similarity NPC254163
0.7606 Intermediate Similarity NPC100566
0.7606 Intermediate Similarity NPC252960
0.7604 Intermediate Similarity NPC329816
0.7604 Intermediate Similarity NPC15919
0.76 Intermediate Similarity NPC71124
0.7594 Intermediate Similarity NPC180306
0.7592 Intermediate Similarity NPC187678
0.7582 Intermediate Similarity NPC223124
0.7582 Intermediate Similarity NPC148898
0.7577 Intermediate Similarity NPC73492
0.7577 Intermediate Similarity NPC299990
0.7563 Intermediate Similarity NPC470642
0.755 Intermediate Similarity NPC66909
0.7546 Intermediate Similarity NPC315914
0.7545 Intermediate Similarity NPC120239
0.754 Intermediate Similarity NPC320104
0.7537 Intermediate Similarity NPC475747
0.7536 Intermediate Similarity NPC195120
0.7536 Intermediate Similarity NPC87560
0.7527 Intermediate Similarity NPC232924
0.7527 Intermediate Similarity NPC306902
0.7527 Intermediate Similarity NPC477559
0.7527 Intermediate Similarity NPC160298
0.7527 Intermediate Similarity NPC266753
0.7526 Intermediate Similarity NPC474506
0.7526 Intermediate Similarity NPC471923
0.7526 Intermediate Similarity NPC32413
0.7525 Intermediate Similarity NPC475597
0.7525 Intermediate Similarity NPC473716
0.7513 Intermediate Similarity NPC320223
0.7513 Intermediate Similarity NPC114364
0.7513 Intermediate Similarity NPC190332
0.7513 Intermediate Similarity NPC181653
0.7512 Intermediate Similarity NPC476500
0.75 Intermediate Similarity NPC214629
0.75 Intermediate Similarity NPC232514
0.75 Intermediate Similarity NPC258322
0.75 Intermediate Similarity NPC308555
0.75 Intermediate Similarity NPC276944
0.75 Intermediate Similarity NPC93593
0.75 Intermediate Similarity NPC191352
0.75 Intermediate Similarity NPC238530
0.7487 Intermediate Similarity NPC473531
0.7487 Intermediate Similarity NPC275132
0.7487 Intermediate Similarity NPC254957
0.7487 Intermediate Similarity NPC475453
0.7475 Intermediate Similarity NPC5374
0.7474 Intermediate Similarity NPC241055
0.7474 Intermediate Similarity NPC149285
0.7474 Intermediate Similarity NPC470879

  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 NPC226652 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
0.9887 High Similarity NPD4420 Approved
0.9669 High Similarity NPD5005 Approved
0.9669 High Similarity NPD5006 Approved
0.8066 Intermediate Similarity NPD6625 Approved
0.7989 Intermediate Similarity NPD5242 Approved
0.7735 Intermediate Similarity NPD6386 Approved
0.7735 Intermediate Similarity NPD6385 Approved
0.7725 Intermediate Similarity NPD5313 Approved
0.7725 Intermediate Similarity NPD5312 Approved
0.7704 Intermediate Similarity NPD7296 Approved
0.77 Intermediate Similarity NPD5457 Discontinued
0.7692 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD2975 Approved
0.755 Intermediate Similarity NPD2974 Approved
0.755 Intermediate Similarity NPD2973 Approved
0.7525 Intermediate Similarity NPD4107 Approved
0.7525 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5977 Approved
0.7514 Intermediate Similarity NPD5978 Approved
0.75 Intermediate Similarity NPD6107 Approved
0.7487 Intermediate Similarity NPD6853 Approved
0.7487 Intermediate Similarity NPD6851 Approved
0.7487 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD6997 Phase 2
0.7474 Intermediate Similarity NPD4481 Phase 3
0.7458 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3050 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD4580 Approved
0.7436 Intermediate Similarity NPD7281 Phase 3
0.7436 Intermediate Similarity NPD2971 Approved
0.7436 Intermediate Similarity NPD7280 Phase 3
0.7436 Intermediate Similarity NPD2968 Approved
0.7419 Intermediate Similarity NPD5353 Approved
0.7418 Intermediate Similarity NPD3641 Approved
0.7418 Intermediate Similarity NPD3640 Phase 3
0.7418 Intermediate Similarity NPD3639 Approved
0.7403 Intermediate Similarity NPD4584 Approved
0.7402 Intermediate Similarity NPD2494 Approved
0.7402 Intermediate Similarity NPD3452 Approved
0.7402 Intermediate Similarity NPD3450 Approved
0.7402 Intermediate Similarity NPD2493 Approved
0.7402 Intermediate Similarity NPD4482 Phase 3
0.7393 Intermediate Similarity NPD7930 Approved
0.7389 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD4846 Phase 2
0.7371 Intermediate Similarity NPD6297 Approved
0.7349 Intermediate Similarity NPD7907 Approved
0.7309 Intermediate Similarity NPD7048 Phase 3
0.73 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7827 Phase 1
0.7296 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD4582 Approved
0.7295 Intermediate Similarity NPD4583 Approved
0.7277 Intermediate Similarity NPD7047 Phase 3
0.7277 Intermediate Similarity NPD5711 Approved
0.7277 Intermediate Similarity NPD5710 Approved
0.7273 Intermediate Similarity NPD7701 Phase 2
0.7269 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD8156 Discontinued
0.7263 Intermediate Similarity NPD5677 Discontinued
0.726 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD4665 Approved
0.7256 Intermediate Similarity NPD4111 Phase 1
0.7246 Intermediate Similarity NPD4004 Approved
0.7246 Intermediate Similarity NPD4002 Approved
0.7245 Intermediate Similarity NPD7039 Approved
0.7245 Intermediate Similarity NPD7038 Approved
0.7238 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD8285 Discontinued
0.7216 Intermediate Similarity NPD8251 Approved
0.7216 Intermediate Similarity NPD8099 Discontinued
0.7216 Intermediate Similarity NPD8252 Approved
0.72 Intermediate Similarity NPD7291 Discontinued
0.7177 Intermediate Similarity NPD7999 Approved
0.7157 Intermediate Similarity NPD5582 Discontinued
0.7129 Intermediate Similarity NPD2488 Approved
0.7129 Intermediate Similarity NPD2490 Approved
0.7122 Intermediate Similarity NPD5564 Approved
0.7115 Intermediate Similarity NPD3057 Approved
0.7112 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4965 Approved
0.7105 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4966 Approved
0.7105 Intermediate Similarity NPD4967 Phase 2
0.7098 Intermediate Similarity NPD6071 Discontinued
0.709 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5676 Approved
0.7074 Intermediate Similarity NPD5890 Approved
0.7074 Intermediate Similarity NPD5889 Approved
0.7062 Intermediate Similarity NPD6973 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD2560 Approved
0.7053 Intermediate Similarity NPD2563 Approved
0.705 Intermediate Similarity NPD6618 Phase 2
0.7048 Intermediate Similarity NPD8319 Approved
0.7048 Intermediate Similarity NPD8320 Phase 1
0.7033 Intermediate Similarity NPD2972 Approved
0.7033 Intermediate Similarity NPD3533 Approved
0.7031 Intermediate Similarity NPD6234 Discontinued
0.703 Intermediate Similarity NPD7906 Approved
0.7028 Intermediate Similarity NPD4859 Phase 1
0.7018 Intermediate Similarity NPD2899 Discontinued
0.7016 Intermediate Similarity NPD6788 Approved
0.701 Intermediate Similarity NPD3051 Approved
0.7009 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7783 Phase 2
0.7005 Intermediate Similarity NPD4210 Discontinued
0.7005 Intermediate Similarity NPD5980 Discovery
0.7 Intermediate Similarity NPD2978 Approved
0.7 Intermediate Similarity NPD2977 Approved
0.6995 Remote Similarity NPD5494 Approved
0.6984 Remote Similarity NPD6873 Phase 2
0.6981 Remote Similarity NPD7583 Approved
0.6974 Remote Similarity NPD2970 Approved
0.6974 Remote Similarity NPD2969 Approved
0.6968 Remote Similarity NPD4017 Approved
0.6965 Remote Similarity NPD8053 Approved
0.6965 Remote Similarity NPD8054 Approved
0.6957 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6954 Remote Similarity NPD3818 Discontinued
0.6954 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6030 Approved
0.6952 Remote Similarity NPD3448 Approved
0.6952 Remote Similarity NPD2491 Approved
0.6952 Remote Similarity NPD6031 Approved
0.6948 Remote Similarity NPD7585 Approved
0.6947 Remote Similarity NPD37 Approved
0.6944 Remote Similarity NPD5688 Approved
0.6944 Remote Similarity NPD5689 Approved
0.6939 Remote Similarity NPD2898 Approved
0.6931 Remote Similarity NPD6585 Discontinued
0.6927 Remote Similarity NPD8404 Phase 2
0.6923 Remote Similarity NPD6808 Phase 2
0.6919 Remote Similarity NPD7497 Discontinued
0.6915 Remote Similarity NPD4578 Approved
0.6915 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4577 Approved
0.6908 Remote Similarity NPD4361 Phase 2
0.6908 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7584 Approved
0.6897 Remote Similarity NPD4663 Approved
0.6895 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6895 Remote Similarity NPD4773 Phase 2
0.6895 Remote Similarity NPD7110 Phase 1
0.6895 Remote Similarity NPD4772 Phase 2
0.6891 Remote Similarity NPD8005 Clinical (unspecified phase)
0.689 Remote Similarity NPD6874 Approved
0.6885 Remote Similarity NPD2897 Discontinued
0.6884 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7228 Approved
0.6865 Remote Similarity NPD5241 Discontinued
0.6862 Remote Similarity NPD5976 Discontinued
0.686 Remote Similarity NPD4360 Phase 2
0.686 Remote Similarity NPD4363 Phase 3
0.6859 Remote Similarity NPD7298 Approved
0.6859 Remote Similarity NPD6844 Discontinued
0.6857 Remote Similarity NPD6778 Approved
0.6857 Remote Similarity NPD6776 Approved
0.6857 Remote Similarity NPD6781 Approved
0.6857 Remote Similarity NPD6782 Approved
0.6857 Remote Similarity NPD6780 Approved
0.6857 Remote Similarity NPD6779 Approved
0.6857 Remote Similarity NPD6777 Approved
0.6853 Remote Similarity NPD27 Approved
0.6853 Remote Similarity NPD2489 Approved
0.6851 Remote Similarity NPD8153 Approved
0.6851 Remote Similarity NPD8152 Approved
0.6848 Remote Similarity NPD4236 Phase 3
0.6848 Remote Similarity NPD4237 Approved
0.684 Remote Similarity NPD7696 Phase 3
0.684 Remote Similarity NPD7697 Approved
0.684 Remote Similarity NPD7698 Approved
0.6837 Remote Similarity NPD4166 Phase 2
0.6837 Remote Similarity NPD6232 Discontinued
0.6837 Remote Similarity NPD8151 Discontinued
0.6837 Remote Similarity NPD7315 Approved
0.6833 Remote Similarity NPD4618 Approved
0.6833 Remote Similarity NPD4622 Approved
0.6833 Remote Similarity NPD1933 Approved
0.6832 Remote Similarity NPD7311 Approved
0.6832 Remote Similarity NPD7312 Approved
0.6832 Remote Similarity NPD4078 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7313 Approved
0.6832 Remote Similarity NPD7310 Approved
0.683 Remote Similarity NPD7223 Discontinued
0.683 Remote Similarity NPD7224 Discontinued
0.6821 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6814 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6029 Clinical (unspecified phase)
0.681 Remote Similarity NPD7810 Phase 3
0.681 Remote Similarity NPD7811 Phase 3
0.681 Remote Similarity NPD7565 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