Structure

Physi-Chem Properties

Molecular Weight:  416.18
Volume:  417.851
LogP:  3.398
LogD:  3.272
LogS:  -3.987
# Rotatable Bonds:  4
TPSA:  75.61
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.816
Synthetic Accessibility Score:  3.616
Fsp3:  0.478
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:  -4.738
MDCK Permeability:  3.246857158956118e-05
Pgp-inhibitor:  0.843
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.065
Plasma Protein Binding (PPB):  79.38968658447266%
Volume Distribution (VD):  0.725
Pgp-substrate:  13.244933128356934%

ADMET: Metabolism

CYP1A2-inhibitor:  0.254
CYP1A2-substrate:  0.973
CYP2C19-inhibitor:  0.666
CYP2C19-substrate:  0.885
CYP2C9-inhibitor:  0.097
CYP2C9-substrate:  0.907
CYP2D6-inhibitor:  0.115
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.913
CYP3A4-substrate:  0.749

ADMET: Excretion

Clearance (CL):  8.432
Half-life (T1/2):  0.117

ADMET: Toxicity

hERG Blockers:  0.244
Human Hepatotoxicity (H-HT):  0.102
Drug-inuced Liver Injury (DILI):  0.13
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.069
Maximum Recommended Daily Dose:  0.2
Skin Sensitization:  0.187
Carcinogencity:  0.858
Eye Corrosion:  0.003
Eye Irritation:  0.052
Respiratory Toxicity:  0.148

Download Data

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

  Natural Product: NPC201404

Natural Product ID:  NPC201404
Common Name*:   Besigomsin
IUPAC Name:   n.a.
Synonyms:   Besigomsin
Standard InCHIKey:  ZWRRJEICIPUPHZ-MYODQAERSA-N
Standard InCHI:  InChI=1S/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3/t12-,23-/m0/s1
SMILES:  C[C@H]1Cc2cc3c(c(c2-c2c(cc(c(c2OC)OC)OC)C[C@]1(C)O)OC)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL403578
PubChem CID:   3001662
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10075755]
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11000019]
NPO11248 Tachigalia paniculata n.a. n.a. n.a. leaves n.a. n.a. PMID[12444671]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[2026709]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14255 Streptomyces flocculus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11642 Dacrydium cupressinum Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19635 Coreopsis nodosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12684 Trigonella grandiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7998 Senecio paludaffinis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22666 Haematococcus lacustris Species Haematococcaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11248 Tachigalia paniculata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13568 Hypoxylon rubiginosum Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13166 Nicotiana undulata Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5189 Glycine tomentella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO731 Panax schinseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12001 Saccharomyces pastori Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21854 Pterocladiella tenuis Species Gelidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11488 Alstonia muelleriana Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18805 Tripolium pannonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14354 Artemisia cina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10540 Passiflora incarnata Species Passifloraceae 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
NPT47 Individual Protein ATP-dependent DNA helicase Q1 Homo sapiens Potency = 1000.0 nM PMID[487581]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[487581]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 20596.2 nM PMID[487581]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Drug metabolism = 10.0 pmol/min PMID[487582]
NPT4023 Individual Protein Cytochrome P450 3A5 Homo sapiens Drug metabolism = 1.0 pmol/min PMID[487582]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 16511.3 nM PMID[487581]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 5.65 % PMID[487583]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 18.28 % PMID[487584]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.08 % PMID[487585]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[487586]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[487586]

☑ 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 NPC201404 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 NPC53722
1.0 High Similarity NPC290714
0.9695 High Similarity NPC145722
0.9695 High Similarity NPC256776
0.9695 High Similarity NPC185680
0.963 High Similarity NPC103637
0.963 High Similarity NPC230538
0.963 High Similarity NPC184641
0.963 High Similarity NPC229172
0.963 High Similarity NPC184684
0.963 High Similarity NPC133934
0.963 High Similarity NPC36531
0.9559 High Similarity NPC324962
0.9549 High Similarity NPC32189
0.9489 High Similarity NPC73467
0.9489 High Similarity NPC172171
0.9489 High Similarity NPC121661
0.9489 High Similarity NPC239254
0.942 High Similarity NPC110763
0.942 High Similarity NPC197352
0.942 High Similarity NPC166506
0.942 High Similarity NPC189239
0.942 High Similarity NPC475868
0.9394 High Similarity NPC102256
0.9353 High Similarity NPC154971
0.9353 High Similarity NPC252286
0.9259 High Similarity NPC197166
0.922 High Similarity NPC325720
0.922 High Similarity NPC316676
0.9185 High Similarity NPC180602
0.9185 High Similarity NPC240279
0.9185 High Similarity NPC214853
0.9185 High Similarity NPC55239
0.9179 High Similarity NPC196937
0.9161 High Similarity NPC224472
0.9137 High Similarity NPC218510
0.9137 High Similarity NPC76415
0.9124 High Similarity NPC6369
0.9124 High Similarity NPC9068
0.9124 High Similarity NPC30951
0.9111 High Similarity NPC469659
0.9111 High Similarity NPC206737
0.9111 High Similarity NPC56764
0.9111 High Similarity NPC188378
0.9111 High Similarity NPC276026
0.9111 High Similarity NPC555
0.9111 High Similarity NPC289258
0.9111 High Similarity NPC7515
0.9091 High Similarity NPC473989
0.9091 High Similarity NPC207702
0.9091 High Similarity NPC283114
0.9091 High Similarity NPC149008
0.9071 High Similarity NPC326144
0.9065 High Similarity NPC191231
0.9058 High Similarity NPC216434
0.9058 High Similarity NPC284464
0.9058 High Similarity NPC103448
0.9051 High Similarity NPC196420
0.9044 High Similarity NPC150534
0.9034 High Similarity NPC126405
0.9034 High Similarity NPC53669
0.9034 High Similarity NPC308739
0.9034 High Similarity NPC16791
0.9034 High Similarity NPC77237
0.9034 High Similarity NPC217708
0.9034 High Similarity NPC297271
0.9028 High Similarity NPC475756
0.9007 High Similarity NPC327651
0.9007 High Similarity NPC318286
0.8978 High Similarity NPC133025
0.8973 High Similarity NPC198461
0.8966 High Similarity NPC471154
0.8955 High Similarity NPC184814
0.8955 High Similarity NPC63574
0.8951 High Similarity NPC304821
0.8944 High Similarity NPC33832
0.8944 High Similarity NPC321958
0.8944 High Similarity NPC321696
0.8929 High Similarity NPC474295
0.8913 High Similarity NPC474039
0.8913 High Similarity NPC3072
0.8913 High Similarity NPC46277
0.8913 High Similarity NPC185908
0.8913 High Similarity NPC156948
0.8913 High Similarity NPC86605
0.8913 High Similarity NPC283949
0.8913 High Similarity NPC301765
0.8905 High Similarity NPC236522
0.8904 High Similarity NPC474606
0.8904 High Similarity NPC24562
0.8897 High Similarity NPC471390
0.8897 High Similarity NPC471391
0.8897 High Similarity NPC58585
0.8889 High Similarity NPC184928
0.8889 High Similarity NPC141493
0.8881 High Similarity NPC116019
0.8865 High Similarity NPC474808
0.8851 High Similarity NPC29727
0.8849 High Similarity NPC471183
0.8844 High Similarity NPC473425
0.8844 High Similarity NPC312763
0.8824 High Similarity NPC475856
0.8824 High Similarity NPC261812
0.8824 High Similarity NPC72046
0.8824 High Similarity NPC65183
0.8819 High Similarity NPC252281
0.8819 High Similarity NPC198129
0.8819 High Similarity NPC477375
0.8819 High Similarity NPC327352
0.8794 High Similarity NPC470917
0.8794 High Similarity NPC41782
0.8792 High Similarity NPC475592
0.8786 High Similarity NPC56091
0.8786 High Similarity NPC226547
0.8786 High Similarity NPC177868
0.8786 High Similarity NPC46591
0.8784 High Similarity NPC476065
0.8784 High Similarity NPC238834
0.8759 High Similarity NPC477376
0.8759 High Similarity NPC322426
0.8759 High Similarity NPC1474
0.8759 High Similarity NPC266848
0.8759 High Similarity NPC477374
0.8759 High Similarity NPC85141
0.8759 High Similarity NPC136750
0.8759 High Similarity NPC112237
0.875 High Similarity NPC192255
0.8741 High Similarity NPC180953
0.8741 High Similarity NPC307466
0.8725 High Similarity NPC473323
0.8705 High Similarity NPC121651
0.8699 High Similarity NPC316989
0.8699 High Similarity NPC24425
0.8696 High Similarity NPC31530
0.8686 High Similarity NPC97316
0.8686 High Similarity NPC7744
0.8676 High Similarity NPC258483
0.8676 High Similarity NPC224157
0.8676 High Similarity NPC192687
0.8676 High Similarity NPC126836
0.8675 High Similarity NPC63061
0.8671 High Similarity NPC87883
0.8662 High Similarity NPC287124
0.8657 High Similarity NPC223953
0.8652 High Similarity NPC109240
0.8643 High Similarity NPC865
0.8643 High Similarity NPC261714
0.8639 High Similarity NPC303519
0.8633 High Similarity NPC25333
0.8633 High Similarity NPC189474
0.8633 High Similarity NPC148893
0.8633 High Similarity NPC474139
0.8633 High Similarity NPC49235
0.8623 High Similarity NPC32778
0.8621 High Similarity NPC183083
0.8621 High Similarity NPC295297
0.8621 High Similarity NPC137352
0.8609 High Similarity NPC230531
0.8609 High Similarity NPC215400
0.8603 High Similarity NPC190144
0.8603 High Similarity NPC228769
0.8603 High Similarity NPC470633
0.8601 High Similarity NPC255566
0.8601 High Similarity NPC185071
0.8601 High Similarity NPC298317
0.8601 High Similarity NPC265154
0.8601 High Similarity NPC469630
0.8601 High Similarity NPC81638
0.8601 High Similarity NPC12728
0.8593 High Similarity NPC242032
0.8593 High Similarity NPC471986
0.8592 High Similarity NPC312199
0.8582 High Similarity NPC292487
0.8582 High Similarity NPC105925
0.8582 High Similarity NPC113550
0.8581 High Similarity NPC220577
0.8581 High Similarity NPC477378
0.8581 High Similarity NPC475229
0.8571 High Similarity NPC11453
0.8571 High Similarity NPC143895
0.8571 High Similarity NPC143139
0.8571 High Similarity NPC205442
0.8571 High Similarity NPC25695
0.8571 High Similarity NPC172818
0.8571 High Similarity NPC202846
0.8562 High Similarity NPC469512
0.8562 High Similarity NPC71726
0.8562 High Similarity NPC270751
0.8561 High Similarity NPC209199
0.8561 High Similarity NPC125649
0.8552 High Similarity NPC87295
0.8552 High Similarity NPC162193
0.8552 High Similarity NPC474054
0.8551 High Similarity NPC204215
0.8551 High Similarity NPC147616
0.8551 High Similarity NPC219671
0.8551 High Similarity NPC259742
0.8551 High Similarity NPC471505
0.8551 High Similarity NPC104077
0.8551 High Similarity NPC6451

  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 NPC201404 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
0.8421 Intermediate Similarity NPD3705 Approved
0.84 Intermediate Similarity NPD37 Approved
0.8235 Intermediate Similarity NPD4966 Approved
0.8235 Intermediate Similarity NPD4967 Phase 2
0.8235 Intermediate Similarity NPD4965 Approved
0.8201 Intermediate Similarity NPD3027 Phase 3
0.8129 Intermediate Similarity NPD6234 Discontinued
0.8025 Intermediate Similarity NPD7199 Phase 2
0.7929 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD3018 Phase 2
0.7925 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD5283 Phase 1
0.7872 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD6674 Discontinued
0.7778 Intermediate Similarity NPD1613 Approved
0.7778 Intermediate Similarity NPD7228 Approved
0.7778 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2982 Phase 2
0.777 Intermediate Similarity NPD2983 Phase 2
0.7698 Intermediate Similarity NPD2981 Phase 2
0.7692 Intermediate Similarity NPD4625 Phase 3
0.7622 Intermediate Similarity NPD4908 Phase 1
0.761 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7240 Approved
0.7536 Intermediate Similarity NPD1357 Approved
0.7518 Intermediate Similarity NPD4749 Approved
0.7517 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1610 Phase 2
0.7483 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6232 Discontinued
0.7419 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7473 Discontinued
0.7394 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD4005 Discontinued
0.7386 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD3540 Phase 1
0.7349 Intermediate Similarity NPD3818 Discontinued
0.7325 Intermediate Similarity NPD1653 Approved
0.731 Intermediate Similarity NPD2861 Phase 2
0.7297 Intermediate Similarity NPD4060 Phase 1
0.7297 Intermediate Similarity NPD3620 Phase 2
0.7297 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3539 Phase 1
0.7284 Intermediate Similarity NPD4055 Discovery
0.7279 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD1091 Approved
0.7251 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD709 Approved
0.7237 Intermediate Similarity NPD1375 Discontinued
0.7233 Intermediate Similarity NPD7028 Phase 2
0.7226 Intermediate Similarity NPD7124 Phase 2
0.7219 Intermediate Similarity NPD4108 Discontinued
0.7214 Intermediate Similarity NPD1548 Phase 1
0.7208 Intermediate Similarity NPD3892 Phase 2
0.7206 Intermediate Similarity NPD228 Approved
0.7202 Intermediate Similarity NPD5844 Phase 1
0.7162 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD5109 Approved
0.7162 Intermediate Similarity NPD5111 Phase 2
0.7162 Intermediate Similarity NPD5110 Phase 2
0.716 Intermediate Similarity NPD7074 Phase 3
0.7152 Intermediate Similarity NPD6111 Discontinued
0.7143 Intermediate Similarity NPD1934 Approved
0.7143 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3882 Suspended
0.7115 Intermediate Similarity NPD5058 Phase 3
0.7108 Intermediate Similarity NPD7229 Phase 3
0.7108 Intermediate Similarity NPD3787 Discontinued
0.7103 Intermediate Similarity NPD6696 Suspended
0.7101 Intermediate Similarity NPD7054 Approved
0.7099 Intermediate Similarity NPD1465 Phase 2
0.7099 Intermediate Similarity NPD2801 Approved
0.7091 Intermediate Similarity NPD5494 Approved
0.7081 Intermediate Similarity NPD5090 Approved
0.7081 Intermediate Similarity NPD5089 Approved
0.7078 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD4357 Discontinued
0.7067 Intermediate Similarity NPD2238 Phase 2
0.7063 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4750 Phase 3
0.7059 Intermediate Similarity NPD6100 Approved
0.7059 Intermediate Similarity NPD6099 Approved
0.7059 Intermediate Similarity NPD3021 Approved
0.7059 Intermediate Similarity NPD3022 Approved
0.7059 Intermediate Similarity NPD7472 Approved
0.7055 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3817 Phase 2
0.7034 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD5536 Phase 2
0.702 Intermediate Similarity NPD3657 Discovery
0.7013 Intermediate Similarity NPD5762 Approved
0.7013 Intermediate Similarity NPD7266 Discontinued
0.7013 Intermediate Similarity NPD5763 Approved
0.7012 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4624 Approved
0.6994 Remote Similarity NPD2978 Approved
0.6994 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2977 Approved
0.6993 Remote Similarity NPD5126 Approved
0.6993 Remote Similarity NPD5125 Phase 3
0.6993 Remote Similarity NPD4626 Approved
0.6986 Remote Similarity NPD1283 Approved
0.6977 Remote Similarity NPD6559 Discontinued
0.6974 Remote Similarity NPD4097 Suspended
0.6966 Remote Similarity NPD2232 Approved
0.6966 Remote Similarity NPD2230 Approved
0.6966 Remote Similarity NPD2233 Approved
0.6961 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6943 Remote Similarity NPD2219 Phase 1
0.6936 Remote Similarity NPD7808 Phase 3
0.6936 Remote Similarity NPD7549 Discontinued
0.6933 Remote Similarity NPD3384 Approved
0.6933 Remote Similarity NPD3382 Approved
0.6933 Remote Similarity NPD3383 Approved
0.6932 Remote Similarity NPD6841 Approved
0.6932 Remote Similarity NPD6843 Phase 3
0.6932 Remote Similarity NPD6842 Approved
0.6923 Remote Similarity NPD4237 Approved
0.6923 Remote Similarity NPD5177 Phase 3
0.6923 Remote Similarity NPD4236 Phase 3
0.6919 Remote Similarity NPD6797 Phase 2
0.6918 Remote Similarity NPD2532 Approved
0.6918 Remote Similarity NPD2533 Approved
0.6918 Remote Similarity NPD2534 Approved
0.6914 Remote Similarity NPD4675 Approved
0.6914 Remote Similarity NPD4678 Approved
0.6908 Remote Similarity NPD6355 Discontinued
0.6897 Remote Similarity NPD422 Phase 1
0.689 Remote Similarity NPD7819 Suspended
0.689 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6879 Remote Similarity NPD3750 Approved
0.6879 Remote Similarity NPD7251 Discontinued
0.6879 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7466 Approved
0.6879 Remote Similarity NPD4110 Phase 3
0.6879 Remote Similarity NPD6671 Approved
0.6875 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7095 Approved
0.6864 Remote Similarity NPD3926 Phase 2
0.6855 Remote Similarity NPD1511 Approved
0.6848 Remote Similarity NPD2560 Approved
0.6848 Remote Similarity NPD2563 Approved
0.6842 Remote Similarity NPD3751 Discontinued
0.6839 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2677 Approved
0.6824 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6166 Phase 2
0.6811 Remote Similarity NPD7680 Approved
0.6806 Remote Similarity NPD5691 Approved
0.6806 Remote Similarity NPD1651 Approved
0.6803 Remote Similarity NPD1669 Approved
0.6797 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5735 Approved
0.6797 Remote Similarity NPD5124 Phase 1
0.6795 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6791 Remote Similarity NPD846 Approved
0.6791 Remote Similarity NPD940 Approved
0.6788 Remote Similarity NPD8455 Phase 2
0.6788 Remote Similarity NPD4585 Approved
0.6786 Remote Similarity NPD1138 Approved
0.6781 Remote Similarity NPD1611 Approved
0.6781 Remote Similarity NPD1281 Approved
0.6774 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6774 Remote Similarity NPD3748 Approved
0.6772 Remote Similarity NPD6331 Phase 2
0.677 Remote Similarity NPD1512 Approved
0.677 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6766 Remote Similarity NPD5604 Discontinued
0.6761 Remote Similarity NPD6387 Discontinued
0.6761 Remote Similarity NPD7157 Approved
0.6759 Remote Similarity NPD2668 Approved
0.6759 Remote Similarity NPD2667 Approved
0.6757 Remote Similarity NPD8651 Approved
0.6757 Remote Similarity NPD2922 Phase 1
0.6753 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6739 Remote Similarity NPD2684 Approved
0.6735 Remote Similarity NPD1608 Approved
0.6732 Remote Similarity NPD2979 Phase 3
0.6732 Remote Similarity NPD1558 Phase 1
0.6732 Remote Similarity NPD4140 Approved
0.6732 Remote Similarity NPD1240 Approved
0.6731 Remote Similarity NPD2935 Discontinued
0.6731 Remote Similarity NPD2438 Suspended
0.6726 Remote Similarity NPD919 Approved
0.6716 Remote Similarity NPD1242 Phase 1
0.6714 Remote Similarity NPD1139 Approved
0.6714 Remote Similarity NPD1137 Approved
0.671 Remote Similarity NPD6895 Approved
0.671 Remote Similarity NPD6896 Approved
0.671 Remote Similarity NPD7097 Phase 1
0.6709 Remote Similarity NPD3060 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