Structure

Physi-Chem Properties

Molecular Weight:  316.13
Volume:  322.347
LogP:  2.741
LogD:  2.608
LogS:  -3.19
# Rotatable Bonds:  4
TPSA:  79.15
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.808
Synthetic Accessibility Score:  3.037
Fsp3:  0.333
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:  -4.782
MDCK Permeability:  1.1013078619726002e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.773
30% Bioavailability (F30%):  0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.116
Plasma Protein Binding (PPB):  95.39212036132812%
Volume Distribution (VD):  0.893
Pgp-substrate:  5.407965183258057%

ADMET: Metabolism

CYP1A2-inhibitor:  0.954
CYP1A2-substrate:  0.949
CYP2C19-inhibitor:  0.789
CYP2C19-substrate:  0.269
CYP2C9-inhibitor:  0.555
CYP2C9-substrate:  0.951
CYP2D6-inhibitor:  0.691
CYP2D6-substrate:  0.914
CYP3A4-inhibitor:  0.526
CYP3A4-substrate:  0.516

ADMET: Excretion

Clearance (CL):  11.884
Half-life (T1/2):  0.867

ADMET: Toxicity

hERG Blockers:  0.123
Human Hepatotoxicity (H-HT):  0.387
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.141
Rat Oral Acute Toxicity:  0.471
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.938
Carcinogencity:  0.783
Eye Corrosion:  0.003
Eye Irritation:  0.403
Respiratory Toxicity:  0.783

Download Data

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

  Natural Product: NPC274716

Natural Product ID:  NPC274716
Common Name*:   Cocsuline
IUPAC Name:   n.a.
Synonyms:   (+)-Cocsuline; Cocsuline
Standard InCHIKey:  GOYCVNCWKXBQBF-SVBPBHIXSA-N
Standard InCHI:  InChI=1S/C35H34N2O5/c1-36-12-10-22-17-30-31-19-25(22)26(36)15-21-6-9-28(38)29(16-21)40-24-7-4-20(5-8-24)14-27-33-23(11-13-37(27)2)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,38H,10-15H2,1-3H3/t26-,27-/m0/s1
SMILES:  CN1CCc2cc3c4cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2c(CCN1C)cc(c(c2O4)O3)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL447886
PubChem CID:   21579625
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO27739 Erythrina mildbraedii Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(88)80746-5]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94986-0]
NPO25388 Siliquariaspongia japonica n.a. n.a. n.a. n.a. n.a. n.a. PMID[10425118]
NPO12170 Solanum indicum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[11575964]
NPO27931 Caulerpa taxifolia Species Caulerpaceae Eukaryota n.a. n.a. n.a. PMID[16563751]
NPO27739 Erythrina mildbraedii Species Fabaceae Eukaryota root bark Buea, Southwest Province, Cameroon 1997-JUL PMID[17125223]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. flower n.a. PMID[17679444]
NPO27646 Cystoseira baccata Species Sargassaceae Eukaryota n.a. n.a. n.a. PMID[18980381]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. fruit n.a. PMID[23132311]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[8759160]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota Fruits n.a. Database[FooDB]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. n.a. Database[FooDB]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27666 Sophora tetraptera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27803 Cercidiphyllum japonicum Species Cercidiphyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27803 Cercidiphyllum japonicum Species Cercidiphyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12170 Solanum indicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27666 Sophora tetraptera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27803 Cercidiphyllum japonicum Species Cercidiphyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27666 Sophora tetraptera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12170 Solanum indicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18354 Meiothermus ruber Species Thermaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26332 Ramalina tumidula Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27617 Phoenix dactylifera Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27666 Sophora tetraptera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27976 Astragalus wootoni Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27869 Bombacopsis glabra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27726 Diplocarpon mali Species Dermateaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27522 Gongronella urceolifera Species Cunninghamellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27703 Eclipta erecta Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27686 Aglaia odorata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27838 Rebutia marsoneri Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27931 Caulerpa taxifolia Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27468 Rhizopogon roseolus Species Rhizopogonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27216 Oreodaphne porosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27646 Cystoseira baccata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25388 Siliquariaspongia japonica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27803 Cercidiphyllum japonicum Species Cercidiphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27739 Erythrina mildbraedii 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 = 10000.0 nM PMID[528425]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 15.56 ug.mL-1 PMID[528424]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 87.0 nM PMID[528425]
NPT2 Others Unspecified Selectivity Index = 110.0 n.a. PMID[528425]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 502.0 nM PMID[528425]
NPT2 Others Unspecified Selectivity Index = 7.0 n.a. PMID[528425]
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 13.21 ug.mL-1 PMID[528426]

☑ 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 NPC274716 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 NPC254441
1.0 High Similarity NPC167116
0.9939 High Similarity NPC42663
0.9939 High Similarity NPC279228
0.9939 High Similarity NPC271013
0.9939 High Similarity NPC54654
0.9939 High Similarity NPC285931
0.9939 High Similarity NPC290582
0.9939 High Similarity NPC222661
0.9939 High Similarity NPC7715
0.9939 High Similarity NPC104196
0.9939 High Similarity NPC217748
0.9939 High Similarity NPC239824
0.9939 High Similarity NPC8836
0.9939 High Similarity NPC229373
0.9939 High Similarity NPC185639
0.9939 High Similarity NPC182052
0.9939 High Similarity NPC290005
0.9939 High Similarity NPC258657
0.9939 High Similarity NPC90998
0.9939 High Similarity NPC15414
0.9939 High Similarity NPC223690
0.9939 High Similarity NPC49075
0.9939 High Similarity NPC328155
0.9939 High Similarity NPC251735
0.9939 High Similarity NPC311973
0.9939 High Similarity NPC181796
0.9879 High Similarity NPC286119
0.9819 High Similarity NPC30779
0.9762 High Similarity NPC212237
0.9762 High Similarity NPC116465
0.9706 High Similarity NPC60295
0.9706 High Similarity NPC191132
0.9704 High Similarity NPC275680
0.9704 High Similarity NPC22115
0.9647 High Similarity NPC11296
0.9647 High Similarity NPC82457
0.9647 High Similarity NPC274661
0.9647 High Similarity NPC175890
0.9647 High Similarity NPC206900
0.9647 High Similarity NPC48490
0.9645 High Similarity NPC65312
0.9645 High Similarity NPC139783
0.9586 High Similarity NPC95426
0.9586 High Similarity NPC302245
0.9586 High Similarity NPC16357
0.9576 High Similarity NPC129518
0.9576 High Similarity NPC41376
0.9576 High Similarity NPC12424
0.9576 High Similarity NPC251580
0.9535 High Similarity NPC24260
0.9515 High Similarity NPC276890
0.9515 High Similarity NPC63646
0.9515 High Similarity NPC115284
0.9515 High Similarity NPC198498
0.9515 High Similarity NPC227060
0.9515 High Similarity NPC317145
0.9515 High Similarity NPC76682
0.9515 High Similarity NPC10908
0.9515 High Similarity NPC317439
0.9422 High Similarity NPC478093
0.9368 High Similarity NPC478091
0.9368 High Similarity NPC30182
0.9368 High Similarity NPC478092
0.9368 High Similarity NPC473589
0.9368 High Similarity NPC256124
0.9345 High Similarity NPC293093
0.9294 High Similarity NPC239584
0.9273 High Similarity NPC13916
0.9273 High Similarity NPC264850
0.9273 High Similarity NPC268503
0.9273 High Similarity NPC250846
0.9273 High Similarity NPC317272
0.9273 High Similarity NPC256012
0.9273 High Similarity NPC240841
0.9273 High Similarity NPC42549
0.9257 High Similarity NPC85381
0.9253 High Similarity NPC41122
0.9253 High Similarity NPC318805
0.9235 High Similarity NPC475479
0.9235 High Similarity NPC243454
0.9213 High Similarity NPC475654
0.9212 High Similarity NPC24465
0.9162 High Similarity NPC204908
0.9162 High Similarity NPC83198
0.9153 High Similarity NPC234318
0.9128 High Similarity NPC73492
0.9128 High Similarity NPC299990
0.9 High Similarity NPC152680
0.9 High Similarity NPC232386
0.9 High Similarity NPC190783
0.8966 High Similarity NPC302275
0.8956 High Similarity NPC254581
0.8941 High Similarity NPC475215
0.8941 High Similarity NPC108434
0.8914 High Similarity NPC249996
0.887 High Similarity NPC281581
0.8851 High Similarity NPC195538
0.8848 High Similarity NPC247639
0.8848 High Similarity NPC25084
0.882 High Similarity NPC475597
0.882 High Similarity NPC473716
0.88 High Similarity NPC476202
0.8788 High Similarity NPC39701
0.8788 High Similarity NPC204828
0.8788 High Similarity NPC127674
0.8788 High Similarity NPC189266
0.8788 High Similarity NPC276588
0.8788 High Similarity NPC2413
0.8788 High Similarity NPC249797
0.8788 High Similarity NPC207757
0.8788 High Similarity NPC295691
0.8788 High Similarity NPC184026
0.8788 High Similarity NPC469817
0.8788 High Similarity NPC278799
0.8788 High Similarity NPC54379
0.8788 High Similarity NPC193949
0.8788 High Similarity NPC172765
0.8788 High Similarity NPC110416
0.8788 High Similarity NPC5238
0.8757 High Similarity NPC14507
0.8757 High Similarity NPC47077
0.8721 High Similarity NPC239775
0.8663 High Similarity NPC168753
0.8663 High Similarity NPC118274
0.8613 High Similarity NPC10871
0.8588 High Similarity NPC475393
0.8545 High Similarity NPC151895
0.8545 High Similarity NPC220858
0.8545 High Similarity NPC88249
0.8545 High Similarity NPC192768
0.8545 High Similarity NPC97221
0.8529 High Similarity NPC60186
0.8485 Intermediate Similarity NPC103379
0.8485 Intermediate Similarity NPC477565
0.8475 Intermediate Similarity NPC474507
0.8471 Intermediate Similarity NPC119649
0.8471 Intermediate Similarity NPC230956
0.8471 Intermediate Similarity NPC205255
0.8471 Intermediate Similarity NPC271388
0.8471 Intermediate Similarity NPC235143
0.8454 Intermediate Similarity NPC82056
0.8448 Intermediate Similarity NPC109925
0.8446 Intermediate Similarity NPC38964
0.8439 Intermediate Similarity NPC474931
0.8439 Intermediate Similarity NPC306555
0.8439 Intermediate Similarity NPC145832
0.8439 Intermediate Similarity NPC158376
0.8439 Intermediate Similarity NPC117188
0.8439 Intermediate Similarity NPC205421
0.8439 Intermediate Similarity NPC12053
0.8439 Intermediate Similarity NPC81218
0.843 Intermediate Similarity NPC96603
0.843 Intermediate Similarity NPC276944
0.843 Intermediate Similarity NPC284183
0.843 Intermediate Similarity NPC306843
0.843 Intermediate Similarity NPC232514
0.843 Intermediate Similarity NPC253043
0.843 Intermediate Similarity NPC238530
0.843 Intermediate Similarity NPC78222
0.843 Intermediate Similarity NPC212794
0.843 Intermediate Similarity NPC4138
0.843 Intermediate Similarity NPC196447
0.843 Intermediate Similarity NPC136508
0.843 Intermediate Similarity NPC121275
0.843 Intermediate Similarity NPC477563
0.843 Intermediate Similarity NPC13504
0.8427 Intermediate Similarity NPC257269
0.8427 Intermediate Similarity NPC230276
0.8424 Intermediate Similarity NPC24233
0.8424 Intermediate Similarity NPC147390
0.8424 Intermediate Similarity NPC246587
0.8424 Intermediate Similarity NPC135538
0.8424 Intermediate Similarity NPC428
0.8424 Intermediate Similarity NPC476571
0.8421 Intermediate Similarity NPC80759
0.8421 Intermediate Similarity NPC79402
0.8412 Intermediate Similarity NPC221864
0.8372 Intermediate Similarity NPC324144
0.8371 Intermediate Similarity NPC40496
0.8371 Intermediate Similarity NPC32154
0.8371 Intermediate Similarity NPC119068
0.8364 Intermediate Similarity NPC210437
0.8364 Intermediate Similarity NPC476151
0.8364 Intermediate Similarity NPC476144
0.8364 Intermediate Similarity NPC179825
0.8364 Intermediate Similarity NPC321505
0.8364 Intermediate Similarity NPC191376
0.8364 Intermediate Similarity NPC51957
0.8364 Intermediate Similarity NPC106295
0.8364 Intermediate Similarity NPC16107
0.8362 Intermediate Similarity NPC148709
0.8362 Intermediate Similarity NPC476577
0.8362 Intermediate Similarity NPC173416
0.8313 Intermediate Similarity NPC7467
0.8266 Intermediate Similarity NPC1229
0.8258 Intermediate Similarity NPC241704
0.8256 Intermediate Similarity NPC166014
0.8256 Intermediate Similarity NPC27410
0.8242 Intermediate Similarity NPC185838

  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 NPC274716 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
0.9939 High Similarity NPD8053 Approved
0.9939 High Similarity NPD8054 Approved
0.9515 High Similarity NPD8252 Approved
0.9515 High Similarity NPD8251 Approved
0.9515 High Similarity NPD8099 Discontinued
0.9458 High Similarity NPD8156 Discontinued
0.8533 High Similarity NPD8095 Phase 1
0.8371 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD4584 Approved
0.8304 Intermediate Similarity NPD6788 Approved
0.8142 Intermediate Similarity NPD7906 Approved
0.807 Intermediate Similarity NPD4772 Phase 2
0.807 Intermediate Similarity NPD4773 Phase 2
0.8023 Intermediate Similarity NPD7298 Approved
0.8 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6071 Discontinued
0.7943 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD7833 Phase 2
0.7943 Intermediate Similarity NPD7831 Phase 2
0.7923 Intermediate Similarity NPD7310 Approved
0.7923 Intermediate Similarity NPD7313 Approved
0.7923 Intermediate Similarity NPD7311 Approved
0.7923 Intermediate Similarity NPD7312 Approved
0.788 Intermediate Similarity NPD7309 Approved
0.7877 Intermediate Similarity NPD27 Approved
0.7877 Intermediate Similarity NPD2489 Approved
0.7865 Intermediate Similarity NPD3051 Approved
0.7849 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD4577 Approved
0.7826 Intermediate Similarity NPD4578 Approved
0.7824 Intermediate Similarity NPD7447 Phase 1
0.7824 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD2969 Approved
0.7821 Intermediate Similarity NPD2970 Approved
0.7796 Intermediate Similarity NPD4663 Approved
0.7753 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2563 Approved
0.7727 Intermediate Similarity NPD2560 Approved
0.7676 Intermediate Similarity NPD7549 Discontinued
0.7667 Intermediate Similarity NPD4010 Discontinued
0.7661 Intermediate Similarity NPD7212 Phase 2
0.7661 Intermediate Similarity NPD7213 Phase 3
0.7616 Intermediate Similarity NPD1424 Approved
0.7605 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD2898 Approved
0.7558 Intermediate Similarity NPD2420 Approved
0.7558 Intermediate Similarity NPD2421 Approved
0.7544 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4055 Discovery
0.7529 Intermediate Similarity NPD6031 Approved
0.7529 Intermediate Similarity NPD6030 Approved
0.75 Intermediate Similarity NPD7124 Phase 2
0.75 Intermediate Similarity NPD4678 Approved
0.75 Intermediate Similarity NPD4675 Approved
0.7459 Intermediate Similarity NPD5677 Discontinued
0.7443 Intermediate Similarity NPD4017 Approved
0.7442 Intermediate Similarity NPD5241 Discontinued
0.7429 Intermediate Similarity NPD3641 Approved
0.7429 Intermediate Similarity NPD3640 Phase 3
0.7429 Intermediate Similarity NPD3639 Approved
0.7418 Intermediate Similarity NPD7802 Discontinued
0.7418 Intermediate Similarity NPD6107 Approved
0.7411 Intermediate Similarity NPD2494 Approved
0.7411 Intermediate Similarity NPD3452 Approved
0.7411 Intermediate Similarity NPD3450 Approved
0.7411 Intermediate Similarity NPD2493 Approved
0.7399 Intermediate Similarity NPD3845 Phase 1
0.7396 Intermediate Similarity NPD2488 Approved
0.7396 Intermediate Similarity NPD2490 Approved
0.7391 Intermediate Similarity NPD4481 Phase 3
0.7389 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4005 Discontinued
0.733 Intermediate Similarity NPD2122 Discontinued
0.7321 Intermediate Similarity NPD6997 Phase 2
0.7316 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4474 Approved
0.7305 Intermediate Similarity NPD4475 Approved
0.73 Intermediate Similarity NPD4582 Approved
0.73 Intermediate Similarity NPD4583 Approved
0.7297 Intermediate Similarity NPD8152 Approved
0.7297 Intermediate Similarity NPD8153 Approved
0.7283 Intermediate Similarity NPD6748 Discontinued
0.7282 Intermediate Similarity NPD7047 Phase 3
0.7278 Intermediate Similarity NPD5772 Approved
0.7278 Intermediate Similarity NPD5773 Approved
0.7263 Intermediate Similarity NPD6072 Discontinued
0.7257 Intermediate Similarity NPD3124 Discontinued
0.7257 Intermediate Similarity NPD7598 Phase 2
0.7253 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4002 Approved
0.725 Intermediate Similarity NPD4004 Approved
0.7246 Intermediate Similarity NPD5718 Phase 2
0.7235 Intermediate Similarity NPD2200 Suspended
0.7229 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD5177 Phase 3
0.7216 Intermediate Similarity NPD4123 Phase 3
0.7208 Intermediate Similarity NPD2974 Approved
0.7208 Intermediate Similarity NPD2975 Approved
0.7208 Intermediate Similarity NPD2973 Approved
0.72 Intermediate Similarity NPD5005 Approved
0.72 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD5006 Approved
0.7196 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7466 Approved
0.7182 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD5312 Approved
0.7181 Intermediate Similarity NPD5313 Approved
0.7175 Intermediate Similarity NPD6090 Discontinued
0.7169 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1613 Approved
0.7151 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7827 Phase 1
0.7135 Intermediate Similarity NPD6853 Approved
0.7135 Intermediate Similarity NPD6851 Approved
0.7127 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4908 Phase 1
0.712 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6297 Approved
0.71 Intermediate Similarity NPD4580 Approved
0.709 Intermediate Similarity NPD42 Phase 2
0.709 Intermediate Similarity NPD6042 Phase 2
0.7083 Intermediate Similarity NPD2968 Approved
0.7083 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2971 Approved
0.7074 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD3692 Discontinued
0.7044 Intermediate Similarity NPD4040 Phase 1
0.7041 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6896 Approved
0.7035 Intermediate Similarity NPD6111 Discontinued
0.7035 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6895 Approved
0.7029 Intermediate Similarity NPD4236 Phase 3
0.7029 Intermediate Similarity NPD3060 Approved
0.7029 Intermediate Similarity NPD4237 Approved
0.7029 Intermediate Similarity NPD4162 Approved
0.7022 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6667 Approved
0.7006 Intermediate Similarity NPD6666 Approved
0.7006 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD4166 Phase 2
0.7 Intermediate Similarity NPD2674 Phase 3
0.7 Intermediate Similarity NPD4420 Approved
0.7 Intermediate Similarity NPD4873 Discontinued
0.6995 Remote Similarity NPD2978 Approved
0.6995 Remote Similarity NPD4585 Approved
0.6995 Remote Similarity NPD2977 Approved
0.6984 Remote Similarity NPD5938 Phase 3
0.6982 Remote Similarity NPD3027 Phase 3
0.6982 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5089 Approved
0.6978 Remote Similarity NPD5090 Approved
0.6973 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7037 Approved
0.6968 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6965 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7479 Phase 2
0.6959 Remote Similarity NPD2238 Phase 2
0.6949 Remote Similarity NPD2677 Approved
0.6949 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6949 Remote Similarity NPD5160 Discontinued
0.6939 Remote Similarity NPD7291 Discontinued
0.6936 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6904 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6898 Remote Similarity NPD4666 Phase 3
0.6897 Remote Similarity NPD1753 Discontinued
0.6893 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6869 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7907 Approved
0.6864 Remote Similarity NPD6723 Discontinued
0.6859 Remote Similarity NPD5940 Clinical (unspecified phase)
0.6859 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6856 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6841 Approved
0.6853 Remote Similarity NPD6842 Approved
0.6853 Remote Similarity NPD6843 Phase 3
0.6851 Remote Similarity NPD5976 Discontinued
0.6845 Remote Similarity NPD5709 Phase 3
0.6842 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3144 Approved
0.6842 Remote Similarity NPD6166 Phase 2
0.6842 Remote Similarity NPD3145 Approved
0.6842 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7280 Phase 3
0.6821 Remote Similarity NPD7281 Phase 3
0.6818 Remote Similarity NPD3656 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