Structure

Physi-Chem Properties

Molecular Weight:  576.26
Volume:  597.067
LogP:  6.905
LogD:  3.9
LogS:  -7.822
# Rotatable Bonds:  2
TPSA:  52.63
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  9
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.219
Synthetic Accessibility Score:  5.872
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.824
MDCK Permeability:  2.452706394251436e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.972
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.844
30% Bioavailability (F30%):  0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.089
Plasma Protein Binding (PPB):  54.98469924926758%
Volume Distribution (VD):  0.949
Pgp-substrate:  20.824687957763672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.09
CYP1A2-substrate:  0.967
CYP2C19-inhibitor:  0.083
CYP2C19-substrate:  0.974
CYP2C9-inhibitor:  0.06
CYP2C9-substrate:  0.724
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.958
CYP3A4-inhibitor:  0.096
CYP3A4-substrate:  0.955

ADMET: Excretion

Clearance (CL):  10.774
Half-life (T1/2):  0.095

ADMET: Toxicity

hERG Blockers:  0.961
Human Hepatotoxicity (H-HT):  0.015
Drug-inuced Liver Injury (DILI):  0.767
AMES Toxicity:  0.13
Rat Oral Acute Toxicity:  0.754
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.693
Carcinogencity:  0.06
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.425

Download Data

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

  Natural Product: NPC251580

Natural Product ID:  NPC251580
Common Name*:   Isotrilobine
IUPAC Name:   n.a.
Synonyms:   (+)-Isotrilobine; Isotrilobine
Standard InCHIKey:  SVMNNRZZJAFEJM-NSOVKSMOSA-N
Standard InCHI:  InChI=1S/C36H36N2O5/c1-37-13-11-23-18-31-32-20-26(23)27(37)16-22-7-10-29(39-3)30(17-22)41-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)19-33(40-4)35(42-31)36(34)43-32/h5-10,17-20,27-28H,11-16H2,1-4H3/t27-,28-/m0/s1
SMILES:  CN1CCc2cc3c4cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2c(CCN1C)cc(c(c2O4)O3)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503241
PubChem CID:   12310578
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
NPO23690 Cocculus orbiculatus Species Menispermaceae Eukaryota n.a. Formosan n.a. PMID[16038548]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota Aerial parts n.a. n.a. PMID[20426456]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9392886]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23690 Cocculus orbiculatus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6730 Crossopteryx febrifuga Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19931 Pyrus x nivalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1516 Passiflora suberosa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae 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
NPT2477 Cell Line NUGC-3 Homo sapiens Inhibition = 0.0 % PMID[515709]
NPT2477 Cell Line NUGC-3 Homo sapiens Inhibition = 100.0 % PMID[515709]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 1.6 ug.mL-1 PMID[515709]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 3.9 ug.mL-1 PMID[515709]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[515709]
NPT91 Cell Line KB Homo sapiens ED50 = 24000.0 nM PMID[515710]
NPT2 Others Unspecified Ratio ED50 = 70.0 n.a. PMID[515708]
NPT2 Others Unspecified Ratio ED50 = 57.0 n.a. PMID[515708]
NPT2 Others Unspecified Ratio ED50 = 32.0 n.a. PMID[515708]
NPT2 Others Unspecified Ratio ED50 = 10.0 n.a. PMID[515708]
NPT2 Others Unspecified Ratio ED50 = 5.0 n.a. PMID[515708]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 79.0 % PMID[515709]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 100.0 % PMID[515709]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.75 ug.mL-1 PMID[515709]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 388.0 nM PMID[515710]
NPT2 Others Unspecified Selectivity Index = 62.0 n.a. PMID[515710]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 788.0 nM PMID[515710]
NPT2 Others Unspecified Selectivity Index = 30.0 n.a. PMID[515710]
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 6.22 ug.mL-1 PMID[515711]
NPT2 Others Unspecified ED50 = 2 ug/ml PMID[9392886]
NPT2 Others Unspecified Activity = 0.2 n.a. PMID[9392886]
NPT2 Others Unspecified Activity = 0.16 n.a. PMID[9392886]
NPT2 Others Unspecified Activity = 0.12 n.a. PMID[9392886]
NPT2 Others Unspecified Activity = 0.06 n.a. PMID[9392886]
NPT2 Others Unspecified Activity = 0.03 n.a. PMID[9392886]

☑ 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 NPC251580 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 NPC129518
1.0 High Similarity NPC41376
1.0 High Similarity NPC12424
0.9937 High Similarity NPC198498
0.9937 High Similarity NPC227060
0.9937 High Similarity NPC63646
0.9937 High Similarity NPC10908
0.9937 High Similarity NPC76682
0.9937 High Similarity NPC276890
0.9937 High Similarity NPC317145
0.9937 High Similarity NPC115284
0.9937 High Similarity NPC317439
0.9752 High Similarity NPC293093
0.9693 High Similarity NPC239584
0.9632 High Similarity NPC243454
0.9632 High Similarity NPC475479
0.9576 High Similarity NPC274716
0.9576 High Similarity NPC167116
0.9576 High Similarity NPC254441
0.9515 High Similarity NPC73492
0.9515 High Similarity NPC251735
0.9515 High Similarity NPC223690
0.9515 High Similarity NPC222661
0.9515 High Similarity NPC271013
0.9515 High Similarity NPC311973
0.9515 High Similarity NPC15414
0.9515 High Similarity NPC181796
0.9515 High Similarity NPC7715
0.9515 High Similarity NPC279228
0.9515 High Similarity NPC328155
0.9515 High Similarity NPC49075
0.9515 High Similarity NPC239824
0.9515 High Similarity NPC290582
0.9515 High Similarity NPC182052
0.9515 High Similarity NPC185639
0.9515 High Similarity NPC90998
0.9515 High Similarity NPC42663
0.9515 High Similarity NPC299990
0.9515 High Similarity NPC229373
0.9515 High Similarity NPC54654
0.9515 High Similarity NPC285931
0.9515 High Similarity NPC290005
0.9515 High Similarity NPC217748
0.9515 High Similarity NPC104196
0.9515 High Similarity NPC8836
0.9515 High Similarity NPC258657
0.9461 High Similarity NPC139783
0.9461 High Similarity NPC65312
0.9455 High Similarity NPC286119
0.9401 High Similarity NPC16357
0.9401 High Similarity NPC95426
0.9401 High Similarity NPC302245
0.9398 High Similarity NPC30779
0.9345 High Similarity NPC116465
0.9345 High Similarity NPC212237
0.9341 High Similarity NPC302275
0.9294 High Similarity NPC60295
0.9294 High Similarity NPC191132
0.929 High Similarity NPC22115
0.929 High Similarity NPC275680
0.9286 High Similarity NPC249996
0.9241 High Similarity NPC25084
0.9241 High Similarity NPC247639
0.9235 High Similarity NPC82457
0.9235 High Similarity NPC11296
0.9235 High Similarity NPC281581
0.9235 High Similarity NPC48490
0.9235 High Similarity NPC175890
0.9235 High Similarity NPC274661
0.9235 High Similarity NPC206900
0.9222 High Similarity NPC195538
0.9186 High Similarity NPC256124
0.9181 High Similarity NPC473716
0.9181 High Similarity NPC475597
0.9167 High Similarity NPC476202
0.9128 High Similarity NPC24260
0.9118 High Similarity NPC14507
0.9118 High Similarity NPC47077
0.9017 High Similarity NPC478093
0.8976 High Similarity NPC10871
0.8966 High Similarity NPC30182
0.8966 High Similarity NPC473589
0.8966 High Similarity NPC478092
0.8966 High Similarity NPC478091
0.8957 High Similarity NPC475393
0.8857 High Similarity NPC85381
0.8851 High Similarity NPC318805
0.8851 High Similarity NPC41122
0.8848 High Similarity NPC317272
0.8848 High Similarity NPC240841
0.8848 High Similarity NPC13916
0.8848 High Similarity NPC268503
0.8848 High Similarity NPC250846
0.8848 High Similarity NPC42549
0.8848 High Similarity NPC264850
0.8848 High Similarity NPC256012
0.882 High Similarity NPC475654
0.8788 High Similarity NPC24465
0.8778 High Similarity NPC254581
0.8757 High Similarity NPC234318
0.8743 High Similarity NPC83198
0.8743 High Similarity NPC204908
0.8734 High Similarity NPC106295
0.8734 High Similarity NPC16107
0.8734 High Similarity NPC51957
0.8734 High Similarity NPC210437
0.8734 High Similarity NPC476144
0.8679 High Similarity NPC7467
0.8589 High Similarity NPC123323
0.8588 High Similarity NPC232386
0.8588 High Similarity NPC152680
0.8588 High Similarity NPC190783
0.8529 High Similarity NPC108434
0.8529 High Similarity NPC475215
0.8481 Intermediate Similarity NPC128019
0.8481 Intermediate Similarity NPC136860
0.8481 Intermediate Similarity NPC476567
0.8373 Intermediate Similarity NPC476572
0.8364 Intermediate Similarity NPC207757
0.8364 Intermediate Similarity NPC278799
0.8364 Intermediate Similarity NPC469817
0.8364 Intermediate Similarity NPC110416
0.8364 Intermediate Similarity NPC39701
0.8364 Intermediate Similarity NPC172765
0.8364 Intermediate Similarity NPC325871
0.8364 Intermediate Similarity NPC54379
0.8364 Intermediate Similarity NPC41178
0.8364 Intermediate Similarity NPC189266
0.8364 Intermediate Similarity NPC2413
0.8364 Intermediate Similarity NPC204828
0.8364 Intermediate Similarity NPC187022
0.8364 Intermediate Similarity NPC138487
0.8364 Intermediate Similarity NPC193949
0.8364 Intermediate Similarity NPC127674
0.8364 Intermediate Similarity NPC249797
0.8364 Intermediate Similarity NPC295691
0.8364 Intermediate Similarity NPC184026
0.8364 Intermediate Similarity NPC99659
0.8364 Intermediate Similarity NPC80129
0.8364 Intermediate Similarity NPC216459
0.8364 Intermediate Similarity NPC276588
0.8364 Intermediate Similarity NPC5238
0.8354 Intermediate Similarity NPC474915
0.8354 Intermediate Similarity NPC213206
0.8354 Intermediate Similarity NPC188163
0.8354 Intermediate Similarity NPC328750
0.8353 Intermediate Similarity NPC204947
0.8314 Intermediate Similarity NPC149090
0.8314 Intermediate Similarity NPC239775
0.8314 Intermediate Similarity NPC19520
0.8313 Intermediate Similarity NPC146288
0.8291 Intermediate Similarity NPC314682
0.8282 Intermediate Similarity NPC92541
0.8274 Intermediate Similarity NPC205255
0.8274 Intermediate Similarity NPC230956
0.8274 Intermediate Similarity NPC119649
0.8274 Intermediate Similarity NPC235143
0.8274 Intermediate Similarity NPC271388
0.8272 Intermediate Similarity NPC38964
0.8256 Intermediate Similarity NPC118274
0.8256 Intermediate Similarity NPC168753
0.8253 Intermediate Similarity NPC244112
0.8239 Intermediate Similarity NPC230276
0.8239 Intermediate Similarity NPC257269
0.8225 Intermediate Similarity NPC79402
0.8225 Intermediate Similarity NPC80759
0.8214 Intermediate Similarity NPC7393
0.8214 Intermediate Similarity NPC221864
0.8204 Intermediate Similarity NPC31311
0.8204 Intermediate Similarity NPC234392
0.8182 Intermediate Similarity NPC326316
0.8182 Intermediate Similarity NPC40496
0.8182 Intermediate Similarity NPC119068
0.8182 Intermediate Similarity NPC81733
0.816 Intermediate Similarity NPC144863
0.816 Intermediate Similarity NPC476151
0.815 Intermediate Similarity NPC75958
0.8121 Intermediate Similarity NPC97221
0.8121 Intermediate Similarity NPC151895
0.8121 Intermediate Similarity NPC192768
0.8121 Intermediate Similarity NPC220858
0.8121 Intermediate Similarity NPC88249
0.8118 Intermediate Similarity NPC60186
0.8111 Intermediate Similarity NPC208890
0.8107 Intermediate Similarity NPC216816
0.8098 Intermediate Similarity NPC473934
0.8095 Intermediate Similarity NPC323443
0.8095 Intermediate Similarity NPC180756
0.8093 Intermediate Similarity NPC82056
0.8081 Intermediate Similarity NPC476432
0.8081 Intermediate Similarity NPC24264
0.8079 Intermediate Similarity NPC474507
0.8068 Intermediate Similarity NPC241704
0.8061 Intermediate Similarity NPC103379
0.8061 Intermediate Similarity NPC477565
0.8057 Intermediate Similarity NPC2314
0.8046 Intermediate Similarity NPC109925
0.8037 Intermediate Similarity NPC185838
0.8035 Intermediate Similarity NPC12053
0.8035 Intermediate Similarity NPC247389

  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 NPC251580 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
0.9937 High Similarity NPD8252 Approved
0.9937 High Similarity NPD8251 Approved
0.9937 High Similarity NPD8099 Discontinued
0.9874 High Similarity NPD8156 Discontinued
0.9515 High Similarity NPD8053 Approved
0.9515 High Similarity NPD8054 Approved
0.887 High Similarity NPD8095 Phase 1
0.8734 High Similarity NPD4584 Approved
0.8659 High Similarity NPD6788 Approved
0.8364 Intermediate Similarity NPD7298 Approved
0.8354 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.8084 Intermediate Similarity NPD4772 Phase 2
0.8084 Intermediate Similarity NPD4773 Phase 2
0.7989 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1424 Approved
0.7937 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD6071 Discontinued
0.7866 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6031 Approved
0.7844 Intermediate Similarity NPD6030 Approved
0.7818 Intermediate Similarity NPD7124 Phase 2
0.7771 Intermediate Similarity NPD3051 Approved
0.776 Intermediate Similarity NPD7906 Approved
0.7759 Intermediate Similarity NPD5677 Discontinued
0.7759 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD4017 Approved
0.7746 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7831 Phase 2
0.7746 Intermediate Similarity NPD7833 Phase 2
0.7738 Intermediate Similarity NPD3641 Approved
0.7738 Intermediate Similarity NPD3640 Phase 3
0.7738 Intermediate Similarity NPD3639 Approved
0.7714 Intermediate Similarity NPD6107 Approved
0.7714 Intermediate Similarity NPD7802 Discontinued
0.7684 Intermediate Similarity NPD4481 Phase 3
0.7644 Intermediate Similarity NPD4055 Discovery
0.763 Intermediate Similarity NPD2563 Approved
0.763 Intermediate Similarity NPD2560 Approved
0.7627 Intermediate Similarity NPD2969 Approved
0.7627 Intermediate Similarity NPD2970 Approved
0.7625 Intermediate Similarity NPD4474 Approved
0.7625 Intermediate Similarity NPD4475 Approved
0.7619 Intermediate Similarity NPD7447 Phase 1
0.759 Intermediate Similarity NPD6748 Discontinued
0.7582 Intermediate Similarity NPD7549 Discontinued
0.7562 Intermediate Similarity NPD5718 Phase 2
0.756 Intermediate Similarity NPD7598 Phase 2
0.756 Intermediate Similarity NPD3124 Discontinued
0.7547 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD2200 Suspended
0.7541 Intermediate Similarity NPD7313 Approved
0.7541 Intermediate Similarity NPD7312 Approved
0.7541 Intermediate Similarity NPD7311 Approved
0.7541 Intermediate Similarity NPD7310 Approved
0.75 Intermediate Similarity NPD7309 Approved
0.7486 Intermediate Similarity NPD2489 Approved
0.7486 Intermediate Similarity NPD27 Approved
0.7485 Intermediate Similarity NPD7466 Approved
0.7473 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD5005 Approved
0.7461 Intermediate Similarity NPD5006 Approved
0.7459 Intermediate Similarity NPD5312 Approved
0.7459 Intermediate Similarity NPD5313 Approved
0.7456 Intermediate Similarity NPD7213 Phase 3
0.7456 Intermediate Similarity NPD7212 Phase 2
0.7446 Intermediate Similarity NPD4577 Approved
0.7446 Intermediate Similarity NPD4578 Approved
0.7442 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4663 Approved
0.7412 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4678 Approved
0.7399 Intermediate Similarity NPD4675 Approved
0.7351 Intermediate Similarity NPD2971 Approved
0.7351 Intermediate Similarity NPD2968 Approved
0.7341 Intermediate Similarity NPD4005 Discontinued
0.7337 Intermediate Similarity NPD5241 Discontinued
0.7333 Intermediate Similarity NPD6896 Approved
0.7333 Intermediate Similarity NPD6895 Approved
0.7333 Intermediate Similarity NPD6111 Discontinued
0.7294 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4166 Phase 2
0.7278 Intermediate Similarity NPD4010 Discontinued
0.7273 Intermediate Similarity NPD4585 Approved
0.7254 Intermediate Similarity NPD4420 Approved
0.7247 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD2122 Discontinued
0.7202 Intermediate Similarity NPD2974 Approved
0.7202 Intermediate Similarity NPD2975 Approved
0.7202 Intermediate Similarity NPD2973 Approved
0.7198 Intermediate Similarity NPD2898 Approved
0.7196 Intermediate Similarity NPD7291 Discontinued
0.7176 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD5772 Approved
0.7175 Intermediate Similarity NPD5773 Approved
0.7168 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD2420 Approved
0.7151 Intermediate Similarity NPD2421 Approved
0.7134 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6853 Approved
0.7128 Intermediate Similarity NPD6851 Approved
0.7126 Intermediate Similarity NPD5976 Discontinued
0.7119 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5177 Phase 3
0.7112 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD4123 Phase 3
0.7097 Intermediate Similarity NPD6297 Approved
0.7092 Intermediate Similarity NPD4580 Approved
0.7081 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5089 Approved
0.7062 Intermediate Similarity NPD7110 Phase 1
0.7062 Intermediate Similarity NPD6072 Discontinued
0.7062 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5090 Approved
0.7056 Intermediate Similarity NPD3452 Approved
0.7056 Intermediate Similarity NPD3450 Approved
0.7056 Intermediate Similarity NPD2494 Approved
0.7056 Intermediate Similarity NPD2493 Approved
0.7049 Intermediate Similarity NPD5242 Approved
0.7048 Intermediate Similarity NPD3110 Approved
0.7048 Intermediate Similarity NPD3109 Approved
0.7037 Intermediate Similarity NPD6618 Phase 2
0.7031 Intermediate Similarity NPD2488 Approved
0.7031 Intermediate Similarity NPD2490 Approved
0.7022 Intermediate Similarity NPD5720 Discontinued
0.7022 Intermediate Similarity NPD3382 Approved
0.7022 Intermediate Similarity NPD3383 Approved
0.7022 Intermediate Similarity NPD3384 Approved
0.7018 Intermediate Similarity NPD4237 Approved
0.7018 Intermediate Similarity NPD4162 Approved
0.7018 Intermediate Similarity NPD4236 Phase 3
0.7005 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3845 Phase 1
0.6989 Remote Similarity NPD4210 Discontinued
0.6986 Remote Similarity NPD6997 Phase 2
0.6983 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6982 Remote Similarity NPD8152 Approved
0.6982 Remote Similarity NPD8153 Approved
0.6977 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6973 Remote Similarity NPD5938 Phase 3
0.6971 Remote Similarity NPD6090 Discontinued
0.6957 Remote Similarity NPD6688 Approved
0.6957 Remote Similarity NPD6687 Approved
0.6954 Remote Similarity NPD5297 Approved
0.6954 Remote Similarity NPD7837 Clinical (unspecified phase)
0.695 Remote Similarity NPD4583 Approved
0.695 Remote Similarity NPD4582 Approved
0.6949 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6947 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5978 Approved
0.6944 Remote Similarity NPD5977 Approved
0.6942 Remote Similarity NPD7047 Phase 3
0.6936 Remote Similarity NPD5160 Discontinued
0.6936 Remote Similarity NPD3692 Discontinued
0.6935 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4098 Discontinued
0.6932 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4908 Phase 1
0.69 Remote Similarity NPD4004 Approved
0.69 Remote Similarity NPD4002 Approved
0.6898 Remote Similarity NPD42 Phase 2
0.6898 Remote Similarity NPD6042 Phase 2
0.6897 Remote Similarity NPD6666 Approved
0.6897 Remote Similarity NPD6667 Approved
0.689 Remote Similarity NPD7905 Discontinued
0.6889 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6882 Remote Similarity NPD3489 Phase 3
0.6879 Remote Similarity NPD5754 Discontinued
0.6872 Remote Similarity NPD6386 Approved
0.6872 Remote Similarity NPD6385 Approved
0.6872 Remote Similarity NPD7125 Discontinued
0.6868 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6865 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6856 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6357 Discontinued
0.6853 Remote Similarity NPD7034 Discontinued
0.685 Remote Similarity NPD7590 Clinical (unspecified phase)
0.6845 Remote Similarity NPD2238 Phase 2
0.6842 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2677 Approved
0.6826 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6823 Remote Similarity NPD5087 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6364 Approved
0.6821 Remote Similarity NPD3060 Approved
0.6821 Remote Similarity NPD44 Approved
0.6816 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6876 Approved
0.6816 Remote Similarity NPD6875 Approved
0.6807 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7280 Phase 3

  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