Structure

Physi-Chem Properties

Molecular Weight:  640.31
Volume:  666.353
LogP:  4.986
LogD:  3.816
LogS:  -4.088
# Rotatable Bonds:  10
TPSA:  93.09
# H-Bond Aceptor:  9
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.202
Synthetic Accessibility Score:  3.788
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.632
MDCK Permeability:  2.666631007741671e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.717
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.838
30% Bioavailability (F30%):  0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.052
Plasma Protein Binding (PPB):  62.41015625%
Volume Distribution (VD):  1.121
Pgp-substrate:  29.444795608520508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.977
CYP2C19-inhibitor:  0.066
CYP2C19-substrate:  0.968
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.634
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.965
CYP3A4-inhibitor:  0.124
CYP3A4-substrate:  0.956

ADMET: Excretion

Clearance (CL):  14.117
Half-life (T1/2):  0.59

ADMET: Toxicity

hERG Blockers:  0.962
Human Hepatotoxicity (H-HT):  0.083
Drug-inuced Liver Injury (DILI):  0.799
AMES Toxicity:  0.07
Rat Oral Acute Toxicity:  0.322
Maximum Recommended Daily Dose:  0.989
Skin Sensitization:  0.927
Carcinogencity:  0.029
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.488

Download Data

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

  Natural Product: NPC286119

Natural Product ID:  NPC286119
Common Name*:   Thalirugine
IUPAC Name:   (1S)-1-[[4-[5-[[(1S)-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenoxy]phenyl]methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-5-ol
Synonyms:   Thalirugine
Standard InCHIKey:  RRBKPDNMJPPISI-CONSDPRKSA-N
Standard InCHI:  InChI=1S/C38H44N2O7/c1-39-15-13-25-20-34(44-4)32(41)21-28(25)30(39)18-24-9-12-33(43-3)35(19-24)47-26-10-7-23(8-11-26)17-31-29-22-36(45-5)38(46-6)37(42)27(29)14-16-40(31)2/h7-12,19-22,30-31,41-42H,13-18H2,1-6H3/t30-,31-/m0/s1
SMILES:  CN1CCc2cc(c(cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2cc(c(c(c2CCN1C)O)OC)OC)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445049
PubChem CID:   44584030
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO20891 Coleonema pulchellum Species Rutaceae Eukaryota n.a. Costa Rica; Bartica, Guyana n.a. PMID[16124770]
NPO22044 Tamarix chinensis Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22044 Tamarix chinensis Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20891 Coleonema pulchellum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22044 Tamarix chinensis Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22044 Tamarix chinensis Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20320 Cryptostegia madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21985 Koenigia coriaria Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20451 Vitex scabra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20891 Coleonema pulchellum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22625 Copris tripartitus Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22044 Tamarix chinensis Species Tamaricaceae 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity = 1000.0 ug ml-1 PMID[573605]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis Activity = 1000.0 ug ml-1 PMID[573605]

☑ 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 NPC286119 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
0.9939 High Similarity NPC279228
0.9939 High Similarity NPC271013
0.9939 High Similarity NPC42663
0.9939 High Similarity NPC54654
0.9939 High Similarity NPC328155
0.9939 High Similarity NPC285931
0.9939 High Similarity NPC104196
0.9939 High Similarity NPC290582
0.9939 High Similarity NPC222661
0.9939 High Similarity NPC7715
0.9939 High Similarity NPC15414
0.9939 High Similarity NPC217748
0.9939 High Similarity NPC239824
0.9939 High Similarity NPC8836
0.9939 High Similarity NPC229373
0.9939 High Similarity NPC182052
0.9939 High Similarity NPC290005
0.9939 High Similarity NPC258657
0.9939 High Similarity NPC90998
0.9939 High Similarity NPC223690
0.9939 High Similarity NPC49075
0.9939 High Similarity NPC251735
0.9939 High Similarity NPC185639
0.9939 High Similarity NPC311973
0.9939 High Similarity NPC30779
0.9939 High Similarity NPC181796
0.9879 High Similarity NPC254441
0.9879 High Similarity NPC274716
0.9879 High Similarity NPC167116
0.976 High Similarity NPC116465
0.976 High Similarity NPC212237
0.9702 High Similarity NPC275680
0.9702 High Similarity NPC22115
0.9645 High Similarity NPC11296
0.9645 High Similarity NPC175890
0.9645 High Similarity NPC274661
0.9645 High Similarity NPC82457
0.9645 High Similarity NPC206900
0.9645 High Similarity NPC48490
0.9588 High Similarity NPC191132
0.9588 High Similarity NPC60295
0.9583 High Similarity NPC95426
0.9583 High Similarity NPC16357
0.9583 High Similarity NPC302245
0.9532 High Similarity NPC478093
0.9532 High Similarity NPC24260
0.9527 High Similarity NPC65312
0.9527 High Similarity NPC139783
0.9512 High Similarity NPC276890
0.9512 High Similarity NPC63646
0.9512 High Similarity NPC115284
0.9512 High Similarity NPC198498
0.9512 High Similarity NPC317145
0.9512 High Similarity NPC227060
0.9512 High Similarity NPC76682
0.9512 High Similarity NPC10908
0.9512 High Similarity NPC317439
0.9477 High Similarity NPC30182
0.9477 High Similarity NPC473589
0.9477 High Similarity NPC478091
0.9477 High Similarity NPC478092
0.9455 High Similarity NPC12424
0.9455 High Similarity NPC251580
0.9455 High Similarity NPC41376
0.9455 High Similarity NPC129518
0.9387 High Similarity NPC240841
0.9387 High Similarity NPC268503
0.9387 High Similarity NPC256012
0.9387 High Similarity NPC42549
0.9387 High Similarity NPC250846
0.9387 High Similarity NPC317272
0.936 High Similarity NPC41122
0.936 High Similarity NPC318805
0.9341 High Similarity NPC293093
0.9268 High Similarity NPC13916
0.9268 High Similarity NPC264850
0.9253 High Similarity NPC256124
0.9253 High Similarity NPC85381
0.9231 High Similarity NPC475479
0.9231 High Similarity NPC243454
0.9209 High Similarity NPC475654
0.9207 High Similarity NPC24465
0.9176 High Similarity NPC239584
0.9157 High Similarity NPC83198
0.9157 High Similarity NPC204908
0.9148 High Similarity NPC234318
0.9123 High Similarity NPC73492
0.9123 High Similarity NPC299990
0.907 High Similarity NPC302275
0.9048 High Similarity NPC475215
0.9048 High Similarity NPC108434
0.8994 High Similarity NPC232386
0.8994 High Similarity NPC152680
0.8994 High Similarity NPC190783
0.8957 High Similarity NPC25084
0.8957 High Similarity NPC247639
0.8953 High Similarity NPC195538
0.8908 High Similarity NPC249996
0.8902 High Similarity NPC476202
0.8864 High Similarity NPC281581
0.8857 High Similarity NPC14507
0.8857 High Similarity NPC47077
0.8846 High Similarity NPC254581
0.8824 High Similarity NPC239775
0.8814 High Similarity NPC473716
0.8814 High Similarity NPC475597
0.878 High Similarity NPC172765
0.878 High Similarity NPC278799
0.878 High Similarity NPC39701
0.878 High Similarity NPC2413
0.878 High Similarity NPC249797
0.878 High Similarity NPC193949
0.878 High Similarity NPC127674
0.878 High Similarity NPC204828
0.878 High Similarity NPC110416
0.878 High Similarity NPC54379
0.878 High Similarity NPC189266
0.878 High Similarity NPC184026
0.878 High Similarity NPC276588
0.878 High Similarity NPC295691
0.878 High Similarity NPC5238
0.878 High Similarity NPC207757
0.878 High Similarity NPC469817
0.8765 High Similarity NPC168753
0.8765 High Similarity NPC118274
0.869 High Similarity NPC475393
0.865 High Similarity NPC97221
0.865 High Similarity NPC151895
0.865 High Similarity NPC88249
0.865 High Similarity NPC220858
0.865 High Similarity NPC192768
0.8605 High Similarity NPC10871
0.8571 High Similarity NPC474507
0.8538 High Similarity NPC12053
0.8538 High Similarity NPC474931
0.8538 High Similarity NPC306555
0.8538 High Similarity NPC158376
0.8538 High Similarity NPC81218
0.8538 High Similarity NPC205421
0.8538 High Similarity NPC145832
0.8538 High Similarity NPC117188
0.8529 High Similarity NPC212794
0.8529 High Similarity NPC306843
0.8529 High Similarity NPC13504
0.8529 High Similarity NPC253043
0.8529 High Similarity NPC78222
0.8529 High Similarity NPC96603
0.8529 High Similarity NPC477563
0.8529 High Similarity NPC136508
0.8529 High Similarity NPC196447
0.8528 High Similarity NPC147390
0.8528 High Similarity NPC135538
0.8528 High Similarity NPC246587
0.8528 High Similarity NPC476571
0.8528 High Similarity NPC428
0.8528 High Similarity NPC24233
0.8521 High Similarity NPC60186
0.8476 Intermediate Similarity NPC103379
0.8476 Intermediate Similarity NPC477565
0.8471 Intermediate Similarity NPC324144
0.8466 Intermediate Similarity NPC321505
0.8466 Intermediate Similarity NPC179825
0.8466 Intermediate Similarity NPC191376
0.8462 Intermediate Similarity NPC205255
0.8462 Intermediate Similarity NPC271388
0.8462 Intermediate Similarity NPC235143
0.8462 Intermediate Similarity NPC119649
0.8462 Intermediate Similarity NPC230956
0.8457 Intermediate Similarity NPC173416
0.8457 Intermediate Similarity NPC148709
0.8457 Intermediate Similarity NPC476577
0.8446 Intermediate Similarity NPC82056
0.8439 Intermediate Similarity NPC109925
0.8421 Intermediate Similarity NPC276944
0.8421 Intermediate Similarity NPC232514
0.8421 Intermediate Similarity NPC4138
0.8421 Intermediate Similarity NPC121275
0.8421 Intermediate Similarity NPC284183
0.8421 Intermediate Similarity NPC238530
0.8418 Intermediate Similarity NPC230276
0.8418 Intermediate Similarity NPC257269
0.8412 Intermediate Similarity NPC80759
0.8412 Intermediate Similarity NPC79402
0.8402 Intermediate Similarity NPC221864
0.8363 Intermediate Similarity NPC1229
0.8362 Intermediate Similarity NPC32154
0.8362 Intermediate Similarity NPC40496
0.8362 Intermediate Similarity NPC119068
0.8354 Intermediate Similarity NPC476151
0.8354 Intermediate Similarity NPC106295
0.8354 Intermediate Similarity NPC51957
0.8354 Intermediate Similarity NPC16107
0.8354 Intermediate Similarity NPC210437
0.8354 Intermediate Similarity NPC476144
0.8353 Intermediate Similarity NPC166014
0.8353 Intermediate Similarity NPC27410
0.8344 Intermediate Similarity NPC185838
0.8342 Intermediate Similarity NPC38964
0.8303 Intermediate Similarity NPC7467
0.8294 Intermediate Similarity NPC111485

  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 NPC286119 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
0.9512 High Similarity NPD8251 Approved
0.9512 High Similarity NPD8252 Approved
0.9512 High Similarity NPD8099 Discontinued
0.9455 High Similarity NPD8156 Discontinued
0.8525 High Similarity NPD8095 Phase 1
0.8362 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD4584 Approved
0.8294 Intermediate Similarity NPD6788 Approved
0.8232 Intermediate Similarity NPD7906 Approved
0.8098 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD4773 Phase 2
0.8059 Intermediate Similarity NPD4772 Phase 2
0.8057 Intermediate Similarity NPD6071 Discontinued
0.8035 Intermediate Similarity NPD7831 Phase 2
0.8035 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD7833 Phase 2
0.8012 Intermediate Similarity NPD7298 Approved
0.8011 Intermediate Similarity NPD7310 Approved
0.8011 Intermediate Similarity NPD7312 Approved
0.8011 Intermediate Similarity NPD7313 Approved
0.8011 Intermediate Similarity NPD7311 Approved
0.7967 Intermediate Similarity NPD7309 Approved
0.7966 Intermediate Similarity NPD2489 Approved
0.7966 Intermediate Similarity NPD27 Approved
0.7955 Intermediate Similarity NPD3051 Approved
0.7941 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD7447 Phase 1
0.7917 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7912 Intermediate Similarity NPD4578 Approved
0.7912 Intermediate Similarity NPD4577 Approved
0.791 Intermediate Similarity NPD2969 Approved
0.791 Intermediate Similarity NPD2970 Approved
0.788 Intermediate Similarity NPD4663 Approved
0.7841 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD2560 Approved
0.7816 Intermediate Similarity NPD2563 Approved
0.7753 Intermediate Similarity NPD4010 Discontinued
0.7751 Intermediate Similarity NPD7213 Phase 3
0.7751 Intermediate Similarity NPD7212 Phase 2
0.7697 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD2898 Approved
0.7663 Intermediate Similarity NPD7549 Discontinued
0.7647 Intermediate Similarity NPD2421 Approved
0.7647 Intermediate Similarity NPD2420 Approved
0.7633 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD4055 Discovery
0.7616 Intermediate Similarity NPD6031 Approved
0.7616 Intermediate Similarity NPD6030 Approved
0.7602 Intermediate Similarity NPD1424 Approved
0.7588 Intermediate Similarity NPD7124 Phase 2
0.7586 Intermediate Similarity NPD4675 Approved
0.7586 Intermediate Similarity NPD4678 Approved
0.7542 Intermediate Similarity NPD5677 Discontinued
0.7529 Intermediate Similarity NPD5241 Discontinued
0.7529 Intermediate Similarity NPD4017 Approved
0.7514 Intermediate Similarity NPD3641 Approved
0.7514 Intermediate Similarity NPD3639 Approved
0.7514 Intermediate Similarity NPD3640 Phase 3
0.75 Intermediate Similarity NPD7802 Discontinued
0.7487 Intermediate Similarity NPD2494 Approved
0.7487 Intermediate Similarity NPD3450 Approved
0.7487 Intermediate Similarity NPD2493 Approved
0.7487 Intermediate Similarity NPD3452 Approved
0.7485 Intermediate Similarity NPD3845 Phase 1
0.7474 Intermediate Similarity NPD2490 Approved
0.7474 Intermediate Similarity NPD2488 Approved
0.7473 Intermediate Similarity NPD4481 Phase 3
0.7472 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4005 Discontinued
0.7403 Intermediate Similarity NPD6107 Approved
0.7394 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6997 Phase 2
0.7374 Intermediate Similarity NPD4582 Approved
0.7374 Intermediate Similarity NPD4583 Approved
0.7353 Intermediate Similarity NPD7047 Phase 3
0.7345 Intermediate Similarity NPD6072 Discontinued
0.7333 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5718 Phase 2
0.7323 Intermediate Similarity NPD4004 Approved
0.7323 Intermediate Similarity NPD4002 Approved
0.7321 Intermediate Similarity NPD2200 Suspended
0.7317 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD2122 Discontinued
0.731 Intermediate Similarity NPD5177 Phase 3
0.7299 Intermediate Similarity NPD4123 Phase 3
0.7289 Intermediate Similarity NPD4474 Approved
0.7289 Intermediate Similarity NPD4475 Approved
0.7283 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD2975 Approved
0.7282 Intermediate Similarity NPD2974 Approved
0.7282 Intermediate Similarity NPD2973 Approved
0.7273 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7466 Approved
0.7267 Intermediate Similarity NPD6748 Discontinued
0.7263 Intermediate Similarity NPD5772 Approved
0.7263 Intermediate Similarity NPD5773 Approved
0.7263 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1613 Approved
0.7246 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3124 Discontinued
0.7241 Intermediate Similarity NPD7598 Phase 2
0.7235 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4908 Phase 1
0.7211 Intermediate Similarity NPD6853 Approved
0.7211 Intermediate Similarity NPD6851 Approved
0.7207 Intermediate Similarity NPD8153 Approved
0.7207 Intermediate Similarity NPD8152 Approved
0.7196 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5005 Approved
0.7186 Intermediate Similarity NPD5006 Approved
0.7181 Intermediate Similarity NPD6297 Approved
0.7172 Intermediate Similarity NPD4580 Approved
0.7166 Intermediate Similarity NPD5313 Approved
0.7166 Intermediate Similarity NPD42 Phase 2
0.7166 Intermediate Similarity NPD6042 Phase 2
0.7166 Intermediate Similarity NPD5312 Approved
0.7159 Intermediate Similarity NPD6090 Discontinued
0.7158 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD2971 Approved
0.7158 Intermediate Similarity NPD2968 Approved
0.7151 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD3692 Discontinued
0.7126 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD7827 Phase 1
0.7121 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD6896 Approved
0.7118 Intermediate Similarity NPD6111 Discontinued
0.7118 Intermediate Similarity NPD6895 Approved
0.7111 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD3060 Approved
0.7102 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6666 Approved
0.7086 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6667 Approved
0.7083 Intermediate Similarity NPD2674 Phase 3
0.7081 Intermediate Similarity NPD4166 Phase 2
0.7072 Intermediate Similarity NPD2977 Approved
0.7072 Intermediate Similarity NPD2978 Approved
0.7072 Intermediate Similarity NPD4585 Approved
0.7071 Intermediate Similarity NPD4420 Approved
0.7066 Intermediate Similarity NPD3027 Phase 3
0.7066 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5090 Approved
0.7056 Intermediate Similarity NPD5089 Approved
0.7052 Intermediate Similarity NPD7037 Approved
0.7049 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4040 Phase 1
0.7029 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4237 Approved
0.7011 Intermediate Similarity NPD4236 Phase 3
0.7011 Intermediate Similarity NPD4162 Approved
0.701 Intermediate Similarity NPD7291 Discontinued
0.6984 Remote Similarity NPD4873 Discontinued
0.6977 Remote Similarity NPD1753 Discontinued
0.6974 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6973 Remote Similarity NPD4666 Phase 3
0.6971 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5938 Phase 3
0.6966 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6952 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6947 Remote Similarity NPD7479 Phase 2
0.6941 Remote Similarity NPD2238 Phase 2
0.6934 Remote Similarity NPD7907 Approved
0.6932 Remote Similarity NPD5160 Discontinued
0.6932 Remote Similarity NPD2677 Approved
0.6931 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5976 Discontinued
0.6927 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3145 Approved
0.6923 Remote Similarity NPD6842 Approved
0.6923 Remote Similarity NPD3144 Approved
0.6923 Remote Similarity NPD6841 Approved
0.6923 Remote Similarity NPD6843 Phase 3
0.6923 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6919 Remote Similarity NPD5709 Phase 3
0.6915 Remote Similarity NPD6166 Phase 2
0.6915 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6911 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6886 Remote Similarity NPD6584 Phase 3
0.6882 Remote Similarity NPD7477 Discontinued
0.6872 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6868 Remote Similarity NPD7110 Phase 1
0.6868 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6866 Remote Similarity NPD3837 Clinical (unspecified phase)

  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