Structure

Physi-Chem Properties

Molecular Weight:  670.33
Volume:  692.439
LogP:  4.902
LogD:  3.59
LogS:  -4.111
# Rotatable Bonds:  11
TPSA:  102.32
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.185
Synthetic Accessibility Score:  3.921
Fsp3:  0.385
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:  -5.564
MDCK Permeability:  3.147134339087643e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.846
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.168
30% Bioavailability (F30%):  0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.055
Plasma Protein Binding (PPB):  58.55740737915039%
Volume Distribution (VD):  1.194
Pgp-substrate:  41.49444580078125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.976
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.972
CYP2C9-inhibitor:  0.028
CYP2C9-substrate:  0.704
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.957
CYP3A4-inhibitor:  0.114
CYP3A4-substrate:  0.961

ADMET: Excretion

Clearance (CL):  13.124
Half-life (T1/2):  0.597

ADMET: Toxicity

hERG Blockers:  0.966
Human Hepatotoxicity (H-HT):  0.064
Drug-inuced Liver Injury (DILI):  0.662
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.403
Maximum Recommended Daily Dose:  0.986
Skin Sensitization:  0.922
Carcinogencity:  0.019
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.479

Download Data

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

  Natural Product: NPC30779

Natural Product ID:  NPC30779
Common Name*:   Thalirugidine
IUPAC Name:   (1S)-1-[[4-[5-[[(1S)-5-hydroxy-6,7-dimethoxy-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:   Thalirugidine
Standard InCHIKey:  DITCAWDOTGUOAZ-CONSDPRKSA-N
Standard InCHI:  InChI=1S/C39H46N2O8/c1-40-16-14-26-28(21-34(45-4)38(47-6)36(26)42)30(40)18-23-8-11-25(12-9-23)49-33-20-24(10-13-32(33)44-3)19-31-29-22-35(46-5)39(48-7)37(43)27(29)15-17-41(31)2/h8-13,20-22,30-31,42-43H,14-19H2,1-7H3/t30-,31-/m0/s1
SMILES:  COc1ccc(cc1Oc1ccc(cc1)C[C@@H]1N(C)CCc2c1cc(OC)c(c2O)OC)C[C@@H]1N(C)CCc2c1cc(OC)c(c2O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504612
PubChem CID:   44584027
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[504557]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis Activity = 1000.0 ug ml-1 PMID[504557]

☑ 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 NPC30779 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 NPC286119
0.9879 High Similarity NPC90998
0.9879 High Similarity NPC290582
0.9879 High Similarity NPC328155
0.9879 High Similarity NPC251735
0.9879 High Similarity NPC7715
0.9879 High Similarity NPC49075
0.9879 High Similarity NPC42663
0.9879 High Similarity NPC239824
0.9879 High Similarity NPC229373
0.9879 High Similarity NPC54654
0.9879 High Similarity NPC104196
0.9879 High Similarity NPC182052
0.9879 High Similarity NPC222661
0.9879 High Similarity NPC290005
0.9879 High Similarity NPC311973
0.9879 High Similarity NPC223690
0.9879 High Similarity NPC217748
0.9879 High Similarity NPC8836
0.9879 High Similarity NPC258657
0.9879 High Similarity NPC181796
0.9879 High Similarity NPC285931
0.9879 High Similarity NPC279228
0.9879 High Similarity NPC185639
0.9879 High Similarity NPC271013
0.9879 High Similarity NPC15414
0.9819 High Similarity NPC254441
0.9819 High Similarity NPC167116
0.9819 High Similarity NPC274716
0.9702 High Similarity NPC212237
0.9702 High Similarity NPC116465
0.9645 High Similarity NPC22115
0.9645 High Similarity NPC275680
0.9588 High Similarity NPC274661
0.9588 High Similarity NPC82457
0.9588 High Similarity NPC206900
0.9588 High Similarity NPC11296
0.9588 High Similarity NPC175890
0.9588 High Similarity NPC48490
0.9535 High Similarity NPC30182
0.9535 High Similarity NPC478091
0.9535 High Similarity NPC473589
0.9535 High Similarity NPC478092
0.9532 High Similarity NPC60295
0.9532 High Similarity NPC191132
0.9527 High Similarity NPC16357
0.9527 High Similarity NPC95426
0.9527 High Similarity NPC302245
0.9477 High Similarity NPC24260
0.9477 High Similarity NPC478093
0.9471 High Similarity NPC139783
0.9471 High Similarity NPC65312
0.9455 High Similarity NPC276890
0.9455 High Similarity NPC317439
0.9455 High Similarity NPC115284
0.9455 High Similarity NPC198498
0.9455 High Similarity NPC317145
0.9455 High Similarity NPC227060
0.9455 High Similarity NPC63646
0.9455 High Similarity NPC76682
0.9455 High Similarity NPC10908
0.9398 High Similarity NPC129518
0.9398 High Similarity NPC41376
0.9398 High Similarity NPC251580
0.9398 High Similarity NPC12424
0.9329 High Similarity NPC317272
0.9329 High Similarity NPC240841
0.9329 High Similarity NPC256012
0.9329 High Similarity NPC268503
0.9329 High Similarity NPC42549
0.9329 High Similarity NPC250846
0.9306 High Similarity NPC318805
0.9306 High Similarity NPC41122
0.9286 High Similarity NPC293093
0.9212 High Similarity NPC13916
0.9212 High Similarity NPC264850
0.92 High Similarity NPC256124
0.92 High Similarity NPC85381
0.9176 High Similarity NPC243454
0.9176 High Similarity NPC475479
0.9157 High Similarity NPC475654
0.9152 High Similarity NPC24465
0.9128 High Similarity NPC302275
0.9123 High Similarity NPC239584
0.9102 High Similarity NPC204908
0.9102 High Similarity NPC83198
0.9096 High Similarity NPC234318
0.907 High Similarity NPC73492
0.907 High Similarity NPC299990
0.8994 High Similarity NPC475215
0.8994 High Similarity NPC108434
0.8941 High Similarity NPC232386
0.8941 High Similarity NPC152680
0.8941 High Similarity NPC190783
0.8914 High Similarity NPC14507
0.8914 High Similarity NPC47077
0.8902 High Similarity NPC247639
0.8902 High Similarity NPC195538
0.8902 High Similarity NPC25084
0.8857 High Similarity NPC249996
0.8851 High Similarity NPC476202
0.8814 High Similarity NPC281581
0.8798 High Similarity NPC254581
0.8772 High Similarity NPC239775
0.8764 High Similarity NPC475597
0.8764 High Similarity NPC473716
0.8727 High Similarity NPC110416
0.8727 High Similarity NPC276588
0.8727 High Similarity NPC295691
0.8727 High Similarity NPC2413
0.8727 High Similarity NPC204828
0.8727 High Similarity NPC127674
0.8727 High Similarity NPC469817
0.8727 High Similarity NPC189266
0.8727 High Similarity NPC207757
0.8727 High Similarity NPC278799
0.8727 High Similarity NPC249797
0.8727 High Similarity NPC39701
0.8727 High Similarity NPC54379
0.8727 High Similarity NPC193949
0.8727 High Similarity NPC184026
0.8727 High Similarity NPC172765
0.8727 High Similarity NPC5238
0.8713 High Similarity NPC118274
0.8713 High Similarity NPC168753
0.8639 High Similarity NPC475393
0.8598 High Similarity NPC151895
0.8598 High Similarity NPC97221
0.8598 High Similarity NPC88249
0.8598 High Similarity NPC220858
0.8598 High Similarity NPC192768
0.8555 High Similarity NPC10871
0.8523 High Similarity NPC474507
0.8497 Intermediate Similarity NPC82056
0.8488 Intermediate Similarity NPC81218
0.8488 Intermediate Similarity NPC205421
0.8488 Intermediate Similarity NPC117188
0.8488 Intermediate Similarity NPC145832
0.8488 Intermediate Similarity NPC474931
0.8488 Intermediate Similarity NPC306555
0.8488 Intermediate Similarity NPC158376
0.8488 Intermediate Similarity NPC12053
0.848 Intermediate Similarity NPC306843
0.848 Intermediate Similarity NPC253043
0.848 Intermediate Similarity NPC78222
0.848 Intermediate Similarity NPC212794
0.848 Intermediate Similarity NPC96603
0.848 Intermediate Similarity NPC196447
0.848 Intermediate Similarity NPC136508
0.848 Intermediate Similarity NPC13504
0.848 Intermediate Similarity NPC477563
0.8476 Intermediate Similarity NPC428
0.8476 Intermediate Similarity NPC476571
0.8476 Intermediate Similarity NPC147390
0.8476 Intermediate Similarity NPC24233
0.8476 Intermediate Similarity NPC246587
0.8476 Intermediate Similarity NPC135538
0.8475 Intermediate Similarity NPC257269
0.8475 Intermediate Similarity NPC230276
0.8471 Intermediate Similarity NPC60186
0.8424 Intermediate Similarity NPC477565
0.8424 Intermediate Similarity NPC103379
0.8421 Intermediate Similarity NPC324144
0.8418 Intermediate Similarity NPC40496
0.8418 Intermediate Similarity NPC119068
0.8415 Intermediate Similarity NPC321505
0.8415 Intermediate Similarity NPC179825
0.8415 Intermediate Similarity NPC191376
0.8412 Intermediate Similarity NPC271388
0.8412 Intermediate Similarity NPC119649
0.8412 Intermediate Similarity NPC230956
0.8412 Intermediate Similarity NPC205255
0.8412 Intermediate Similarity NPC235143
0.8409 Intermediate Similarity NPC148709
0.8409 Intermediate Similarity NPC476577
0.8409 Intermediate Similarity NPC173416
0.8391 Intermediate Similarity NPC109925
0.8372 Intermediate Similarity NPC284183
0.8372 Intermediate Similarity NPC232514
0.8372 Intermediate Similarity NPC276944
0.8372 Intermediate Similarity NPC4138
0.8372 Intermediate Similarity NPC121275
0.8372 Intermediate Similarity NPC238530
0.8363 Intermediate Similarity NPC80759
0.8363 Intermediate Similarity NPC79402
0.8353 Intermediate Similarity NPC221864
0.8315 Intermediate Similarity NPC32154
0.8314 Intermediate Similarity NPC1229
0.8304 Intermediate Similarity NPC27410
0.8304 Intermediate Similarity NPC166014
0.8303 Intermediate Similarity NPC476144
0.8303 Intermediate Similarity NPC476151
0.8303 Intermediate Similarity NPC51957
0.8303 Intermediate Similarity NPC106295
0.8303 Intermediate Similarity NPC16107
0.8303 Intermediate Similarity NPC210437
0.8299 Intermediate Similarity NPC38964
0.8293 Intermediate Similarity NPC185838
0.8253 Intermediate Similarity NPC7467
0.8246 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 NPC30779 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
0.9879 High Similarity NPD8054 Approved
0.9879 High Similarity NPD8053 Approved
0.9455 High Similarity NPD8252 Approved
0.9455 High Similarity NPD8099 Discontinued
0.9455 High Similarity NPD8251 Approved
0.9398 High Similarity NPD8156 Discontinued
0.8478 Intermediate Similarity NPD8095 Phase 1
0.8418 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD4584 Approved
0.8287 Intermediate Similarity NPD7906 Approved
0.8246 Intermediate Similarity NPD6788 Approved
0.8049 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8021 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD4772 Phase 2
0.8012 Intermediate Similarity NPD4773 Phase 2
0.8011 Intermediate Similarity NPD6071 Discontinued
0.7989 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7833 Phase 2
0.7989 Intermediate Similarity NPD7831 Phase 2
0.7967 Intermediate Similarity NPD7310 Approved
0.7967 Intermediate Similarity NPD7313 Approved
0.7967 Intermediate Similarity NPD7311 Approved
0.7967 Intermediate Similarity NPD7312 Approved
0.7965 Intermediate Similarity NPD7298 Approved
0.7923 Intermediate Similarity NPD7309 Approved
0.7921 Intermediate Similarity NPD27 Approved
0.7921 Intermediate Similarity NPD2489 Approved
0.791 Intermediate Similarity NPD3051 Approved
0.7895 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7447 Phase 1
0.787 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7869 Intermediate Similarity NPD4577 Approved
0.7869 Intermediate Similarity NPD4578 Approved
0.7865 Intermediate Similarity NPD2969 Approved
0.7865 Intermediate Similarity NPD2970 Approved
0.7838 Intermediate Similarity NPD4663 Approved
0.7797 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD2560 Approved
0.7771 Intermediate Similarity NPD2563 Approved
0.7709 Intermediate Similarity NPD4010 Discontinued
0.7706 Intermediate Similarity NPD7212 Phase 2
0.7706 Intermediate Similarity NPD7213 Phase 3
0.7684 Intermediate Similarity NPD4055 Discovery
0.7651 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD2898 Approved
0.7622 Intermediate Similarity NPD7549 Discontinued
0.7602 Intermediate Similarity NPD2420 Approved
0.7602 Intermediate Similarity NPD2421 Approved
0.7588 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD6030 Approved
0.7572 Intermediate Similarity NPD6031 Approved
0.7558 Intermediate Similarity NPD1424 Approved
0.7544 Intermediate Similarity NPD7124 Phase 2
0.7543 Intermediate Similarity NPD4678 Approved
0.7543 Intermediate Similarity NPD4675 Approved
0.75 Intermediate Similarity NPD5677 Discontinued
0.7486 Intermediate Similarity NPD4017 Approved
0.7485 Intermediate Similarity NPD5241 Discontinued
0.7471 Intermediate Similarity NPD3639 Approved
0.7471 Intermediate Similarity NPD3640 Phase 3
0.7471 Intermediate Similarity NPD3641 Approved
0.7459 Intermediate Similarity NPD7802 Discontinued
0.7449 Intermediate Similarity NPD3452 Approved
0.7449 Intermediate Similarity NPD3450 Approved
0.7449 Intermediate Similarity NPD2493 Approved
0.7449 Intermediate Similarity NPD2494 Approved
0.7442 Intermediate Similarity NPD3845 Phase 1
0.7435 Intermediate Similarity NPD2488 Approved
0.7435 Intermediate Similarity NPD2490 Approved
0.7432 Intermediate Similarity NPD4481 Phase 3
0.743 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4005 Discontinued
0.7363 Intermediate Similarity NPD6107 Approved
0.7356 Intermediate Similarity NPD6997 Phase 2
0.7354 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD4582 Approved
0.7337 Intermediate Similarity NPD4583 Approved
0.7317 Intermediate Similarity NPD7047 Phase 3
0.731 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6072 Discontinued
0.7289 Intermediate Similarity NPD5718 Phase 2
0.7286 Intermediate Similarity NPD4004 Approved
0.7286 Intermediate Similarity NPD4002 Approved
0.7278 Intermediate Similarity NPD2200 Suspended
0.7273 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2122 Discontinued
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5177 Phase 3
0.7257 Intermediate Similarity NPD4123 Phase 3
0.7252 Intermediate Similarity NPD8152 Approved
0.7252 Intermediate Similarity NPD8153 Approved
0.7246 Intermediate Similarity NPD4474 Approved
0.7246 Intermediate Similarity NPD4475 Approved
0.7245 Intermediate Similarity NPD2975 Approved
0.7245 Intermediate Similarity NPD2973 Approved
0.7245 Intermediate Similarity NPD2974 Approved
0.7241 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6748 Discontinued
0.7225 Intermediate Similarity NPD7466 Approved
0.7222 Intermediate Similarity NPD5773 Approved
0.7222 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5772 Approved
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD1613 Approved
0.72 Intermediate Similarity NPD3124 Discontinued
0.72 Intermediate Similarity NPD7598 Phase 2
0.7193 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD6851 Approved
0.7173 Intermediate Similarity NPD6853 Approved
0.7172 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7827 Phase 1
0.7169 Intermediate Similarity NPD4908 Phase 1
0.7158 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD5005 Approved
0.715 Intermediate Similarity NPD5006 Approved
0.7143 Intermediate Similarity NPD6297 Approved
0.7136 Intermediate Similarity NPD4580 Approved
0.7128 Intermediate Similarity NPD42 Phase 2
0.7128 Intermediate Similarity NPD6042 Phase 2
0.7128 Intermediate Similarity NPD5312 Approved
0.7128 Intermediate Similarity NPD5313 Approved
0.712 Intermediate Similarity NPD2971 Approved
0.712 Intermediate Similarity NPD2968 Approved
0.712 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6090 Discontinued
0.7112 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3692 Discontinued
0.7083 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6111 Discontinued
0.7076 Intermediate Similarity NPD6895 Approved
0.7076 Intermediate Similarity NPD6896 Approved
0.7072 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD3060 Approved
0.7062 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6666 Approved
0.7045 Intermediate Similarity NPD6667 Approved
0.7045 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD4166 Phase 2
0.7041 Intermediate Similarity NPD2674 Phase 3
0.7035 Intermediate Similarity NPD4420 Approved
0.7033 Intermediate Similarity NPD2978 Approved
0.7033 Intermediate Similarity NPD4585 Approved
0.7033 Intermediate Similarity NPD2977 Approved
0.7024 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD3027 Phase 3
0.7017 Intermediate Similarity NPD5089 Approved
0.7017 Intermediate Similarity NPD5090 Approved
0.7011 Intermediate Similarity NPD7037 Approved
0.7011 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.6995 Remote Similarity NPD4040 Phase 1
0.6989 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6984 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7907 Approved
0.6974 Remote Similarity NPD7291 Discontinued
0.6974 Remote Similarity NPD6841 Approved
0.6974 Remote Similarity NPD6843 Phase 3
0.6974 Remote Similarity NPD6842 Approved
0.6971 Remote Similarity NPD4236 Phase 3
0.6971 Remote Similarity NPD4162 Approved
0.6971 Remote Similarity NPD4237 Approved
0.6968 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6166 Phase 2
0.6947 Remote Similarity NPD4873 Discontinued
0.6939 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6936 Remote Similarity NPD1753 Discontinued
0.6935 Remote Similarity NPD4666 Phase 3
0.6932 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5938 Phase 3
0.6927 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6915 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6911 Remote Similarity NPD7479 Phase 2
0.6901 Remote Similarity NPD2238 Phase 2
0.6895 Remote Similarity NPD6723 Discontinued
0.6893 Remote Similarity NPD5160 Discontinued
0.6893 Remote Similarity NPD2677 Approved
0.6891 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5976 Discontinued
0.6882 Remote Similarity NPD5709 Phase 3
0.6882 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6882 Remote Similarity NPD3145 Approved
0.6882 Remote Similarity NPD3144 Approved
0.6879 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6584 Phase 3
0.6842 Remote Similarity NPD7477 Discontinued
0.6834 Remote Similarity NPD7125 Discontinued
0.6833 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6832 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6831 Remote Similarity NPD7109 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