Structure

Physi-Chem Properties

Molecular Weight:  385.15
Volume:  388.749
LogP:  0.975
LogD:  1.453
LogS:  -3.593
# Rotatable Bonds:  5
TPSA:  94.09
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.84
Synthetic Accessibility Score:  3.046
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.77
MDCK Permeability:  1.0385901987319812e-05
Pgp-inhibitor:  0.04
Pgp-substrate:  0.928
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.571
Plasma Protein Binding (PPB):  64.40018463134766%
Volume Distribution (VD):  0.719
Pgp-substrate:  17.562206268310547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.13
CYP1A2-substrate:  0.94
CYP2C19-inhibitor:  0.112
CYP2C19-substrate:  0.627
CYP2C9-inhibitor:  0.057
CYP2C9-substrate:  0.623
CYP2D6-inhibitor:  0.09
CYP2D6-substrate:  0.332
CYP3A4-inhibitor:  0.361
CYP3A4-substrate:  0.844

ADMET: Excretion

Clearance (CL):  1.814
Half-life (T1/2):  0.409

ADMET: Toxicity

hERG Blockers:  0.042
Human Hepatotoxicity (H-HT):  0.596
Drug-inuced Liver Injury (DILI):  0.2
AMES Toxicity:  0.257
Rat Oral Acute Toxicity:  0.048
Maximum Recommended Daily Dose:  0.701
Skin Sensitization:  0.085
Carcinogencity:  0.041
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.043

Download Data

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

  Natural Product: NPC66678

Natural Product ID:  NPC66678
Common Name*:   3-Desmethylcolchicin
IUPAC Name:   N-[(7S)-3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Synonyms:   3-Desmethylcolchicin
Standard InCHIKey:  JRRUSQGIRBEMRN-HNNXBMFYSA-N
Standard InCHI:  InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-17(25)20(27-3)21(28-4)19(12)13-6-8-18(26-2)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
SMILES:  COc1ccc2c(cc1=O)[C@H](CCc1c2c(OC)c(c(c1)O)OC)N=C(O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1081
PubChem CID:   299664
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004150] Hydrocarbon derivatives
      • [CHEMONTID:0001650] Tropones

*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
NPO24146 Colchicum brachyphyllum Species Colchicaceae Eukaryota n.a. Jordanian n.a. PMID[15730238]
NPO22241 Alangium villosum Species Cornaceae Eukaryota stem bark Ceram, Indonesia 1998 PMID[18327911]
NPO22241 Alangium villosum Species Cornaceae Eukaryota n.a. n.a. n.a. PMID[32372642]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. PMID[32372642]
NPO11746 Delphinium consolida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11746 Delphinium consolida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22316 Mycena pura Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19531 Chamaecytisus prolifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4250 Gloriosa superba Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5913 Cneorum tricoccon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16993 Pinus roxburghii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13973 Centaurea behen Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11746 Delphinium consolida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24146 Colchicum brachyphyllum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17754 Coscoroba coscoroba Species Anatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22241 Alangium villosum Species Cornaceae 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
NPT3597 Individual Protein Tubulin beta chain Bos taurus Tubulin binding = 68.0 % PMID[494355]
NPT168 Cell Line P388 Mus musculus Potency = 3.6 uM kg-1 PMID[494356]
NPT3597 Individual Protein Tubulin beta chain Bos taurus IC50 = 2900.0 nM PMID[494357]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 180.0 nM PMID[494358]
NPT397 Cell Line NCI-H460 Homo sapiens EC50 = 510.0 nM PMID[494358]
NPT395 Cell Line SF-268 Homo sapiens EC50 = 280.0 nM PMID[494358]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 239.33 nM PMID[494359]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 137.09 nM PMID[494359]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 5834.45 nM PMID[494359]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 47.21 nM PMID[494359]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 34.59 nM PMID[494359]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 140.93 nM PMID[494359]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 32.51 nM PMID[494359]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 85.51 nM PMID[494359]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 219.79 nM PMID[494359]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 90.36 nM PMID[494359]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 6966.27 nM PMID[494359]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 311888.96 nM PMID[494359]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 118.3 nM PMID[494359]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 33.27 nM PMID[494359]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 191.43 nM PMID[494359]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 59.57 nM PMID[494359]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 81.1 nM PMID[494359]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 43.85 nM PMID[494359]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 69.82 nM PMID[494359]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 41.5 nM PMID[494359]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 32.51 nM PMID[494359]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 157.4 nM PMID[494359]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 379.31 nM PMID[494359]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 31.19 nM PMID[494359]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 89.74 nM PMID[494359]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 43.75 nM PMID[494359]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 835.6 nM PMID[494359]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 63.97 nM PMID[494359]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 119.4 nM PMID[494359]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 4852.89 nM PMID[494359]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 355.63 nM PMID[494359]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 61.8 nM PMID[494359]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 87.3 nM PMID[494359]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 60.12 nM PMID[494359]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 32.51 nM PMID[494359]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 177.01 nM PMID[494359]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 92.04 nM PMID[494359]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 77.62 nM PMID[494359]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 9527.96 nM PMID[494359]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 95.72 nM PMID[494359]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 162.93 nM PMID[494359]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 82.41 nM PMID[494359]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 4456.56 nM PMID[494359]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 32.51 nM PMID[494359]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 123.59 nM PMID[494359]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 89.54 nM PMID[494359]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 32.51 nM PMID[494359]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 106.66 nM PMID[494359]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 84.33 nM PMID[494359]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 84.14 nM PMID[494359]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 31.19 nM PMID[494359]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 19230.92 nM PMID[494359]
NPT518 Protein Complex Tubulin Homo sapiens Tubulin binding = 68.0 % PMID[494356]
NPT32 Organism Mus musculus Mus musculus Toxicity = 26.0 uM kg-1 PMID[494356]
NPT32 Organism Mus musculus Mus musculus Toxicity = 31.7 uM kg-1 PMID[494356]
NPT32 Organism Mus musculus Mus musculus Toxicity = 26.0 mg kg-1 PMID[494357]
NPT140 Organism Artemia Artemia LC50 = 74.6 ug.mL-1 PMID[494358]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC > 500.0 ug.mL-1 PMID[494358]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC > 500.0 ug.mL-1 PMID[494358]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC > 500.0 ug.mL-1 PMID[494358]
NPT21 Organism Aspergillus niger Aspergillus niger MIC > 500.0 ug.mL-1 PMID[494358]

☑ 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 NPC66678 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 NPC202839
0.9664 High Similarity NPC226941
0.9664 High Similarity NPC14005
0.9664 High Similarity NPC108957
0.9404 High Similarity NPC44642
0.9236 High Similarity NPC53146
0.9236 High Similarity NPC286790
0.9236 High Similarity NPC188120
0.9231 High Similarity NPC189782
0.902 High Similarity NPC218575
0.8875 High Similarity NPC3906
0.879 High Similarity NPC190931
0.8679 High Similarity NPC329837
0.8013 Intermediate Similarity NPC144284
0.8 Intermediate Similarity NPC296898
0.7917 Intermediate Similarity NPC3375
0.7917 Intermediate Similarity NPC255607
0.7895 Intermediate Similarity NPC231371
0.7857 Intermediate Similarity NPC32778
0.7853 Intermediate Similarity NPC127402
0.7844 Intermediate Similarity NPC226428
0.7811 Intermediate Similarity NPC24465
0.7778 Intermediate Similarity NPC204908
0.7778 Intermediate Similarity NPC126836
0.7778 Intermediate Similarity NPC83198
0.7765 Intermediate Similarity NPC13916
0.7765 Intermediate Similarity NPC264850
0.7758 Intermediate Similarity NPC475557
0.7711 Intermediate Similarity NPC107602
0.7697 Intermediate Similarity NPC153990
0.7674 Intermediate Similarity NPC182257
0.7667 Intermediate Similarity NPC238810
0.7661 Intermediate Similarity NPC68328
0.7654 Intermediate Similarity NPC476841
0.7654 Intermediate Similarity NPC476843
0.7644 Intermediate Similarity NPC232386
0.7644 Intermediate Similarity NPC152680
0.7644 Intermediate Similarity NPC190783
0.7628 Intermediate Similarity NPC218530
0.7613 Intermediate Similarity NPC93882
0.7613 Intermediate Similarity NPC214869
0.7613 Intermediate Similarity NPC130595
0.7593 Intermediate Similarity NPC16353
0.759 Intermediate Similarity NPC275027
0.7586 Intermediate Similarity NPC239775
0.7582 Intermediate Similarity NPC169474
0.7582 Intermediate Similarity NPC282000
0.7582 Intermediate Similarity NPC293054
0.7582 Intermediate Similarity NPC82679
0.7582 Intermediate Similarity NPC124452
0.7582 Intermediate Similarity NPC159968
0.7582 Intermediate Similarity NPC246620
0.7582 Intermediate Similarity NPC236791
0.7582 Intermediate Similarity NPC74817
0.7582 Intermediate Similarity NPC324112
0.758 Intermediate Similarity NPC289258
0.758 Intermediate Similarity NPC125649
0.758 Intermediate Similarity NPC188378
0.758 Intermediate Similarity NPC555
0.758 Intermediate Similarity NPC56764
0.758 Intermediate Similarity NPC276026
0.758 Intermediate Similarity NPC469659
0.758 Intermediate Similarity NPC7515
0.758 Intermediate Similarity NPC206737
0.758 Intermediate Similarity NPC209199
0.7564 Intermediate Similarity NPC6854
0.7564 Intermediate Similarity NPC313737
0.7564 Intermediate Similarity NPC285078
0.7561 Intermediate Similarity NPC178129
0.7548 Intermediate Similarity NPC114102
0.7547 Intermediate Similarity NPC299583
0.7546 Intermediate Similarity NPC474982
0.7532 Intermediate Similarity NPC69029
0.7532 Intermediate Similarity NPC158142
0.7532 Intermediate Similarity NPC294884
0.7532 Intermediate Similarity NPC154866
0.7532 Intermediate Similarity NPC28765
0.7532 Intermediate Similarity NPC200557
0.7532 Intermediate Similarity NPC240279
0.7532 Intermediate Similarity NPC55239
0.7532 Intermediate Similarity NPC313081
0.7532 Intermediate Similarity NPC10314
0.7532 Intermediate Similarity NPC214853
0.7532 Intermediate Similarity NPC108198
0.7532 Intermediate Similarity NPC180602
0.7516 Intermediate Similarity NPC76451
0.7516 Intermediate Similarity NPC18924
0.7516 Intermediate Similarity NPC28730
0.7516 Intermediate Similarity NPC44748
0.7516 Intermediate Similarity NPC223136
0.7516 Intermediate Similarity NPC78974
0.7516 Intermediate Similarity NPC214406
0.7516 Intermediate Similarity NPC103823
0.7515 Intermediate Similarity NPC77598
0.7515 Intermediate Similarity NPC195766
0.7515 Intermediate Similarity NPC206736
0.75 Intermediate Similarity NPC15543
0.75 Intermediate Similarity NPC469907
0.7485 Intermediate Similarity NPC5462
0.7485 Intermediate Similarity NPC477410
0.7484 Intermediate Similarity NPC14600
0.7484 Intermediate Similarity NPC52029
0.7484 Intermediate Similarity NPC41473
0.7484 Intermediate Similarity NPC143139
0.7484 Intermediate Similarity NPC312770
0.7484 Intermediate Similarity NPC204848
0.7484 Intermediate Similarity NPC160607
0.7484 Intermediate Similarity NPC35961
0.7484 Intermediate Similarity NPC195749
0.7484 Intermediate Similarity NPC133025
0.7484 Intermediate Similarity NPC202846
0.747 Intermediate Similarity NPC474347
0.747 Intermediate Similarity NPC474393
0.7468 Intermediate Similarity NPC266555
0.7468 Intermediate Similarity NPC127587
0.7468 Intermediate Similarity NPC252131
0.7468 Intermediate Similarity NPC291847
0.7452 Intermediate Similarity NPC14224
0.7452 Intermediate Similarity NPC161958
0.7452 Intermediate Similarity NPC6451
0.7451 Intermediate Similarity NPC251855
0.7451 Intermediate Similarity NPC234400
0.7451 Intermediate Similarity NPC472093
0.7451 Intermediate Similarity NPC298757
0.7451 Intermediate Similarity NPC57490
0.7451 Intermediate Similarity NPC17943
0.7451 Intermediate Similarity NPC299584
0.7451 Intermediate Similarity NPC265483
0.7451 Intermediate Similarity NPC117214
0.7451 Intermediate Similarity NPC475169
0.7451 Intermediate Similarity NPC203133
0.7451 Intermediate Similarity NPC221077
0.7451 Intermediate Similarity NPC300326
0.7451 Intermediate Similarity NPC105925
0.7451 Intermediate Similarity NPC116907
0.7451 Intermediate Similarity NPC58279
0.7451 Intermediate Similarity NPC271985
0.7451 Intermediate Similarity NPC60885
0.7451 Intermediate Similarity NPC82483
0.7451 Intermediate Similarity NPC233410
0.7451 Intermediate Similarity NPC208950
0.7451 Intermediate Similarity NPC193544
0.7443 Intermediate Similarity NPC289743
0.7443 Intermediate Similarity NPC110374
0.744 Intermediate Similarity NPC272566
0.7439 Intermediate Similarity NPC207732
0.7438 Intermediate Similarity NPC156948
0.7438 Intermediate Similarity NPC46277
0.7438 Intermediate Similarity NPC3072
0.7438 Intermediate Similarity NPC22902
0.7438 Intermediate Similarity NPC105493
0.7438 Intermediate Similarity NPC301765
0.7438 Intermediate Similarity NPC56329
0.7438 Intermediate Similarity NPC86605
0.7438 Intermediate Similarity NPC242715
0.7436 Intermediate Similarity NPC299221
0.7436 Intermediate Similarity NPC311680
0.7436 Intermediate Similarity NPC234488
0.7436 Intermediate Similarity NPC308885
0.7436 Intermediate Similarity NPC255550
0.7436 Intermediate Similarity NPC51840
0.7432 Intermediate Similarity NPC318805
0.7432 Intermediate Similarity NPC41122
0.7429 Intermediate Similarity NPC118274
0.7429 Intermediate Similarity NPC168753
0.7425 Intermediate Similarity NPC241636
0.7425 Intermediate Similarity NPC177830
0.7425 Intermediate Similarity NPC470916
0.7425 Intermediate Similarity NPC85747
0.7425 Intermediate Similarity NPC8337
0.7423 Intermediate Similarity NPC6568
0.7421 Intermediate Similarity NPC241241
0.7419 Intermediate Similarity NPC109275
0.7419 Intermediate Similarity NPC155838
0.7417 Intermediate Similarity NPC49341
0.7412 Intermediate Similarity NPC234485
0.7407 Intermediate Similarity NPC19158
0.7403 Intermediate Similarity NPC112596
0.7403 Intermediate Similarity NPC223953
0.7394 Intermediate Similarity NPC474799
0.7394 Intermediate Similarity NPC157133
0.7391 Intermediate Similarity NPC243996
0.7391 Intermediate Similarity NPC114171
0.7391 Intermediate Similarity NPC132804
0.7391 Intermediate Similarity NPC230124
0.7391 Intermediate Similarity NPC477838
0.7391 Intermediate Similarity NPC79622
0.7391 Intermediate Similarity NPC471183
0.7391 Intermediate Similarity NPC6300
0.7391 Intermediate Similarity NPC212942
0.7391 Intermediate Similarity NPC220344
0.7391 Intermediate Similarity NPC477837
0.7391 Intermediate Similarity NPC29868
0.7391 Intermediate Similarity NPC275061
0.7391 Intermediate Similarity NPC184613
0.7389 Intermediate Similarity NPC12275
0.7389 Intermediate Similarity NPC45715
0.7389 Intermediate Similarity NPC232275
0.7389 Intermediate Similarity NPC474356
0.7386 Intermediate Similarity NPC183446

  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 NPC66678 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
0.9664 High Similarity NPD5089 Approved
0.9664 High Similarity NPD5090 Approved
0.879 High Similarity NPD4585 Approved
0.8266 Intermediate Similarity NPD6843 Phase 3
0.8266 Intermediate Similarity NPD6841 Approved
0.8266 Intermediate Similarity NPD6842 Approved
0.8061 Intermediate Similarity NPD4055 Discovery
0.7853 Intermediate Similarity NPD4005 Discontinued
0.7613 Intermediate Similarity NPD2674 Phase 3
0.7529 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD4357 Discontinued
0.7436 Intermediate Similarity NPD3145 Approved
0.7436 Intermediate Similarity NPD3144 Approved
0.7371 Intermediate Similarity NPD2898 Approved
0.7333 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2219 Phase 1
0.7293 Intermediate Similarity NPD8053 Approved
0.7293 Intermediate Similarity NPD8054 Approved
0.7261 Intermediate Similarity NPD3027 Phase 3
0.7176 Intermediate Similarity NPD4675 Approved
0.7176 Intermediate Similarity NPD4678 Approved
0.7168 Intermediate Similarity NPD3882 Suspended
0.7143 Intermediate Similarity NPD7526 Approved
0.7143 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD52 Approved
0.7099 Intermediate Similarity NPD6111 Discontinued
0.7044 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD2161 Phase 2
0.7011 Intermediate Similarity NPD2563 Approved
0.7011 Intermediate Similarity NPD2560 Approved
0.7006 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.6987 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6981 Remote Similarity NPD1529 Clinical (unspecified phase)
0.697 Remote Similarity NPD1375 Discontinued
0.6964 Remote Similarity NPD7124 Phase 2
0.6954 Remote Similarity NPD5772 Approved
0.6954 Remote Similarity NPD5773 Approved
0.6949 Remote Similarity NPD4666 Phase 3
0.6946 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3450 Approved
0.6943 Remote Similarity NPD3452 Approved
0.6943 Remote Similarity NPD2493 Approved
0.6943 Remote Similarity NPD2494 Approved
0.6933 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5297 Approved
0.6919 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6915 Remote Similarity NPD2488 Approved
0.6915 Remote Similarity NPD2490 Approved
0.6914 Remote Similarity NPD1613 Approved
0.6914 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6906 Remote Similarity NPD8251 Approved
0.6906 Remote Similarity NPD8099 Discontinued
0.6906 Remote Similarity NPD8252 Approved
0.6905 Remote Similarity NPD5241 Discontinued
0.6902 Remote Similarity NPD7549 Discontinued
0.6898 Remote Similarity NPD7906 Approved
0.6897 Remote Similarity NPD1934 Approved
0.6893 Remote Similarity NPD5709 Phase 3
0.6889 Remote Similarity NPD27 Approved
0.6889 Remote Similarity NPD2489 Approved
0.6882 Remote Similarity NPD4123 Phase 3
0.6882 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6882 Remote Similarity NPD4739 Approved
0.6882 Remote Similarity NPD4584 Approved
0.6879 Remote Similarity NPD1669 Approved
0.6868 Remote Similarity NPD8156 Discontinued
0.6867 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6857 Remote Similarity NPD2801 Approved
0.6853 Remote Similarity NPD7263 Phase 2
0.6848 Remote Similarity NPD651 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6331 Phase 2
0.6839 Remote Similarity NPD6072 Discontinued
0.6837 Remote Similarity NPD4583 Approved
0.6837 Remote Similarity NPD4582 Approved
0.6833 Remote Similarity NPD2970 Approved
0.6833 Remote Similarity NPD2969 Approved
0.6829 Remote Similarity NPD2157 Approved
0.6826 Remote Similarity NPD7153 Discontinued
0.6813 Remote Similarity NPD1712 Approved
0.681 Remote Similarity NPD4060 Phase 1
0.681 Remote Similarity NPD2238 Phase 2
0.6802 Remote Similarity NPD3639 Approved
0.6802 Remote Similarity NPD3641 Approved
0.6802 Remote Similarity NPD3640 Phase 3
0.68 Remote Similarity NPD228 Approved
0.6796 Remote Similarity NPD6166 Phase 2
0.6796 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6168 Clinical (unspecified phase)
0.679 Remote Similarity NPD5109 Approved
0.679 Remote Similarity NPD5111 Phase 2
0.679 Remote Similarity NPD5110 Phase 2
0.6786 Remote Similarity NPD3060 Approved
0.6786 Remote Similarity NPD4237 Approved
0.6786 Remote Similarity NPD4004 Approved
0.6786 Remote Similarity NPD4002 Approved
0.6786 Remote Similarity NPD4236 Phase 3
0.678 Remote Similarity NPD6788 Approved
0.6778 Remote Similarity NPD4010 Discontinued
0.6778 Remote Similarity NPD6071 Discontinued
0.6778 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6778 Remote Similarity NPD3051 Approved
0.6774 Remote Similarity NPD7312 Approved
0.6774 Remote Similarity NPD7310 Approved
0.6774 Remote Similarity NPD4577 Approved
0.6774 Remote Similarity NPD4578 Approved
0.6774 Remote Similarity NPD7311 Approved
0.6774 Remote Similarity NPD7313 Approved
0.6772 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7827 Phase 1
0.6763 Remote Similarity NPD1653 Approved
0.6761 Remote Similarity NPD2978 Approved
0.6761 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6761 Remote Similarity NPD2977 Approved
0.676 Remote Similarity NPD6746 Phase 2
0.676 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6755 Remote Similarity NPD4663 Approved
0.6753 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6748 Remote Similarity NPD839 Approved
0.6748 Remote Similarity NPD840 Approved
0.6744 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6744 Remote Similarity NPD1512 Approved
0.674 Remote Similarity NPD5242 Approved
0.6738 Remote Similarity NPD7309 Approved
0.6736 Remote Similarity NPD2975 Approved
0.6736 Remote Similarity NPD2973 Approved
0.6736 Remote Similarity NPD2974 Approved
0.6728 Remote Similarity NPD1024 Discontinued
0.6723 Remote Similarity NPD3817 Phase 2
0.6721 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6718 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6708 Remote Similarity NPD3018 Phase 2
0.6706 Remote Similarity NPD302 Approved
0.6704 Remote Similarity NPD6234 Discontinued
0.6703 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6687 Remote Similarity NPD1048 Approved
0.6686 Remote Similarity NPD1424 Approved
0.6685 Remote Similarity NPD6232 Discontinued
0.6685 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7315 Approved
0.6667 Remote Similarity NPD7907 Approved
0.6667 Remote Similarity NPD3686 Approved
0.6667 Remote Similarity NPD7473 Discontinued
0.6667 Remote Similarity NPD3687 Approved
0.6667 Remote Similarity NPD1465 Phase 2
0.665 Remote Similarity NPD3057 Approved
0.6648 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4772 Phase 2
0.6648 Remote Similarity NPD4773 Phase 2
0.6647 Remote Similarity NPD1349 Approved
0.6647 Remote Similarity NPD1351 Approved
0.6647 Remote Similarity NPD1350 Approved
0.6633 Remote Similarity NPD4580 Approved
0.6629 Remote Similarity NPD824 Approved
0.6629 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6629 Remote Similarity NPD3455 Phase 2
0.6628 Remote Similarity NPD1511 Approved
0.6627 Remote Similarity NPD970 Clinical (unspecified phase)
0.6625 Remote Similarity NPD2922 Phase 1
0.6624 Remote Similarity NPD4626 Approved
0.6615 Remote Similarity NPD7296 Approved
0.6612 Remote Similarity NPD4481 Phase 3
0.661 Remote Similarity NPD37 Approved
0.6609 Remote Similarity NPD2122 Discontinued
0.6608 Remote Similarity NPD2677 Approved
0.6608 Remote Similarity NPD3692 Discontinued
0.6606 Remote Similarity NPD1558 Phase 1
0.6604 Remote Similarity NPD2230 Approved
0.6604 Remote Similarity NPD2233 Approved
0.6604 Remote Similarity NPD2232 Approved
0.6596 Remote Similarity NPD2968 Approved
0.6596 Remote Similarity NPD2971 Approved
0.6595 Remote Similarity NPD6042 Phase 2
0.6595 Remote Similarity NPD42 Phase 2
0.659 Remote Similarity NPD7447 Phase 1
0.659 Remote Similarity NPD3536 Discontinued
0.659 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5177 Phase 3
0.6588 Remote Similarity NPD2654 Approved
0.6578 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6576 Remote Similarity NPD3489 Phase 3
0.6573 Remote Similarity NPD6818 Clinical (unspecified phase)
0.657 Remote Similarity NPD6667 Approved
0.657 Remote Similarity NPD6666 Approved
0.6566 Remote Similarity NPD3448 Approved
0.6566 Remote Similarity NPD230 Phase 1
0.6566 Remote Similarity NPD3533 Approved
0.6566 Remote Similarity NPD2491 Approved
0.6566 Remote Similarity NPD2972 Approved
0.6564 Remote Similarity NPD596 Approved
0.6564 Remote Similarity NPD600 Approved
0.6564 Remote Similarity NPD4908 Phase 1
0.6562 Remote Similarity NPD9622 Approved
0.6562 Remote Similarity NPD2983 Phase 2
0.6562 Remote Similarity NPD2982 Phase 2
0.6562 Remote Similarity NPD4749 Approved
0.6556 Remote Similarity NPD7075 Discontinued
0.6554 Remote Similarity NPD6386 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