Structure

Physi-Chem Properties

Molecular Weight:  294.17
Volume:  317.919
LogP:  2.85
LogD:  2.916
LogS:  -2.2
# Rotatable Bonds:  3
TPSA:  36.36
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.883
Synthetic Accessibility Score:  4.484
Fsp3:  0.421
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.839
MDCK Permeability:  1.979087210202124e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.231
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.604
Plasma Protein Binding (PPB):  70.0735092163086%
Volume Distribution (VD):  3.48
Pgp-substrate:  42.143821716308594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.228
CYP1A2-substrate:  0.855
CYP2C19-inhibitor:  0.165
CYP2C19-substrate:  0.871
CYP2C9-inhibitor:  0.051
CYP2C9-substrate:  0.192
CYP2D6-inhibitor:  0.912
CYP2D6-substrate:  0.895
CYP3A4-inhibitor:  0.415
CYP3A4-substrate:  0.735

ADMET: Excretion

Clearance (CL):  2.474
Half-life (T1/2):  0.408

ADMET: Toxicity

hERG Blockers:  0.426
Human Hepatotoxicity (H-HT):  0.956
Drug-inuced Liver Injury (DILI):  0.624
AMES Toxicity:  0.073
Rat Oral Acute Toxicity:  0.816
Maximum Recommended Daily Dose:  0.336
Skin Sensitization:  0.204
Carcinogencity:  0.351
Eye Corrosion:  0.003
Eye Irritation:  0.108
Respiratory Toxicity:  0.955

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

  Natural Product: NPC150048

Natural Product ID:  NPC150048
Common Name*:   Cinchonine
IUPAC Name:   (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
Synonyms:   GNF-Pf-3189; TCMDC-123933
Standard InCHIKey:  KMPWYEUPVWOPIM-QAMTZSDWSA-N
Standard InCHI:  InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
SMILES:  C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL588619
PubChem CID:   90454
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002246] Cinchona alkaloids

*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
NPO25089 Cinchona calisaya Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[11992775]
NPO25089 Cinchona calisaya Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25089 Cinchona calisaya Species Rubiaceae 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
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Ki = 21000.0 nM PMID[453248]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens IC50 = 1800.0 nM PMID[453248]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[453249]
NPT65 Cell Line HepG2 Homo sapiens Inhibition = 0.0 % PMID[453250]
NPT1229 Cell Line Huh-7 Homo sapiens CC50 > 6250.0 nM PMID[453251]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 32642.7 nM PMID[453253]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 52722.99 nM PMID[453255]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 62950.62 nM PMID[453255]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 55207.74 nM PMID[453255]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 89949.76 nM PMID[453255]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 38106.58 nM PMID[453255]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 22908.68 nM PMID[453255]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 58613.82 nM PMID[453255]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 5395.11 nM PMID[453255]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 22803.42 nM PMID[453255]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 73282.45 nM PMID[453255]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 19588.45 nM PMID[453255]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 1258.93 nM PMID[453255]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 46773.51 nM PMID[453255]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[453255]
NPT5068 Cell Line Spermatozoa Activity = 0.5 % PMID[453257]
NPT165 Cell Line HeLa Homo sapiens EC50 = 697.0 ug.mL-1 PMID[453257]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 130.0 nM PMID[453253]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 5.94 % PMID[453258]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 12995.3 nM PMID[453253]
NPT1374 Cell Line WI-38 Homo sapiens IC50 > 20.0 ug.mL-1 PMID[453260]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 220.0 nM PMID[453246]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 51.0 nM PMID[453246]
NPT2 Others Unspecified IC50 = 370000.0 nM PMID[453247]
NPT2 Others Unspecified IFI = 0.73 % PMID[453250]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 2.0 % PMID[453250]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 3.0 % PMID[453250]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Inhibition = 100.0 % PMID[453250]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum XC50 = 766.16 nM PMID[453250]
NPT2 Others Unspecified IFI = 4.688 % PMID[453251]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 110.0 nM PMID[453251]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 95.3 nM PMID[453251]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 23000.0 nM PMID[453252]
NPT2 Others Unspecified Potency = 920.0 nM PMID[453253]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5.0 nM PMID[453254]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 4.1 nM PMID[453253]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 32.9 nM PMID[453253]
NPT2 Others Unspecified Potency n.a. 251.2 nM PMID[453253]
NPT2 Others Unspecified Potency n.a. 199.5 nM PMID[453253]
NPT2 Others Unspecified IC50 = 370000.0 nM PMID[453256]
NPT2 Others Unspecified IC50 = 170000.0 nM PMID[453256]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 22.0 nM PMID[453256]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 82.0 nM PMID[453256]
NPT27 Others Unspecified EC50 = 428.0 ug.mL-1 PMID[453257]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 9.07 % PMID[453258]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 56.0 nM PMID[453259]
NPT757 Organism Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 IC50 = 21.0 nM PMID[453259]
NPT20576 SMALL MOLECULE Heme n.a. IC50 = 23000.0 nM PMID[453259]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 > 20.0 ug.mL-1 PMID[453260]
NPT2 Others Unspecified Ratio IC50 > 222.0 n.a. PMID[453260]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.09 ug.mL-1 PMID[453260]
NPT3694 Organism Leishmania mexicana mexicana Leishmania mexicana mexicana IC50 > 20.0 ug.mL-1 PMID[453260]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 105.27 % PMID[453261]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 122.27 % PMID[453261]
NPT942 Individual Protein Glucose transporter Homo sapiens Inhibition = -1.24 % PMID[453262]
NPT943 Individual Protein Hexose transporter 1 Plasmodium falciparum Inhibition = 1.12 % PMID[453262]
NPT944 Individual Protein Glucose transporter Leishmania mexicana Inhibition = 0.13 % PMID[453262]
NPT27 Others Unspecified IC50 > 68030.0 nM PMID[453263]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 > 68030.0 nM PMID[453263]
NPT757 Organism Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 IC50 = 292.5 nM PMID[453263]
NPT2 Others Unspecified Ratio IC50 > 222.0 n.a. PMID[453263]

☑ 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 NPC150048 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 NPC203754
0.8674 High Similarity NPC118832
0.8674 High Similarity NPC47059
0.8674 High Similarity NPC165349
0.8674 High Similarity NPC274291
0.8674 High Similarity NPC264166
0.8674 High Similarity NPC329708
0.8266 Intermediate Similarity NPC133261
0.8208 Intermediate Similarity NPC326575
0.8125 Intermediate Similarity NPC48938
0.8107 Intermediate Similarity NPC102423
0.8081 Intermediate Similarity NPC158129
0.8047 Intermediate Similarity NPC59779
0.8047 Intermediate Similarity NPC124542
0.8047 Intermediate Similarity NPC471177
0.8046 Intermediate Similarity NPC24594
0.8046 Intermediate Similarity NPC472122
0.8011 Intermediate Similarity NPC187827
0.8011 Intermediate Similarity NPC472105
0.8 Intermediate Similarity NPC469813
0.8 Intermediate Similarity NPC78375
0.8 Intermediate Similarity NPC476446
0.7988 Intermediate Similarity NPC131718
0.7965 Intermediate Similarity NPC317430
0.7956 Intermediate Similarity NPC95783
0.7933 Intermediate Similarity NPC62510
0.7931 Intermediate Similarity NPC472123
0.7931 Intermediate Similarity NPC313791
0.7919 Intermediate Similarity NPC473764
0.7919 Intermediate Similarity NPC314940
0.7898 Intermediate Similarity NPC256893
0.7882 Intermediate Similarity NPC81229
0.7882 Intermediate Similarity NPC255229
0.7872 Intermediate Similarity NPC328318
0.7872 Intermediate Similarity NPC328596
0.7861 Intermediate Similarity NPC249040
0.7849 Intermediate Similarity NPC265576
0.7849 Intermediate Similarity NPC471178
0.7821 Intermediate Similarity NPC472109
0.7821 Intermediate Similarity NPC472110
0.7811 Intermediate Similarity NPC469785
0.7797 Intermediate Similarity NPC151939
0.7791 Intermediate Similarity NPC311276
0.7765 Intermediate Similarity NPC129721
0.7765 Intermediate Similarity NPC469762
0.774 Intermediate Similarity NPC134586
0.7722 Intermediate Similarity NPC139291
0.7722 Intermediate Similarity NPC472108
0.7719 Intermediate Similarity NPC230869
0.7719 Intermediate Similarity NPC84508
0.7701 Intermediate Similarity NPC474561
0.7701 Intermediate Similarity NPC49954
0.7701 Intermediate Similarity NPC54988
0.7697 Intermediate Similarity NPC211997
0.7696 Intermediate Similarity NPC470505
0.7696 Intermediate Similarity NPC470500
0.7688 Intermediate Similarity NPC97367
0.768 Intermediate Similarity NPC5145
0.767 Intermediate Similarity NPC252590
0.7668 Intermediate Similarity NPC477111
0.7667 Intermediate Similarity NPC233936
0.7665 Intermediate Similarity NPC477110
0.7663 Intermediate Similarity NPC3715
0.766 Intermediate Similarity NPC212213
0.7657 Intermediate Similarity NPC201700
0.7657 Intermediate Similarity NPC63751
0.7656 Intermediate Similarity NPC317373
0.7656 Intermediate Similarity NPC477113
0.7656 Intermediate Similarity NPC472111
0.7654 Intermediate Similarity NPC251722
0.7654 Intermediate Similarity NPC314102
0.7634 Intermediate Similarity NPC474177
0.7627 Intermediate Similarity NPC34508
0.7626 Intermediate Similarity NPC476041
0.7626 Intermediate Similarity NPC304926
0.7611 Intermediate Similarity NPC300688
0.7611 Intermediate Similarity NPC15840
0.7604 Intermediate Similarity NPC327592
0.76 Intermediate Similarity NPC98187
0.76 Intermediate Similarity NPC160105
0.7596 Intermediate Similarity NPC171171
0.7594 Intermediate Similarity NPC133366
0.7588 Intermediate Similarity NPC469760
0.7588 Intermediate Similarity NPC73952
0.7588 Intermediate Similarity NPC469763
0.7588 Intermediate Similarity NPC469786
0.7588 Intermediate Similarity NPC259644
0.7588 Intermediate Similarity NPC469765
0.7588 Intermediate Similarity NPC25008
0.7586 Intermediate Similarity NPC40779
0.7582 Intermediate Similarity NPC284678
0.7582 Intermediate Similarity NPC207851
0.7572 Intermediate Similarity NPC279918
0.7565 Intermediate Similarity NPC475288
0.7556 Intermediate Similarity NPC176199
0.7556 Intermediate Similarity NPC215795
0.7544 Intermediate Similarity NPC70922
0.7544 Intermediate Similarity NPC212376
0.7544 Intermediate Similarity NPC80597
0.7544 Intermediate Similarity NPC75540
0.7544 Intermediate Similarity NPC211572
0.754 Intermediate Similarity NPC329541
0.7538 Intermediate Similarity NPC469589
0.7529 Intermediate Similarity NPC282231
0.7527 Intermediate Similarity NPC117244
0.7527 Intermediate Similarity NPC473763
0.7527 Intermediate Similarity NPC19679
0.7527 Intermediate Similarity NPC220765
0.7527 Intermediate Similarity NPC472104
0.7526 Intermediate Similarity NPC166492
0.7526 Intermediate Similarity NPC473362
0.7513 Intermediate Similarity NPC475070
0.75 Intermediate Similarity NPC141353
0.75 Intermediate Similarity NPC478077
0.75 Intermediate Similarity NPC68354
0.75 Intermediate Similarity NPC474707
0.75 Intermediate Similarity NPC293472
0.7487 Intermediate Similarity NPC99666
0.7487 Intermediate Similarity NPC324149
0.7486 Intermediate Similarity NPC204717
0.7486 Intermediate Similarity NPC37423
0.7486 Intermediate Similarity NPC194640
0.7486 Intermediate Similarity NPC329688
0.7486 Intermediate Similarity NPC189812
0.7486 Intermediate Similarity NPC284559
0.7486 Intermediate Similarity NPC275305
0.7474 Intermediate Similarity NPC239954
0.7473 Intermediate Similarity NPC314394
0.7471 Intermediate Similarity NPC40070
0.7471 Intermediate Similarity NPC24678
0.7471 Intermediate Similarity NPC105818
0.7463 Intermediate Similarity NPC476492
0.7459 Intermediate Similarity NPC270009
0.7459 Intermediate Similarity NPC204565
0.7459 Intermediate Similarity NPC472443
0.7458 Intermediate Similarity NPC44161
0.7453 Intermediate Similarity NPC324611
0.7447 Intermediate Similarity NPC198673
0.7446 Intermediate Similarity NPC15102
0.7446 Intermediate Similarity NPC314002
0.744 Intermediate Similarity NPC159856
0.743 Intermediate Similarity NPC314603
0.7419 Intermediate Similarity NPC173028
0.7419 Intermediate Similarity NPC65215
0.7403 Intermediate Similarity NPC59269
0.7391 Intermediate Similarity NPC472294
0.7389 Intermediate Similarity NPC471506
0.7389 Intermediate Similarity NPC46358
0.7389 Intermediate Similarity NPC469938
0.7387 Intermediate Similarity NPC317752
0.7382 Intermediate Similarity NPC192315
0.7382 Intermediate Similarity NPC168911
0.738 Intermediate Similarity NPC469470
0.738 Intermediate Similarity NPC469501
0.7377 Intermediate Similarity NPC192270
0.7374 Intermediate Similarity NPC470498
0.7371 Intermediate Similarity NPC25899
0.7366 Intermediate Similarity NPC472323
0.7366 Intermediate Similarity NPC317030
0.7366 Intermediate Similarity NPC46580
0.7365 Intermediate Similarity NPC60553
0.7358 Intermediate Similarity NPC300183
0.7351 Intermediate Similarity NPC472107
0.7351 Intermediate Similarity NPC188387
0.7351 Intermediate Similarity NPC163421
0.7351 Intermediate Similarity NPC79062
0.7344 Intermediate Similarity NPC476167
0.7337 Intermediate Similarity NPC318299
0.7337 Intermediate Similarity NPC163055
0.7337 Intermediate Similarity NPC143533
0.7337 Intermediate Similarity NPC472444
0.7337 Intermediate Similarity NPC314372
0.733 Intermediate Similarity NPC48192
0.7322 Intermediate Similarity NPC24864
0.7321 Intermediate Similarity NPC20144
0.732 Intermediate Similarity NPC211813
0.7318 Intermediate Similarity NPC194411
0.7314 Intermediate Similarity NPC92796
0.7314 Intermediate Similarity NPC135141
0.7312 Intermediate Similarity NPC165370
0.7312 Intermediate Similarity NPC471311
0.7312 Intermediate Similarity NPC471313
0.731 Intermediate Similarity NPC314957
0.731 Intermediate Similarity NPC288445
0.7308 Intermediate Similarity NPC184964
0.73 Intermediate Similarity NPC471080
0.73 Intermediate Similarity NPC469592
0.7299 Intermediate Similarity NPC51054
0.7296 Intermediate Similarity NPC474145
0.7296 Intermediate Similarity NPC475841
0.7295 Intermediate Similarity NPC6215
0.7292 Intermediate Similarity NPC474916
0.7292 Intermediate Similarity NPC149708
0.7288 Intermediate Similarity NPC474217
0.7288 Intermediate Similarity NPC473057
0.7283 Intermediate Similarity NPC219963
0.7282 Intermediate Similarity NPC98715
0.7282 Intermediate Similarity NPC475774
0.7273 Intermediate Similarity NPC328029
0.7268 Intermediate Similarity NPC232340

  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 NPC150048 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
0.8938 High Similarity NPD5255 Approved
0.8674 High Similarity NPD4122 Approved
0.8674 High Similarity NPD4039 Approved
0.8674 High Similarity NPD4033 Approved
0.8674 High Similarity NPD4035 Approved
0.8674 High Similarity NPD4038 Approved
0.8674 High Similarity NPD4037 Approved
0.8674 High Similarity NPD4036 Approved
0.8674 High Similarity NPD32 Approved
0.8674 High Similarity NPD31 Approved
0.8674 High Similarity NPD4034 Approved
0.858 High Similarity NPD2381 Approved
0.858 High Similarity NPD2380 Approved
0.858 High Similarity NPD2382 Approved
0.8395 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD6158 Phase 2
0.8304 Intermediate Similarity NPD5065 Approved
0.8303 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD5862 Discovery
0.8193 Intermediate Similarity NPD2581 Approved
0.8193 Intermediate Similarity NPD2582 Approved
0.8156 Intermediate Similarity NPD8063 Discontinued
0.8132 Intermediate Similarity NPD3477 Phase 2
0.8132 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD4702 Approved
0.8098 Intermediate Similarity NPD4703 Approved
0.8061 Intermediate Similarity NPD2882 Phase 1
0.8025 Intermediate Similarity NPD3813 Approved
0.7967 Intermediate Similarity NPD6569 Phase 2
0.7956 Intermediate Similarity NPD6281 Approved
0.7943 Intermediate Similarity NPD5100 Phase 3
0.7933 Intermediate Similarity NPD3082 Discontinued
0.7927 Intermediate Similarity NPD7469 Discontinued
0.7898 Intermediate Similarity NPD6159 Phase 2
0.7865 Intermediate Similarity NPD8408 Discontinued
0.7861 Intermediate Similarity NPD4638 Approved
0.7861 Intermediate Similarity NPD4640 Approved
0.7861 Intermediate Similarity NPD4639 Approved
0.7853 Intermediate Similarity NPD3525 Discontinued
0.7841 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD8122 Approved
0.7797 Intermediate Similarity NPD8123 Approved
0.7784 Intermediate Similarity NPD9690 Approved
0.7778 Intermediate Similarity NPD9705 Discontinued
0.7778 Intermediate Similarity NPD112 Approved
0.7771 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD3321 Discontinued
0.7747 Intermediate Similarity NPD8020 Approved
0.7747 Intermediate Similarity NPD2383 Phase 1
0.7747 Intermediate Similarity NPD8021 Approved
0.7746 Intermediate Similarity NPD925 Approved
0.7746 Intermediate Similarity NPD926 Approved
0.7744 Intermediate Similarity NPD3717 Discontinued
0.773 Intermediate Similarity NPD4526 Approved
0.773 Intermediate Similarity NPD4529 Approved
0.773 Intermediate Similarity NPD4528 Approved
0.7727 Intermediate Similarity NPD2077 Approved
0.7727 Intermediate Similarity NPD2076 Approved
0.7706 Intermediate Similarity NPD6026 Approved
0.7684 Intermediate Similarity NPD6492 Phase 2
0.766 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7637 Intermediate Similarity NPD6227 Discontinued
0.7634 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD3330 Phase 1
0.76 Intermediate Similarity NPD424 Approved
0.76 Intermediate Similarity NPD425 Approved
0.7581 Intermediate Similarity NPD3404 Approved
0.7576 Intermediate Similarity NPD3393 Approved
0.7576 Intermediate Similarity NPD3389 Approved
0.7576 Intermediate Similarity NPD7112 Discontinued
0.7576 Intermediate Similarity NPD3394 Approved
0.756 Intermediate Similarity NPD1661 Suspended
0.7557 Intermediate Similarity NPD2781 Approved
0.7556 Intermediate Similarity NPD4076 Approved
0.7556 Intermediate Similarity NPD4079 Approved
0.7543 Intermediate Similarity NPD2780 Approved
0.7543 Intermediate Similarity NPD2720 Phase 1
0.7543 Intermediate Similarity NPD2719 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD2782 Approved
0.7532 Intermediate Similarity NPD2119 Approved
0.7532 Intermediate Similarity NPD2118 Approved
0.7527 Intermediate Similarity NPD5596 Phase 2
0.7527 Intermediate Similarity NPD4699 Discontinued
0.7526 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1649 Discontinued
0.7514 Intermediate Similarity NPD3433 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD7948 Phase 1
0.75 Intermediate Similarity NPD8321 Discontinued
0.75 Intermediate Similarity NPD1032 Phase 2
0.75 Intermediate Similarity NPD3505 Approved
0.75 Intermediate Similarity NPD8289 Discontinued
0.75 Intermediate Similarity NPD3506 Approved
0.7473 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD4203 Approved
0.7473 Intermediate Similarity NPD4204 Approved
0.7471 Intermediate Similarity NPD2511 Approved
0.7469 Intermediate Similarity NPD3942 Approved
0.7469 Intermediate Similarity NPD3944 Approved
0.7463 Intermediate Similarity NPD3402 Phase 1
0.7459 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD4547 Phase 3
0.7449 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5428 Discontinued
0.7446 Intermediate Similarity NPD5555 Phase 1
0.7446 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD2176 Approved
0.7435 Intermediate Similarity NPD2177 Approved
0.7435 Intermediate Similarity NPD2175 Phase 3
0.7432 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD3262 Approved
0.7427 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD6595 Phase 3
0.7407 Intermediate Similarity NPD7944 Discontinued
0.7396 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD3117 Approved
0.7374 Intermediate Similarity NPD3116 Approved
0.7371 Intermediate Similarity NPD4886 Phase 2
0.7354 Intermediate Similarity NPD9695 Approved
0.7344 Intermediate Similarity NPD6999 Discontinued
0.7344 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD2391 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7675 Phase 3
0.733 Intermediate Similarity NPD7674 Phase 3
0.7326 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD6452 Discontinued
0.732 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD1325 Approved
0.7318 Intermediate Similarity NPD1326 Approved
0.7316 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7666 Phase 3
0.731 Intermediate Similarity NPD3575 Approved
0.731 Intermediate Similarity NPD7665 Phase 2
0.731 Intermediate Similarity NPD3576 Approved
0.7308 Intermediate Similarity NPD2144 Approved
0.7308 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6178 Phase 3
0.7296 Intermediate Similarity NPD7001 Phase 3
0.7283 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3038 Discontinued
0.7283 Intermediate Similarity NPD2837 Discontinued
0.7282 Intermediate Similarity NPD7586 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2123 Phase 3
0.7277 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1034 Phase 3
0.7273 Intermediate Similarity NPD3002 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7287 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD1722 Approved
0.7259 Intermediate Similarity NPD7222 Phase 2
0.7258 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD5541 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD4028 Approved
0.7256 Intermediate Similarity NPD4030 Approved
0.7256 Intermediate Similarity NPD4029 Approved
0.7249 Intermediate Similarity NPD6022 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7426 Phase 1
0.7238 Intermediate Similarity NPD7418 Discontinued
0.7238 Intermediate Similarity NPD750 Phase 2
0.7234 Intermediate Similarity NPD7234 Approved
0.7234 Intermediate Similarity NPD7233 Approved
0.7231 Intermediate Similarity NPD3928 Approved
0.7231 Intermediate Similarity NPD6132 Phase 1
0.7231 Intermediate Similarity NPD3931 Approved
0.7229 Intermediate Similarity NPD9506 Approved
0.7225 Intermediate Similarity NPD4602 Approved
0.7222 Intermediate Similarity NPD7474 Suspended
0.7222 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD9689 Approved
0.7211 Intermediate Similarity NPD6887 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD9284 Approved
0.7202 Intermediate Similarity NPD53 Approved
0.7202 Intermediate Similarity NPD7778 Approved
0.7202 Intermediate Similarity NPD7777 Approved
0.72 Intermediate Similarity NPD7470 Discontinued
0.7196 Intermediate Similarity NPD3439 Approved
0.7194 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD4044 Discontinued
0.7192 Intermediate Similarity NPD8326 Phase 3
0.7192 Intermediate Similarity NPD8325 Phase 3
0.7192 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD7867 Phase 1
0.7188 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7935 Phase 2
0.7186 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2896 Discontinued

  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