Structure

Physi-Chem Properties

Molecular Weight:  295.16
Volume:  321.633
LogP:  5.337
LogD:  4.092
LogS:  -3.98
# Rotatable Bonds:  3
TPSA:  45.25
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.678
Synthetic Accessibility Score:  2.625
Fsp3:  0.263
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.027
MDCK Permeability:  1.3216418665251695e-05
Pgp-inhibitor:  0.937
Pgp-substrate:  0.037
Human Intestinal Absorption (HIA):  0.023
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.142
Plasma Protein Binding (PPB):  94.48136901855469%
Volume Distribution (VD):  2.181
Pgp-substrate:  4.769333839416504%

ADMET: Metabolism

CYP1A2-inhibitor:  0.98
CYP1A2-substrate:  0.919
CYP2C19-inhibitor:  0.944
CYP2C19-substrate:  0.211
CYP2C9-inhibitor:  0.787
CYP2C9-substrate:  0.928
CYP2D6-inhibitor:  0.87
CYP2D6-substrate:  0.91
CYP3A4-inhibitor:  0.45
CYP3A4-substrate:  0.24

ADMET: Excretion

Clearance (CL):  10.327
Half-life (T1/2):  0.303

ADMET: Toxicity

hERG Blockers:  0.066
Human Hepatotoxicity (H-HT):  0.687
Drug-inuced Liver Injury (DILI):  0.573
AMES Toxicity:  0.642
Rat Oral Acute Toxicity:  0.473
Maximum Recommended Daily Dose:  0.922
Skin Sensitization:  0.888
Carcinogencity:  0.547
Eye Corrosion:  0.005
Eye Irritation:  0.918
Respiratory Toxicity:  0.961

Download Data

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

  Natural Product: NPC243834

Natural Product ID:  NPC243834
Common Name*:   Sid506287
IUPAC Name:   7-methoxy-3-methyl-8-(3-methylbut-2-enyl)-9H-carbazol-2-ol
Synonyms:  
Standard InCHIKey:  XFLPKTCBCLWABD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H21NO2/c1-11(2)5-6-14-18(22-4)8-7-13-15-9-12(3)17(21)10-16(15)20-19(13)14/h5,7-10,20-21H,6H2,1-4H3
SMILES:  CC(=CCc1c(ccc2c3cc(C)c(cc3[nH]c12)O)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507794
PubChem CID:   375146
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota root bark Kuantaochi, Nantou Hsien, Taiwan n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota stem bark;fruit n.a. n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3118 Murraya euchrestifolia Species Rutaceae 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
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 = 5370.32 nM PMID[538197]
NPT111 Cell Line K562 Homo sapiens GI50 = 5754.4 nM PMID[538197]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 = 4897.79 nM PMID[538197]
NPT385 Cell Line SR Homo sapiens GI50 = 7244.36 nM PMID[538197]
NPT81 Cell Line A549 Homo sapiens GI50 = 8511.38 nM PMID[538197]
NPT372 Cell Line HOP-92 Homo sapiens GI50 = 7943.28 nM PMID[538197]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 = 10715.19 nM PMID[538197]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 5623.41 nM PMID[538197]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 = 5888.44 nM PMID[538197]
NPT572 Cell Line DMS-273 Homo sapiens GI50 = 8511.38 nM PMID[538197]
NPT407 Cell Line COLO 205 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT579 Cell Line DLD-1 Homo sapiens GI50 = 9120.11 nM PMID[538197]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 = 5495.41 nM PMID[538197]
NPT393 Cell Line HCT-116 Homo sapiens GI50 = 12022.64 nM PMID[538197]
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 5128.61 nM PMID[538197]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 72443.6 nM PMID[538197]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 16218.1 nM PMID[538197]
NPT323 Cell Line SW-620 Homo sapiens GI50 = 6760.83 nM PMID[538197]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 9549.93 nM PMID[538197]
NPT374 Cell Line SF-539 Homo sapiens GI50 = 7943.28 nM PMID[538197]
NPT383 Cell Line SNB-19 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT392 Cell Line SNB-75 Homo sapiens GI50 = 11481.54 nM PMID[538197]
NPT380 Cell Line U-251 Homo sapiens GI50 = 5888.44 nM PMID[538197]
NPT574 Cell Line XF498 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 = 4365.16 nM PMID[538197]
NPT375 Cell Line Malme-3M Homo sapiens GI50 = 17378.01 nM PMID[538197]
NPT387 Cell Line M14 Homo sapiens GI50 = 1621.81 nM PMID[538197]
NPT573 Cell Line M19-MEL Homo sapiens GI50 = 12302.69 nM PMID[538197]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 = 8128.31 nM PMID[538197]
NPT398 Cell Line UACC-62 Homo sapiens GI50 = 9120.11 nM PMID[538197]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 = 2290.87 nM PMID[538197]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 = 25118.86 nM PMID[538197]
NPT401 Cell Line 786-0 Homo sapiens GI50 = 4365.16 nM PMID[538197]
NPT369 Cell Line ACHN Homo sapiens GI50 = 9332.54 nM PMID[538197]
NPT384 Cell Line TK-10 Homo sapiens GI50 = 5011.87 nM PMID[538197]
NPT371 Cell Line UO-31 Homo sapiens GI50 = 14454.4 nM PMID[538197]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 5035.01 nM PMID[538198]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 9354.06 nM PMID[538198]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14288.94 nM PMID[538198]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 8035.26 nM PMID[538198]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 7943.28 nM PMID[538198]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 8016.78 nM PMID[538198]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 8035.26 nM PMID[538198]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 17338.04 nM PMID[538198]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 5780.96 nM PMID[538198]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 5321.08 nM PMID[538198]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 4931.74 nM PMID[538198]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 2500.35 nM PMID[538198]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 5888.44 nM PMID[538198]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 4415.7 nM PMID[538198]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 8433.35 nM PMID[538198]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 7177.94 nM PMID[538198]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 6760.83 nM PMID[538198]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 12246.16 nM PMID[538198]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 5915.62 nM PMID[538198]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2500.35 nM PMID[538198]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1621.81 nM PMID[538198]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10568.18 nM PMID[538198]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 8375.29 nM PMID[538198]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 4355.12 nM PMID[538198]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 22490.55 nM PMID[538198]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 8472.27 nM PMID[538198]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 16255.49 nM PMID[538198]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 5482.77 nM PMID[538198]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 5140.44 nM PMID[538198]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 11857.69 nM PMID[538198]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 9660.51 nM PMID[538198]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 8629.79 nM PMID[538198]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 20892.96 nM PMID[538198]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 5559.04 nM PMID[538198]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 9099.13 nM PMID[538198]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 23120.65 nM PMID[538198]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 4395.42 nM PMID[538198]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 11534.53 nM PMID[538198]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 5395.11 nM PMID[538198]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 9225.71 nM PMID[538198]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 7244.36 nM PMID[538198]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 25003.45 nM PMID[538198]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 50000.0 nM PMID[538199]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 7943.28 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 8317.64 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 8709.64 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 20892.96 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 5370.32 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 22387.21 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 25118.86 nM PMID[538197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 4466.84 nM PMID[538197]
NPT2 Others Unspecified Selectivity Index > 4.2 n.a. PMID[538199]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC90 = 11900.0 nM PMID[538199]

☑ 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 NPC243834 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 NPC70956
0.9611 High Similarity NPC291535
0.9611 High Similarity NPC475085
0.9611 High Similarity NPC475112
0.9508 High Similarity NPC193777
0.9425 High Similarity NPC94943
0.9389 High Similarity NPC72211
0.9368 High Similarity NPC190007
0.9348 High Similarity NPC476106
0.933 High Similarity NPC131017
0.931 High Similarity NPC212535
0.9278 High Similarity NPC70259
0.9222 High Similarity NPC205934
0.9222 High Similarity NPC43787
0.9153 High Similarity NPC48353
0.9135 High Similarity NPC162484
0.9016 High Similarity NPC153042
0.8969 High Similarity NPC473179
0.8925 High Similarity NPC476044
0.8925 High Similarity NPC267423
0.8923 High Similarity NPC150239
0.8895 High Similarity NPC209769
0.8878 High Similarity NPC477532
0.8877 High Similarity NPC199277
0.8877 High Similarity NPC135887
0.8827 High Similarity NPC84478
0.8821 High Similarity NPC247803
0.8802 High Similarity NPC87413
0.88 High Similarity NPC474409
0.8796 High Similarity NPC201697
0.875 High Similarity NPC11464
0.8717 High Similarity NPC128823
0.8684 High Similarity NPC470930
0.867 High Similarity NPC329747
0.8657 High Similarity NPC473185
0.8646 High Similarity NPC39679
0.8646 High Similarity NPC475910
0.8646 High Similarity NPC470931
0.8636 High Similarity NPC174760
0.8634 High Similarity NPC246700
0.8632 High Similarity NPC223427
0.8614 High Similarity NPC252251
0.8603 High Similarity NPC88363
0.8603 High Similarity NPC72980
0.8594 High Similarity NPC4687
0.8594 High Similarity NPC249583
0.8564 High Similarity NPC310211
0.8564 High Similarity NPC308137
0.8533 High Similarity NPC242928
0.8529 High Similarity NPC477531
0.8528 High Similarity NPC3207
0.8513 High Similarity NPC23294
0.8485 Intermediate Similarity NPC169402
0.848 Intermediate Similarity NPC209174
0.8477 Intermediate Similarity NPC116238
0.8462 Intermediate Similarity NPC303951
0.8447 Intermediate Similarity NPC473182
0.8434 Intermediate Similarity NPC170114
0.8432 Intermediate Similarity NPC128751
0.8408 Intermediate Similarity NPC198503
0.8394 Intermediate Similarity NPC285558
0.8387 Intermediate Similarity NPC469497
0.8387 Intermediate Similarity NPC106833
0.8384 Intermediate Similarity NPC470549
0.8374 Intermediate Similarity NPC179287
0.8365 Intermediate Similarity NPC473187
0.8359 Intermediate Similarity NPC210828
0.8359 Intermediate Similarity NPC86834
0.8358 Intermediate Similarity NPC477533
0.835 Intermediate Similarity NPC46561
0.8333 Intermediate Similarity NPC471080
0.8333 Intermediate Similarity NPC202503
0.8333 Intermediate Similarity NPC469592
0.8325 Intermediate Similarity NPC473183
0.8317 Intermediate Similarity NPC473184
0.8308 Intermediate Similarity NPC213530
0.8308 Intermediate Similarity NPC193267
0.8281 Intermediate Similarity NPC11017
0.8261 Intermediate Similarity NPC176127
0.8238 Intermediate Similarity NPC6786
0.8238 Intermediate Similarity NPC232727
0.8216 Intermediate Similarity NPC62069
0.8207 Intermediate Similarity NPC474798
0.8201 Intermediate Similarity NPC141915
0.8201 Intermediate Similarity NPC114335
0.8201 Intermediate Similarity NPC280964
0.8191 Intermediate Similarity NPC316981
0.8182 Intermediate Similarity NPC46580
0.8182 Intermediate Similarity NPC199667
0.8168 Intermediate Similarity NPC13880
0.8168 Intermediate Similarity NPC469594
0.815 Intermediate Similarity NPC266931
0.815 Intermediate Similarity NPC478074
0.8131 Intermediate Similarity NPC473181
0.8128 Intermediate Similarity NPC208084
0.81 Intermediate Similarity NPC473180
0.809 Intermediate Similarity NPC167860
0.809 Intermediate Similarity NPC123976
0.8088 Intermediate Similarity NPC132642
0.8086 Intermediate Similarity NPC475253
0.8079 Intermediate Similarity NPC473041
0.8079 Intermediate Similarity NPC303658
0.8073 Intermediate Similarity NPC251090
0.8071 Intermediate Similarity NPC45190
0.8071 Intermediate Similarity NPC300156
0.8063 Intermediate Similarity NPC307963
0.8057 Intermediate Similarity NPC277351
0.8049 Intermediate Similarity NPC310118
0.8043 Intermediate Similarity NPC283152
0.8041 Intermediate Similarity NPC18487
0.8023 Intermediate Similarity NPC26850
0.801 Intermediate Similarity NPC99666
0.801 Intermediate Similarity NPC94157
0.801 Intermediate Similarity NPC294620
0.8 Intermediate Similarity NPC329793
0.8 Intermediate Similarity NPC86078
0.799 Intermediate Similarity NPC184408
0.799 Intermediate Similarity NPC306376
0.798 Intermediate Similarity NPC330009
0.798 Intermediate Similarity NPC183407
0.796 Intermediate Similarity NPC9894
0.796 Intermediate Similarity NPC208284
0.7955 Intermediate Similarity NPC26872
0.7946 Intermediate Similarity NPC96890
0.7923 Intermediate Similarity NPC280272
0.7906 Intermediate Similarity NPC76748
0.7905 Intermediate Similarity NPC274640
0.7885 Intermediate Similarity NPC51388
0.7884 Intermediate Similarity NPC473189
0.7876 Intermediate Similarity NPC475190
0.7874 Intermediate Similarity NPC280799
0.7874 Intermediate Similarity NPC60621
0.7865 Intermediate Similarity NPC92111
0.7861 Intermediate Similarity NPC469589
0.7857 Intermediate Similarity NPC110151
0.7854 Intermediate Similarity NPC314552
0.7854 Intermediate Similarity NPC305984
0.7853 Intermediate Similarity NPC296527
0.7843 Intermediate Similarity NPC118228
0.7842 Intermediate Similarity NPC204385
0.7838 Intermediate Similarity NPC312872
0.7837 Intermediate Similarity NPC144452
0.7826 Intermediate Similarity NPC225279
0.7822 Intermediate Similarity NPC471304
0.7817 Intermediate Similarity NPC121772
0.781 Intermediate Similarity NPC227908
0.7805 Intermediate Similarity NPC148183
0.7805 Intermediate Similarity NPC152768
0.7796 Intermediate Similarity NPC288943
0.7795 Intermediate Similarity NPC242209
0.7794 Intermediate Similarity NPC39500
0.7783 Intermediate Similarity NPC187501
0.7757 Intermediate Similarity NPC473105
0.775 Intermediate Similarity NPC137929
0.775 Intermediate Similarity NPC164374
0.7736 Intermediate Similarity NPC194740
0.7727 Intermediate Similarity NPC176538
0.7727 Intermediate Similarity NPC249040
0.7725 Intermediate Similarity NPC200888
0.7708 Intermediate Similarity NPC66083
0.77 Intermediate Similarity NPC134848
0.7696 Intermediate Similarity NPC42591
0.7696 Intermediate Similarity NPC11408
0.7696 Intermediate Similarity NPC314002
0.7692 Intermediate Similarity NPC106937
0.7688 Intermediate Similarity NPC34508
0.7681 Intermediate Similarity NPC293151
0.7665 Intermediate Similarity NPC89549
0.7656 Intermediate Similarity NPC171171
0.7656 Intermediate Similarity NPC160381
0.7653 Intermediate Similarity NPC326634
0.765 Intermediate Similarity NPC295898
0.7647 Intermediate Similarity NPC475666
0.7644 Intermediate Similarity NPC204717
0.7644 Intermediate Similarity NPC96321
0.7633 Intermediate Similarity NPC74969
0.7632 Intermediate Similarity NPC206201
0.763 Intermediate Similarity NPC211416
0.7626 Intermediate Similarity NPC217554
0.7602 Intermediate Similarity NPC279401
0.7602 Intermediate Similarity NPC79293
0.7602 Intermediate Similarity NPC81939
0.7596 Intermediate Similarity NPC177404
0.7596 Intermediate Similarity NPC16667
0.7594 Intermediate Similarity NPC21638
0.7592 Intermediate Similarity NPC220765
0.759 Intermediate Similarity NPC469390
0.7589 Intermediate Similarity NPC473188
0.7586 Intermediate Similarity NPC321428
0.7586 Intermediate Similarity NPC283117
0.7583 Intermediate Similarity NPC162748
0.7581 Intermediate Similarity NPC474688
0.7581 Intermediate Similarity NPC474701
0.7579 Intermediate Similarity NPC478032
0.7576 Intermediate Similarity NPC77555
0.7576 Intermediate Similarity NPC224928
0.7573 Intermediate Similarity NPC202605
0.7573 Intermediate Similarity NPC112206
0.757 Intermediate Similarity NPC471762
0.7565 Intermediate Similarity NPC61350

  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 NPC243834 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
0.8542 High Similarity NPD3003 Approved
0.8359 Intermediate Similarity NPD5658 Approved
0.8229 Intermediate Similarity NPD1768 Approved
0.82 Intermediate Similarity NPD5902 Approved
0.82 Intermediate Similarity NPD5903 Approved
0.8135 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD1038 Approved
0.798 Intermediate Similarity NPD5612 Discontinued
0.7967 Intermediate Similarity NPD1325 Approved
0.7967 Intermediate Similarity NPD1326 Approved
0.794 Intermediate Similarity NPD1392 Approved
0.7927 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD7558 Phase 2
0.7902 Intermediate Similarity NPD6985 Discontinued
0.7876 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7868 Intermediate Similarity NPD4511 Phase 1
0.7864 Intermediate Similarity NPD7194 Discontinued
0.7854 Intermediate Similarity NPD5164 Discontinued
0.785 Intermediate Similarity NPD7222 Phase 2
0.785 Intermediate Similarity NPD7453 Approved
0.785 Intermediate Similarity NPD7452 Approved
0.7846 Intermediate Similarity NPD7948 Phase 1
0.7789 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7783 Intermediate Similarity NPD5067 Phase 2
0.7783 Intermediate Similarity NPD5066 Phase 2
0.7744 Intermediate Similarity NPD4418 Discontinued
0.7744 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7729 Intermediate Similarity NPD5632 Approved
0.7713 Intermediate Similarity NPD3920 Phase 2
0.7711 Intermediate Similarity NPD8403 Phase 1
0.7711 Intermediate Similarity NPD5530 Phase 1
0.7692 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD802 Phase 2
0.7676 Intermediate Similarity NPD4724 Clinical (unspecified phase)
0.7653 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD4203 Approved
0.7632 Intermediate Similarity NPD4204 Approved
0.761 Intermediate Similarity NPD4502 Phase 2
0.761 Intermediate Similarity NPD6220 Phase 3
0.7596 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD3825 Phase 3
0.7583 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7563 Intermediate Similarity NPD6590 Discontinued
0.7549 Intermediate Similarity NPD2916 Discontinued
0.7525 Intermediate Similarity NPD5512 Phase 3
0.75 Intermediate Similarity NPD8395 Approved
0.75 Intermediate Similarity NPD3814 Phase 1
0.75 Intermediate Similarity NPD5913 Phase 3
0.75 Intermediate Similarity NPD7221 Approved
0.75 Intermediate Similarity NPD8396 Approved
0.75 Intermediate Similarity NPD7219 Approved
0.75 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD4795 Phase 2
0.7487 Intermediate Similarity NPD5003 Discontinued
0.7431 Intermediate Similarity NPD6494 Phase 2
0.7418 Intermediate Similarity NPD5617 Suspended
0.7407 Intermediate Similarity NPD7555 Discontinued
0.7406 Intermediate Similarity NPD5930 Phase 3
0.7387 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD2189 Approved
0.7379 Intermediate Similarity NPD2187 Approved
0.7376 Intermediate Similarity NPD1739 Approved
0.7376 Intermediate Similarity NPD1740 Approved
0.7366 Intermediate Similarity NPD4349 Approved
0.7366 Intermediate Similarity NPD4350 Approved
0.7366 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD4305 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD2727 Phase 2
0.736 Intermediate Similarity NPD2564 Approved
0.736 Intermediate Similarity NPD2565 Phase 2
0.7358 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD6473 Phase 1
0.7344 Intermediate Similarity NPD7479 Phase 2
0.734 Intermediate Similarity NPD1921 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD1954 Phase 1
0.7336 Intermediate Similarity NPD6736 Discontinued
0.7336 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD5429 Discontinued
0.7324 Intermediate Similarity NPD6242 Discontinued
0.7321 Intermediate Similarity NPD7069 Discontinued
0.7321 Intermediate Similarity NPD3330 Phase 1
0.7321 Intermediate Similarity NPD2794 Discontinued
0.7321 Intermediate Similarity NPD3816 Phase 1
0.7321 Intermediate Similarity NPD3815 Phase 1
0.7296 Intermediate Similarity NPD5256 Discontinued
0.7295 Intermediate Similarity NPD7672 Approved
0.7295 Intermediate Similarity NPD7671 Approved
0.7288 Intermediate Similarity NPD8364 Approved
0.7288 Intermediate Similarity NPD8363 Approved
0.7286 Intermediate Similarity NPD6569 Phase 2
0.7286 Intermediate Similarity NPD3924 Approved
0.7286 Intermediate Similarity NPD3922 Approved
0.7286 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD3923 Approved
0.7286 Intermediate Similarity NPD3921 Approved
0.7281 Intermediate Similarity NPD3259 Approved
0.7277 Intermediate Similarity NPD3875 Discontinued
0.7273 Intermediate Similarity NPD5939 Approved
0.7273 Intermediate Similarity NPD5936 Approved
0.7268 Intermediate Similarity NPD6991 Approved
0.7265 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD6962 Phase 2
0.7259 Intermediate Similarity NPD2749 Discontinued
0.7259 Intermediate Similarity NPD2383 Phase 1
0.7254 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD2177 Approved
0.7241 Intermediate Similarity NPD2176 Approved
0.7241 Intermediate Similarity NPD2175 Phase 3
0.7233 Intermediate Similarity NPD3397 Phase 2
0.7232 Intermediate Similarity NPD6790 Phase 1
0.7231 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6988 Phase 1
0.7227 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD4885 Approved
0.722 Intermediate Similarity NPD6975 Discontinued
0.7219 Intermediate Similarity NPD1684 Approved
0.7219 Intermediate Similarity NPD1685 Approved
0.7214 Intermediate Similarity NPD6251 Discontinued
0.7202 Intermediate Similarity NPD6159 Phase 2
0.7198 Intermediate Similarity NPD6150 Discontinued
0.7195 Intermediate Similarity NPD4373 Phase 2
0.7189 Intermediate Similarity NPD6246 Approved
0.7188 Intermediate Similarity NPD5065 Approved
0.7184 Intermediate Similarity NPD6324 Phase 1
0.7179 Intermediate Similarity NPD3037 Phase 1
0.7178 Intermediate Similarity NPD6550 Discontinued
0.7169 Intermediate Similarity NPD5559 Phase 2
0.7165 Intermediate Similarity NPD8386 Phase 2
0.7165 Intermediate Similarity NPD1503 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD4463 Approved
0.7158 Intermediate Similarity NPD4462 Approved
0.7157 Intermediate Similarity NPD2151 Approved
0.7151 Intermediate Similarity NPD1592 Phase 3
0.7143 Intermediate Similarity NPD2952 Discontinued
0.7136 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD4952 Phase 3
0.7129 Intermediate Similarity NPD3791 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD484 Approved
0.7121 Intermediate Similarity NPD4375 Approved
0.712 Intermediate Similarity NPD2882 Phase 1
0.712 Intermediate Similarity NPD814 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD3763 Approved
0.7116 Intermediate Similarity NPD3402 Phase 1
0.7116 Intermediate Similarity NPD3258 Approved
0.7115 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD5416 Discontinued
0.7107 Intermediate Similarity NPD8428 Approved
0.7107 Intermediate Similarity NPD8467 Approved
0.7107 Intermediate Similarity NPD8427 Approved
0.7107 Intermediate Similarity NPD8465 Approved
0.7107 Intermediate Similarity NPD8466 Approved
0.7107 Intermediate Similarity NPD8429 Approved
0.71 Intermediate Similarity NPD3342 Phase 2
0.7094 Intermediate Similarity NPD3127 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD5140 Approved
0.709 Intermediate Similarity NPD5138 Approved
0.7087 Intermediate Similarity NPD5482 Discontinued
0.7085 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7082 Intermediate Similarity NPD8244 Phase 2
0.7081 Intermediate Similarity NPD6290 Phase 2
0.7079 Intermediate Similarity NPD4590 Approved
0.7079 Intermediate Similarity NPD4591 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD8358 Approved
0.7071 Intermediate Similarity NPD4889 Approved
0.707 Intermediate Similarity NPD3354 Phase 2
0.7068 Intermediate Similarity NPD2844 Phase 3
0.7067 Intermediate Similarity NPD5901 Discontinued
0.7065 Intermediate Similarity NPD3835 Phase 3
0.7065 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD3833 Phase 3
0.7062 Intermediate Similarity NPD4354 Approved
0.7059 Intermediate Similarity NPD8512 Phase 3
0.7059 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD6208 Discontinued
0.7045 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD5488 Discontinued
0.703 Intermediate Similarity NPD3404 Approved
0.703 Intermediate Similarity NPD3963 Phase 1
0.7027 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6158 Phase 2
0.7021 Intermediate Similarity NPD7956 Approved
0.7021 Intermediate Similarity NPD7955 Approved
0.7017 Intermediate Similarity NPD8284 Discontinued
0.7009 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD7417 Discontinued
0.6995 Remote Similarity NPD6202 Discontinued
0.6995 Remote Similarity NPD4083 Discontinued
0.6992 Remote Similarity NPD8459 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