Structure

Physi-Chem Properties

Molecular Weight:  256.18
Volume:  304.299
LogP:  5.395
LogD:  4.322
LogS:  -4.272
# Rotatable Bonds:  6
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.681
Synthetic Accessibility Score:  3.363
Fsp3:  0.333
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:  -4.617
MDCK Permeability:  3.0163231713231653e-05
Pgp-inhibitor:  0.762
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.083
30% Bioavailability (F30%):  0.12

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.06
Plasma Protein Binding (PPB):  99.1821060180664%
Volume Distribution (VD):  3.598
Pgp-substrate:  2.903329610824585%

ADMET: Metabolism

CYP1A2-inhibitor:  0.94
CYP1A2-substrate:  0.157
CYP2C19-inhibitor:  0.914
CYP2C19-substrate:  0.405
CYP2C9-inhibitor:  0.62
CYP2C9-substrate:  0.883
CYP2D6-inhibitor:  0.942
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.915
CYP3A4-substrate:  0.312

ADMET: Excretion

Clearance (CL):  14.169
Half-life (T1/2):  0.44

ADMET: Toxicity

hERG Blockers:  0.24
Human Hepatotoxicity (H-HT):  0.561
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.142
Maximum Recommended Daily Dose:  0.24
Skin Sensitization:  0.952
Carcinogencity:  0.205
Eye Corrosion:  0.137
Eye Irritation:  0.779
Respiratory Toxicity:  0.729

Download Data

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

  Natural Product: NPC98772

Natural Product ID:  NPC98772
Common Name*:   Bakuchiol
IUPAC Name:   4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
Synonyms:   (S)-Bakuchiol; Bakuchiol
Standard InCHIKey:  LFYJSSARVMHQJB-QIXNEVBVSA-N
Standard InCHI:  InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1
SMILES:  C=C[C@@](/C=C/c1ccc(cc1)O)(CCC=C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL262344
PubChem CID:   5468522
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota seeds n.a. n.a. PMID[18359631]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. fruit n.a. PMID[20663508]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24507928]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota Fruits n.a. n.a. PMID[25710081]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[3069958]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. seed n.a. PMID[8759164]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9544566]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26610 Spiraea formosana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18535 Psoralea drupacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18535 Psoralea drupacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28809 Cullen corylifolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26610 Spiraea formosana Species Rosaceae 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
NPT196 Cell Line AGS Homo sapiens IC50 = 15300.0 nM PMID[476631]
NPT165 Cell Line HeLa Homo sapiens IC50 = 11000.0 nM PMID[476631]
NPT382 Cell Line OVCAR-5 Homo sapiens GI = 66.0 % PMID[476635]
NPT744 Cell Line IMR-32 Homo sapiens GI = 58.0 % PMID[476635]
NPT165 Cell Line HeLa Homo sapiens GI = 55.0 % PMID[476635]
NPT1970 Cell Line THP-1 Homo sapiens GI = 74.0 % PMID[476635]
NPT83 Cell Line MCF7 Homo sapiens GI = 33.0 % PMID[476635]
NPT81 Cell Line A549 Homo sapiens GI = 30.0 % PMID[476635]
NPT306 Cell Line PC-3 Homo sapiens GI = 21.0 % PMID[476635]
NPT382 Cell Line OVCAR-5 Homo sapiens GI = 25.0 % PMID[476635]
NPT744 Cell Line IMR-32 Homo sapiens GI = 31.0 % PMID[476635]
NPT165 Cell Line HeLa Homo sapiens GI = 20.0 % PMID[476635]
NPT1970 Cell Line THP-1 Homo sapiens GI = 44.0 % PMID[476635]
NPT1171 Cell Line HEp-2 Homo sapiens GI = 53.0 % PMID[476635]
NPT1171 Cell Line HEp-2 Homo sapiens GI = 20.0 % PMID[476635]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 8290000.0 nM PMID[476635]
NPT396 Cell Line T47D Homo sapiens IC50 = 28900.0 nM PMID[476635]
NPT81 Cell Line A549 Homo sapiens GI = 63.0 % PMID[476635]
NPT83 Cell Line MCF7 Homo sapiens GI = 63.0 % PMID[476635]
NPT306 Cell Line PC-3 Homo sapiens GI = 58.0 % PMID[476635]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 18535.32 nM PMID[476636]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 17258.38 nM PMID[476636]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 10592.54 nM PMID[476636]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 16710.91 nM PMID[476636]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 16519.62 nM PMID[476636]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 17660.38 nM PMID[476636]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 14125.38 nM PMID[476636]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 13182.57 nM PMID[476636]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 16032.45 nM PMID[476636]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 15703.63 nM PMID[476636]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 21232.44 nM PMID[476636]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 18281.0 nM PMID[476636]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 13091.82 nM PMID[476636]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 16180.8 nM PMID[476636]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 19054.61 nM PMID[476636]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 16943.38 nM PMID[476636]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 16943.38 nM PMID[476636]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 19186.69 nM PMID[476636]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 18620.87 nM PMID[476636]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 19054.61 nM PMID[476636]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 16481.62 nM PMID[476636]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 17060.82 nM PMID[476636]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 16982.44 nM PMID[476636]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 17139.57 nM PMID[476636]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 19142.56 nM PMID[476636]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 14927.94 nM PMID[476636]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 13995.87 nM PMID[476636]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 18238.96 nM PMID[476636]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 22029.26 nM PMID[476636]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 20558.91 nM PMID[476636]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 17823.79 nM PMID[476636]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 13963.68 nM PMID[476636]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 18113.4 nM PMID[476636]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16826.74 nM PMID[476636]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 16788.04 nM PMID[476636]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 19543.39 nM PMID[476636]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 16255.49 nM PMID[476636]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 15595.53 nM PMID[476636]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 14028.14 nM PMID[476636]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 18578.04 nM PMID[476636]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 20183.66 nM PMID[476636]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 18197.01 nM PMID[476636]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 15812.48 nM PMID[476636]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 20941.12 nM PMID[476636]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 17660.38 nM PMID[476636]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 14757.07 nM PMID[476636]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 16481.62 nM PMID[476636]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 18967.06 nM PMID[476636]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 19952.62 nM PMID[476636]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 17660.38 nM PMID[476636]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -7.92 % PMID[476637]
NPT65 Cell Line HepG2 Homo sapiens EC50 > 52083.3 nM PMID[476638]
NPT80 Cell Line Raji Homo sapiens EC50 > 26041.7 nM PMID[476638]
NPT15 Cell Line Jurkat Homo sapiens EC50 > 49019.6 nM PMID[476638]
NPT1160 Cell Line BJ Homo sapiens EC50 > 36630.0 nM PMID[476638]
NPT71 Cell Line HEK293 Homo sapiens EC50 > 36630.0 nM PMID[476638]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 19000.0 nM PMID[476628]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 10000.0 nM PMID[476628]
NPT19 Organism Escherichia coli Escherichia coli MIC > 780000.0 nM PMID[476628]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 780000.0 nM PMID[476628]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -14.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -27.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -18.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -21.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -39.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -32.0 % PMID[476629]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -19.0 % PMID[476630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -45.0 % PMID[476630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -100.0 % PMID[476630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -26.0 % PMID[476630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -99.0 % PMID[476630]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = -42.0 % PMID[476630]
NPT21802 PROTEIN FAMILY Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 6100.0 nM PMID[476631]
NPT2 Others Unspecified IC50 = 6900.0 nM PMID[476631]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition < 30.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition < 20.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 81.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 84.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 91.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 0.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 43.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 28.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 92.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 79.0 % PMID[476632]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 75.0 % PMID[476632]
NPT1484 Organism Fusobacterium nucleatum Fusobacterium nucleatum MIC = 32.0 ug.mL-1 PMID[476634]
NPT1172 Organism Streptococcus sanguinis Streptococcus sanguinis MBC = 2.0 ug ml-1 PMID[476634]
NPT1172 Organism Streptococcus sanguinis Streptococcus sanguinis MIC = 1.0 ug.mL-1 PMID[476634]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC = 2.0 ug ml-1 PMID[476634]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus MIC = 1.0 ug.mL-1 PMID[476634]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus MBC = 2.0 ug ml-1 PMID[476634]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC = 1.0 ug.mL-1 PMID[476634]
NPT1484 Organism Fusobacterium nucleatum Fusobacterium nucleatum MBC = 64.0 ug ml-1 PMID[476634]
NPT1128 Organism Prevotella intermedia Prevotella intermedia MIC = 1.0 ug.mL-1 PMID[476634]
NPT1128 Organism Prevotella intermedia Prevotella intermedia MBC = 2.0 ug ml-1 PMID[476634]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis MIC = 1.0 ug.mL-1 PMID[476634]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis MBC = 1.0 ug ml-1 PMID[476634]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBIC50 = 4.0 ug ml-1 PMID[476634]
NPT878 Organism Streptococcus mutans Streptococcus mutans Activity > 80.0 % PMID[476634]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 13.38 % PMID[476637]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 15286.6 nM PMID[476638]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 38000.0 nM PMID[476638]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 2.33 % PMID[476639]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 4.323 % PMID[476640]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.02 % PMID[476641]
NPT20972 CELL-LINE SU.86.86 Homo sapiens Activity > 20.0 % PMID[476642]

☑ 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 NPC98772 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9767 High Similarity NPC270547
0.9762 High Similarity NPC184169
0.9535 High Similarity NPC280347
0.9535 High Similarity NPC177420
0.9524 High Similarity NPC248817
0.9425 High Similarity NPC55561
0.9419 High Similarity NPC113460
0.9419 High Similarity NPC25493
0.9412 High Similarity NPC197783
0.9405 High Similarity NPC265146
0.9405 High Similarity NPC124436
0.9326 High Similarity NPC27323
0.9326 High Similarity NPC316301
0.9318 High Similarity NPC155908
0.931 High Similarity NPC242240
0.931 High Similarity NPC123273
0.931 High Similarity NPC318325
0.9302 High Similarity NPC23167
0.9294 High Similarity NPC175313
0.9091 High Similarity NPC258219
0.9032 High Similarity NPC225506
0.9022 High Similarity NPC225464
0.9011 High Similarity NPC26244
0.8977 High Similarity NPC104216
0.8936 High Similarity NPC471578
0.8936 High Similarity NPC101025
0.8936 High Similarity NPC472585
0.8925 High Similarity NPC252821
0.8925 High Similarity NPC122005
0.8925 High Similarity NPC92730
0.8913 High Similarity NPC473388
0.8901 High Similarity NPC151715
0.8901 High Similarity NPC152415
0.8889 High Similarity NPC304541
0.8889 High Similarity NPC204210
0.8889 High Similarity NPC306074
0.8864 High Similarity NPC307235
0.8864 High Similarity NPC407
0.8851 High Similarity NPC286904
0.8851 High Similarity NPC150837
0.8842 High Similarity NPC62351
0.8804 High Similarity NPC144682
0.8791 High Similarity NPC181709
0.8791 High Similarity NPC210497
0.8791 High Similarity NPC162314
0.8791 High Similarity NPC94139
0.8791 High Similarity NPC3358
0.8791 High Similarity NPC147284
0.8791 High Similarity NPC306884
0.8791 High Similarity NPC55903
0.8791 High Similarity NPC138117
0.8791 High Similarity NPC325292
0.8778 High Similarity NPC300017
0.8778 High Similarity NPC192
0.8764 High Similarity NPC27974
0.875 High Similarity NPC155393
0.871 High Similarity NPC132271
0.871 High Similarity NPC292730
0.871 High Similarity NPC82664
0.871 High Similarity NPC216520
0.8696 High Similarity NPC289769
0.8681 High Similarity NPC45040
0.8667 High Similarity NPC70436
0.8632 High Similarity NPC211885
0.8617 High Similarity NPC77492
0.8617 High Similarity NPC201967
0.8602 High Similarity NPC222146
0.8602 High Similarity NPC313650
0.8602 High Similarity NPC8392
0.8571 High Similarity NPC300478
0.8571 High Similarity NPC477814
0.8556 High Similarity NPC19680
0.8542 High Similarity NPC252105
0.8526 High Similarity NPC78119
0.8526 High Similarity NPC130193
0.8526 High Similarity NPC128723
0.8526 High Similarity NPC132078
0.8526 High Similarity NPC216468
0.8526 High Similarity NPC299762
0.8526 High Similarity NPC33675
0.8526 High Similarity NPC51333
0.8495 Intermediate Similarity NPC76938
0.8495 Intermediate Similarity NPC81010
0.8495 Intermediate Similarity NPC32977
0.8495 Intermediate Similarity NPC471581
0.8495 Intermediate Similarity NPC128062
0.8478 Intermediate Similarity NPC231150
0.8454 Intermediate Similarity NPC196479
0.8438 Intermediate Similarity NPC213730
0.8421 Intermediate Similarity NPC152097
0.8421 Intermediate Similarity NPC260000
0.8421 Intermediate Similarity NPC475078
0.8404 Intermediate Similarity NPC274678
0.8404 Intermediate Similarity NPC286006
0.8404 Intermediate Similarity NPC32714
0.8404 Intermediate Similarity NPC107522
0.837 Intermediate Similarity NPC151764
0.8367 Intermediate Similarity NPC120719
0.8351 Intermediate Similarity NPC40258
0.8351 Intermediate Similarity NPC7686
0.8351 Intermediate Similarity NPC91461
0.8333 Intermediate Similarity NPC80027
0.8333 Intermediate Similarity NPC171843
0.8333 Intermediate Similarity NPC280869
0.8333 Intermediate Similarity NPC260775
0.8316 Intermediate Similarity NPC202986
0.8298 Intermediate Similarity NPC245187
0.8283 Intermediate Similarity NPC233396
0.8283 Intermediate Similarity NPC99557
0.8283 Intermediate Similarity NPC219286
0.8283 Intermediate Similarity NPC154899
0.8283 Intermediate Similarity NPC47284
0.8283 Intermediate Similarity NPC138942
0.8265 Intermediate Similarity NPC168829
0.8265 Intermediate Similarity NPC68269
0.8247 Intermediate Similarity NPC155847
0.8247 Intermediate Similarity NPC130756
0.8247 Intermediate Similarity NPC12931
0.8247 Intermediate Similarity NPC129373
0.8247 Intermediate Similarity NPC48730
0.8247 Intermediate Similarity NPC166761
0.8247 Intermediate Similarity NPC253746
0.8247 Intermediate Similarity NPC248396
0.8247 Intermediate Similarity NPC70677
0.8247 Intermediate Similarity NPC289381
0.8235 Intermediate Similarity NPC13482
0.8235 Intermediate Similarity NPC222905
0.8229 Intermediate Similarity NPC6597
0.8229 Intermediate Similarity NPC32674
0.8229 Intermediate Similarity NPC474073
0.8229 Intermediate Similarity NPC79241
0.8229 Intermediate Similarity NPC109955
0.8229 Intermediate Similarity NPC107619
0.8218 Intermediate Similarity NPC470039
0.82 Intermediate Similarity NPC53740
0.82 Intermediate Similarity NPC135464
0.82 Intermediate Similarity NPC92623
0.82 Intermediate Similarity NPC113457
0.82 Intermediate Similarity NPC231705
0.82 Intermediate Similarity NPC271274
0.82 Intermediate Similarity NPC155072
0.8191 Intermediate Similarity NPC29373
0.8191 Intermediate Similarity NPC271440
0.8182 Intermediate Similarity NPC288411
0.8182 Intermediate Similarity NPC8931
0.8182 Intermediate Similarity NPC261573
0.8182 Intermediate Similarity NPC120693
0.8172 Intermediate Similarity NPC47950
0.8172 Intermediate Similarity NPC312304
0.8163 Intermediate Similarity NPC80800
0.8155 Intermediate Similarity NPC322753
0.8155 Intermediate Similarity NPC139946
0.8144 Intermediate Similarity NPC131587
0.8144 Intermediate Similarity NPC275104
0.8144 Intermediate Similarity NPC125732
0.8144 Intermediate Similarity NPC245561
0.8144 Intermediate Similarity NPC471576
0.8125 Intermediate Similarity NPC312132
0.8125 Intermediate Similarity NPC259512
0.8119 Intermediate Similarity NPC320439
0.8119 Intermediate Similarity NPC142297
0.81 Intermediate Similarity NPC303141
0.81 Intermediate Similarity NPC243677
0.81 Intermediate Similarity NPC474839
0.8095 Intermediate Similarity NPC100980
0.8081 Intermediate Similarity NPC249828
0.8081 Intermediate Similarity NPC135784
0.8081 Intermediate Similarity NPC108497
0.8081 Intermediate Similarity NPC313030
0.8081 Intermediate Similarity NPC71002
0.8081 Intermediate Similarity NPC85479
0.8081 Intermediate Similarity NPC304638
0.8081 Intermediate Similarity NPC106396
0.8081 Intermediate Similarity NPC269212
0.8081 Intermediate Similarity NPC242342
0.8081 Intermediate Similarity NPC146798
0.8081 Intermediate Similarity NPC178902
0.8081 Intermediate Similarity NPC302219
0.8081 Intermediate Similarity NPC53051
0.8081 Intermediate Similarity NPC222522
0.8081 Intermediate Similarity NPC24404
0.8081 Intermediate Similarity NPC192596
0.8081 Intermediate Similarity NPC94351
0.8081 Intermediate Similarity NPC168303
0.8077 Intermediate Similarity NPC250323
0.8077 Intermediate Similarity NPC228425
0.8065 Intermediate Similarity NPC259134
0.8065 Intermediate Similarity NPC177844
0.8065 Intermediate Similarity NPC99886
0.8065 Intermediate Similarity NPC8002
0.8061 Intermediate Similarity NPC223393
0.8061 Intermediate Similarity NPC52472
0.8061 Intermediate Similarity NPC161571
0.8061 Intermediate Similarity NPC294741
0.8061 Intermediate Similarity NPC248573
0.8061 Intermediate Similarity NPC275053
0.8061 Intermediate Similarity NPC72729
0.8061 Intermediate Similarity NPC10588
0.8058 Intermediate Similarity NPC141782
0.8039 Intermediate Similarity NPC317305

  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 NPC98772 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
0.9405 High Similarity NPD111 Approved
0.9326 High Similarity NPD1432 Clinical (unspecified phase)
0.9111 High Similarity NPD2934 Approved
0.9111 High Similarity NPD2933 Approved
0.9011 High Similarity NPD2860 Approved
0.9011 High Similarity NPD2859 Approved
0.8804 High Similarity NPD1809 Phase 2
0.8723 High Similarity NPD3020 Approved
0.8404 Intermediate Similarity NPD844 Approved
0.8387 Intermediate Similarity NPD845 Approved
0.8351 Intermediate Similarity NPD846 Approved
0.8351 Intermediate Similarity NPD940 Approved
0.8247 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD288 Approved
0.8095 Intermediate Similarity NPD9087 Approved
0.8061 Intermediate Similarity NPD1242 Phase 1
0.8 Intermediate Similarity NPD9610 Approved
0.8 Intermediate Similarity NPD9608 Approved
0.7961 Intermediate Similarity NPD3022 Approved
0.7961 Intermediate Similarity NPD3021 Approved
0.7879 Intermediate Similarity NPD3028 Approved
0.781 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD9088 Approved
0.767 Intermediate Similarity NPD1444 Approved
0.767 Intermediate Similarity NPD1445 Approved
0.7664 Intermediate Similarity NPD2229 Approved
0.7664 Intermediate Similarity NPD2234 Approved
0.7664 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD2228 Approved
0.7636 Intermediate Similarity NPD3091 Approved
0.7614 Intermediate Similarity NPD9294 Approved
0.7549 Intermediate Similarity NPD9500 Approved
0.7524 Intermediate Similarity NPD2684 Approved
0.75 Intermediate Similarity NPD9273 Approved
0.75 Intermediate Similarity NPD4589 Approved
0.75 Intermediate Similarity NPD3019 Approved
0.75 Intermediate Similarity NPD4059 Approved
0.75 Intermediate Similarity NPD2932 Approved
0.7477 Intermediate Similarity NPD228 Approved
0.7453 Intermediate Similarity NPD1792 Phase 2
0.7453 Intermediate Similarity NPD4750 Phase 3
0.7453 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1791 Approved
0.7431 Intermediate Similarity NPD1793 Approved
0.7391 Intermediate Similarity NPD9089 Approved
0.7368 Intermediate Similarity NPD3092 Approved
0.7364 Intermediate Similarity NPD7157 Approved
0.7345 Intermediate Similarity NPD1751 Approved
0.7333 Intermediate Similarity NPD968 Approved
0.7333 Intermediate Similarity NPD3134 Approved
0.7321 Intermediate Similarity NPD5304 Approved
0.7321 Intermediate Similarity NPD5303 Approved
0.7283 Intermediate Similarity NPD9093 Approved
0.7264 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD2342 Discontinued
0.7257 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD1357 Approved
0.7257 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD4093 Discontinued
0.7248 Intermediate Similarity NPD7843 Approved
0.7248 Intermediate Similarity NPD821 Approved
0.7248 Intermediate Similarity NPD7635 Approved
0.7248 Intermediate Similarity NPD9379 Approved
0.7248 Intermediate Similarity NPD9377 Approved
0.7232 Intermediate Similarity NPD16 Approved
0.7232 Intermediate Similarity NPD856 Approved
0.7216 Intermediate Similarity NPD9295 Approved
0.7207 Intermediate Similarity NPD255 Approved
0.7207 Intermediate Similarity NPD6671 Approved
0.7207 Intermediate Similarity NPD256 Approved
0.7193 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD3095 Discontinued
0.7158 Intermediate Similarity NPD9073 Approved
0.713 Intermediate Similarity NPD3421 Phase 3
0.713 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD3143 Discontinued
0.713 Intermediate Similarity NPD5451 Approved
0.7119 Intermediate Similarity NPD3094 Phase 2
0.7103 Intermediate Similarity NPD1358 Approved
0.7103 Intermediate Similarity NPD290 Approved
0.708 Intermediate Similarity NPD317 Approved
0.708 Intermediate Similarity NPD318 Approved
0.7069 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2195 Approved
0.7059 Intermediate Similarity NPD2194 Approved
0.7018 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7330 Discontinued
0.7018 Intermediate Similarity NPD9545 Approved
0.7009 Intermediate Similarity NPD2561 Approved
0.7009 Intermediate Similarity NPD3070 Discontinued
0.7009 Intermediate Similarity NPD2562 Approved
0.7 Intermediate Similarity NPD5736 Approved
0.7 Intermediate Similarity NPD3637 Approved
0.7 Intermediate Similarity NPD3635 Approved
0.7 Intermediate Similarity NPD3636 Approved
0.6991 Remote Similarity NPD9568 Approved
0.6964 Remote Similarity NPD475 Phase 2
0.6964 Remote Similarity NPD9618 Approved
0.6964 Remote Similarity NPD9614 Approved
0.6949 Remote Similarity NPD4659 Approved
0.6949 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6949 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6583 Phase 3
0.6949 Remote Similarity NPD6582 Phase 2
0.6942 Remote Similarity NPD2606 Approved
0.6942 Remote Similarity NPD2605 Approved
0.6939 Remote Similarity NPD9094 Approved
0.6937 Remote Similarity NPD5535 Approved
0.6897 Remote Similarity NPD2667 Approved
0.6897 Remote Similarity NPD2668 Approved
0.6897 Remote Similarity NPD2286 Discontinued
0.6897 Remote Similarity NPD4626 Approved
0.6885 Remote Similarity NPD5156 Approved
0.6885 Remote Similarity NPD5155 Approved
0.6881 Remote Similarity NPD74 Approved
0.6881 Remote Similarity NPD9266 Approved
0.6875 Remote Similarity NPD5283 Phase 1
0.687 Remote Similarity NPD1548 Phase 1
0.6863 Remote Similarity NPD9296 Approved
0.6842 Remote Similarity NPD9493 Approved
0.6842 Remote Similarity NPD7636 Approved
0.6838 Remote Similarity NPD3023 Approved
0.6838 Remote Similarity NPD3847 Discontinued
0.6838 Remote Similarity NPD3026 Approved
0.6833 Remote Similarity NPD3053 Approved
0.6833 Remote Similarity NPD4103 Phase 2
0.6833 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6833 Remote Similarity NPD3055 Approved
0.6833 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6822 Remote Similarity NPD9244 Approved
0.6814 Remote Similarity NPD1476 Clinical (unspecified phase)
0.681 Remote Similarity NPD3024 Approved
0.681 Remote Similarity NPD3025 Approved
0.6807 Remote Similarity NPD1755 Approved
0.6803 Remote Similarity NPD3595 Approved
0.6803 Remote Similarity NPD3594 Approved
0.6792 Remote Similarity NPD4817 Approved
0.6792 Remote Similarity NPD4818 Approved
0.6789 Remote Similarity NPD9263 Approved
0.6789 Remote Similarity NPD9267 Approved
0.6789 Remote Similarity NPD9264 Approved
0.6783 Remote Similarity NPD9616 Approved
0.6783 Remote Similarity NPD9615 Approved
0.6783 Remote Similarity NPD9613 Approved
0.678 Remote Similarity NPD422 Phase 1
0.6777 Remote Similarity NPD7451 Discontinued
0.6777 Remote Similarity NPD4624 Approved
0.6777 Remote Similarity NPD6584 Phase 3
0.6774 Remote Similarity NPD6663 Approved
0.6752 Remote Similarity NPD1778 Approved
0.6752 Remote Similarity NPD9384 Approved
0.6752 Remote Similarity NPD9381 Approved
0.675 Remote Similarity NPD5310 Approved
0.675 Remote Similarity NPD5311 Approved
0.6729 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6724 Remote Similarity NPD316 Approved
0.6724 Remote Similarity NPD1759 Phase 1
0.6723 Remote Similarity NPD2337 Clinical (unspecified phase)
0.6721 Remote Similarity NPD4208 Discontinued
0.6721 Remote Similarity NPD4212 Discontinued
0.6696 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6696 Remote Similarity NPD3596 Phase 2
0.6695 Remote Similarity NPD1981 Approved
0.6695 Remote Similarity NPD1980 Approved
0.6695 Remote Similarity NPD1671 Clinical (unspecified phase)
0.6695 Remote Similarity NPD1983 Approved
0.6695 Remote Similarity NPD3496 Discontinued
0.6694 Remote Similarity NPD1133 Approved
0.6694 Remote Similarity NPD1134 Approved
0.6694 Remote Similarity NPD1135 Approved
0.6694 Remote Similarity NPD1131 Approved
0.6694 Remote Similarity NPD1129 Approved
0.6667 Remote Similarity NPD4908 Phase 1
0.6667 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4207 Discontinued
0.6667 Remote Similarity NPD3685 Discontinued
0.6667 Remote Similarity NPD159 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9612 Approved
0.6667 Remote Similarity NPD9611 Approved
0.6667 Remote Similarity NPD9622 Approved
0.6667 Remote Similarity NPD9609 Approved
0.6639 Remote Similarity NPD1610 Phase 2
0.6639 Remote Similarity NPD1535 Discovery
0.6638 Remote Similarity NPD1758 Phase 1
0.6638 Remote Similarity NPD5536 Phase 2
0.6636 Remote Similarity NPD854 Approved
0.6636 Remote Similarity NPD855 Approved
0.6633 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6613 Remote Similarity NPD3027 Phase 3
0.6613 Remote Similarity NPD7095 Approved
0.6613 Remote Similarity NPD3136 Phase 2
0.6612 Remote Similarity NPD9634 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6696 Suspended
0.661 Remote Similarity NPD6516 Phase 2
0.661 Remote Similarity NPD5846 Approved
0.6587 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6587 Remote Similarity NPD3620 Phase 2
0.6585 Remote Similarity NPD2861 Phase 2

  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