Structure

Physi-Chem Properties

Molecular Weight:  354.1
Volume:  363.956
LogP:  5.267
LogD:  4.315
LogS:  -4.991
# Rotatable Bonds:  3
TPSA:  53.6
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.748
Synthetic Accessibility Score:  2.838
Fsp3:  0.143
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:  -4.98
MDCK Permeability:  2.249194039904978e-05
Pgp-inhibitor:  0.021
Pgp-substrate:  0.149
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  100.57118225097656%
Volume Distribution (VD):  0.837
Pgp-substrate:  0.6549697518348694%

ADMET: Metabolism

CYP1A2-inhibitor:  0.883
CYP1A2-substrate:  0.54
CYP2C19-inhibitor:  0.711
CYP2C19-substrate:  0.117
CYP2C9-inhibitor:  0.684
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.721
CYP2D6-substrate:  0.347
CYP3A4-inhibitor:  0.146
CYP3A4-substrate:  0.667

ADMET: Excretion

Clearance (CL):  9.847
Half-life (T1/2):  0.71

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.559
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.253
Rat Oral Acute Toxicity:  0.315
Maximum Recommended Daily Dose:  0.404
Skin Sensitization:  0.533
Carcinogencity:  0.469
Eye Corrosion:  0.003
Eye Irritation:  0.333
Respiratory Toxicity:  0.953

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  Natural Product: NPC30390

Natural Product ID:  NPC30390
Common Name*:   (5Z)-3-Benzyl-5-[(3-Chloro-4-Hydroxyphenyl)Methylidene]-4-Propan-2-Ylfuran-2-One
IUPAC Name:   (5Z)-3-benzyl-5-[(3-chloro-4-hydroxyphenyl)methylidene]-4-propan-2-ylfuran-2-one
Synonyms:  
Standard InCHIKey:  FJCMKDBQNWQPBT-UNOMPAQXSA-N
Standard InCHI:  InChI=1S/C21H19ClO3/c1-13(2)20-16(10-14-6-4-3-5-7-14)21(24)25-19(20)12-15-8-9-18(23)17(22)11-15/h3-9,11-13,23H,10H2,1-2H3/b19-12-
SMILES:  CC(C1=C(Cc2ccccc2)C(=O)O/C/1=Cc1ccc(c(c1)Cl)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1972163
PubChem CID:   5468143
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0002320] Halophenols
          • [CHEMONTID:0002766] Chlorophenols
            • [CHEMONTID:0002771] O-chlorophenols

*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
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1021/jo00416a020]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11473413]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[12608844]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota leaves n.a. n.a. PMID[17243726]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24476550]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. Database[FooDB]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7788 Rana catesbeiana Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19541 Smilax moranensis Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1537 Vaccinium arctostaphylos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8426 Tinospora rumphii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7240 Osteospermum oppositifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4198 Ungernia vvedenskyi Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23436 Cladrastis sikokiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8811 Cytisus prolifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28833 Eleutherococcus sieboldianus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19804 Lycopodium saururus Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5335 0stoc sp Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO834 Peperomia clusiifolia Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8623 Anneissia japonica Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9705 Meyerozyma guilliermondii Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18618 Neurolaena lobata Species Asteraceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 16481.62 nM PMID[493746]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 16904.41 nM PMID[493746]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 14893.61 nM PMID[493746]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 13091.82 nM PMID[493746]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14387.99 nM PMID[493746]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 15739.83 nM PMID[493746]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 18197.01 nM PMID[493746]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 18620.87 nM PMID[493746]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 16672.47 nM PMID[493746]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 15812.48 nM PMID[493746]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 17619.76 nM PMID[493746]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 16032.45 nM PMID[493746]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10914.4 nM PMID[493746]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 14791.08 nM PMID[493746]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 17741.89 nM PMID[493746]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 10000.0 nM PMID[493746]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 18323.14 nM PMID[493746]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 16710.91 nM PMID[493746]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 18365.38 nM PMID[493746]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 11534.53 nM PMID[493746]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 16218.1 nM PMID[493746]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 10399.2 nM PMID[493746]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 17701.09 nM PMID[493746]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 19098.53 nM PMID[493746]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 18071.74 nM PMID[493746]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 17498.47 nM PMID[493746]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 16904.41 nM PMID[493746]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 12387.97 nM PMID[493746]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 14655.48 nM PMID[493746]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 18365.38 nM PMID[493746]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 22233.1 nM PMID[493746]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 14621.77 nM PMID[493746]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 15100.8 nM PMID[493746]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 16943.38 nM PMID[493746]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 15488.17 nM PMID[493746]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 16032.45 nM PMID[493746]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 16634.13 nM PMID[493746]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 16557.7 nM PMID[493746]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 17864.88 nM PMID[493746]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 15739.83 nM PMID[493746]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 19543.39 nM PMID[493746]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 17378.01 nM PMID[493746]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 14791.08 nM PMID[493746]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 18578.04 nM PMID[493746]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 17021.59 nM PMID[493746]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 16826.74 nM PMID[493746]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 15995.58 nM PMID[493746]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 16519.62 nM PMID[493746]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 13645.83 nM PMID[493746]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 18793.17 nM PMID[493746]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 15523.87 nM PMID[493746]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 18793.17 nM PMID[493746]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 16634.13 nM PMID[493746]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 16943.38 nM PMID[493746]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 20370.42 nM PMID[493746]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 17458.22 nM PMID[493746]

☑ 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 NPC30390 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
0.9683 High Similarity NPC76453
0.8955 High Similarity NPC86087
0.8759 High Similarity NPC182475
0.8203 Intermediate Similarity NPC471033
0.8203 Intermediate Similarity NPC311091
0.8189 Intermediate Similarity NPC128249
0.816 Intermediate Similarity NPC17693
0.8065 Intermediate Similarity NPC79543
0.797 Intermediate Similarity NPC14141
0.7829 Intermediate Similarity NPC472623
0.7829 Intermediate Similarity NPC296526
0.7769 Intermediate Similarity NPC19290
0.7727 Intermediate Similarity NPC264976
0.7717 Intermediate Similarity NPC183700
0.7698 Intermediate Similarity NPC31274
0.7698 Intermediate Similarity NPC48909
0.7692 Intermediate Similarity NPC51345
0.7681 Intermediate Similarity NPC217431
0.768 Intermediate Similarity NPC29989
0.768 Intermediate Similarity NPC70843
0.768 Intermediate Similarity NPC95178
0.768 Intermediate Similarity NPC69332
0.7647 Intermediate Similarity NPC288945
0.7619 Intermediate Similarity NPC260952
0.7591 Intermediate Similarity NPC137416
0.7574 Intermediate Similarity NPC473942
0.7559 Intermediate Similarity NPC206341
0.7554 Intermediate Similarity NPC2596
0.7536 Intermediate Similarity NPC474476
0.752 Intermediate Similarity NPC261573
0.752 Intermediate Similarity NPC120693
0.752 Intermediate Similarity NPC8931
0.7519 Intermediate Similarity NPC293424
0.7518 Intermediate Similarity NPC89630
0.75 Intermediate Similarity NPC88141
0.75 Intermediate Similarity NPC246991
0.748 Intermediate Similarity NPC245561
0.7465 Intermediate Similarity NPC173034
0.746 Intermediate Similarity NPC127676
0.7444 Intermediate Similarity NPC325295
0.7444 Intermediate Similarity NPC76308
0.7429 Intermediate Similarity NPC79332
0.7424 Intermediate Similarity NPC23402
0.7419 Intermediate Similarity NPC52472
0.7413 Intermediate Similarity NPC202743
0.741 Intermediate Similarity NPC8058
0.7407 Intermediate Similarity NPC474874
0.7402 Intermediate Similarity NPC188677
0.7379 Intermediate Similarity NPC90431
0.7376 Intermediate Similarity NPC478071
0.7376 Intermediate Similarity NPC214246
0.7372 Intermediate Similarity NPC90577
0.7372 Intermediate Similarity NPC151237
0.7364 Intermediate Similarity NPC234639
0.7344 Intermediate Similarity NPC156648
0.7343 Intermediate Similarity NPC139335
0.731 Intermediate Similarity NPC311742
0.7308 Intermediate Similarity NPC63345
0.7308 Intermediate Similarity NPC21162
0.7308 Intermediate Similarity NPC116842
0.7302 Intermediate Similarity NPC304638
0.7299 Intermediate Similarity NPC7830
0.7299 Intermediate Similarity NPC42644
0.7293 Intermediate Similarity NPC322197
0.7287 Intermediate Similarity NPC281604
0.7287 Intermediate Similarity NPC146096
0.728 Intermediate Similarity NPC253746
0.7273 Intermediate Similarity NPC109241
0.7266 Intermediate Similarity NPC33402
0.7259 Intermediate Similarity NPC94298
0.7259 Intermediate Similarity NPC27633
0.7258 Intermediate Similarity NPC260000
0.7254 Intermediate Similarity NPC477300
0.7254 Intermediate Similarity NPC64111
0.7254 Intermediate Similarity NPC131684
0.7254 Intermediate Similarity NPC194979
0.7252 Intermediate Similarity NPC139946
0.725 Intermediate Similarity NPC269383
0.725 Intermediate Similarity NPC151030
0.7246 Intermediate Similarity NPC296202
0.7241 Intermediate Similarity NPC5310
0.7241 Intermediate Similarity NPC4982
0.7241 Intermediate Similarity NPC176814
0.7241 Intermediate Similarity NPC68779
0.7241 Intermediate Similarity NPC300776
0.7239 Intermediate Similarity NPC471928
0.7239 Intermediate Similarity NPC471925
0.7239 Intermediate Similarity NPC325646
0.7239 Intermediate Similarity NPC131192
0.7239 Intermediate Similarity NPC471924
0.7239 Intermediate Similarity NPC28951
0.7231 Intermediate Similarity NPC471954
0.7231 Intermediate Similarity NPC75272
0.7226 Intermediate Similarity NPC470848
0.7226 Intermediate Similarity NPC470849
0.7222 Intermediate Similarity NPC66643
0.7218 Intermediate Similarity NPC285350
0.7214 Intermediate Similarity NPC49938
0.7214 Intermediate Similarity NPC197832
0.7214 Intermediate Similarity NPC88403
0.7211 Intermediate Similarity NPC106688
0.7206 Intermediate Similarity NPC263386
0.7206 Intermediate Similarity NPC141791
0.7206 Intermediate Similarity NPC42657
0.7203 Intermediate Similarity NPC285361
0.7203 Intermediate Similarity NPC2989
0.72 Intermediate Similarity NPC171843
0.72 Intermediate Similarity NPC280869
0.7194 Intermediate Similarity NPC212541
0.7194 Intermediate Similarity NPC306100
0.7188 Intermediate Similarity NPC298401
0.7188 Intermediate Similarity NPC13495
0.7185 Intermediate Similarity NPC471926
0.7183 Intermediate Similarity NPC219923
0.7183 Intermediate Similarity NPC46192
0.7183 Intermediate Similarity NPC167463
0.7181 Intermediate Similarity NPC9218
0.7177 Intermediate Similarity NPC473388
0.7176 Intermediate Similarity NPC321252
0.7176 Intermediate Similarity NPC252544
0.7174 Intermediate Similarity NPC472271
0.7172 Intermediate Similarity NPC155209
0.7172 Intermediate Similarity NPC168799
0.7165 Intermediate Similarity NPC291426
0.7165 Intermediate Similarity NPC68269
0.7163 Intermediate Similarity NPC204579
0.7163 Intermediate Similarity NPC110211
0.7163 Intermediate Similarity NPC90128
0.7163 Intermediate Similarity NPC303680
0.7163 Intermediate Similarity NPC179777
0.7163 Intermediate Similarity NPC84076
0.7162 Intermediate Similarity NPC148738
0.7162 Intermediate Similarity NPC327612
0.7162 Intermediate Similarity NPC73078
0.7162 Intermediate Similarity NPC319870
0.716 Intermediate Similarity NPC68850
0.7154 Intermediate Similarity NPC17525
0.7153 Intermediate Similarity NPC233282
0.7153 Intermediate Similarity NPC318799
0.7153 Intermediate Similarity NPC108553
0.7153 Intermediate Similarity NPC198388
0.7153 Intermediate Similarity NPC72977
0.7153 Intermediate Similarity NPC478121
0.7143 Intermediate Similarity NPC223616
0.7143 Intermediate Similarity NPC221798
0.7143 Intermediate Similarity NPC184219
0.7143 Intermediate Similarity NPC246177
0.7143 Intermediate Similarity NPC317045
0.7143 Intermediate Similarity NPC213414
0.7143 Intermediate Similarity NPC473696
0.7133 Intermediate Similarity NPC208536
0.7133 Intermediate Similarity NPC241354
0.7132 Intermediate Similarity NPC1065
0.7132 Intermediate Similarity NPC474890
0.7132 Intermediate Similarity NPC161943
0.7132 Intermediate Similarity NPC135464
0.7132 Intermediate Similarity NPC273282
0.7132 Intermediate Similarity NPC92623
0.7132 Intermediate Similarity NPC113457
0.7132 Intermediate Similarity NPC328694
0.7123 Intermediate Similarity NPC194970
0.7123 Intermediate Similarity NPC106406
0.7123 Intermediate Similarity NPC248150
0.7122 Intermediate Similarity NPC46634
0.7122 Intermediate Similarity NPC132518
0.7122 Intermediate Similarity NPC67300
0.7122 Intermediate Similarity NPC27198
0.7122 Intermediate Similarity NPC68167
0.7122 Intermediate Similarity NPC121168
0.7122 Intermediate Similarity NPC477151
0.7121 Intermediate Similarity NPC177576
0.712 Intermediate Similarity NPC201967
0.7117 Intermediate Similarity NPC227778
0.7115 Intermediate Similarity NPC282294
0.7113 Intermediate Similarity NPC122359
0.7113 Intermediate Similarity NPC276466
0.7113 Intermediate Similarity NPC123228
0.7113 Intermediate Similarity NPC5018
0.7113 Intermediate Similarity NPC123722
0.7113 Intermediate Similarity NPC151167
0.7113 Intermediate Similarity NPC159987
0.7113 Intermediate Similarity NPC78061
0.7111 Intermediate Similarity NPC277394
0.7111 Intermediate Similarity NPC61062
0.7111 Intermediate Similarity NPC33717
0.7111 Intermediate Similarity NPC299252
0.7107 Intermediate Similarity NPC472404
0.7103 Intermediate Similarity NPC25581
0.7103 Intermediate Similarity NPC61
0.7103 Intermediate Similarity NPC18074
0.7103 Intermediate Similarity NPC327204
0.7103 Intermediate Similarity NPC5419
0.7103 Intermediate Similarity NPC323379
0.7101 Intermediate Similarity NPC241001
0.7101 Intermediate Similarity NPC164852
0.7099 Intermediate Similarity NPC259554
0.7099 Intermediate Similarity NPC470081
0.7099 Intermediate Similarity NPC95172
0.7097 Intermediate Similarity NPC26244
0.7092 Intermediate Similarity NPC4164

  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 NPC30390 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
0.8271 Intermediate Similarity NPD454 Approved
0.8207 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1184 Approved
0.7708 Intermediate Similarity NPD5958 Discontinued
0.7586 Intermediate Similarity NPD4534 Discontinued
0.7551 Intermediate Similarity NPD2354 Approved
0.7464 Intermediate Similarity NPD2797 Approved
0.7419 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD2353 Approved
0.7397 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD3887 Approved
0.731 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1535 Discovery
0.7259 Intermediate Similarity NPD9545 Approved
0.7259 Intermediate Similarity NPD1894 Discontinued
0.7246 Intermediate Similarity NPD1481 Phase 2
0.7244 Intermediate Similarity NPD5909 Discontinued
0.7239 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD3268 Approved
0.7203 Intermediate Similarity NPD3764 Approved
0.7154 Intermediate Similarity NPD2933 Approved
0.7154 Intermediate Similarity NPD2934 Approved
0.7115 Intermediate Similarity NPD958 Approved
0.7101 Intermediate Similarity NPD3847 Discontinued
0.7097 Intermediate Similarity NPD2859 Approved
0.7097 Intermediate Similarity NPD2860 Approved
0.7095 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD2379 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD3020 Approved
0.7055 Intermediate Similarity NPD6355 Discontinued
0.7032 Intermediate Similarity NPD957 Approved
0.7027 Intermediate Similarity NPD2799 Discontinued
0.7021 Intermediate Similarity NPD1283 Approved
0.7 Intermediate Similarity NPD3134 Approved
0.7 Intermediate Similarity NPD1608 Approved
0.6985 Remote Similarity NPD9493 Approved
0.698 Remote Similarity NPD2935 Discontinued
0.6972 Remote Similarity NPD1203 Approved
0.697 Remote Similarity NPD5451 Approved
0.6966 Remote Similarity NPD6798 Discontinued
0.6966 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6947 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6944 Remote Similarity NPD2614 Approved
0.694 Remote Similarity NPD5535 Approved
0.6918 Remote Similarity NPD4062 Phase 3
0.6918 Remote Similarity NPD6663 Approved
0.6918 Remote Similarity NPD6233 Phase 2
0.6906 Remote Similarity NPD3019 Approved
0.6906 Remote Similarity NPD4589 Approved
0.6906 Remote Similarity NPD2932 Approved
0.6905 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6889 Remote Similarity NPD1241 Discontinued
0.6883 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6879 Remote Similarity NPD4878 Approved
0.6875 Remote Similarity NPD5736 Approved
0.6853 Remote Similarity NPD987 Approved
0.6853 Remote Similarity NPD3267 Approved
0.6853 Remote Similarity NPD3266 Approved
0.6842 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6831 Remote Similarity NPD4359 Approved
0.6809 Remote Similarity NPD422 Phase 1
0.6809 Remote Similarity NPD1281 Approved
0.6806 Remote Similarity NPD2798 Approved
0.6797 Remote Similarity NPD7003 Approved
0.6797 Remote Similarity NPD4628 Phase 3
0.6797 Remote Similarity NPD8166 Discontinued
0.6788 Remote Similarity NPD256 Approved
0.6788 Remote Similarity NPD255 Approved
0.6786 Remote Similarity NPD17 Approved
0.6783 Remote Similarity NPD3225 Approved
0.6783 Remote Similarity NPD1876 Approved
0.6781 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6761 Remote Similarity NPD9717 Approved
0.6761 Remote Similarity NPD3972 Approved
0.675 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6736 Remote Similarity NPD1164 Approved
0.6731 Remote Similarity NPD1578 Phase 2
0.673 Remote Similarity NPD4972 Discontinued
0.6715 Remote Similarity NPD690 Clinical (unspecified phase)
0.6714 Remote Similarity NPD5585 Approved
0.6713 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6832 Phase 2
0.6711 Remote Similarity NPD2344 Approved
0.6708 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3365 Discontinued
0.6692 Remote Similarity NPD1358 Approved
0.6689 Remote Similarity NPD4308 Phase 3
0.6689 Remote Similarity NPD8032 Phase 2
0.6688 Remote Similarity NPD6273 Approved
0.6688 Remote Similarity NPD3750 Approved
0.6687 Remote Similarity NPD4424 Discontinued
0.6687 Remote Similarity NPD3274 Phase 2
0.6667 Remote Similarity NPD7041 Phase 2
0.6667 Remote Similarity NPD7095 Approved
0.6667 Remote Similarity NPD3097 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4626 Approved
0.6667 Remote Similarity NPD5846 Approved
0.6667 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6516 Phase 2
0.6645 Remote Similarity NPD4476 Approved
0.6645 Remote Similarity NPD4477 Approved
0.6644 Remote Similarity NPD1240 Approved
0.6644 Remote Similarity NPD2979 Phase 3
0.6644 Remote Similarity NPD4060 Phase 1
0.6642 Remote Similarity NPD74 Approved
0.6642 Remote Similarity NPD9266 Approved
0.6623 Remote Similarity NPD4536 Approved
0.6623 Remote Similarity NPD4538 Approved
0.6623 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6622 Remote Similarity NPD2313 Discontinued
0.6619 Remote Similarity NPD9568 Approved
0.6607 Remote Similarity NPD3366 Approved
0.6603 Remote Similarity NPD7440 Discontinued
0.6601 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6596 Remote Similarity NPD1651 Approved
0.6593 Remote Similarity NPD2067 Discontinued
0.6593 Remote Similarity NPD3021 Approved
0.6593 Remote Similarity NPD3022 Approved
0.6581 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4110 Phase 3
0.6579 Remote Similarity NPD7033 Discontinued
0.6579 Remote Similarity NPD5588 Approved
0.6575 Remote Similarity NPD5647 Approved
0.6573 Remote Similarity NPD6312 Discontinued
0.6567 Remote Similarity NPD9264 Approved
0.6567 Remote Similarity NPD9263 Approved
0.6567 Remote Similarity NPD9267 Approved
0.6558 Remote Similarity NPD970 Clinical (unspecified phase)
0.6556 Remote Similarity NPD1607 Approved
0.6554 Remote Similarity NPD5163 Phase 2
0.6552 Remote Similarity NPD1888 Phase 1
0.6538 Remote Similarity NPD2066 Phase 3
0.6538 Remote Similarity NPD2309 Approved
0.6538 Remote Similarity NPD6190 Approved
0.6538 Remote Similarity NPD1238 Approved
0.6536 Remote Similarity NPD1538 Phase 1
0.6536 Remote Similarity NPD1519 Approved
0.6536 Remote Similarity NPD1537 Approved
0.6528 Remote Similarity NPD1157 Approved
0.6516 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6503 Remote Similarity NPD3496 Discontinued
0.6497 Remote Similarity NPD5058 Phase 3
0.6493 Remote Similarity NPD968 Approved
0.6484 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6479 Remote Similarity NPD5691 Approved
0.6479 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6478 Remote Similarity NPD3364 Phase 3
0.6475 Remote Similarity NPD2629 Approved
0.6474 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5960 Phase 3
0.646 Remote Similarity NPD3769 Discontinued
0.646 Remote Similarity NPD7458 Discontinued
0.646 Remote Similarity NPD3455 Phase 2
0.6456 Remote Similarity NPD6799 Approved
0.6454 Remote Similarity NPD5536 Phase 2
0.6452 Remote Similarity NPD7596 Clinical (unspecified phase)
0.645 Remote Similarity NPD2403 Approved
0.6438 Remote Similarity NPD196 Phase 1
0.6434 Remote Similarity NPD1778 Approved
0.6429 Remote Similarity NPD2531 Phase 2
0.6429 Remote Similarity NPD1551 Phase 2
0.6429 Remote Similarity NPD1522 Approved
0.6429 Remote Similarity NPD2438 Suspended
0.6429 Remote Similarity NPD1523 Approved
0.6424 Remote Similarity NPD4140 Approved
0.6424 Remote Similarity NPD4307 Phase 2
0.6423 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6423 Remote Similarity NPD111 Approved
0.6418 Remote Similarity NPD9697 Approved
0.6415 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6408 Remote Similarity NPD1759 Phase 1
0.6406 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6405 Remote Similarity NPD7097 Phase 1
0.6405 Remote Similarity NPD1536 Approved
0.6397 Remote Similarity NPD2684 Approved
0.6397 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6362 Approved
0.6392 Remote Similarity NPD6815 Approved
0.6391 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6391 Remote Similarity NPD6647 Phase 2
0.6391 Remote Similarity NPD1929 Approved
0.6391 Remote Similarity NPD9500 Approved
0.6391 Remote Similarity NPD1930 Approved
0.6389 Remote Similarity NPD3026 Approved
0.6389 Remote Similarity NPD4879 Approved
0.6389 Remote Similarity NPD3023 Approved
0.6387 Remote Similarity NPD6800 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6387 Remote Similarity NPD7611 Approved
0.6387 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6387 Remote Similarity NPD2346 Discontinued
0.6387 Remote Similarity NPD7266 Discontinued
0.6382 Remote Similarity NPD4622 Approved
0.6382 Remote Similarity NPD4618 Approved
0.6382 Remote Similarity NPD4340 Discontinued
0.6382 Remote Similarity NPD230 Phase 1
0.638 Remote Similarity NPD7411 Suspended
0.6375 Remote Similarity NPD1940 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data