Structure

Physi-Chem Properties

Molecular Weight:  280.08
Volume:  278.339
LogP:  2.295
LogD:  2.747
LogS:  -3.232
# Rotatable Bonds:  2
TPSA:  52.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.566
Synthetic Accessibility Score:  2.424
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.777
MDCK Permeability:  2.24996965698665e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.874
Plasma Protein Binding (PPB):  94.0746841430664%
Volume Distribution (VD):  0.483
Pgp-substrate:  3.9808850288391113%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.96
CYP2C19-inhibitor:  0.831
CYP2C19-substrate:  0.873
CYP2C9-inhibitor:  0.699
CYP2C9-substrate:  0.877
CYP2D6-inhibitor:  0.048
CYP2D6-substrate:  0.839
CYP3A4-inhibitor:  0.522
CYP3A4-substrate:  0.624

ADMET: Excretion

Clearance (CL):  5.177
Half-life (T1/2):  0.556

ADMET: Toxicity

hERG Blockers:  0.115
Human Hepatotoxicity (H-HT):  0.189
Drug-inuced Liver Injury (DILI):  0.843
AMES Toxicity:  0.958
Rat Oral Acute Toxicity:  0.148
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.06
Carcinogencity:  0.963
Eye Corrosion:  0.003
Eye Irritation:  0.336
Respiratory Toxicity:  0.833

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  Natural Product: NPC168911

Natural Product ID:  NPC168911
Common Name*:   4,5-Dimethoxycanthin-6-One
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ATONBUGCNDSBBC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12N2O3/c1-20-14-12-13-10(7-8-17-12)9-5-3-4-6-11(9)18(13)16(19)15(14)21-2/h3-8H,1-2H3
SMILES:  COc1c(OC)c2nccc3c2n(c1=O)c1ccccc31
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2386324
PubChem CID:   638215
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota Roots n.a. n.a. PMID[14575431]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. root n.a. PMID[1800638]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[19299148]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19586051]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. PMID[19659728]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19919052]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota stems n.a. n.a. PMID[20095629]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO15986 Alangium chinense Species Cornaceae Eukaryota Roots n.a. n.a. PMID[23734721]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[24467387]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[25066952]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25506718]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. n.a. PMID[25749794]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25905468]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[27494664]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[28368118]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[29667820]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[30917277]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15986 Alangium chinense Species Cornaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15986 Alangium chinense Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1418 Boletinus paluster Species Gyrodontaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12890 Ophryosporus charua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8820 Lophocereus marginatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2084 Acinetobacter calcoaceticus Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8640 Nemuaron humboldtii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8220 Russula sardonia Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6626 Pteris spinulosa Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13692 Leontice kiangnanensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20318 Acinetobacter baumannii Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12577 Pinus glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3428 Undaria pinnatifida Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12026 Papaver radicatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11072 Geigeria schinzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2505 Pachycereus pringlei Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12988 Blainvillea latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6014 Goniothalamus undulatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20383 Stenocereus thurberi Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14280 Helichrysum angustifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9375 Medium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3576 Bersama swinnyi Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13494 Prosopis kuntzei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3924 Penicillium alutaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9024 Aralidium pinnatifidum Species Torricelliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13798 Cheilanthes marantae Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13604 Dermocybe cardinalis Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22888 Lophiostoma vaginatispora Species Lophiostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15986 Alangium chinense Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9965 Eurycoma longifolia Species Simaroubaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 26.5 % PMID[487400]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 130000.0 nM PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 189000.0 nM PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 61.1 % PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 58.3 % PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 59.0 % PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 42.6 % PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 43.8 % PMID[487398]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 33.3 % PMID[487398]
NPT3494 Organism Coxsackievirus Coxsackievirus IC50 = 7400.0 nM PMID[487399]
NPT5110 Organism Meriones unguiculatus Meriones unguiculatus Activity <= 40.0 % PMID[487401]
NPT5110 Organism Meriones unguiculatus Meriones unguiculatus Activity = 20.8 % PMID[487401]

☑ 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 NPC168911 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
0.9774 High Similarity NPC239954
0.9771 High Similarity NPC198673
0.9553 High Similarity NPC212213
0.8995 High Similarity NPC287208
0.8977 High Similarity NPC12649
0.8653 High Similarity NPC174758
0.8601 High Similarity NPC82548
0.8557 High Similarity NPC174672
0.847 Intermediate Similarity NPC284678
0.8392 Intermediate Similarity NPC274982
0.8305 Intermediate Similarity NPC478182
0.8281 Intermediate Similarity NPC81535
0.8272 Intermediate Similarity NPC267928
0.8239 Intermediate Similarity NPC293487
0.8205 Intermediate Similarity NPC53144
0.8154 Intermediate Similarity NPC211813
0.8143 Intermediate Similarity NPC141053
0.8112 Intermediate Similarity NPC200836
0.8111 Intermediate Similarity NPC478183
0.8108 Intermediate Similarity NPC24864
0.8101 Intermediate Similarity NPC478184
0.8051 Intermediate Similarity NPC19872
0.8045 Intermediate Similarity NPC478185
0.804 Intermediate Similarity NPC266249
0.8022 Intermediate Similarity NPC91895
0.8022 Intermediate Similarity NPC32534
0.796 Intermediate Similarity NPC85273
0.796 Intermediate Similarity NPC123839
0.7929 Intermediate Similarity NPC245816
0.7929 Intermediate Similarity NPC476138
0.7926 Intermediate Similarity NPC48938
0.7826 Intermediate Similarity NPC65080
0.7794 Intermediate Similarity NPC118940
0.7789 Intermediate Similarity NPC295898
0.7789 Intermediate Similarity NPC57398
0.7766 Intermediate Similarity NPC474916
0.7761 Intermediate Similarity NPC238457
0.7756 Intermediate Similarity NPC476287
0.7748 Intermediate Similarity NPC26543
0.7739 Intermediate Similarity NPC232727
0.7734 Intermediate Similarity NPC185782
0.7727 Intermediate Similarity NPC478186
0.7727 Intermediate Similarity NPC472434
0.7707 Intermediate Similarity NPC26679
0.7688 Intermediate Similarity NPC176538
0.7662 Intermediate Similarity NPC475774
0.766 Intermediate Similarity NPC134586
0.7633 Intermediate Similarity NPC477979
0.7624 Intermediate Similarity NPC470500
0.7622 Intermediate Similarity NPC56233
0.7619 Intermediate Similarity NPC211997
0.7617 Intermediate Similarity NPC311858
0.761 Intermediate Similarity NPC123976
0.761 Intermediate Similarity NPC167860
0.7604 Intermediate Similarity NPC284559
0.7594 Intermediate Similarity NPC65277
0.7591 Intermediate Similarity NPC99891
0.7546 Intermediate Similarity NPC260434
0.7539 Intermediate Similarity NPC73994
0.7537 Intermediate Similarity NPC285558
0.7535 Intermediate Similarity NPC314954
0.7533 Intermediate Similarity NPC472435
0.7526 Intermediate Similarity NPC14325
0.7526 Intermediate Similarity NPC28848
0.7512 Intermediate Similarity NPC470799
0.7512 Intermediate Similarity NPC8022
0.75 Intermediate Similarity NPC470499
0.75 Intermediate Similarity NPC221100
0.75 Intermediate Similarity NPC234078
0.7463 Intermediate Similarity NPC476167
0.7451 Intermediate Similarity NPC470505
0.744 Intermediate Similarity NPC5145
0.7438 Intermediate Similarity NPC473761
0.7435 Intermediate Similarity NPC472436
0.743 Intermediate Similarity NPC122436
0.7424 Intermediate Similarity NPC324149
0.7423 Intermediate Similarity NPC46895
0.7418 Intermediate Similarity NPC281094
0.7413 Intermediate Similarity NPC192315
0.7406 Intermediate Similarity NPC193267
0.7406 Intermediate Similarity NPC17565
0.7406 Intermediate Similarity NPC213530
0.7385 Intermediate Similarity NPC282103
0.7382 Intermediate Similarity NPC203754
0.7382 Intermediate Similarity NPC150048
0.7374 Intermediate Similarity NPC129909
0.7374 Intermediate Similarity NPC473763
0.7374 Intermediate Similarity NPC117244
0.7366 Intermediate Similarity NPC472259
0.7364 Intermediate Similarity NPC182222
0.736 Intermediate Similarity NPC61435
0.7358 Intermediate Similarity NPC61011
0.7352 Intermediate Similarity NPC101543
0.7352 Intermediate Similarity NPC469554
0.7347 Intermediate Similarity NPC66210
0.7336 Intermediate Similarity NPC60621
0.7333 Intermediate Similarity NPC258480
0.7333 Intermediate Similarity NPC74562
0.7333 Intermediate Similarity NPC151781
0.7333 Intermediate Similarity NPC316181
0.7333 Intermediate Similarity NPC470003
0.7324 Intermediate Similarity NPC292958
0.7316 Intermediate Similarity NPC158129
0.7293 Intermediate Similarity NPC470111
0.7291 Intermediate Similarity NPC74413
0.7286 Intermediate Similarity NPC264176
0.7282 Intermediate Similarity NPC132539
0.7282 Intermediate Similarity NPC327592
0.7282 Intermediate Similarity NPC475070
0.7265 Intermediate Similarity NPC30540
0.7263 Intermediate Similarity NPC476518
0.7256 Intermediate Similarity NPC310118
0.7255 Intermediate Similarity NPC470497
0.7254 Intermediate Similarity NPC326575
0.7254 Intermediate Similarity NPC83774
0.7246 Intermediate Similarity NPC472064
0.7246 Intermediate Similarity NPC317373
0.724 Intermediate Similarity NPC469938
0.7231 Intermediate Similarity NPC314394
0.7231 Intermediate Similarity NPC266551
0.7231 Intermediate Similarity NPC161887
0.7231 Intermediate Similarity NPC219963
0.7225 Intermediate Similarity NPC14651
0.7225 Intermediate Similarity NPC121658
0.722 Intermediate Similarity NPC235685
0.7213 Intermediate Similarity NPC40070
0.7209 Intermediate Similarity NPC128115
0.7208 Intermediate Similarity NPC20249
0.7208 Intermediate Similarity NPC62510
0.7206 Intermediate Similarity NPC123395
0.7204 Intermediate Similarity NPC26850
0.72 Intermediate Similarity NPC138370
0.72 Intermediate Similarity NPC92111
0.7198 Intermediate Similarity NPC329708
0.7198 Intermediate Similarity NPC201380
0.7198 Intermediate Similarity NPC165349
0.7198 Intermediate Similarity NPC118832
0.7198 Intermediate Similarity NPC47059
0.7198 Intermediate Similarity NPC179787
0.7198 Intermediate Similarity NPC264166
0.7198 Intermediate Similarity NPC274291
0.7192 Intermediate Similarity NPC106824
0.7188 Intermediate Similarity NPC101350
0.7186 Intermediate Similarity NPC296527
0.7184 Intermediate Similarity NPC260900
0.7183 Intermediate Similarity NPC36405
0.7181 Intermediate Similarity NPC177404
0.7172 Intermediate Similarity NPC94752
0.7172 Intermediate Similarity NPC118084
0.7158 Intermediate Similarity NPC321911
0.7157 Intermediate Similarity NPC228835
0.7157 Intermediate Similarity NPC165495
0.7151 Intermediate Similarity NPC238499
0.715 Intermediate Similarity NPC76748
0.7143 Intermediate Similarity NPC216612
0.7143 Intermediate Similarity NPC469589
0.7143 Intermediate Similarity NPC63545
0.7135 Intermediate Similarity NPC325903
0.713 Intermediate Similarity NPC323969
0.7129 Intermediate Similarity NPC307963
0.7128 Intermediate Similarity NPC248462
0.7128 Intermediate Similarity NPC131718
0.7124 Intermediate Similarity NPC148889
0.7122 Intermediate Similarity NPC284338
0.7122 Intermediate Similarity NPC192674
0.712 Intermediate Similarity NPC63751
0.7112 Intermediate Similarity NPC129721
0.711 Intermediate Similarity NPC229893
0.7104 Intermediate Similarity NPC469811
0.7101 Intermediate Similarity NPC472062
0.7101 Intermediate Similarity NPC472063
0.7101 Intermediate Similarity NPC472069
0.7101 Intermediate Similarity NPC143977
0.7098 Intermediate Similarity NPC111624
0.7098 Intermediate Similarity NPC477549
0.7097 Intermediate Similarity NPC470502
0.7091 Intermediate Similarity NPC110151
0.7091 Intermediate Similarity NPC257851
0.709 Intermediate Similarity NPC225018
0.709 Intermediate Similarity NPC282231
0.7089 Intermediate Similarity NPC89508
0.7089 Intermediate Similarity NPC152620
0.7087 Intermediate Similarity NPC234197
0.7087 Intermediate Similarity NPC121327
0.7087 Intermediate Similarity NPC477019
0.7087 Intermediate Similarity NPC315957
0.7085 Intermediate Similarity NPC323752
0.7081 Intermediate Similarity NPC472065
0.7081 Intermediate Similarity NPC476121
0.7081 Intermediate Similarity NPC476124
0.7081 Intermediate Similarity NPC472111
0.7075 Intermediate Similarity NPC208284
0.7074 Intermediate Similarity NPC477591
0.7073 Intermediate Similarity NPC265576
0.707 Intermediate Similarity NPC312645
0.707 Intermediate Similarity NPC27041
0.7068 Intermediate Similarity NPC474561
0.7068 Intermediate Similarity NPC49954
0.7064 Intermediate Similarity NPC470501
0.7059 Intermediate Similarity NPC245916

  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 NPC168911 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
0.8053 Intermediate Similarity NPD3321 Discontinued
0.7877 Intermediate Similarity NPD2581 Approved
0.7877 Intermediate Similarity NPD2582 Approved
0.7871 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD4372 Phase 1
0.776 Intermediate Similarity NPD2915 Discontinued
0.7749 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7729 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD5559 Phase 2
0.7617 Intermediate Similarity NPD5444 Phase 1
0.759 Intermediate Similarity NPD6281 Approved
0.75 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD5104 Approved
0.745 Intermediate Similarity NPD6206 Phase 1
0.7449 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD6569 Phase 2
0.7415 Intermediate Similarity NPD7001 Phase 3
0.7413 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6223 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD4897 Phase 2
0.7374 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2076 Approved
0.7368 Intermediate Similarity NPD2077 Approved
0.7366 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4334 Discontinued
0.7351 Intermediate Similarity NPD5255 Approved
0.7333 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD5065 Approved
0.7323 Intermediate Similarity NPD8063 Discontinued
0.7321 Intermediate Similarity NPD5475 Discontinued
0.7317 Intermediate Similarity NPD5487 Phase 1
0.7313 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD3477 Phase 2
0.73 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD6999 Discontinued
0.7282 Intermediate Similarity NPD4795 Phase 2
0.7273 Intermediate Similarity NPD6961 Discontinued
0.7268 Intermediate Similarity NPD2882 Phase 1
0.7264 Intermediate Similarity NPD7944 Discontinued
0.726 Intermediate Similarity NPD2509 Approved
0.726 Intermediate Similarity NPD2510 Approved
0.7241 Intermediate Similarity NPD6261 Phase 3
0.7238 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD112 Approved
0.7219 Intermediate Similarity NPD9705 Discontinued
0.7211 Intermediate Similarity NPD5862 Discovery
0.7211 Intermediate Similarity NPD4640 Approved
0.7211 Intermediate Similarity NPD4639 Approved
0.7211 Intermediate Similarity NPD4638 Approved
0.7209 Intermediate Similarity NPD6242 Discontinued
0.7208 Intermediate Similarity NPD5555 Phase 1
0.7208 Intermediate Similarity NPD5075 Discontinued
0.7208 Intermediate Similarity NPD4889 Approved
0.7206 Intermediate Similarity NPD6248 Phase 2
0.7206 Intermediate Similarity NPD6249 Phase 2
0.7205 Intermediate Similarity NPD5482 Discontinued
0.7202 Intermediate Similarity NPD7603 Discontinued
0.7198 Intermediate Similarity NPD4034 Approved
0.7198 Intermediate Similarity NPD4122 Approved
0.7198 Intermediate Similarity NPD31 Approved
0.7198 Intermediate Similarity NPD32 Approved
0.7198 Intermediate Similarity NPD4038 Approved
0.7198 Intermediate Similarity NPD4039 Approved
0.7198 Intermediate Similarity NPD4033 Approved
0.7198 Intermediate Similarity NPD4035 Approved
0.7198 Intermediate Similarity NPD4036 Approved
0.7198 Intermediate Similarity NPD4037 Approved
0.7182 Intermediate Similarity NPD6968 Phase 2
0.7182 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6969 Phase 2
0.7177 Intermediate Similarity NPD7665 Phase 2
0.7177 Intermediate Similarity NPD7666 Phase 3
0.7176 Intermediate Similarity NPD5507 Approved
0.7176 Intermediate Similarity NPD5506 Approved
0.7171 Intermediate Similarity NPD5427 Suspended
0.7164 Intermediate Similarity NPD4315 Phase 2
0.7163 Intermediate Similarity NPD5601 Phase 2
0.7156 Intermediate Similarity NPD3939 Suspended
0.7156 Intermediate Similarity NPD7470 Discontinued
0.7155 Intermediate Similarity NPD8247 Approved
0.7155 Intermediate Similarity NPD8246 Approved
0.715 Intermediate Similarity NPD5513 Phase 2
0.7143 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1856 Discontinued
0.7136 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD4526 Approved
0.7129 Intermediate Similarity NPD7222 Phase 2
0.7129 Intermediate Similarity NPD4528 Approved
0.7129 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD4529 Approved
0.7129 Intermediate Similarity NPD1038 Approved
0.7123 Intermediate Similarity NPD7426 Phase 1
0.7123 Intermediate Similarity NPD8289 Discontinued
0.7123 Intermediate Similarity NPD7573 Discontinued
0.7122 Intermediate Similarity NPD3800 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD2814 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD6568 Discontinued
0.7116 Intermediate Similarity NPD4429 Discontinued
0.7114 Intermediate Similarity NPD5913 Phase 3
0.7114 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD4547 Phase 3
0.7103 Intermediate Similarity NPD3393 Approved
0.7103 Intermediate Similarity NPD3394 Approved
0.7103 Intermediate Similarity NPD3389 Approved
0.7098 Intermediate Similarity NPD5891 Approved
0.7097 Intermediate Similarity NPD4881 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD1739 Approved
0.7087 Intermediate Similarity NPD4896 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD1740 Approved
0.7085 Intermediate Similarity NPD706 Phase 1
0.7083 Intermediate Similarity NPD4555 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD4886 Phase 2
0.7067 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1274 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4204 Approved
0.7056 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4203 Approved
0.7056 Intermediate Similarity NPD5293 Phase 2
0.7056 Intermediate Similarity NPD3386 Phase 2
0.7051 Intermediate Similarity NPD8049 Phase 2
0.705 Intermediate Similarity NPD1034 Phase 3
0.705 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6790 Phase 1
0.7044 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD3330 Phase 1
0.704 Intermediate Similarity NPD7797 Approved
0.704 Intermediate Similarity NPD7796 Approved
0.7039 Intermediate Similarity NPD6239 Discontinued
0.7039 Intermediate Similarity NPD4548 Discontinued
0.7037 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5948 Phase 2
0.7033 Intermediate Similarity NPD3947 Discontinued
0.7031 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD4326 Phase 2
0.7016 Intermediate Similarity NPD2780 Approved
0.7016 Intermediate Similarity NPD2782 Approved
0.7014 Intermediate Similarity NPD7467 Discontinued
0.701 Intermediate Similarity NPD4418 Discontinued
0.7005 Intermediate Similarity NPD7404 Approved
0.7005 Intermediate Similarity NPD3402 Phase 1
0.7005 Intermediate Similarity NPD6452 Discontinued
0.7004 Intermediate Similarity NPD6992 Phase 2
0.6995 Remote Similarity NPD3922 Approved
0.6995 Remote Similarity NPD3923 Approved
0.6995 Remote Similarity NPD5066 Phase 2
0.6995 Remote Similarity NPD4376 Phase 3
0.6995 Remote Similarity NPD3921 Approved
0.6995 Remote Similarity NPD3924 Approved
0.6995 Remote Similarity NPD5067 Phase 2
0.699 Remote Similarity NPD1032 Phase 2
0.6989 Remote Similarity NPD6476 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6158 Phase 2
0.6986 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6986 Remote Similarity NPD3777 Phase 3
0.6985 Remote Similarity NPD5083 Clinical (unspecified phase)
0.698 Remote Similarity NPD3439 Approved
0.6974 Remote Similarity NPD6492 Phase 2
0.6972 Remote Similarity NPD1996 Discontinued
0.6971 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5640 Discontinued
0.6967 Remote Similarity NPD7453 Approved
0.6967 Remote Similarity NPD7452 Approved
0.6963 Remote Similarity NPD8093 Discontinued
0.6963 Remote Similarity NPD3816 Phase 1
0.6963 Remote Similarity NPD3815 Phase 1
0.6959 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3825 Phase 3
0.6952 Remote Similarity NPD5901 Discontinued
0.6947 Remote Similarity NPD6454 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6022 Clinical (unspecified phase)
0.6943 Remote Similarity NPD2781 Approved
0.6943 Remote Similarity NPD2390 Clinical (unspecified phase)
0.6942 Remote Similarity NPD4899 Clinical (unspecified phase)
0.694 Remote Similarity NPD4558 Phase 2
0.6939 Remote Similarity NPD5100 Phase 3
0.6937 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7161 Clinical (unspecified phase)
0.6934 Remote Similarity NPD5658 Approved
0.6933 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6927 Remote Similarity NPD2720 Phase 1
0.6927 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6927 Remote Similarity NPD3396 Approved
0.6927 Remote Similarity NPD3395 Approved
0.6923 Remote Similarity NPD750 Phase 2
0.6923 Remote Similarity NPD6479 Discontinued
0.6919 Remote Similarity NPD4703 Approved
0.6919 Remote Similarity NPD7010 Phase 3
0.6919 Remote Similarity NPD4702 Approved
0.6919 Remote Similarity NPD5530 Phase 1
0.6913 Remote Similarity NPD3264 Phase 3

  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