Structure

Physi-Chem Properties

Molecular Weight:  196.07
Volume:  197.575
LogP:  1.868
LogD:  1.711
LogS:  -2.022
# Rotatable Bonds:  3
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.746
Synthetic Accessibility Score:  1.93
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.642
MDCK Permeability:  1.627568417461589e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.78
Plasma Protein Binding (PPB):  83.70343780517578%
Volume Distribution (VD):  0.95
Pgp-substrate:  18.750015258789062%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.924
CYP2C19-inhibitor:  0.403
CYP2C19-substrate:  0.72
CYP2C9-inhibitor:  0.201
CYP2C9-substrate:  0.905
CYP2D6-inhibitor:  0.426
CYP2D6-substrate:  0.881
CYP3A4-inhibitor:  0.333
CYP3A4-substrate:  0.319

ADMET: Excretion

Clearance (CL):  9.963
Half-life (T1/2):  0.66

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.658
AMES Toxicity:  0.136
Rat Oral Acute Toxicity:  0.387
Maximum Recommended Daily Dose:  0.108
Skin Sensitization:  0.274
Carcinogencity:  0.041
Eye Corrosion:  0.269
Eye Irritation:  0.984
Respiratory Toxicity:  0.869

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC305518

Natural Product ID:  NPC305518
Common Name*:   Xanthoxylin
IUPAC Name:   1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone
Synonyms:   Xanthoxylin
Standard InCHIKey:  FBUBVLUPUDBFME-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
SMILES:  CC(=O)c1c(cc(cc1OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL450288
PubChem CID:   66654
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003670] Aryl ketones
              • [CHEMONTID:0004296] Phenylketones
                • [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11000023]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15787457]
NPO9553 Phyllodium pulchellum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[15921433]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. leaf n.a. PMID[21319848]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[26281591]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[3404159]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota Latex n.a. n.a. PMID[6481361]
NPO31224 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[7513748]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31224 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27527 Artemisia brevifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27527 Artemisia brevifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22060 Hippomane mancinella Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31224 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28988 Euphorbia maculata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13555 Beaucarnea recurvata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7870 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9361 Aplophyllum villosum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12233 Diospyros peregrina Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12819 Clitocybe subilludens Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21559 Blumea balsamifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11333 Trapa japonica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28988 Euphorbia maculata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1326 Cratystylis conocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9989 Cotylelobium scabriusculum Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25140 Sapium sebiferum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12591 Archaster typicus Species Archasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6386 Gutenbergia cordifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27527 Artemisia brevifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8601 Petrosia volcano Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13526 Medicago hybrida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4746 Centaurea arenaria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22899 Phaeotremella fagi Species Phaeotremellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9553 Phyllodium pulchellum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13042 Diospyros abyssinica Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12367 Diospyros elliptifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22060 Hippomane mancinella Species Euphorbiaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[494618]
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[494618]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 100000.0 nM PMID[494618]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 100000.0 nM PMID[494618]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 28183.8 nM PMID[494619]
NPT45 Individual Protein Ubiquitin carboxyl-terminal hydrolase 2 Homo sapiens Potency = 15848.9 nM PMID[494619]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 25118.9 nM PMID[494619]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 1122.0 nM PMID[494619]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 206.0 nM PMID[494620]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 2592.9 nM PMID[494620]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 25929.0 nM PMID[494620]
NPT165 Cell Line HeLa Homo sapiens IC50 = 18700.0 nM PMID[494622]
NPT466 Cell Line U-937 Homo sapiens IC50 > 20000.0 nM PMID[494622]
NPT81 Cell Line A549 Homo sapiens IC50 > 20000.0 nM PMID[494622]
NPT783 Cell Line MIA PaCa-2 Homo sapiens IC50 > 20000.0 nM PMID[494622]
NPT2142 Cell Line REH Homo sapiens IC50 > 20000.0 nM PMID[494622]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 20000.0 nM PMID[494622]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[494617]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 100.0 % PMID[494617]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 891.3 nM PMID[494619]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 104.34 % PMID[494621]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 128.73 % PMID[494621]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[494619]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 26679.5 nM PMID[494620]
NPT2 Others Unspecified Potency n.a. 8912.5 nM PMID[494619]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[494623]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[494623]

☑ 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 NPC305518 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC128428
0.9836 High Similarity NPC212379
0.9836 High Similarity NPC69235
0.9754 High Similarity NPC186098
0.9754 High Similarity NPC80694
0.9675 High Similarity NPC230818
0.96 High Similarity NPC31872
0.96 High Similarity NPC473584
0.96 High Similarity NPC475589
0.9597 High Similarity NPC84772
0.9593 High Similarity NPC293453
0.9524 High Similarity NPC129132
0.9524 High Similarity NPC205468
0.9524 High Similarity NPC87231
0.9524 High Similarity NPC257756
0.9524 High Similarity NPC212631
0.9524 High Similarity NPC203817
0.9524 High Similarity NPC25937
0.952 High Similarity NPC270369
0.952 High Similarity NPC5515
0.952 High Similarity NPC324482
0.9449 High Similarity NPC144051
0.9449 High Similarity NPC175098
0.9449 High Similarity NPC263670
0.9449 High Similarity NPC56031
0.9449 High Similarity NPC18877
0.9449 High Similarity NPC82225
0.9449 High Similarity NPC204960
0.9449 High Similarity NPC312318
0.9449 High Similarity NPC223457
0.9449 High Similarity NPC20560
0.9449 High Similarity NPC472365
0.9449 High Similarity NPC188646
0.9449 High Similarity NPC139813
0.9449 High Similarity NPC28753
0.9449 High Similarity NPC192304
0.9449 High Similarity NPC242294
0.9449 High Similarity NPC294593
0.9449 High Similarity NPC159623
0.9449 High Similarity NPC337373
0.9444 High Similarity NPC27490
0.9444 High Similarity NPC262359
0.9444 High Similarity NPC308037
0.9444 High Similarity NPC64359
0.9444 High Similarity NPC313618
0.944 High Similarity NPC42292
0.944 High Similarity NPC185497
0.944 High Similarity NPC307732
0.9375 High Similarity NPC125920
0.9375 High Similarity NPC236974
0.9375 High Similarity NPC164136
0.9375 High Similarity NPC286336
0.9375 High Similarity NPC144027
0.937 High Similarity NPC10971
0.936 High Similarity NPC78662
0.936 High Similarity NPC8005
0.936 High Similarity NPC60558
0.935 High Similarity NPC65041
0.9302 High Similarity NPC60667
0.9302 High Similarity NPC13575
0.9302 High Similarity NPC84699
0.9297 High Similarity NPC93756
0.9297 High Similarity NPC108113
0.9291 High Similarity NPC186097
0.9291 High Similarity NPC475009
0.9291 High Similarity NPC65060
0.9291 High Similarity NPC475008
0.9286 High Similarity NPC247779
0.9231 High Similarity NPC150399
0.9231 High Similarity NPC240147
0.9231 High Similarity NPC194281
0.9231 High Similarity NPC47815
0.9231 High Similarity NPC473887
0.9231 High Similarity NPC477244
0.9231 High Similarity NPC1486
0.9231 High Similarity NPC231772
0.9231 High Similarity NPC121243
0.9231 High Similarity NPC473391
0.9231 High Similarity NPC470398
0.9231 High Similarity NPC274109
0.9231 High Similarity NPC174999
0.9231 High Similarity NPC186838
0.9231 High Similarity NPC66349
0.9231 High Similarity NPC168105
0.9231 High Similarity NPC477243
0.9231 High Similarity NPC127447
0.9231 High Similarity NPC472364
0.9231 High Similarity NPC98115
0.9231 High Similarity NPC476333
0.9231 High Similarity NPC234133
0.9231 High Similarity NPC249606
0.9231 High Similarity NPC12165
0.9231 High Similarity NPC156910
0.9231 High Similarity NPC29353
0.9231 High Similarity NPC477242
0.9231 High Similarity NPC124784
0.9231 High Similarity NPC472367
0.9231 High Similarity NPC41461
0.9231 High Similarity NPC470397
0.9231 High Similarity NPC25287
0.9231 High Similarity NPC222633
0.9231 High Similarity NPC187826
0.9225 High Similarity NPC182496
0.9225 High Similarity NPC103842
0.9225 High Similarity NPC180905
0.92 High Similarity NPC475496
0.92 High Similarity NPC49852
0.9167 High Similarity NPC40649
0.9167 High Similarity NPC209486
0.916 High Similarity NPC303644
0.916 High Similarity NPC317119
0.916 High Similarity NPC209560
0.916 High Similarity NPC472419
0.916 High Similarity NPC162680
0.916 High Similarity NPC153979
0.916 High Similarity NPC266597
0.916 High Similarity NPC188879
0.916 High Similarity NPC7013
0.916 High Similarity NPC294409
0.916 High Similarity NPC250266
0.916 High Similarity NPC116632
0.916 High Similarity NPC181124
0.9154 High Similarity NPC234560
0.9154 High Similarity NPC131039
0.9154 High Similarity NPC39426
0.9154 High Similarity NPC156092
0.9147 High Similarity NPC274121
0.9147 High Similarity NPC213216
0.9147 High Similarity NPC50898
0.9147 High Similarity NPC78540
0.9141 High Similarity NPC164236
0.9141 High Similarity NPC66384
0.9141 High Similarity NPC189106
0.9141 High Similarity NPC112192
0.9141 High Similarity NPC309717
0.9141 High Similarity NPC128348
0.9127 High Similarity NPC473907
0.912 High Similarity NPC95309
0.9113 High Similarity NPC6888
0.9091 High Similarity NPC99333
0.9091 High Similarity NPC470399
0.9091 High Similarity NPC124269
0.9091 High Similarity NPC477055
0.9091 High Similarity NPC188947
0.9091 High Similarity NPC55162
0.9091 High Similarity NPC309154
0.9091 High Similarity NPC472368
0.9091 High Similarity NPC280284
0.9091 High Similarity NPC25427
0.9091 High Similarity NPC243528
0.9091 High Similarity NPC90665
0.9091 High Similarity NPC12175
0.9091 High Similarity NPC21350
0.9091 High Similarity NPC131130
0.9091 High Similarity NPC279668
0.9091 High Similarity NPC278323
0.9091 High Similarity NPC477056
0.9091 High Similarity NPC251681
0.9084 High Similarity NPC235428
0.9084 High Similarity NPC213603
0.9084 High Similarity NPC87545
0.9084 High Similarity NPC135837
0.9084 High Similarity NPC193792
0.9084 High Similarity NPC13408
0.9084 High Similarity NPC240593
0.9077 High Similarity NPC172262
0.907 High Similarity NPC215875
0.907 High Similarity NPC15834
0.907 High Similarity NPC285054
0.907 High Similarity NPC103105
0.9062 High Similarity NPC250057
0.9055 High Similarity NPC211120
0.9055 High Similarity NPC473894
0.9023 High Similarity NPC295384
0.9023 High Similarity NPC470211
0.9023 High Similarity NPC472366
0.9023 High Similarity NPC241838
0.9023 High Similarity NPC310135
0.9023 High Similarity NPC265871
0.9023 High Similarity NPC222342
0.9023 High Similarity NPC150648
0.9023 High Similarity NPC20709
0.9023 High Similarity NPC78913
0.9023 High Similarity NPC143799
0.9023 High Similarity NPC139554
0.9023 High Similarity NPC18260
0.9023 High Similarity NPC37206
0.9023 High Similarity NPC225153
0.9023 High Similarity NPC152042
0.9023 High Similarity NPC49242
0.9023 High Similarity NPC140890
0.9023 High Similarity NPC477956
0.9023 High Similarity NPC471697
0.9023 High Similarity NPC329203
0.9023 High Similarity NPC274784
0.9023 High Similarity NPC23257
0.9016 High Similarity NPC294037
0.9015 High Similarity NPC287246
0.9015 High Similarity NPC212767
0.9015 High Similarity NPC296490

  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 NPC305518 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
0.9444 High Similarity NPD1240 Approved
0.9297 High Similarity NPD1607 Approved
0.9154 High Similarity NPD1510 Phase 2
0.9015 High Similarity NPD1552 Clinical (unspecified phase)
0.9015 High Similarity NPD1550 Clinical (unspecified phase)
0.8947 High Similarity NPD1549 Phase 2
0.8947 High Similarity NPD970 Clinical (unspecified phase)
0.8696 High Similarity NPD4378 Clinical (unspecified phase)
0.8571 High Similarity NPD6651 Approved
0.8489 Intermediate Similarity NPD1511 Approved
0.8429 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD2796 Approved
0.8369 Intermediate Similarity NPD1512 Approved
0.8357 Intermediate Similarity NPD6799 Approved
0.8333 Intermediate Similarity NPD2654 Approved
0.8333 Intermediate Similarity NPD2800 Approved
0.8276 Intermediate Similarity NPD1934 Approved
0.8264 Intermediate Similarity NPD4380 Phase 2
0.8248 Intermediate Similarity NPD1551 Phase 2
0.824 Intermediate Similarity NPD9493 Approved
0.8219 Intermediate Similarity NPD2801 Approved
0.8219 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD9717 Approved
0.8207 Intermediate Similarity NPD7411 Suspended
0.8169 Intermediate Similarity NPD2533 Approved
0.8169 Intermediate Similarity NPD2532 Approved
0.8169 Intermediate Similarity NPD2534 Approved
0.8163 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8134 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.811 Intermediate Similarity NPD9545 Approved
0.8108 Intermediate Similarity NPD3882 Suspended
0.8071 Intermediate Similarity NPD1243 Approved
0.8054 Intermediate Similarity NPD7075 Discontinued
0.803 Intermediate Similarity NPD1203 Approved
0.8015 Intermediate Similarity NPD943 Approved
0.8014 Intermediate Similarity NPD6599 Discontinued
0.8014 Intermediate Similarity NPD3750 Approved
0.8 Intermediate Similarity NPD422 Phase 1
0.7986 Intermediate Similarity NPD2935 Discontinued
0.7973 Intermediate Similarity NPD7819 Suspended
0.7973 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD230 Phase 1
0.7933 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD6801 Discontinued
0.7817 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD3749 Approved
0.7808 Intermediate Similarity NPD920 Approved
0.7801 Intermediate Similarity NPD2344 Approved
0.78 Intermediate Similarity NPD3817 Phase 2
0.7786 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6959 Discontinued
0.7778 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD7768 Phase 2
0.7742 Intermediate Similarity NPD6166 Phase 2
0.7742 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6232 Discontinued
0.7692 Intermediate Similarity NPD1548 Phase 1
0.7692 Intermediate Similarity NPD7473 Discontinued
0.7687 Intermediate Similarity NPD5403 Approved
0.7671 Intermediate Similarity NPD5401 Approved
0.7671 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD3748 Approved
0.7609 Intermediate Similarity NPD411 Approved
0.7606 Intermediate Similarity NPD6099 Approved
0.7606 Intermediate Similarity NPD6100 Approved
0.76 Intermediate Similarity NPD9266 Approved
0.76 Intermediate Similarity NPD74 Approved
0.7595 Intermediate Similarity NPD7054 Approved
0.7595 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD6832 Phase 2
0.7586 Intermediate Similarity NPD2309 Approved
0.7578 Intermediate Similarity NPD1241 Discontinued
0.7574 Intermediate Similarity NPD2798 Approved
0.7574 Intermediate Similarity NPD1019 Discontinued
0.7571 Intermediate Similarity NPD447 Suspended
0.7547 Intermediate Similarity NPD7472 Approved
0.7547 Intermediate Similarity NPD7074 Phase 3
0.7537 Intermediate Similarity NPD3972 Approved
0.7535 Intermediate Similarity NPD2799 Discontinued
0.7532 Intermediate Similarity NPD3818 Discontinued
0.752 Intermediate Similarity NPD9267 Approved
0.752 Intermediate Similarity NPD9264 Approved
0.752 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD9263 Approved
0.7518 Intermediate Similarity NPD9494 Approved
0.7516 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5953 Discontinued
0.75 Intermediate Similarity NPD6797 Phase 2
0.7484 Intermediate Similarity NPD7286 Phase 2
0.7483 Intermediate Similarity NPD7390 Discontinued
0.7482 Intermediate Similarity NPD1296 Phase 2
0.7463 Intermediate Similarity NPD1610 Phase 2
0.7453 Intermediate Similarity NPD7251 Discontinued
0.7419 Intermediate Similarity NPD919 Approved
0.7407 Intermediate Similarity NPD7808 Phase 3
0.7407 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD9269 Phase 2
0.7398 Intermediate Similarity NPD846 Approved
0.7398 Intermediate Similarity NPD940 Approved
0.7397 Intermediate Similarity NPD4628 Phase 3
0.7397 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5711 Approved
0.7389 Intermediate Similarity NPD5710 Approved
0.7372 Intermediate Similarity NPD5494 Approved
0.7368 Intermediate Similarity NPD9268 Approved
0.7368 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD2313 Discontinued
0.7357 Intermediate Similarity NPD3268 Approved
0.7338 Intermediate Similarity NPD4908 Phase 1
0.7338 Intermediate Similarity NPD5402 Approved
0.7333 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1201 Approved
0.7329 Intermediate Similarity NPD1729 Discontinued
0.7325 Intermediate Similarity NPD1247 Approved
0.7301 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3225 Approved
0.7292 Intermediate Similarity NPD7033 Discontinued
0.7279 Intermediate Similarity NPD1608 Approved
0.7273 Intermediate Similarity NPD1465 Phase 2
0.7273 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD9281 Approved
0.7246 Intermediate Similarity NPD1470 Approved
0.7246 Intermediate Similarity NPD2797 Approved
0.7246 Intermediate Similarity NPD1164 Approved
0.7239 Intermediate Similarity NPD6559 Discontinued
0.7237 Intermediate Similarity NPD3226 Approved
0.7234 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD3926 Phase 2
0.7214 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD1933 Approved
0.7203 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD9261 Approved
0.7174 Intermediate Similarity NPD1876 Approved
0.7172 Intermediate Similarity NPD4308 Phase 3
0.7153 Intermediate Similarity NPD1481 Phase 2
0.7143 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6104 Discontinued
0.7122 Intermediate Similarity NPD3266 Approved
0.7122 Intermediate Similarity NPD3267 Approved
0.7113 Intermediate Similarity NPD3764 Approved
0.7101 Intermediate Similarity NPD4749 Approved
0.7092 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5124 Phase 1
0.7081 Intermediate Similarity NPD2403 Approved
0.708 Intermediate Similarity NPD1535 Discovery
0.7075 Intermediate Similarity NPD2346 Discontinued
0.7073 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1778 Approved
0.7059 Intermediate Similarity NPD17 Approved
0.7055 Intermediate Similarity NPD5844 Phase 1
0.7042 Intermediate Similarity NPD3027 Phase 3
0.702 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD3140 Approved
0.7014 Intermediate Similarity NPD3142 Approved
0.7014 Intermediate Similarity NPD1613 Approved
0.7013 Intermediate Similarity NPD7458 Discontinued
0.7006 Intermediate Similarity NPD2296 Approved
0.7006 Intermediate Similarity NPD4288 Approved
0.698 Remote Similarity NPD1652 Phase 2
0.6978 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4363 Phase 3
0.6977 Remote Similarity NPD4360 Phase 2
0.6959 Remote Similarity NPD1471 Phase 3
0.695 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6944 Remote Similarity NPD520 Approved
0.6936 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6936 Remote Similarity NPD4361 Phase 2
0.6934 Remote Similarity NPD4626 Approved
0.6933 Remote Similarity NPD7003 Approved
0.6929 Remote Similarity NPD1283 Approved
0.6923 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6912 Remote Similarity NPD1894 Discontinued
0.6897 Remote Similarity NPD4307 Phase 2
0.6897 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6894 Remote Similarity NPD228 Approved
0.6892 Remote Similarity NPD5404 Approved
0.6892 Remote Similarity NPD5406 Approved
0.6892 Remote Similarity NPD5405 Approved
0.6892 Remote Similarity NPD5408 Approved
0.6887 Remote Similarity NPD2354 Approved
0.6884 Remote Similarity NPD3847 Discontinued
0.6875 Remote Similarity NPD6798 Discontinued
0.6875 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6863 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6861 Remote Similarity NPD1651 Approved
0.6846 Remote Similarity NPD290 Approved
0.6846 Remote Similarity NPD1358 Approved
0.6842 Remote Similarity NPD4287 Approved
0.6826 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4625 Phase 3
0.6792 Remote Similarity NPD5353 Approved
0.6788 Remote Similarity NPD3751 Discontinued
0.6783 Remote Similarity NPD3018 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