NPASS Compound

Structure

CID120593 OpenBabel06191715472D 30 34 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 23 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 28 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 12 1 1 0 0 0 19 21 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 25 2 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.14
Volume:	404.022
LogP:	4.615
LogD:	3.91
LogS:	-3.971
# Rotatable Bonds:	2
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	3.821
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.838
MDCK Permeability:	2.7097368729300797e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	98.53961944580078%
Volume Distribution (VD):	0.622
Pgp-substrate:	4.362648963928223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.742
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.706
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	4.602
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.707
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.33
Carcinogencity:	0.664
Eye Corrosion:	0.003
Eye Irritation:	0.107
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC120593

Natural Product ID:	NPC120593
*Common Name:**	Toxicarol
IUPAC Name:	n.a.
Synonyms:	Alpha-Toxicarol; Toxicarol
Standard InCHIKey:	JLTNCZQNGBLBGO-MOPGFXCFSA-N
Standard InCHI:	InChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1
SMILES:	COc1cc2OC[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C=CC(Oc2cc1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508992
PubChem CID:	442826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO32669	derris malaccensis plain	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975515]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10600	Dysoxylum spectabile	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO323	Trachelanthus hissaricus	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11864	Aflatunia ulmifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5368	Achillea cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12750	Cordia americana	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2671	Pedicularis semitorta	Species	Orobanchaceae	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

Activity Type	# Activity
IC50	2
MIC	1
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	23.0	uM	PMID[483522]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	200.0	nM	PMID[483525]
NPT27	Others	Unspecified		IC50	>	47000.0	nM	PMID[483522]
NPT2	Others	Unspecified		Inhibition	=	80.0	%	PMID[483522]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	0.3	ug.mL-1	PMID[483523]
NPT1093	Organism	Callosobruchus maculatus	Callosobruchus maculatus	LC50	<	10.0	ppm	PMID[483524]
NPT1093	Organism	Callosobruchus maculatus	Callosobruchus maculatus	Ratio	=	2.2	n.a.	PMID[483524]

☑ 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 NPC120593 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	1603
0.2-0.3	3702
0.3-0.4	9235
0.4-0.5	9159
0.5-0.6	3415
0.6-0.7	4905
0.7-0.8	5584
0.8-0.85	2771
0.85-0.9	1593
0.9-0.95	291
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC177480
0.962	High Similarity	NPC273959
0.9618	High Similarity	NPC165549
0.9565	High Similarity	NPC103307
0.9563	High Similarity	NPC8965
0.9557	High Similarity	NPC474162
0.9557	High Similarity	NPC229632
0.9557	High Similarity	NPC474150
0.9551	High Similarity	NPC473272
0.9551	High Similarity	NPC284820
0.95	High Similarity	NPC472449
0.95	High Similarity	NPC128293
0.95	High Similarity	NPC173292
0.9494	High Similarity	NPC40037
0.9441	High Similarity	NPC6588
0.9441	High Similarity	NPC117854
0.9441	High Similarity	NPC477154
0.9437	High Similarity	NPC224280
0.9437	High Similarity	NPC234052
0.9437	High Similarity	NPC239752
0.9437	High Similarity	NPC472450
0.9437	High Similarity	NPC275780
0.9437	High Similarity	NPC62261
0.9434	High Similarity	NPC83922
0.9434	High Similarity	NPC472448
0.9434	High Similarity	NPC52204
0.943	High Similarity	NPC119209
0.943	High Similarity	NPC475784
0.943	High Similarity	NPC204290
0.943	High Similarity	NPC118256
0.943	High Similarity	NPC192686
0.9427	High Similarity	NPC476981
0.9427	High Similarity	NPC181960
0.9423	High Similarity	NPC37392
0.9423	High Similarity	NPC472909
0.9387	High Similarity	NPC223375
0.9387	High Similarity	NPC475825
0.9383	High Similarity	NPC326877
0.9383	High Similarity	NPC152477
0.9379	High Similarity	NPC39091
0.9379	High Similarity	NPC272502
0.9375	High Similarity	NPC236521
0.9375	High Similarity	NPC152659
0.9375	High Similarity	NPC186686
0.9375	High Similarity	NPC248638
0.9375	High Similarity	NPC189473
0.9375	High Similarity	NPC23298
0.9371	High Similarity	NPC167678
0.9371	High Similarity	NPC266314
0.9371	High Similarity	NPC472632
0.9371	High Similarity	NPC474187
0.9371	High Similarity	NPC471210
0.9371	High Similarity	NPC29876
0.9371	High Similarity	NPC474186
0.9371	High Similarity	NPC134783
0.9371	High Similarity	NPC474038
0.9367	High Similarity	NPC95936
0.9367	High Similarity	NPC473990
0.9367	High Similarity	NPC250214
0.9325	High Similarity	NPC472276
0.9325	High Similarity	NPC74559
0.9317	High Similarity	NPC25361
0.9317	High Similarity	NPC293319
0.9313	High Similarity	NPC194427
0.9313	High Similarity	NPC261470
0.9313	High Similarity	NPC25152
0.9313	High Similarity	NPC474034
0.9313	High Similarity	NPC474033
0.9308	High Similarity	NPC174953
0.9308	High Similarity	NPC475886
0.9308	High Similarity	NPC476980
0.9308	High Similarity	NPC471976
0.9308	High Similarity	NPC298093
0.9308	High Similarity	NPC474287
0.9304	High Similarity	NPC165977
0.9304	High Similarity	NPC472914
0.9304	High Similarity	NPC27337
0.9304	High Similarity	NPC156057
0.9304	High Similarity	NPC162869
0.9304	High Similarity	NPC222814
0.9304	High Similarity	NPC474208
0.9304	High Similarity	NPC472913
0.9304	High Similarity	NPC78225
0.9304	High Similarity	NPC472910
0.9304	High Similarity	NPC475267
0.9304	High Similarity	NPC217677
0.9304	High Similarity	NPC472911
0.9304	High Similarity	NPC48208
0.9304	High Similarity	NPC469584
0.9304	High Similarity	NPC471209
0.9304	High Similarity	NPC474836
0.9304	High Similarity	NPC245758
0.9304	High Similarity	NPC96167
0.9304	High Similarity	NPC223787
0.9299	High Similarity	NPC226025
0.9299	High Similarity	NPC255807
0.9299	High Similarity	NPC31018
0.9268	High Similarity	NPC121333
0.9264	High Similarity	NPC242395
0.9264	High Similarity	NPC288813
0.9259	High Similarity	NPC43319
0.9259	High Similarity	NPC37870
0.9259	High Similarity	NPC170245
0.9255	High Similarity	NPC41301
0.9255	High Similarity	NPC472625
0.9255	High Similarity	NPC303460
0.9255	High Similarity	NPC306321
0.9255	High Similarity	NPC197168
0.9255	High Similarity	NPC146134
0.925	High Similarity	NPC26326
0.925	High Similarity	NPC474351
0.925	High Similarity	NPC259456
0.925	High Similarity	NPC475883
0.925	High Similarity	NPC471211
0.925	High Similarity	NPC3629
0.925	High Similarity	NPC61010
0.925	High Similarity	NPC173137
0.925	High Similarity	NPC471212
0.9245	High Similarity	NPC152904
0.9245	High Similarity	NPC204879
0.9241	High Similarity	NPC68093
0.9241	High Similarity	NPC255106
0.9241	High Similarity	NPC35038
0.9241	High Similarity	NPC195796
0.9241	High Similarity	NPC278778
0.9241	High Similarity	NPC235165
0.9241	High Similarity	NPC191146
0.9241	High Similarity	NPC291878
0.9236	High Similarity	NPC280937
0.9236	High Similarity	NPC472915
0.9231	High Similarity	NPC208043
0.9231	High Similarity	NPC226973
0.9231	High Similarity	NPC117579
0.9222	High Similarity	NPC324742
0.9212	High Similarity	NPC310794
0.9202	High Similarity	NPC225419
0.9202	High Similarity	NPC14662
0.9202	High Similarity	NPC218226
0.9202	High Similarity	NPC243877
0.9198	High Similarity	NPC326520
0.9198	High Similarity	NPC50960
0.9193	High Similarity	NPC472402
0.9193	High Similarity	NPC220912
0.9193	High Similarity	NPC329760
0.9193	High Similarity	NPC81679
0.9187	High Similarity	NPC200746
0.9187	High Similarity	NPC472624
0.9187	High Similarity	NPC471973
0.9187	High Similarity	NPC139036
0.9187	High Similarity	NPC228785
0.9187	High Similarity	NPC36217
0.9187	High Similarity	NPC56085
0.9187	High Similarity	NPC14353
0.9187	High Similarity	NPC299436
0.9182	High Similarity	NPC299520
0.9182	High Similarity	NPC218313
0.9182	High Similarity	NPC470402
0.9182	High Similarity	NPC129684
0.9182	High Similarity	NPC472598
0.9182	High Similarity	NPC291508
0.9182	High Similarity	NPC99597
0.9182	High Similarity	NPC36852
0.9182	High Similarity	NPC474055
0.9182	High Similarity	NPC210084
0.9182	High Similarity	NPC262286
0.9182	High Similarity	NPC52889
0.9182	High Similarity	NPC474681
0.9177	High Similarity	NPC470327
0.9177	High Similarity	NPC213622
0.9177	High Similarity	NPC477503
0.9177	High Similarity	NPC45849
0.9177	High Similarity	NPC200761
0.9172	High Similarity	NPC166201
0.9172	High Similarity	NPC40033
0.9167	High Similarity	NPC471115
0.9167	High Similarity	NPC472633
0.9167	High Similarity	NPC29777
0.9167	High Similarity	NPC306821
0.9167	High Similarity	NPC338131
0.9162	High Similarity	NPC67302
0.9152	High Similarity	NPC475669
0.9146	High Similarity	NPC476637
0.9141	High Similarity	NPC471213
0.9141	High Similarity	NPC224851
0.9141	High Similarity	NPC320741
0.9141	High Similarity	NPC235610
0.9141	High Similarity	NPC171985
0.9136	High Similarity	NPC475985
0.9136	High Similarity	NPC124038
0.9136	High Similarity	NPC7483
0.9136	High Similarity	NPC207690
0.9136	High Similarity	NPC220313
0.9136	High Similarity	NPC12461
0.913	High Similarity	NPC258331
0.913	High Similarity	NPC472634
0.913	High Similarity	NPC198829
0.913	High Similarity	NPC66288
0.913	High Similarity	NPC57715
0.913	High Similarity	NPC278052
0.913	High Similarity	NPC472275

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 NPC120593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	942
0.2-0.3	1762
0.3-0.4	2589
0.4-0.5	1819
0.5-0.6	986
0.6-0.7	477
0.7-0.8	155
0.8-0.85	33
0.85-0.9	10
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9308	High Similarity	NPD5494	Approved
0.9114	High Similarity	NPD2801	Approved
0.9114	High Similarity	NPD2393	Clinical (unspecified phase)
0.9051	High Similarity	NPD1934	Approved
0.8963	High Similarity	NPD6168	Clinical (unspecified phase)
0.8963	High Similarity	NPD6167	Clinical (unspecified phase)
0.8963	High Similarity	NPD6166	Phase 2
0.8802	High Similarity	NPD7054	Approved
0.875	High Similarity	NPD7472	Approved
0.875	High Similarity	NPD7074	Phase 3
0.8688	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD4378	Clinical (unspecified phase)
0.8596	High Similarity	NPD7808	Phase 3
0.8596	High Similarity	NPD4338	Clinical (unspecified phase)
0.8589	High Similarity	NPD8443	Clinical (unspecified phase)
0.8588	High Similarity	NPD6797	Phase 2
0.858	High Similarity	NPD5844	Phase 1
0.8554	High Similarity	NPD6959	Discontinued
0.8544	High Similarity	NPD1511	Approved
0.8538	High Similarity	NPD7251	Discontinued
0.8537	High Similarity	NPD3882	Suspended
0.8521	High Similarity	NPD3818	Discontinued
0.8476	Intermediate Similarity	NPD3817	Phase 2
0.8471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7473	Discontinued
0.8438	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD6232	Discontinued
0.8375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8373	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8303	Intermediate Similarity	NPD7819	Suspended
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD1247	Approved
0.8217	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8161	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1510	Phase 2
0.8144	Intermediate Similarity	NPD5402	Approved
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.8081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1240	Approved
0.7895	Intermediate Similarity	NPD919	Approved
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD2935	Discontinued
0.7866	Intermediate Similarity	NPD6799	Approved
0.784	Intermediate Similarity	NPD2800	Approved
0.7836	Intermediate Similarity	NPD3749	Approved
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7816	Intermediate Similarity	NPD3926	Phase 2
0.7799	Intermediate Similarity	NPD1607	Approved
0.7798	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD3750	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7713	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1613	Approved
0.7673	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6100	Approved
0.7654	Intermediate Similarity	NPD6099	Approved
0.7634	Intermediate Similarity	NPD4363	Phase 3
0.7634	Intermediate Similarity	NPD4360	Phase 2
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD920	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7605	Intermediate Similarity	NPD5401	Approved
0.7602	Intermediate Similarity	NPD37	Approved
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7593	Intermediate Similarity	NPD2799	Discontinued
0.7592	Intermediate Similarity	NPD7697	Approved
0.7592	Intermediate Similarity	NPD7696	Phase 3
0.7592	Intermediate Similarity	NPD7698	Approved
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD7390	Discontinued
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3748	Approved
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7473	Intermediate Similarity	NPD7549	Discontinued
0.7471	Intermediate Similarity	NPD1653	Approved
0.747	Intermediate Similarity	NPD4628	Phase 3
0.747	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6651	Approved
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7459	Intermediate Similarity	NPD5953	Discontinued
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7416	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD5124	Phase 1
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7407	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD6844	Discontinued
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7381	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5710	Approved
0.736	Intermediate Similarity	NPD5711	Approved
0.7358	Intermediate Similarity	NPD2861	Phase 2
0.7358	Intermediate Similarity	NPD6823	Phase 2
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD6534	Approved
0.7341	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7323	Intermediate Similarity	NPD7801	Approved
0.7322	Intermediate Similarity	NPD7240	Approved
0.7321	Intermediate Similarity	NPD6190	Approved
0.7308	Intermediate Similarity	NPD1610	Phase 2
0.7301	Intermediate Similarity	NPD1933	Approved
0.7296	Intermediate Similarity	NPD7584	Approved
0.7294	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7263	Intermediate Similarity	NPD7229	Phase 3
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5242	Approved
0.7222	Intermediate Similarity	NPD3268	Approved
0.7219	Intermediate Similarity	NPD2309	Approved
0.7216	Intermediate Similarity	NPD5353	Approved
0.7197	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2798	Approved
0.7182	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD2797	Approved
0.7117	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7107	Intermediate Similarity	NPD8319	Approved
0.7107	Intermediate Similarity	NPD4749	Approved
0.7062	Intermediate Similarity	NPD5760	Phase 2
0.7062	Intermediate Similarity	NPD5761	Phase 2
0.7051	Intermediate Similarity	NPD1548	Phase 1
0.7044	Intermediate Similarity	NPD1608	Approved
0.7031	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6213	Phase 3
0.7031	Intermediate Similarity	NPD6212	Phase 3
0.703	Intermediate Similarity	NPD4060	Phase 1
0.7026	Intermediate Similarity	NPD8285	Discontinued
0.7019	Intermediate Similarity	NPD1203	Approved
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD6674	Discontinued
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6832	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