NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.08
Volume:	228.803
LogP:	2.494
LogD:	2.352
LogS:	-4.377
# Rotatable Bonds:	0
TPSA:	34.89
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.437
Fsp3:	0.143
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:	-4.679
MDCK Permeability:	2.3905538910184987e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.121
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	91.32906341552734%
Volume Distribution (VD):	0.958
Pgp-substrate:	3.6508374214172363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.839
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.647
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	2.709
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.514
AMES Toxicity:	0.878
Rat Oral Acute Toxicity:	0.634
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.13
Carcinogencity:	0.956
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC56233

Natural Product ID:	NPC56233
*Common Name:**	KXBQYMQMSNZAKO-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KXBQYMQMSNZAKO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-4,7-8H,5-6H2
SMILES:	c1ccc2c(c1)c1ccnc3CCC(=O)n2c13
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2296051
PubChem CID:	76316632
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]
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]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
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]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
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]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	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[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	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]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	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]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	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]
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]
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]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	30.0	ug.mL-1	PMID[449609]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	42.0	ug.mL-1	PMID[449609]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	49.3	ug.mL-1	PMID[449609]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	7.81	ug.mL-1	PMID[449611]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	15.63	ug.mL-1	PMID[449611]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	125.0	ug.mL-1	PMID[449611]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	15.63	ug.mL-1	PMID[449611]

☑ 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 NPC56233 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	724
0.1-0.2	7603
0.2-0.3	20526
0.3-0.4	8022
0.4-0.5	2086
0.5-0.6	2035
0.6-0.7	1264
0.7-0.8	403
0.8-0.85	25
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9038	High Similarity	NPC293487
0.8868	High Similarity	NPC478182
0.8868	High Similarity	NPC478184
0.8805	High Similarity	NPC478185
0.8758	High Similarity	NPC478183
0.8688	High Similarity	NPC194881
0.865	High Similarity	NPC91895
0.865	High Similarity	NPC32534
0.8402	Intermediate Similarity	NPC24864
0.8344	Intermediate Similarity	NPC478186
0.8343	Intermediate Similarity	NPC12649
0.8302	Intermediate Similarity	NPC40070
0.8291	Intermediate Similarity	NPC470111
0.8266	Intermediate Similarity	NPC62749
0.8228	Intermediate Similarity	NPC63545
0.8208	Intermediate Similarity	NPC308931
0.8208	Intermediate Similarity	NPC99939
0.8182	Intermediate Similarity	NPC271797
0.8182	Intermediate Similarity	NPC21174
0.8176	Intermediate Similarity	NPC201380
0.8176	Intermediate Similarity	NPC469811
0.8176	Intermediate Similarity	NPC179787
0.814	Intermediate Similarity	NPC191415
0.8129	Intermediate Similarity	NPC248462
0.8125	Intermediate Similarity	NPC321911
0.8107	Intermediate Similarity	NPC161861
0.8092	Intermediate Similarity	NPC102755
0.8086	Intermediate Similarity	NPC325903
0.8084	Intermediate Similarity	NPC114637
0.8065	Intermediate Similarity	NPC65408
0.8023	Intermediate Similarity	NPC11126
0.8	Intermediate Similarity	NPC477591
0.7953	Intermediate Similarity	NPC469529
0.7939	Intermediate Similarity	NPC236711
0.7937	Intermediate Similarity	NPC470440
0.7904	Intermediate Similarity	NPC225018
0.7903	Intermediate Similarity	NPC238457
0.7901	Intermediate Similarity	NPC128244
0.7892	Intermediate Similarity	NPC317701
0.7889	Intermediate Similarity	NPC326422
0.7866	Intermediate Similarity	NPC281094
0.7861	Intermediate Similarity	NPC157583
0.7853	Intermediate Similarity	NPC478077
0.7844	Intermediate Similarity	NPC122141
0.7841	Intermediate Similarity	NPC467063
0.7841	Intermediate Similarity	NPC228835
0.7834	Intermediate Similarity	NPC251722
0.7834	Intermediate Similarity	NPC314102
0.7818	Intermediate Similarity	NPC476219
0.7814	Intermediate Similarity	NPC474916
0.7812	Intermediate Similarity	NPC20144
0.779	Intermediate Similarity	NPC198673
0.7772	Intermediate Similarity	NPC81535
0.7771	Intermediate Similarity	NPC15840
0.7759	Intermediate Similarity	NPC237188
0.7759	Intermediate Similarity	NPC64436
0.7751	Intermediate Similarity	NPC317105
0.7742	Intermediate Similarity	NPC57398
0.774	Intermediate Similarity	NPC472119
0.7738	Intermediate Similarity	NPC470204
0.7722	Intermediate Similarity	NPC150259
0.7722	Intermediate Similarity	NPC324091
0.7709	Intermediate Similarity	NPC17059
0.7701	Intermediate Similarity	NPC280852
0.7701	Intermediate Similarity	NPC151635
0.7697	Intermediate Similarity	NPC470233
0.7692	Intermediate Similarity	NPC242116
0.7692	Intermediate Similarity	NPC470203
0.7684	Intermediate Similarity	NPC143533
0.7682	Intermediate Similarity	NPC46358
0.768	Intermediate Similarity	NPC117244
0.768	Intermediate Similarity	NPC476460
0.768	Intermediate Similarity	NPC473763
0.7676	Intermediate Similarity	NPC474318
0.7676	Intermediate Similarity	NPC220797
0.7676	Intermediate Similarity	NPC475914
0.7676	Intermediate Similarity	NPC268744
0.7676	Intermediate Similarity	NPC153123
0.7676	Intermediate Similarity	NPC201266
0.767	Intermediate Similarity	NPC73994
0.7647	Intermediate Similarity	NPC265100
0.7644	Intermediate Similarity	NPC471579
0.764	Intermediate Similarity	NPC258480
0.764	Intermediate Similarity	NPC477003
0.7637	Intermediate Similarity	NPC471386
0.7637	Intermediate Similarity	NPC216550
0.7634	Intermediate Similarity	NPC166209
0.7634	Intermediate Similarity	NPC269203
0.7634	Intermediate Similarity	NPC77241
0.7634	Intermediate Similarity	NPC13456
0.7625	Intermediate Similarity	NPC88097
0.7622	Intermediate Similarity	NPC168911
0.7622	Intermediate Similarity	NPC239954
0.7622	Intermediate Similarity	NPC212213
0.7617	Intermediate Similarity	NPC234078
0.7617	Intermediate Similarity	NPC221100
0.7607	Intermediate Similarity	NPC86288
0.7602	Intermediate Similarity	NPC274229
0.7598	Intermediate Similarity	NPC133003
0.7598	Intermediate Similarity	NPC472107
0.7598	Intermediate Similarity	NPC79062
0.7593	Intermediate Similarity	NPC190296
0.759	Intermediate Similarity	NPC472260
0.7584	Intermediate Similarity	NPC470205
0.7578	Intermediate Similarity	NPC115611
0.7578	Intermediate Similarity	NPC238499
0.7568	Intermediate Similarity	NPC167710
0.7562	Intermediate Similarity	NPC169433
0.7557	Intermediate Similarity	NPC234987
0.7556	Intermediate Similarity	NPC94752
0.7556	Intermediate Similarity	NPC141612
0.7556	Intermediate Similarity	NPC135601
0.7556	Intermediate Similarity	NPC17273
0.7556	Intermediate Similarity	NPC66210
0.7547	Intermediate Similarity	NPC96102
0.7545	Intermediate Similarity	NPC200214
0.7543	Intermediate Similarity	NPC469938
0.7529	Intermediate Similarity	NPC82331
0.7516	Intermediate Similarity	NPC110126
0.7516	Intermediate Similarity	NPC73767
0.7516	Intermediate Similarity	NPC104483
0.7515	Intermediate Similarity	NPC129721
0.7514	Intermediate Similarity	NPC78020
0.7514	Intermediate Similarity	NPC472323
0.75	Intermediate Similarity	NPC105127
0.75	Intermediate Similarity	NPC42372
0.75	Intermediate Similarity	NPC476297
0.75	Intermediate Similarity	NPC314372
0.75	Intermediate Similarity	NPC84911
0.75	Intermediate Similarity	NPC159856
0.7487	Intermediate Similarity	NPC237414
0.7484	Intermediate Similarity	NPC198988
0.7473	Intermediate Similarity	NPC255909
0.7473	Intermediate Similarity	NPC103119
0.7471	Intermediate Similarity	NPC97343
0.7471	Intermediate Similarity	NPC80681
0.746	Intermediate Similarity	NPC211813
0.7459	Intermediate Similarity	NPC294693
0.7458	Intermediate Similarity	NPC284775
0.7458	Intermediate Similarity	NPC145885
0.7458	Intermediate Similarity	NPC14113
0.7458	Intermediate Similarity	NPC84827
0.7458	Intermediate Similarity	NPC111275
0.7455	Intermediate Similarity	NPC288838
0.7444	Intermediate Similarity	NPC21429
0.7443	Intermediate Similarity	NPC203468
0.7443	Intermediate Similarity	NPC149155
0.7443	Intermediate Similarity	NPC317054
0.7443	Intermediate Similarity	NPC110500
0.744	Intermediate Similarity	NPC138842
0.7438	Intermediate Similarity	NPC29886
0.7438	Intermediate Similarity	NPC261195
0.743	Intermediate Similarity	NPC113626
0.7427	Intermediate Similarity	NPC81229
0.7427	Intermediate Similarity	NPC255229
0.7425	Intermediate Similarity	NPC473878
0.7421	Intermediate Similarity	NPC53144
0.7421	Intermediate Similarity	NPC200836
0.7419	Intermediate Similarity	NPC79356
0.7419	Intermediate Similarity	NPC102592
0.7416	Intermediate Similarity	NPC55772
0.7405	Intermediate Similarity	NPC304203
0.7401	Intermediate Similarity	NPC267885
0.7394	Intermediate Similarity	NPC285731
0.7389	Intermediate Similarity	NPC48938
0.7386	Intermediate Similarity	NPC252572
0.7381	Intermediate Similarity	NPC470679
0.7381	Intermediate Similarity	NPC217021
0.7374	Intermediate Similarity	NPC91179
0.7371	Intermediate Similarity	NPC65080
0.7368	Intermediate Similarity	NPC92796
0.7368	Intermediate Similarity	NPC135141
0.7362	Intermediate Similarity	NPC469780
0.7362	Intermediate Similarity	NPC469768
0.7362	Intermediate Similarity	NPC469779
0.7362	Intermediate Similarity	NPC469761
0.7362	Intermediate Similarity	NPC469784
0.7362	Intermediate Similarity	NPC469783
0.7362	Intermediate Similarity	NPC279081
0.7362	Intermediate Similarity	NPC284635
0.7362	Intermediate Similarity	NPC469767
0.736	Intermediate Similarity	NPC83774
0.7353	Intermediate Similarity	NPC51054
0.7351	Intermediate Similarity	NPC91958
0.7348	Intermediate Similarity	NPC284678
0.7345	Intermediate Similarity	NPC293216
0.7345	Intermediate Similarity	NPC297034
0.7342	Intermediate Similarity	NPC69914
0.734	Intermediate Similarity	NPC131887
0.7329	Intermediate Similarity	NPC325252
0.7326	Intermediate Similarity	NPC44773
0.7326	Intermediate Similarity	NPC472116
0.7326	Intermediate Similarity	NPC215584
0.7321	Intermediate Similarity	NPC105818
0.7321	Intermediate Similarity	NPC53947
0.7321	Intermediate Similarity	NPC24678
0.7318	Intermediate Similarity	NPC248041
0.7318	Intermediate Similarity	NPC283219
0.7318	Intermediate Similarity	NPC126709
0.7317	Intermediate Similarity	NPC469766

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 NPC56233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	709
0.2-0.3	1024
0.3-0.4	2140
0.4-0.5	2048
0.5-0.6	1795
0.6-0.7	883
0.7-0.8	168
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD6454	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4547	Phase 3
0.8101	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD201	Phase 2
0.8065	Intermediate Similarity	NPD200	Phase 2
0.8026	Intermediate Similarity	NPD715	Phase 3
0.7956	Intermediate Similarity	NPD2880	Discontinued
0.7933	Intermediate Similarity	NPD3430	Approved
0.7933	Intermediate Similarity	NPD3431	Approved
0.7866	Intermediate Similarity	NPD2837	Discontinued
0.7853	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD7618	Phase 3
0.7845	Intermediate Similarity	NPD7619	Phase 3
0.7841	Intermediate Similarity	NPD7564	Discontinued
0.7819	Intermediate Similarity	NPD7665	Phase 2
0.7819	Intermediate Similarity	NPD7666	Phase 3
0.7798	Intermediate Similarity	NPD5400	Approved
0.7772	Intermediate Similarity	NPD6999	Discontinued
0.7772	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD3905	Phase 3
0.7756	Intermediate Similarity	NPD3385	Approved
0.7754	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6178	Phase 3
0.7727	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7394	Phase 2
0.7706	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2720	Phase 1
0.7688	Intermediate Similarity	NPD750	Phase 2
0.7654	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7944	Discontinued
0.7647	Intermediate Similarity	NPD2881	Approved
0.7647	Intermediate Similarity	NPD3583	Phase 2
0.7647	Intermediate Similarity	NPD2879	Approved
0.764	Intermediate Similarity	NPD1722	Approved
0.7637	Intermediate Similarity	NPD5505	Discontinued
0.7632	Intermediate Similarity	NPD6520	Phase 3
0.7632	Intermediate Similarity	NPD6521	Phase 3
0.7622	Intermediate Similarity	NPD1661	Suspended
0.7609	Intermediate Similarity	NPD4848	Phase 1
0.76	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2006	Phase 2
0.7593	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6771	Discontinued
0.7582	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1658	Discontinued
0.7576	Intermediate Similarity	NPD2430	Phase 2
0.7568	Intermediate Similarity	NPD6664	Approved
0.7566	Intermediate Similarity	NPD5426	Phase 3
0.7564	Intermediate Similarity	NPD3476	Approved
0.7564	Intermediate Similarity	NPD3475	Approved
0.7561	Intermediate Similarity	NPD7469	Discontinued
0.7554	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4922	Phase 2
0.7539	Intermediate Similarity	NPD2442	Approved
0.7539	Intermediate Similarity	NPD2443	Approved
0.7532	Intermediate Similarity	NPD3942	Approved
0.7532	Intermediate Similarity	NPD3944	Approved
0.7515	Intermediate Similarity	NPD4326	Phase 2
0.7515	Intermediate Similarity	NPD1270	Approved
0.7514	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD977	Approved
0.75	Intermediate Similarity	NPD975	Approved
0.75	Intermediate Similarity	NPD4075	Phase 2
0.75	Intermediate Similarity	NPD976	Approved
0.75	Intermediate Similarity	NPD5017	Discontinued
0.7487	Intermediate Similarity	NPD1506	Discontinued
0.7485	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2119	Approved
0.7484	Intermediate Similarity	NPD2118	Approved
0.7474	Intermediate Similarity	NPD4446	Approved
0.7471	Intermediate Similarity	NPD5418	Discontinued
0.7468	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7111	Discontinued
0.7457	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD482	Approved
0.7436	Intermediate Similarity	NPD6787	Phase 2
0.7435	Intermediate Similarity	NPD2008	Discontinued
0.7419	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2333	Discontinued
0.7414	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD786	Approved
0.7403	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5555	Phase 1
0.7401	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6554	Approved
0.7391	Intermediate Similarity	NPD7434	Approved
0.7391	Intermediate Similarity	NPD45	Approved
0.7389	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3654	Approved
0.7385	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4902	Discontinued
0.7363	Intermediate Similarity	NPD5809	Phase 3
0.7349	Intermediate Similarity	NPD1683	Approved
0.734	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5198	Approved
0.7337	Intermediate Similarity	NPD5199	Approved
0.733	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6507	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4988	Discontinued
0.732	Intermediate Similarity	NPD2408	Discontinued
0.7314	Intermediate Similarity	NPD1343	Approved
0.7312	Intermediate Similarity	NPD4029	Approved
0.7312	Intermediate Similarity	NPD4030	Approved
0.7312	Intermediate Similarity	NPD4028	Approved
0.7303	Intermediate Similarity	NPD6044	Discontinued
0.7302	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6954	Phase 2
0.7296	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2411	Approved
0.7293	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6470	Phase 3
0.7283	Intermediate Similarity	NPD5315	Discontinued
0.7278	Intermediate Similarity	NPD3927	Phase 2
0.7268	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6721	Phase 1
0.7262	Intermediate Similarity	NPD3100	Discontinued
0.7261	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD991	Phase 2
0.7254	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7001	Phase 3
0.7253	Intermediate Similarity	NPD2096	Phase 2
0.7253	Intermediate Similarity	NPD2091	Phase 2
0.7253	Intermediate Similarity	NPD4957	Phase 2
0.7247	Intermediate Similarity	NPD5065	Approved
0.7247	Intermediate Similarity	NPD4883	Approved
0.7243	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3323	Discontinued
0.7239	Intermediate Similarity	NPD2896	Discontinued
0.7225	Intermediate Similarity	NPD2511	Approved
0.7222	Intermediate Similarity	NPD3078	Approved
0.7222	Intermediate Similarity	NPD3079	Approved
0.7222	Intermediate Similarity	NPD3076	Approved
0.7222	Intermediate Similarity	NPD3077	Approved
0.7219	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4640	Approved
0.7216	Intermediate Similarity	NPD4639	Approved
0.7216	Intermediate Similarity	NPD4638	Approved
0.7208	Intermediate Similarity	NPD271	Approved
0.7208	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD268	Approved
0.7207	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2751	Phase 1
0.7202	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2915	Discontinued
0.7198	Intermediate Similarity	NPD2092	Phase 2
0.7198	Intermediate Similarity	NPD3320	Approved
0.7198	Intermediate Similarity	NPD2095	Phase 2
0.7198	Intermediate Similarity	NPD2094	Phase 2
0.7198	Intermediate Similarity	NPD3319	Phase 1
0.7198	Intermediate Similarity	NPD3318	Approved
0.7196	Intermediate Similarity	NPD5446	Phase 2
0.7191	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2481	Approved
0.7182	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5473	Discontinued
0.7182	Intermediate Similarity	NPD2479	Phase 3
0.7181	Intermediate Similarity	NPD4602	Approved
0.7174	Intermediate Similarity	NPD6217	Discontinued
0.7167	Intermediate Similarity	NPD4181	Approved
0.7159	Intermediate Similarity	NPD6446	Discontinued
0.7159	Intermediate Similarity	NPD5636	Discontinued
0.7158	Intermediate Similarity	NPD5892	Approved
0.7158	Intermediate Similarity	NPD4397	Phase 1
0.7135	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3961	Discontinued
0.712	Intermediate Similarity	NPD5854	Approved
0.7119	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1255	Approved
0.7117	Intermediate Similarity	NPD1253	Approved
0.7117	Intermediate Similarity	NPD1256	Approved
0.7117	Intermediate Similarity	NPD1254	Approved
0.7113	Intermediate Similarity	NPD7207	Approved
0.7113	Intermediate Similarity	NPD7208	Approved
0.7113	Intermediate Similarity	NPD7209	Approved
0.7111	Intermediate Similarity	NPD5104	Approved
0.711	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1031	Discontinued
0.7098	Intermediate Similarity	NPD6268	Phase 1
0.7098	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6474	Phase 2
0.7088	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5508	Phase 1
0.7083	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7026	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