NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.05
Volume:	261.972
LogP:	2.96
LogD:	3.499
LogS:	-4.623
# Rotatable Bonds:	1
TPSA:	34.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	2.54
Fsp3:	0.067
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:	-4.771
MDCK Permeability:	2.3541249902336858e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	94.61669158935547%
Volume Distribution (VD):	0.725
Pgp-substrate:	2.106532335281372%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.559
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	7.602
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.45
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.203
Carcinogencity:	0.967
Eye Corrosion:	0.004
Eye Irritation:	0.817
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC91895

Natural Product ID:	NPC91895
*Common Name:**	HCKATCNEEDQXNJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HCKATCNEEDQXNJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10N2OS/c1-19-12-8-13(18)17-11-5-3-2-4-9(11)10-6-7-16-14(12)15(10)17/h2-8H,1H3
SMILES:	CSc1cc(=O)n2c3ccccc3c3ccnc1c23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1981482
PubChem CID:	259217
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
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21067210]
NPO21885	Furcraea elegans	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21012	Mikania sessilifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20992	Tarenna graveolens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18753	Sideritis serrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21697	Irpex pachyodon	Species	Irpicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19973	Cupania glabra	Species	Sapindaceae	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
GI50	57

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	45603.69	nM	PMID[520953]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	65313.06	nM	PMID[520953]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[520953]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	43351.09	nM	PMID[520953]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	86696.19	nM	PMID[520953]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	91411.32	nM	PMID[520953]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	35481.34	nM	PMID[520953]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	73790.42	nM	PMID[520953]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	55590.43	nM	PMID[520953]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	67920.36	nM	PMID[520953]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	97051.0	nM	PMID[520953]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	64268.77	nM	PMID[520953]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	79615.94	nM	PMID[520953]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	81846.48	nM	PMID[520953]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	82224.26	nM	PMID[520953]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	10.0	nM	PMID[520953]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	90782.05	nM	PMID[520953]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	100000.0	nM	PMID[520953]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	61801.64	nM	PMID[520953]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	69342.58	nM	PMID[520953]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	39719.15	nM	PMID[520953]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	49888.45	nM	PMID[520953]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	24434.31	nM	PMID[520953]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	34593.94	nM	PMID[520953]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	25585.86	nM	PMID[520953]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	41399.97	nM	PMID[520953]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	57016.43	nM	PMID[520953]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	100000.0	nM	PMID[520953]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25703.96	nM	PMID[520953]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	65162.84	nM	PMID[520953]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	70794.58	nM	PMID[520953]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	54450.27	nM	PMID[520953]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	49659.23	nM	PMID[520953]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	14157.94	nM	PMID[520953]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[520953]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	49203.95	nM	PMID[520953]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	81470.43	nM	PMID[520953]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	7161.43	nM	PMID[520953]

☑ 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 NPC91895 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	846
0.1-0.2	9251
0.2-0.3	18185
0.3-0.4	9211
0.4-0.5	1928
0.5-0.6	2193
0.6-0.7	939
0.7-0.8	131
0.8-0.85	3
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC293487
0.9359	High Similarity	NPC478182
0.9236	High Similarity	NPC478184
0.9172	High Similarity	NPC478185
0.9119	High Similarity	NPC478183
0.9006	High Similarity	NPC32534
0.8831	High Similarity	NPC478186
0.8795	High Similarity	NPC12649
0.865	High Similarity	NPC56233
0.8631	High Similarity	NPC24864
0.8302	Intermediate Similarity	NPC470111
0.821	Intermediate Similarity	NPC281094
0.8202	Intermediate Similarity	NPC198673
0.8187	Intermediate Similarity	NPC201380
0.8187	Intermediate Similarity	NPC179787
0.8137	Intermediate Similarity	NPC321911
0.8125	Intermediate Similarity	NPC63545
0.8086	Intermediate Similarity	NPC40070
0.8075	Intermediate Similarity	NPC469811
0.8038	Intermediate Similarity	NPC238499
0.8024	Intermediate Similarity	NPC225018
0.8022	Intermediate Similarity	NPC168911
0.8022	Intermediate Similarity	NPC239954
0.8022	Intermediate Similarity	NPC212213
0.8012	Intermediate Similarity	NPC477591
0.7988	Intermediate Similarity	NPC325903
0.7988	Intermediate Similarity	NPC200214
0.7964	Intermediate Similarity	NPC122141
0.7952	Intermediate Similarity	NPC236711
0.795	Intermediate Similarity	NPC470440
0.7848	Intermediate Similarity	NPC314102
0.7848	Intermediate Similarity	NPC251722
0.7841	Intermediate Similarity	NPC191415
0.784	Intermediate Similarity	NPC285731
0.7826	Intermediate Similarity	NPC20144
0.7818	Intermediate Similarity	NPC216713
0.7764	Intermediate Similarity	NPC277157
0.776	Intermediate Similarity	NPC294693
0.7754	Intermediate Similarity	NPC211813
0.7744	Intermediate Similarity	NPC471957
0.7736	Intermediate Similarity	NPC150259
0.7713	Intermediate Similarity	NPC200836
0.7713	Intermediate Similarity	NPC53144
0.7711	Intermediate Similarity	NPC470823
0.7697	Intermediate Similarity	NPC102755
0.7688	Intermediate Similarity	NPC65080
0.7688	Intermediate Similarity	NPC81535
0.7674	Intermediate Similarity	NPC114637
0.7661	Intermediate Similarity	NPC317105
0.7657	Intermediate Similarity	NPC469529
0.7647	Intermediate Similarity	NPC470204
0.7644	Intermediate Similarity	NPC82548
0.7644	Intermediate Similarity	NPC287208
0.7627	Intermediate Similarity	NPC11126
0.7619	Intermediate Similarity	NPC476219
0.7607	Intermediate Similarity	NPC190296
0.7604	Intermediate Similarity	NPC174672
0.7604	Intermediate Similarity	NPC174758
0.7602	Intermediate Similarity	NPC470203
0.7602	Intermediate Similarity	NPC194881
0.7593	Intermediate Similarity	NPC115611
0.7582	Intermediate Similarity	NPC46358
0.7582	Intermediate Similarity	NPC255909
0.7582	Intermediate Similarity	NPC103119
0.7574	Intermediate Similarity	NPC51054
0.7571	Intermediate Similarity	NPC248454
0.7543	Intermediate Similarity	NPC82331
0.7531	Intermediate Similarity	NPC73767
0.7531	Intermediate Similarity	NPC104483
0.7531	Intermediate Similarity	NPC110126
0.7529	Intermediate Similarity	NPC129721
0.7516	Intermediate Similarity	NPC84911
0.7515	Intermediate Similarity	NPC476297
0.7515	Intermediate Similarity	NPC314372
0.7514	Intermediate Similarity	NPC99939
0.7514	Intermediate Similarity	NPC280852
0.7514	Intermediate Similarity	NPC274229
0.7514	Intermediate Similarity	NPC308931
0.75	Intermediate Similarity	NPC198988
0.75	Intermediate Similarity	NPC470233
0.7486	Intermediate Similarity	NPC73994
0.7474	Intermediate Similarity	NPC85273
0.7472	Intermediate Similarity	NPC240088
0.7472	Intermediate Similarity	NPC473380
0.7469	Intermediate Similarity	NPC169433
0.7459	Intermediate Similarity	NPC228835
0.7458	Intermediate Similarity	NPC317054
0.7453	Intermediate Similarity	NPC29886
0.7453	Intermediate Similarity	NPC96102
0.7453	Intermediate Similarity	NPC261195
0.7447	Intermediate Similarity	NPC474916
0.7435	Intermediate Similarity	NPC317701
0.743	Intermediate Similarity	NPC265710
0.743	Intermediate Similarity	NPC248462
0.7419	Intermediate Similarity	NPC326422
0.741	Intermediate Similarity	NPC159856
0.7407	Intermediate Similarity	NPC105127
0.7407	Intermediate Similarity	NPC65408
0.7403	Intermediate Similarity	NPC163055
0.7396	Intermediate Similarity	NPC472260
0.7389	Intermediate Similarity	NPC16659
0.7386	Intermediate Similarity	NPC97343
0.7378	Intermediate Similarity	NPC469768
0.7378	Intermediate Similarity	NPC469784
0.7378	Intermediate Similarity	NPC469761
0.7378	Intermediate Similarity	NPC469780
0.7378	Intermediate Similarity	NPC469783
0.7378	Intermediate Similarity	NPC469767
0.7378	Intermediate Similarity	NPC469779
0.7377	Intermediate Similarity	NPC62749
0.7374	Intermediate Similarity	NPC14325
0.7374	Intermediate Similarity	NPC28848
0.7374	Intermediate Similarity	NPC274982
0.7365	Intermediate Similarity	NPC288838
0.7365	Intermediate Similarity	NPC143872
0.7363	Intermediate Similarity	NPC284678
0.7363	Intermediate Similarity	NPC467063
0.736	Intermediate Similarity	NPC471579
0.7346	Intermediate Similarity	NPC325252
0.7341	Intermediate Similarity	NPC44773
0.7341	Intermediate Similarity	NPC215584
0.7337	Intermediate Similarity	NPC24678
0.7337	Intermediate Similarity	NPC105818
0.7337	Intermediate Similarity	NPC53947
0.7333	Intermediate Similarity	NPC469766
0.7318	Intermediate Similarity	NPC474958
0.7317	Intermediate Similarity	NPC88097
0.7308	Intermediate Similarity	NPC48938
0.7305	Intermediate Similarity	NPC86288
0.7299	Intermediate Similarity	NPC282231
0.7299	Intermediate Similarity	NPC242116
0.7292	Intermediate Similarity	NPC106757
0.7292	Intermediate Similarity	NPC57398
0.7288	Intermediate Similarity	NPC194411
0.7283	Intermediate Similarity	NPC56765
0.7283	Intermediate Similarity	NPC92796
0.7283	Intermediate Similarity	NPC318065
0.7283	Intermediate Similarity	NPC135141
0.7283	Intermediate Similarity	NPC94752
0.7283	Intermediate Similarity	NPC206819
0.7278	Intermediate Similarity	NPC157583
0.7273	Intermediate Similarity	NPC284635
0.7273	Intermediate Similarity	NPC279081
0.7268	Intermediate Similarity	NPC21429
0.7268	Intermediate Similarity	NPC238457
0.7263	Intermediate Similarity	NPC469938
0.7258	Intermediate Similarity	NPC324091
0.7255	Intermediate Similarity	NPC91958
0.7251	Intermediate Similarity	NPC73952
0.7251	Intermediate Similarity	NPC469786
0.7251	Intermediate Similarity	NPC25008
0.7251	Intermediate Similarity	NPC469760
0.7251	Intermediate Similarity	NPC259644
0.7251	Intermediate Similarity	NPC469765
0.7251	Intermediate Similarity	NPC469763
0.725	Intermediate Similarity	NPC22079
0.7243	Intermediate Similarity	NPC17059
0.7241	Intermediate Similarity	NPC255229
0.7241	Intermediate Similarity	NPC279918
0.7241	Intermediate Similarity	NPC81229
0.7235	Intermediate Similarity	NPC148592
0.7232	Intermediate Similarity	NPC63751
0.7226	Intermediate Similarity	NPC48564
0.7226	Intermediate Similarity	NPC265605
0.7226	Intermediate Similarity	NPC182570
0.7225	Intermediate Similarity	NPC237414
0.7222	Intermediate Similarity	NPC151635
0.7219	Intermediate Similarity	NPC117244
0.7219	Intermediate Similarity	NPC473763
0.7216	Intermediate Similarity	NPC88115
0.7211	Intermediate Similarity	NPC167710
0.7209	Intermediate Similarity	NPC211572
0.7209	Intermediate Similarity	NPC80597
0.7209	Intermediate Similarity	NPC212376
0.7209	Intermediate Similarity	NPC75540
0.7209	Intermediate Similarity	NPC70922
0.7207	Intermediate Similarity	NPC161861
0.7205	Intermediate Similarity	NPC82295
0.7205	Intermediate Similarity	NPC256893
0.7202	Intermediate Similarity	NPC469525
0.7182	Intermediate Similarity	NPC83774
0.7182	Intermediate Similarity	NPC64436
0.7175	Intermediate Similarity	NPC49954
0.7175	Intermediate Similarity	NPC474561
0.7174	Intermediate Similarity	NPC165495
0.7174	Intermediate Similarity	NPC470003
0.7169	Intermediate Similarity	NPC230002
0.7167	Intermediate Similarity	NPC37423
0.7167	Intermediate Similarity	NPC275305
0.7159	Intermediate Similarity	NPC271797
0.7159	Intermediate Similarity	NPC265100
0.7159	Intermediate Similarity	NPC21174
0.7151	Intermediate Similarity	NPC138842
0.7143	Intermediate Similarity	NPC162689
0.7143	Intermediate Similarity	NPC54102
0.7136	Intermediate Similarity	NPC75726
0.7136	Intermediate Similarity	NPC31385
0.7136	Intermediate Similarity	NPC110602
0.7135	Intermediate Similarity	NPC133003
0.7126	Intermediate Similarity	NPC216643

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 NPC91895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	702
0.2-0.3	1106
0.3-0.4	2401
0.4-0.5	1996
0.5-0.6	1849
0.6-0.7	603
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8024	Intermediate Similarity	NPD5315	Discontinued
0.7963	Intermediate Similarity	NPD4547	Phase 3
0.7963	Intermediate Similarity	NPD1661	Suspended
0.7929	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2720	Phase 1
0.7806	Intermediate Similarity	NPD715	Phase 3
0.7771	Intermediate Similarity	NPD3385	Approved
0.7751	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6044	Discontinued
0.7673	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3610	Approved
0.7644	Intermediate Similarity	NPD3609	Approved
0.7616	Intermediate Similarity	NPD2915	Discontinued
0.7614	Intermediate Similarity	NPD4075	Phase 2
0.7607	Intermediate Similarity	NPD2006	Phase 2
0.7607	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5400	Approved
0.759	Intermediate Similarity	NPD2430	Phase 2
0.7584	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3475	Approved
0.758	Intermediate Similarity	NPD3476	Approved
0.7569	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2837	Discontinued
0.7546	Intermediate Similarity	NPD1722	Approved
0.7541	Intermediate Similarity	NPD2818	Discontinued
0.7529	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4326	Phase 2
0.7527	Intermediate Similarity	NPD7394	Phase 2
0.7527	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4436	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2118	Approved
0.75	Intermediate Similarity	NPD2119	Approved
0.7487	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3100	Discontinued
0.7485	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4509	Discontinued
0.7453	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2640	Approved
0.7429	Intermediate Similarity	NPD4640	Approved
0.7429	Intermediate Similarity	NPD4639	Approved
0.7429	Intermediate Similarity	NPD4638	Approved
0.7429	Intermediate Similarity	NPD2641	Approved
0.7423	Intermediate Similarity	NPD786	Approved
0.7418	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD201	Phase 2
0.7407	Intermediate Similarity	NPD45	Approved
0.7407	Intermediate Similarity	NPD6554	Approved
0.7407	Intermediate Similarity	NPD200	Phase 2
0.7405	Intermediate Similarity	NPD3654	Approved
0.7399	Intermediate Similarity	NPD6771	Discontinued
0.7377	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6217	Discontinued
0.7377	Intermediate Similarity	NPD4902	Discontinued
0.7366	Intermediate Similarity	NPD3431	Approved
0.7366	Intermediate Similarity	NPD3430	Approved
0.7365	Intermediate Similarity	NPD1683	Approved
0.7365	Intermediate Similarity	NPD7469	Discontinued
0.7363	Intermediate Similarity	NPD7564	Discontinued
0.7358	Intermediate Similarity	NPD6156	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1403	Approved
0.7341	Intermediate Similarity	NPD1404	Approved
0.7337	Intermediate Similarity	NPD3961	Discontinued
0.733	Intermediate Similarity	NPD2333	Discontinued
0.7329	Intermediate Similarity	NPD3942	Approved
0.7329	Intermediate Similarity	NPD4028	Approved
0.7329	Intermediate Similarity	NPD4030	Approved
0.7329	Intermediate Similarity	NPD3944	Approved
0.7329	Intermediate Similarity	NPD4029	Approved
0.7325	Intermediate Similarity	NPD9583	Approved
0.7322	Intermediate Similarity	NPD5555	Phase 1
0.732	Intermediate Similarity	NPD5864	Phase 2
0.7318	Intermediate Similarity	NPD3348	Phase 2
0.7318	Intermediate Similarity	NPD5104	Approved
0.7312	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7164	Discontinued
0.7299	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4047	Discontinued
0.7287	Intermediate Similarity	NPD7618	Phase 3
0.7287	Intermediate Similarity	NPD7619	Phase 3
0.7278	Intermediate Similarity	NPD7111	Discontinued
0.7273	Intermediate Similarity	NPD5636	Discontinued
0.7273	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4957	Phase 2
0.7263	Intermediate Similarity	NPD4128	Approved
0.7257	Intermediate Similarity	NPD3323	Discontinued
0.7249	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD792	Discontinued
0.7234	Intermediate Similarity	NPD2717	Phase 2
0.7231	Intermediate Similarity	NPD3905	Phase 3
0.7226	Intermediate Similarity	NPD271	Approved
0.7226	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD268	Approved
0.7225	Intermediate Similarity	NPD6999	Discontinued
0.7225	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2771	Approved
0.7213	Intermediate Similarity	NPD5106	Approved
0.7213	Intermediate Similarity	NPD5105	Approved
0.7213	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2880	Discontinued
0.7209	Intermediate Similarity	NPD975	Approved
0.7209	Intermediate Similarity	NPD976	Approved
0.7209	Intermediate Similarity	NPD977	Approved
0.7204	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD9357	Approved
0.7196	Intermediate Similarity	NPD7944	Discontinued
0.7189	Intermediate Similarity	NPD6721	Phase 1
0.7186	Intermediate Similarity	NPD4510	Discontinued
0.7184	Intermediate Similarity	NPD5418	Discontinued
0.7182	Intermediate Similarity	NPD4181	Approved
0.7182	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4922	Phase 2
0.7175	Intermediate Similarity	NPD2639	Approved
0.7175	Intermediate Similarity	NPD2642	Approved
0.717	Intermediate Similarity	NPD991	Phase 2
0.717	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5065	Approved
0.7159	Intermediate Similarity	NPD3583	Phase 2
0.7158	Intermediate Similarity	NPD4848	Phase 1
0.7151	Intermediate Similarity	NPD4988	Discontinued
0.715	Intermediate Similarity	NPD5017	Discontinued
0.7143	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1253	Approved
0.7134	Intermediate Similarity	NPD1255	Approved
0.7134	Intermediate Similarity	NPD1254	Approved
0.7134	Intermediate Similarity	NPD1256	Approved
0.7128	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8272	Phase 2
0.7128	Intermediate Similarity	NPD1658	Discontinued
0.7127	Intermediate Similarity	NPD7402	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5020	Approved
0.7113	Intermediate Similarity	NPD2879	Approved
0.7113	Intermediate Similarity	NPD2881	Approved
0.7111	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD750	Phase 2
0.7107	Intermediate Similarity	NPD7665	Phase 2
0.7107	Intermediate Similarity	NPD2443	Approved
0.7107	Intermediate Similarity	NPD2442	Approved
0.7107	Intermediate Similarity	NPD7666	Phase 3
0.7104	Intermediate Similarity	NPD5508	Phase 1
0.7097	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5444	Phase 1
0.709	Intermediate Similarity	NPD5505	Discontinued
0.709	Intermediate Similarity	NPD7127	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3506	Approved
0.7088	Intermediate Similarity	NPD3505	Approved
0.7086	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5892	Approved
0.7074	Intermediate Similarity	NPD3321	Discontinued
0.7069	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2580	Discontinued
0.7068	Intermediate Similarity	NPD7027	Phase 3
0.7065	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1545	Discontinued
0.7062	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4076	Approved
0.7049	Intermediate Similarity	NPD4079	Approved
0.7047	Intermediate Similarity	NPD6239	Discontinued
0.7043	Intermediate Similarity	NPD5075	Discontinued
0.7043	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1343	Approved
0.7035	Intermediate Similarity	NPD2172	Phase 1
0.7033	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6224	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6206	Phase 1
0.7029	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3015	Discontinued
0.7022	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4334	Discontinued
0.7018	Intermediate Similarity	NPD4702	Approved
0.7018	Intermediate Similarity	NPD4703	Approved
0.7011	Intermediate Similarity	NPD6515	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6514	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5198	Approved
0.701	Intermediate Similarity	NPD5199	Approved
0.7006	Intermediate Similarity	NPD2075	Approved
0.7006	Intermediate Similarity	NPD2068	Approved
0.7006	Intermediate Similarity	NPD2071	Approved
0.7006	Intermediate Similarity	NPD2072	Approved
0.7006	Intermediate Similarity	NPD2070	Approved
0.7006	Intermediate Similarity	NPD2073	Approved

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