NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.09
Volume:	231.111
LogP:	1.996
LogD:	1.806
LogS:	-2.434
# Rotatable Bonds:	3
TPSA:	67.6
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	2.519
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	1.6517766198376194e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	79.67709350585938%
Volume Distribution (VD):	0.521
Pgp-substrate:	12.77978229522705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.607
CYP2C19-inhibitor:	0.181
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	1.156
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.519
AMES Toxicity:	0.805
Rat Oral Acute Toxicity:	0.331
Maximum Recommended Daily Dose:	0.579
Skin Sensitization:	0.269
Carcinogencity:	0.349
Eye Corrosion:	0.75
Eye Irritation:	0.985
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC121658

Natural Product ID:	NPC121658
*Common Name:**	JCTRJRHLGOKMCF-ZSOIEALJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JCTRJRHLGOKMCF-ZSOIEALJSA-N
Standard InCHI:	InChI=1S/C12H11N3O2/c1-17-10-6-9(8-14-16)15-12(7-10)11-4-2-3-5-13-11/h2-8,16H,1H3/b14-8-
SMILES:	COc1cc(/C=NO)nc(c1)c1ccccn1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1970645
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	isolated from marine sediments	the seashore of Weihai, China	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	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	60

Activity Type	# Activity
Cell Line	60

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	263.63	nM	PMID[542958]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	1166.81	nM	PMID[542958]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	92.26	nM	PMID[542958]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	510.5	nM	PMID[542958]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	1442.12	nM	PMID[542958]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	161.06	nM	PMID[542958]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	123.88	nM	PMID[542958]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	236.05	nM	PMID[542958]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	575.44	nM	PMID[542958]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	297.85	nM	PMID[542958]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	741.31	nM	PMID[542958]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	399.02	nM	PMID[542958]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	1297.18	nM	PMID[542958]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	222.33	nM	PMID[542958]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	172.58	nM	PMID[542958]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	359.75	nM	PMID[542958]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	136.77	nM	PMID[542958]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	553.35	nM	PMID[542958]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	199.53	nM	PMID[542958]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	3076.1	nM	PMID[542958]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	1047.13	nM	PMID[542958]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	1114.29	nM	PMID[542958]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	43.75	nM	PMID[542958]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	30831.88	nM	PMID[542958]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	663.74	nM	PMID[542958]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	549.54	nM	PMID[542958]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	128.82	nM	PMID[542958]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	258.82	nM	PMID[542958]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	227.51	nM	PMID[542958]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	337.29	nM	PMID[542958]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	503.5	nM	PMID[542958]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	221.31	nM	PMID[542958]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	1503.14	nM	PMID[542958]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	5533.5	nM	PMID[542958]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	343.56	nM	PMID[542958]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	46773.51	nM	PMID[542958]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1282.33	nM	PMID[542958]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	92.04	nM	PMID[542958]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	301.3	nM	PMID[542958]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	451.86	nM	PMID[542958]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	194.54	nM	PMID[542958]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	474.24	nM	PMID[542958]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	2432.2	nM	PMID[542958]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	449.78	nM	PMID[542958]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	226.99	nM	PMID[542958]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	1180.32	nM	PMID[542958]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	303.39	nM	PMID[542958]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	447.71	nM	PMID[542958]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1603.25	nM	PMID[542958]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	202.3	nM	PMID[542958]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	338.84	nM	PMID[542958]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	47206.3	nM	PMID[542958]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	178.65	nM	PMID[542958]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	2398.83	nM	PMID[542958]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	174.58	nM	PMID[542958]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	568.85	nM	PMID[542958]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	363.08	nM	PMID[542958]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	729.46	nM	PMID[542958]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	363.08	nM	PMID[542958]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	187.5	nM	PMID[542958]

☑ 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 NPC121658 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	565
0.1-0.2	10216
0.2-0.3	7932
0.3-0.4	15510
0.4-0.5	4837
0.5-0.6	2731
0.6-0.7	796
0.7-0.8	93
0.8-0.85	1
0.85-0.9	6
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC14651
0.9935	High Similarity	NPC476518
0.9565	High Similarity	NPC266551
0.9434	High Similarity	NPC111624
0.939	High Similarity	NPC20249
0.9325	High Similarity	NPC161887
0.9325	High Similarity	NPC219963
0.9277	High Similarity	NPC74382
0.9277	High Similarity	NPC206251
0.9114	High Similarity	NPC48192
0.9051	High Similarity	NPC25899
0.8786	High Similarity	NPC226202
0.8772	High Similarity	NPC224327
0.8721	High Similarity	NPC134079
0.8531	High Similarity	NPC267928
0.8528	High Similarity	NPC177404
0.8087	Intermediate Similarity	NPC19872
0.8024	Intermediate Similarity	NPC285635
0.7956	Intermediate Similarity	NPC84853
0.7946	Intermediate Similarity	NPC232727
0.7943	Intermediate Similarity	NPC222592
0.7943	Intermediate Similarity	NPC168486
0.7892	Intermediate Similarity	NPC176538
0.7892	Intermediate Similarity	NPC315957
0.7884	Intermediate Similarity	NPC287208
0.7842	Intermediate Similarity	NPC174672
0.7838	Intermediate Similarity	NPC187558
0.7831	Intermediate Similarity	NPC26872
0.7803	Intermediate Similarity	NPC258773
0.7801	Intermediate Similarity	NPC167860
0.7801	Intermediate Similarity	NPC123976
0.7755	Intermediate Similarity	NPC193267
0.7755	Intermediate Similarity	NPC213530
0.7749	Intermediate Similarity	NPC174758
0.7696	Intermediate Similarity	NPC82548
0.7692	Intermediate Similarity	NPC274982
0.7692	Intermediate Similarity	NPC26850
0.7688	Intermediate Similarity	NPC1527
0.7684	Intermediate Similarity	NPC470164
0.7684	Intermediate Similarity	NPC323345
0.7672	Intermediate Similarity	NPC476138
0.7672	Intermediate Similarity	NPC245816
0.7656	Intermediate Similarity	NPC185782
0.7647	Intermediate Similarity	NPC287437
0.7606	Intermediate Similarity	NPC121772
0.7539	Intermediate Similarity	NPC16452
0.7539	Intermediate Similarity	NPC118832
0.7539	Intermediate Similarity	NPC329708
0.7539	Intermediate Similarity	NPC47059
0.7539	Intermediate Similarity	NPC476581
0.7539	Intermediate Similarity	NPC274291
0.7539	Intermediate Similarity	NPC264166
0.7539	Intermediate Similarity	NPC36229
0.7539	Intermediate Similarity	NPC165349
0.7538	Intermediate Similarity	NPC26679
0.7513	Intermediate Similarity	NPC470799
0.7513	Intermediate Similarity	NPC8022
0.75	Intermediate Similarity	NPC310118
0.75	Intermediate Similarity	NPC60621
0.7473	Intermediate Similarity	NPC307963
0.746	Intermediate Similarity	NPC476578
0.746	Intermediate Similarity	NPC476582
0.746	Intermediate Similarity	NPC4071
0.7446	Intermediate Similarity	NPC296527
0.7419	Intermediate Similarity	NPC195268
0.7419	Intermediate Similarity	NPC133140
0.7418	Intermediate Similarity	NPC284559
0.7405	Intermediate Similarity	NPC76748
0.7403	Intermediate Similarity	NPC118776
0.7394	Intermediate Similarity	NPC13880
0.7382	Intermediate Similarity	NPC31930
0.738	Intermediate Similarity	NPC198673
0.7371	Intermediate Similarity	NPC471178
0.7366	Intermediate Similarity	NPC314954
0.7366	Intermediate Similarity	NPC92111
0.736	Intermediate Similarity	NPC112206
0.736	Intermediate Similarity	NPC202605
0.7358	Intermediate Similarity	NPC285558
0.7356	Intermediate Similarity	NPC124542
0.7356	Intermediate Similarity	NPC471177
0.7356	Intermediate Similarity	NPC59779
0.7323	Intermediate Similarity	NPC476287
0.7322	Intermediate Similarity	NPC284678
0.7321	Intermediate Similarity	NPC220523
0.7317	Intermediate Similarity	NPC110151
0.7316	Intermediate Similarity	NPC239954
0.7314	Intermediate Similarity	NPC118511
0.731	Intermediate Similarity	NPC36168
0.7308	Intermediate Similarity	NPC470474
0.7302	Intermediate Similarity	NPC251090
0.7273	Intermediate Similarity	NPC53069
0.7273	Intermediate Similarity	NPC202768
0.7273	Intermediate Similarity	NPC296482
0.7263	Intermediate Similarity	NPC224928
0.726	Intermediate Similarity	NPC101543
0.726	Intermediate Similarity	NPC469554
0.7258	Intermediate Similarity	NPC110741
0.7255	Intermediate Similarity	NPC122436
0.724	Intermediate Similarity	NPC234197
0.7238	Intermediate Similarity	NPC283152
0.7234	Intermediate Similarity	NPC324149
0.7231	Intermediate Similarity	NPC472111
0.7225	Intermediate Similarity	NPC168911
0.7225	Intermediate Similarity	NPC141053
0.7216	Intermediate Similarity	NPC475774
0.7216	Intermediate Similarity	NPC200836
0.7208	Intermediate Similarity	NPC469589
0.7194	Intermediate Similarity	NPC193238
0.7194	Intermediate Similarity	NPC313189
0.7186	Intermediate Similarity	NPC96405
0.7186	Intermediate Similarity	NPC171409
0.7182	Intermediate Similarity	NPC288943
0.7172	Intermediate Similarity	NPC290689
0.7151	Intermediate Similarity	NPC473764
0.7151	Intermediate Similarity	NPC314940
0.715	Intermediate Similarity	NPC477019
0.7135	Intermediate Similarity	NPC62069
0.7128	Intermediate Similarity	NPC53144
0.7127	Intermediate Similarity	NPC312872
0.7119	Intermediate Similarity	NPC97367
0.7119	Intermediate Similarity	NPC473057
0.7112	Intermediate Similarity	NPC66083
0.7107	Intermediate Similarity	NPC135549
0.7105	Intermediate Similarity	NPC289786
0.7101	Intermediate Similarity	NPC471323
0.7098	Intermediate Similarity	NPC476167
0.7098	Intermediate Similarity	NPC18487
0.7097	Intermediate Similarity	NPC42591
0.7092	Intermediate Similarity	NPC470500
0.7085	Intermediate Similarity	NPC85273
0.7077	Intermediate Similarity	NPC211813
0.7075	Intermediate Similarity	NPC295228
0.7065	Intermediate Similarity	NPC162530
0.7062	Intermediate Similarity	NPC79911
0.7059	Intermediate Similarity	NPC292958
0.7059	Intermediate Similarity	NPC17565
0.705	Intermediate Similarity	NPC208284
0.7048	Intermediate Similarity	NPC260434
0.7047	Intermediate Similarity	NPC192315
0.7047	Intermediate Similarity	NPC212213
0.7043	Intermediate Similarity	NPC84478
0.7041	Intermediate Similarity	NPC470404
0.7041	Intermediate Similarity	NPC470394
0.7041	Intermediate Similarity	NPC470403
0.7041	Intermediate Similarity	NPC223427
0.7017	Intermediate Similarity	NPC252590
0.7016	Intermediate Similarity	NPC329541
0.701	Intermediate Similarity	NPC173080
0.701	Intermediate Similarity	NPC197141
0.7006	Intermediate Similarity	NPC120798
0.7005	Intermediate Similarity	NPC322482
0.7005	Intermediate Similarity	NPC475070
0.7	Intermediate Similarity	NPC5145
0.7	Intermediate Similarity	NPC151489
0.6995	Remote Similarity	NPC170114
0.6989	Remote Similarity	NPC176127
0.6989	Remote Similarity	NPC48938
0.6988	Remote Similarity	NPC328029
0.698	Remote Similarity	NPC471080
0.698	Remote Similarity	NPC469592
0.6968	Remote Similarity	NPC204385
0.6961	Remote Similarity	NPC473513
0.6959	Remote Similarity	NPC470395
0.6957	Remote Similarity	NPC216612
0.6951	Remote Similarity	NPC174421
0.6949	Remote Similarity	NPC84508
0.6946	Remote Similarity	NPC470549
0.6943	Remote Similarity	NPC194967
0.694	Remote Similarity	NPC95898
0.6931	Remote Similarity	NPC264176
0.6931	Remote Similarity	NPC46580
0.6931	Remote Similarity	NPC316981
0.6931	Remote Similarity	NPC472098
0.6927	Remote Similarity	NPC263439
0.6923	Remote Similarity	NPC65277
0.6919	Remote Similarity	NPC42979
0.6919	Remote Similarity	NPC472168
0.6915	Remote Similarity	NPC11464
0.6915	Remote Similarity	NPC314002
0.6915	Remote Similarity	NPC470020
0.6904	Remote Similarity	NPC295898
0.6902	Remote Similarity	NPC203754
0.6902	Remote Similarity	NPC150048
0.6902	Remote Similarity	NPC224764
0.69	Remote Similarity	NPC475910
0.6897	Remote Similarity	NPC266931
0.6895	Remote Similarity	NPC472289
0.6888	Remote Similarity	NPC329793
0.6884	Remote Similarity	NPC476124
0.6884	Remote Similarity	NPC476121
0.6884	Remote Similarity	NPC235685
0.6879	Remote Similarity	NPC470111
0.6866	Remote Similarity	NPC99891
0.6862	Remote Similarity	NPC204717
0.6856	Remote Similarity	NPC473053
0.6853	Remote Similarity	NPC470586
0.6852	Remote Similarity	NPC101350
0.6851	Remote Similarity	NPC108469
0.6849	Remote Similarity	NPC472434
0.6845	Remote Similarity	NPC469594

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 NPC121658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	1001
0.2-0.3	601
0.3-0.4	1832
0.4-0.5	2785
0.5-0.6	1988
0.6-0.7	601
0.7-0.8	76
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD1740	Approved
0.7892	Intermediate Similarity	NPD1739	Approved
0.7826	Intermediate Similarity	NPD1622	Discontinued
0.7802	Intermediate Similarity	NPD4372	Phase 1
0.7725	Intermediate Similarity	NPD4795	Phase 2
0.7705	Intermediate Similarity	NPD6569	Phase 2
0.7692	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1034	Phase 3
0.768	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3477	Phase 2
0.765	Intermediate Similarity	NPD2334	Discontinued
0.7598	Intermediate Similarity	NPD3386	Phase 2
0.7543	Intermediate Similarity	NPD565	Phase 2
0.7543	Intermediate Similarity	NPD5320	Approved
0.7543	Intermediate Similarity	NPD5319	Approved
0.7539	Intermediate Similarity	NPD4122	Approved
0.7539	Intermediate Similarity	NPD31	Approved
0.7539	Intermediate Similarity	NPD4034	Approved
0.7539	Intermediate Similarity	NPD4038	Approved
0.7539	Intermediate Similarity	NPD32	Approved
0.7539	Intermediate Similarity	NPD4039	Approved
0.7539	Intermediate Similarity	NPD4035	Approved
0.7539	Intermediate Similarity	NPD4033	Approved
0.7539	Intermediate Similarity	NPD4036	Approved
0.7539	Intermediate Similarity	NPD4037	Approved
0.7527	Intermediate Similarity	NPD4375	Approved
0.7527	Intermediate Similarity	NPD3396	Approved
0.7527	Intermediate Similarity	NPD3395	Approved
0.7516	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4204	Approved
0.75	Intermediate Similarity	NPD4203	Approved
0.7486	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4889	Approved
0.7473	Intermediate Similarity	NPD1038	Approved
0.7456	Intermediate Similarity	NPD9596	Approved
0.7456	Intermediate Similarity	NPD9595	Approved
0.7442	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD1602	Discontinued
0.7429	Intermediate Similarity	NPD424	Approved
0.7429	Intermediate Similarity	NPD425	Approved
0.7419	Intermediate Similarity	NPD3923	Approved
0.7419	Intermediate Similarity	NPD3924	Approved
0.7419	Intermediate Similarity	NPD3921	Approved
0.7419	Intermediate Similarity	NPD3922	Approved
0.7416	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1856	Discontinued
0.7354	Intermediate Similarity	NPD2952	Discontinued
0.7348	Intermediate Similarity	NPD2599	Approved
0.7348	Intermediate Similarity	NPD2601	Approved
0.7348	Intermediate Similarity	NPD2600	Approved
0.7337	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4072	Approved
0.7333	Intermediate Similarity	NPD4071	Approved
0.7312	Intermediate Similarity	NPD715	Phase 3
0.73	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9705	Discontinued
0.7299	Intermediate Similarity	NPD112	Approved
0.7283	Intermediate Similarity	NPD2582	Approved
0.7283	Intermediate Similarity	NPD2581	Approved
0.7283	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2958	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD926	Approved
0.7273	Intermediate Similarity	NPD3815	Phase 1
0.7273	Intermediate Similarity	NPD925	Approved
0.7273	Intermediate Similarity	NPD3816	Phase 1
0.7263	Intermediate Similarity	NPD2959	Phase 3
0.7238	Intermediate Similarity	NPD1032	Phase 2
0.7231	Intermediate Similarity	NPD5530	Phase 1
0.7207	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4551	Phase 2
0.7194	Intermediate Similarity	NPD1392	Approved
0.7191	Intermediate Similarity	NPD2781	Approved
0.7188	Intermediate Similarity	NPD5999	Phase 2
0.7188	Intermediate Similarity	NPD4548	Discontinued
0.7184	Intermediate Similarity	NPD1603	Discontinued
0.7175	Intermediate Similarity	NPD2782	Approved
0.7175	Intermediate Similarity	NPD2780	Approved
0.7173	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4021	Phase 2
0.7158	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5601	Phase 2
0.7143	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5255	Approved
0.7136	Intermediate Similarity	NPD3570	Phase 2
0.7136	Intermediate Similarity	NPD4131	Phase 3
0.7126	Intermediate Similarity	NPD1649	Discontinued
0.7113	Intermediate Similarity	NPD1621	Discontinued
0.7112	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7069	Discontinued
0.7083	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2816	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1951	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6500	Approved
0.7059	Intermediate Similarity	NPD6501	Approved
0.7043	Intermediate Similarity	NPD3569	Discontinued
0.7043	Intermediate Similarity	NPD1334	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5513	Phase 2
0.703	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD2757	Phase 2
0.7024	Intermediate Similarity	NPD6856	Discontinued
0.7024	Intermediate Similarity	NPD8479	Phase 2
0.7019	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7675	Phase 3
0.7019	Intermediate Similarity	NPD7674	Phase 3
0.7019	Intermediate Similarity	NPD7426	Phase 1
0.701	Intermediate Similarity	NPD3825	Phase 3
0.7006	Intermediate Similarity	NPD1418	Phase 2
0.7005	Intermediate Similarity	NPD3397	Phase 2
0.7005	Intermediate Similarity	NPD6306	Phase 2
0.7	Intermediate Similarity	NPD4148	Approved
0.6985	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5529	Phase 1
0.6985	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7757	Approved
0.6968	Remote Similarity	NPD7758	Approved
0.6967	Remote Similarity	NPD2062	Phase 2
0.6965	Remote Similarity	NPD5067	Phase 2
0.6965	Remote Similarity	NPD5066	Phase 2
0.6965	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8063	Discontinued
0.694	Remote Similarity	NPD9690	Approved
0.6939	Remote Similarity	NPD5259	Phase 3
0.6932	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2848	Discontinued
0.6927	Remote Similarity	NPD6361	Phase 2
0.6927	Remote Similarity	NPD6568	Discontinued
0.6927	Remote Similarity	NPD9695	Approved
0.6923	Remote Similarity	NPD9548	Phase 2
0.6919	Remote Similarity	NPD3920	Phase 2
0.6912	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1286	Suspended
0.6909	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5658	Approved
0.6898	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1258	Discontinued
0.6885	Remote Similarity	NPD2076	Approved
0.6885	Remote Similarity	NPD2077	Approved
0.6881	Remote Similarity	NPD3939	Suspended
0.6881	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4703	Approved
0.6879	Remote Similarity	NPD1661	Suspended
0.6879	Remote Similarity	NPD4702	Approved
0.6878	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4919	Phase 3
0.6878	Remote Similarity	NPD4921	Phase 3
0.6857	Remote Similarity	NPD5640	Discontinued
0.6857	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5045	Phase 2
0.6842	Remote Similarity	NPD3717	Discontinued
0.684	Remote Similarity	NPD6968	Phase 2
0.684	Remote Similarity	NPD8512	Phase 3
0.684	Remote Similarity	NPD6969	Phase 2
0.6839	Remote Similarity	NPD802	Phase 2
0.6837	Remote Similarity	NPD1259	Discontinued
0.6837	Remote Similarity	NPD1768	Approved
0.6833	Remote Similarity	NPD862	Approved
0.6833	Remote Similarity	NPD861	Approved
0.6833	Remote Similarity	NPD863	Approved
0.6827	Remote Similarity	NPD6298	Discontinued
0.6822	Remote Similarity	NPD2471	Approved
0.6822	Remote Similarity	NPD4306	Phase 1
0.6822	Remote Similarity	NPD2472	Approved
0.6821	Remote Similarity	NPD4673	Phase 2
0.682	Remote Similarity	NPD1927	Discontinued
0.6816	Remote Similarity	NPD2189	Approved
0.6816	Remote Similarity	NPD2187	Approved
0.6812	Remote Similarity	NPD3402	Phase 1
0.681	Remote Similarity	NPD3938	Phase 1
0.6804	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD949	Phase 1
0.6796	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5256	Discontinued
0.6774	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3321	Discontinued
0.6771	Remote Similarity	NPD2410	Phase 2
0.6769	Remote Similarity	NPD6550	Discontinued
0.6769	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7222	Phase 2
0.6763	Remote Similarity	NPD4429	Discontinued
0.6763	Remote Similarity	NPD2440	Phase 3
0.6763	Remote Similarity	NPD2441	Approved
0.6761	Remote Similarity	NPD3302	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2882	Phase 1

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