NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	161.05
Volume:	162.502
LogP:	1.763
LogD:	1.741
LogS:	-2.623
# Rotatable Bonds:	0
TPSA:	53.35
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	2.193
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.659
MDCK Permeability:	1.89245147339534e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	83.59813690185547%
Volume Distribution (VD):	0.873
Pgp-substrate:	15.078166007995605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.55
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.476
CYP2D6-substrate:	0.774
CYP3A4-inhibitor:	0.415
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	15.684
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.448
AMES Toxicity:	0.325
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.937
Carcinogencity:	0.438
Eye Corrosion:	0.376
Eye Irritation:	0.974
Respiratory Toxicity:	0.738

Download Data

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

Natural Product: NPC252590

Natural Product ID:	NPC252590
*Common Name:**	Jineol
IUPAC Name:	quinoline-3,8-diol
Synonyms:	Jineol
Standard InCHIKey:	IGDFDIZIHMFYGR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7NO2/c11-7-4-6-2-1-3-8(12)9(6)10-5-7/h1-5,11-12H
SMILES:	Oc1cnc2c(c1)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450230
PubChem CID:	177338
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0003953] 8-hydroxyquinolines

*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
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np960188t]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16595909]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29855	Centipede scolopendra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	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
ED50	5
GI50	52

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.8	ug ml-1	PMID[471425]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	4.5	ug ml-1	PMID[471425]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[471425]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	10.0	ug ml-1	PMID[471425]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[471425]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	57147.86	nM	PMID[471426]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	37497.3	nM	PMID[471426]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	27542.29	nM	PMID[471426]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	41020.41	nM	PMID[471426]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	30760.97	nM	PMID[471426]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	31477.48	nM	PMID[471426]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	57279.6	nM	PMID[471426]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	30338.91	nM	PMID[471426]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[471426]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	51286.14	nM	PMID[471426]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[471426]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	41686.94	nM	PMID[471426]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	20558.91	nM	PMID[471426]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[471426]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	18155.16	nM	PMID[471426]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	26181.83	nM	PMID[471426]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	48865.24	nM	PMID[471426]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	24888.57	nM	PMID[471426]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	51999.6	nM	PMID[471426]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	58884.37	nM	PMID[471426]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	40644.33	nM	PMID[471426]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	53088.44	nM	PMID[471426]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	45498.81	nM	PMID[471426]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	12823.31	nM	PMID[471426]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	19230.92	nM	PMID[471426]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	24547.09	nM	PMID[471426]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	35318.32	nM	PMID[471426]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	38106.58	nM	PMID[471426]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	26242.19	nM	PMID[471426]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	64416.93	nM	PMID[471426]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	43351.09	nM	PMID[471426]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	40738.03	nM	PMID[471426]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	20701.41	nM	PMID[471426]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	40831.94	nM	PMID[471426]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	33496.54	nM	PMID[471426]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	15922.09	nM	PMID[471426]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	33189.45	nM	PMID[471426]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	30690.22	nM	PMID[471426]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	36812.9	nM	PMID[471426]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	32583.67	nM	PMID[471426]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	31915.38	nM	PMID[471426]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	28973.44	nM	PMID[471426]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	32734.07	nM	PMID[471426]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	36812.9	nM	PMID[471426]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	80167.81	nM	PMID[471426]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	20276.83	nM	PMID[471426]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[471426]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	35481.34	nM	PMID[471426]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	56623.93	nM	PMID[471426]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	32734.07	nM	PMID[471426]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	24154.61	nM	PMID[471426]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	76559.66	nM	PMID[471426]

☑ 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 NPC252590 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	634
0.1-0.2	5556
0.2-0.3	11782
0.3-0.4	11491
0.4-0.5	8815
0.5-0.6	2953
0.6-0.7	1261
0.7-0.8	193
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9554	High Similarity	NPC473764
0.9554	High Similarity	NPC314940
0.838	Intermediate Similarity	NPC192315
0.8333	Intermediate Similarity	NPC476167
0.8187	Intermediate Similarity	NPC220523
0.8172	Intermediate Similarity	NPC477111
0.8162	Intermediate Similarity	NPC477113
0.815	Intermediate Similarity	NPC478032
0.814	Intermediate Similarity	NPC184964
0.8098	Intermediate Similarity	NPC470678
0.8063	Intermediate Similarity	NPC470799
0.8063	Intermediate Similarity	NPC8022
0.8	Intermediate Similarity	NPC44161
0.7966	Intermediate Similarity	NPC314002
0.7955	Intermediate Similarity	NPC220765
0.7937	Intermediate Similarity	NPC60553
0.7929	Intermediate Similarity	NPC118511
0.791	Intermediate Similarity	NPC204717
0.7892	Intermediate Similarity	NPC63562
0.7886	Intermediate Similarity	NPC42979
0.7884	Intermediate Similarity	NPC18348
0.7876	Intermediate Similarity	NPC477110
0.7874	Intermediate Similarity	NPC224764
0.7865	Intermediate Similarity	NPC42591
0.7826	Intermediate Similarity	NPC90229
0.7821	Intermediate Similarity	NPC171171
0.7819	Intermediate Similarity	NPC274291
0.7819	Intermediate Similarity	NPC118832
0.7819	Intermediate Similarity	NPC47059
0.7819	Intermediate Similarity	NPC264166
0.7819	Intermediate Similarity	NPC329708
0.7819	Intermediate Similarity	NPC165349
0.7802	Intermediate Similarity	NPC99666
0.7798	Intermediate Similarity	NPC132680
0.7798	Intermediate Similarity	NPC269919
0.779	Intermediate Similarity	NPC3715
0.779	Intermediate Similarity	NPC144381
0.7766	Intermediate Similarity	NPC475774
0.7749	Intermediate Similarity	NPC185782
0.7735	Intermediate Similarity	NPC230805
0.7725	Intermediate Similarity	NPC470500
0.7707	Intermediate Similarity	NPC174421
0.7706	Intermediate Similarity	NPC324203
0.7706	Intermediate Similarity	NPC25899
0.7706	Intermediate Similarity	NPC63338
0.7706	Intermediate Similarity	NPC322976
0.768	Intermediate Similarity	NPC46580
0.7674	Intermediate Similarity	NPC471178
0.767	Intermediate Similarity	NPC203754
0.767	Intermediate Similarity	NPC150048
0.7663	Intermediate Similarity	NPC329541
0.7663	Intermediate Similarity	NPC230403
0.7661	Intermediate Similarity	NPC471177
0.7661	Intermediate Similarity	NPC124542
0.7661	Intermediate Similarity	NPC48192
0.7661	Intermediate Similarity	NPC59779
0.7634	Intermediate Similarity	NPC77555
0.7629	Intermediate Similarity	NPC26679
0.7627	Intermediate Similarity	NPC96890
0.7622	Intermediate Similarity	NPC326634
0.7619	Intermediate Similarity	NPC211813
0.7617	Intermediate Similarity	NPC5145
0.7616	Intermediate Similarity	NPC263439
0.7616	Intermediate Similarity	NPC211187
0.7579	Intermediate Similarity	NPC476138
0.7579	Intermediate Similarity	NPC245816
0.7576	Intermediate Similarity	NPC470395
0.7552	Intermediate Similarity	NPC193238
0.7546	Intermediate Similarity	NPC318935
0.754	Intermediate Similarity	NPC267928
0.754	Intermediate Similarity	NPC156704
0.7525	Intermediate Similarity	NPC173080
0.7525	Intermediate Similarity	NPC103687
0.7525	Intermediate Similarity	NPC132631
0.7514	Intermediate Similarity	NPC324149
0.7514	Intermediate Similarity	NPC473057
0.7513	Intermediate Similarity	NPC142901
0.7513	Intermediate Similarity	NPC315491
0.7513	Intermediate Similarity	NPC45459
0.7487	Intermediate Similarity	NPC222018
0.7456	Intermediate Similarity	NPC153769
0.7455	Intermediate Similarity	NPC470404
0.7455	Intermediate Similarity	NPC470403
0.7455	Intermediate Similarity	NPC470394
0.7448	Intermediate Similarity	NPC475070
0.7446	Intermediate Similarity	NPC32771
0.7443	Intermediate Similarity	NPC256828
0.7435	Intermediate Similarity	NPC66815
0.7432	Intermediate Similarity	NPC314573
0.7429	Intermediate Similarity	NPC108469
0.7421	Intermediate Similarity	NPC213308
0.7414	Intermediate Similarity	NPC97367
0.7399	Intermediate Similarity	NPC131718
0.7394	Intermediate Similarity	NPC251090
0.738	Intermediate Similarity	NPC307963
0.7379	Intermediate Similarity	NPC477112
0.7379	Intermediate Similarity	NPC476451
0.7363	Intermediate Similarity	NPC48938
0.7356	Intermediate Similarity	NPC177404
0.7354	Intermediate Similarity	NPC224928
0.7347	Intermediate Similarity	NPC309845
0.7333	Intermediate Similarity	NPC476157
0.733	Intermediate Similarity	NPC19872
0.7323	Intermediate Similarity	NPC476287
0.7321	Intermediate Similarity	NPC161292
0.732	Intermediate Similarity	NPC476124
0.732	Intermediate Similarity	NPC476121
0.7314	Intermediate Similarity	NPC102423
0.7308	Intermediate Similarity	NPC266551
0.7308	Intermediate Similarity	NPC161887
0.7308	Intermediate Similarity	NPC219963
0.7306	Intermediate Similarity	NPC53144
0.7306	Intermediate Similarity	NPC200836
0.7302	Intermediate Similarity	NPC242209
0.7287	Intermediate Similarity	NPC226202
0.7278	Intermediate Similarity	NPC257142
0.7258	Intermediate Similarity	NPC296527
0.7255	Intermediate Similarity	NPC167908
0.7249	Intermediate Similarity	NPC146724
0.7247	Intermediate Similarity	NPC164664
0.724	Intermediate Similarity	NPC234197
0.7219	Intermediate Similarity	NPC76748
0.7213	Intermediate Similarity	NPC474798
0.7209	Intermediate Similarity	NPC26872
0.7207	Intermediate Similarity	NPC253810
0.7204	Intermediate Similarity	NPC66083
0.7198	Intermediate Similarity	NPC88363
0.7198	Intermediate Similarity	NPC149402
0.7197	Intermediate Similarity	NPC46358
0.7194	Intermediate Similarity	NPC88008
0.7181	Intermediate Similarity	NPC92111
0.7164	Intermediate Similarity	NPC288349
0.7164	Intermediate Similarity	NPC476161
0.716	Intermediate Similarity	NPC256893
0.7159	Intermediate Similarity	NPC79911
0.7158	Intermediate Similarity	NPC52831
0.7158	Intermediate Similarity	NPC325705
0.7157	Intermediate Similarity	NPC171787
0.7157	Intermediate Similarity	NPC287208
0.7151	Intermediate Similarity	NPC284348
0.715	Intermediate Similarity	NPC315957
0.715	Intermediate Similarity	NPC162530
0.715	Intermediate Similarity	NPC176538
0.7143	Intermediate Similarity	NPC195268
0.7143	Intermediate Similarity	NPC133140
0.7135	Intermediate Similarity	NPC41717
0.7135	Intermediate Similarity	NPC212213
0.7135	Intermediate Similarity	NPC62069
0.7129	Intermediate Similarity	NPC469727
0.7128	Intermediate Similarity	NPC476098
0.7127	Intermediate Similarity	NPC303225
0.7122	Intermediate Similarity	NPC470501
0.7111	Intermediate Similarity	NPC158129
0.7109	Intermediate Similarity	NPC182222
0.7107	Intermediate Similarity	NPC151489
0.7104	Intermediate Similarity	NPC164340
0.7104	Intermediate Similarity	NPC72980
0.7102	Intermediate Similarity	NPC120798
0.7102	Intermediate Similarity	NPC322644
0.71	Intermediate Similarity	NPC202605
0.71	Intermediate Similarity	NPC112206
0.7098	Intermediate Similarity	NPC128823
0.7097	Intermediate Similarity	NPC20249
0.7097	Intermediate Similarity	NPC62510
0.7094	Intermediate Similarity	NPC204446
0.7092	Intermediate Similarity	NPC472259
0.7091	Intermediate Similarity	NPC328029
0.7088	Intermediate Similarity	NPC288943
0.7086	Intermediate Similarity	NPC26850
0.7085	Intermediate Similarity	NPC85273
0.7073	Intermediate Similarity	NPC470502
0.7072	Intermediate Similarity	NPC313791
0.7072	Intermediate Similarity	NPC474409
0.707	Intermediate Similarity	NPC473312
0.7068	Intermediate Similarity	NPC276517
0.7065	Intermediate Similarity	NPC271792
0.7065	Intermediate Similarity	NPC266931
0.7062	Intermediate Similarity	NPC249040
0.7059	Intermediate Similarity	NPC148409
0.7056	Intermediate Similarity	NPC304183
0.7056	Intermediate Similarity	NPC475841
0.7056	Intermediate Similarity	NPC474145
0.7053	Intermediate Similarity	NPC471448
0.7049	Intermediate Similarity	NPC283152
0.7044	Intermediate Similarity	NPC304926
0.7044	Intermediate Similarity	NPC476041
0.7044	Intermediate Similarity	NPC473513
0.7043	Intermediate Similarity	NPC207851
0.7033	Intermediate Similarity	NPC312872
0.7029	Intermediate Similarity	NPC141353
0.7029	Intermediate Similarity	NPC477889
0.7026	Intermediate Similarity	NPC31930
0.7024	Intermediate Similarity	NPC174049
0.702	Intermediate Similarity	NPC283117
0.7017	Intermediate Similarity	NPC14651
0.7017	Intermediate Similarity	NPC121658
0.7016	Intermediate Similarity	NPC106937
0.7015	Intermediate Similarity	NPC219087
0.7015	Intermediate Similarity	NPC203168
0.7014	Intermediate Similarity	NPC469554

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 NPC252590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	769
0.2-0.3	782
0.3-0.4	1496
0.4-0.5	3082
0.5-0.6	2034
0.6-0.7	591
0.7-0.8	74
0.8-0.85	5
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9255	High Similarity	NPD9690	Approved
0.9172	High Similarity	NPD112	Approved
0.9172	High Similarity	NPD9705	Discontinued
0.879	High Similarity	NPD9706	Clinical (unspecified phase)
0.8786	High Similarity	NPD9695	Approved
0.8514	High Similarity	NPD9689	Approved
0.8232	Intermediate Similarity	NPD9688	Approved
0.8232	Intermediate Similarity	NPD9687	Approved
0.809	Intermediate Similarity	NPD1213	Phase 3
0.8035	Intermediate Similarity	NPD6159	Phase 2
0.8033	Intermediate Similarity	NPD2176	Approved
0.8033	Intermediate Similarity	NPD2177	Approved
0.8033	Intermediate Similarity	NPD2175	Phase 3
0.7857	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD31	Approved
0.7819	Intermediate Similarity	NPD4039	Approved
0.7819	Intermediate Similarity	NPD4122	Approved
0.7819	Intermediate Similarity	NPD4033	Approved
0.7819	Intermediate Similarity	NPD4035	Approved
0.7819	Intermediate Similarity	NPD4037	Approved
0.7819	Intermediate Similarity	NPD4038	Approved
0.7819	Intermediate Similarity	NPD4034	Approved
0.7819	Intermediate Similarity	NPD32	Approved
0.7819	Intermediate Similarity	NPD4036	Approved
0.7798	Intermediate Similarity	NPD9383	Approved
0.7798	Intermediate Similarity	NPD9382	Approved
0.7737	Intermediate Similarity	NPD6290	Phase 2
0.7735	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD424	Approved
0.7733	Intermediate Similarity	NPD425	Approved
0.7706	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2615	Phase 3
0.768	Intermediate Similarity	NPD2616	Phase 3
0.7663	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5255	Approved
0.7638	Intermediate Similarity	NPD1856	Discontinued
0.7637	Intermediate Similarity	NPD408	Approved
0.7594	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2781	Approved
0.7577	Intermediate Similarity	NPD5939	Approved
0.7577	Intermediate Similarity	NPD4502	Phase 2
0.7577	Intermediate Similarity	NPD5936	Approved
0.7572	Intermediate Similarity	NPD2780	Approved
0.7572	Intermediate Similarity	NPD2782	Approved
0.7572	Intermediate Similarity	NPD926	Approved
0.7572	Intermediate Similarity	NPD925	Approved
0.754	Intermediate Similarity	NPD1229	Phase 2
0.7513	Intermediate Similarity	NPD484	Approved
0.75	Intermediate Similarity	NPD2123	Phase 3
0.7473	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7948	Phase 1
0.7438	Intermediate Similarity	NPD7603	Discontinued
0.7418	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD861	Approved
0.7414	Intermediate Similarity	NPD863	Approved
0.7414	Intermediate Similarity	NPD862	Approved
0.7394	Intermediate Similarity	NPD3477	Phase 2
0.7394	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD1038	Approved
0.735	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6569	Phase 2
0.7277	Intermediate Similarity	NPD5999	Phase 2
0.7264	Intermediate Similarity	NPD4429	Discontinued
0.7254	Intermediate Similarity	NPD3928	Approved
0.7254	Intermediate Similarity	NPD3931	Approved
0.7254	Intermediate Similarity	NPD6975	Discontinued
0.7251	Intermediate Similarity	NPD6158	Phase 2
0.7251	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5065	Approved
0.7213	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2383	Phase 1
0.7198	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6361	Phase 2
0.7184	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2581	Approved
0.7184	Intermediate Similarity	NPD2582	Approved
0.7182	Intermediate Similarity	NPD5100	Phase 3
0.7176	Intermediate Similarity	NPD1661	Suspended
0.7164	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5612	Discontinued
0.7158	Intermediate Similarity	NPD9510	Approved
0.7151	Intermediate Similarity	NPD2882	Phase 1
0.715	Intermediate Similarity	NPD1739	Approved
0.715	Intermediate Similarity	NPD1740	Approved
0.7143	Intermediate Similarity	NPD3924	Approved
0.7143	Intermediate Similarity	NPD3922	Approved
0.7143	Intermediate Similarity	NPD3921	Approved
0.7143	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3525	Discontinued
0.7143	Intermediate Similarity	NPD3923	Approved
0.7127	Intermediate Similarity	NPD158	Discontinued
0.712	Intermediate Similarity	NPD4203	Approved
0.712	Intermediate Similarity	NPD4204	Approved
0.7107	Intermediate Similarity	NPD7222	Phase 2
0.7105	Intermediate Similarity	NPD4551	Phase 2
0.7101	Intermediate Similarity	NPD3813	Approved
0.7097	Intermediate Similarity	NPD2762	Phase 2
0.7081	Intermediate Similarity	NPD5022	Discontinued
0.7079	Intermediate Similarity	NPD7112	Discontinued
0.7076	Intermediate Similarity	NPD4703	Approved
0.7076	Intermediate Similarity	NPD4702	Approved
0.7056	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4945	Discontinued
0.7037	Intermediate Similarity	NPD3321	Discontinued
0.7027	Intermediate Similarity	NPD3386	Phase 2
0.702	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD802	Phase 2
0.7015	Intermediate Similarity	NPD3330	Phase 1
0.7011	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4889	Approved
0.7005	Intermediate Similarity	NPD4795	Phase 2
0.6995	Remote Similarity	NPD2382	Approved
0.6995	Remote Similarity	NPD2380	Approved
0.6995	Remote Similarity	NPD2381	Approved
0.6968	Remote Similarity	NPD4375	Approved
0.6965	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5164	Discontinued
0.6947	Remote Similarity	NPD5316	Approved
0.694	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7452	Approved
0.6935	Remote Similarity	NPD7453	Approved
0.6931	Remote Similarity	NPD9363	Approved
0.6931	Remote Similarity	NPD9364	Phase 2
0.6931	Remote Similarity	NPD1034	Phase 3
0.6931	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3825	Phase 3
0.6916	Remote Similarity	NPD3006	Discontinued
0.6906	Remote Similarity	NPD5862	Discovery
0.6905	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3396	Approved
0.6891	Remote Similarity	NPD3395	Approved
0.6888	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1685	Approved
0.6872	Remote Similarity	NPD1684	Approved
0.6872	Remote Similarity	NPD2727	Phase 2
0.685	Remote Similarity	NPD1392	Approved
0.6847	Remote Similarity	NPD7069	Discontinued
0.6845	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4548	Discontinued
0.6837	Remote Similarity	NPD4454	Phase 2
0.6831	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1649	Discontinued
0.6823	Remote Similarity	NPD2334	Discontinued
0.6822	Remote Similarity	NPD6494	Phase 2
0.6821	Remote Similarity	NPD2952	Discontinued
0.6816	Remote Similarity	NPD1418	Phase 2
0.681	Remote Similarity	NPD9284	Approved
0.681	Remote Similarity	NPD9080	Approved
0.6805	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6590	Discontinued
0.6802	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3809	Discontinued
0.68	Remote Similarity	NPD5530	Phase 1
0.6798	Remote Similarity	NPD4131	Phase 3
0.6794	Remote Similarity	NPD8356	Approved
0.6793	Remote Similarity	NPD2077	Approved
0.6793	Remote Similarity	NPD2076	Approved
0.6788	Remote Similarity	NPD4372	Phase 1
0.6786	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4044	Discontinued
0.6782	Remote Similarity	NPD4437	Phase 3
0.6771	Remote Similarity	NPD8063	Discontinued
0.6769	Remote Similarity	NPD5512	Phase 3
0.6768	Remote Similarity	NPD4511	Phase 1
0.6763	Remote Similarity	NPD3354	Phase 2
0.6757	Remote Similarity	NPD6492	Phase 2
0.6755	Remote Similarity	NPD1570	Approved
0.6754	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD9506	Approved
0.6745	Remote Similarity	NPD8430	Approved
0.6744	Remote Similarity	NPD3717	Discontinued
0.6743	Remote Similarity	NPD3576	Approved
0.6743	Remote Similarity	NPD3575	Approved
0.6738	Remote Similarity	NPD443	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3082	Discontinued
0.6736	Remote Similarity	NPD4699	Discontinued
0.6735	Remote Similarity	NPD1622	Discontinued
0.6733	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4021	Phase 2
0.6718	Remote Similarity	NPD4418	Discontinued
0.6716	Remote Similarity	NPD5066	Phase 2
0.6716	Remote Similarity	NPD5067	Phase 2
0.6716	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2896	Discontinued
0.6703	Remote Similarity	NPD2719	Clinical (unspecified phase)

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