NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	227.09
Volume:	237.789
LogP:	2.664
LogD:	2.794
LogS:	-3.402
# Rotatable Bonds:	2
TPSA:	45.25
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.014
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:	-4.785
MDCK Permeability:	1.2575864275277127e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.84
Plasma Protein Binding (PPB):	81.9900894165039%
Volume Distribution (VD):	0.891
Pgp-substrate:	8.670005798339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.592
CYP2C19-substrate:	0.442
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.898
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.576
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	7.882
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.65
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.687
Carcinogencity:	0.628
Eye Corrosion:	0.01
Eye Irritation:	0.944
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC128823

Natural Product ID:	NPC128823
*Common Name:**	Koenoline
IUPAC Name:	(1-methoxy-9H-carbazol-3-yl)methanol
Synonyms:	Koenoline
Standard InCHIKey:	KNKVHLASDDREQS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H13NO2/c1-17-13-7-9(8-16)6-11-10-4-2-3-5-12(10)15-14(11)13/h2-7,15-16H,8H2,1H3
SMILES:	COc1cc(cc2c3ccccc3[nH]c12)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503498
PubChem CID:	375152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	stem bark;fruit	n.a.	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	root bark	Kuantaochi, Nantou Hsien, Taiwan	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	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	53
Others	1

Activity Type	# Activity
Cell Line	54

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	1737.8	nM	PMID[536087]
NPT405	Cell Line	NCI-H226	Homo sapiens	TGI	=	5248.07	nM	PMID[536087]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	11912.42	nM	PMID[536088]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	20844.91	nM	PMID[536088]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	24603.68	nM	PMID[536088]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	24378.11	nM	PMID[536088]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	1733.8	nM	PMID[536088]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[536088]

☑ 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 NPC128823 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	502
0.1-0.2	3411
0.2-0.3	13671
0.3-0.4	5338
0.4-0.5	14379
0.5-0.6	3267
0.6-0.7	1673
0.7-0.8	371
0.8-0.85	59
0.85-0.9	21
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC242928
0.9148	High Similarity	NPC474798
0.9026	High Similarity	NPC132642
0.8923	High Similarity	NPC184408
0.8782	High Similarity	NPC473179
0.8718	High Similarity	NPC39500
0.8717	High Similarity	NPC70956
0.8717	High Similarity	NPC243834
0.8711	High Similarity	NPC187501
0.8667	High Similarity	NPC94157
0.866	High Similarity	NPC199667
0.8656	High Similarity	NPC475190
0.8611	High Similarity	NPC88363
0.861	High Similarity	NPC131017
0.8608	High Similarity	NPC209769
0.8608	High Similarity	NPC473181
0.8594	High Similarity	NPC470930
0.8579	High Similarity	NPC118228
0.8571	High Similarity	NPC473180
0.8564	High Similarity	NPC478032
0.8564	High Similarity	NPC179287
0.8549	High Similarity	NPC476106
0.8505	High Similarity	NPC193777
0.85	High Similarity	NPC208084
0.848	Intermediate Similarity	NPC473185
0.8439	Intermediate Similarity	NPC274640
0.8394	Intermediate Similarity	NPC291535
0.8394	Intermediate Similarity	NPC475085
0.8394	Intermediate Similarity	NPC475112
0.8378	Intermediate Similarity	NPC42591
0.8374	Intermediate Similarity	NPC144452
0.837	Intermediate Similarity	NPC176127
0.8368	Intermediate Similarity	NPC251090
0.8366	Intermediate Similarity	NPC225279
0.8316	Intermediate Similarity	NPC283117
0.8299	Intermediate Similarity	NPC135887
0.8299	Intermediate Similarity	NPC199277
0.8281	Intermediate Similarity	NPC72211
0.8278	Intermediate Similarity	NPC473182
0.827	Intermediate Similarity	NPC212535
0.8265	Intermediate Similarity	NPC45190
0.8258	Intermediate Similarity	NPC118511
0.8256	Intermediate Similarity	NPC223427
0.8256	Intermediate Similarity	NPC162484
0.8256	Intermediate Similarity	NPC476138
0.8256	Intermediate Similarity	NPC245816
0.8245	Intermediate Similarity	NPC246700
0.8244	Intermediate Similarity	NPC51388
0.8241	Intermediate Similarity	NPC294375
0.82	Intermediate Similarity	NPC48353
0.8182	Intermediate Similarity	NPC474688
0.8182	Intermediate Similarity	NPC94943
0.8177	Intermediate Similarity	NPC70259
0.8173	Intermediate Similarity	NPC300156
0.8164	Intermediate Similarity	NPC202503
0.8163	Intermediate Similarity	NPC475774
0.816	Intermediate Similarity	NPC473183
0.8152	Intermediate Similarity	NPC473184
0.815	Intermediate Similarity	NPC87413
0.8131	Intermediate Similarity	NPC475844
0.8128	Intermediate Similarity	NPC190007
0.8128	Intermediate Similarity	NPC84478
0.8128	Intermediate Similarity	NPC314552
0.8125	Intermediate Similarity	NPC43787
0.8125	Intermediate Similarity	NPC205934
0.8095	Intermediate Similarity	NPC474701
0.8079	Intermediate Similarity	NPC8022
0.8079	Intermediate Similarity	NPC470799
0.8073	Intermediate Similarity	NPC307963
0.8053	Intermediate Similarity	NPC128751
0.8041	Intermediate Similarity	NPC153042
0.804	Intermediate Similarity	NPC249583
0.8039	Intermediate Similarity	NPC293151
0.801	Intermediate Similarity	NPC469497
0.801	Intermediate Similarity	NPC106833
0.8009	Intermediate Similarity	NPC475253
0.8	Intermediate Similarity	NPC247803
0.8	Intermediate Similarity	NPC475910
0.7989	Intermediate Similarity	NPC474409
0.7981	Intermediate Similarity	NPC39370
0.7972	Intermediate Similarity	NPC473186
0.797	Intermediate Similarity	NPC267423
0.796	Intermediate Similarity	NPC185782
0.796	Intermediate Similarity	NPC201697
0.7958	Intermediate Similarity	NPC296527
0.795	Intermediate Similarity	NPC4687
0.795	Intermediate Similarity	NPC321428
0.7931	Intermediate Similarity	NPC26679
0.7923	Intermediate Similarity	NPC150239
0.7919	Intermediate Similarity	NPC329793
0.7917	Intermediate Similarity	NPC76748
0.791	Intermediate Similarity	NPC39679
0.7892	Intermediate Similarity	NPC469592
0.7892	Intermediate Similarity	NPC471080
0.7892	Intermediate Similarity	NPC476287
0.7885	Intermediate Similarity	NPC477532
0.7882	Intermediate Similarity	NPC208284
0.7879	Intermediate Similarity	NPC476044
0.7876	Intermediate Similarity	NPC92111
0.7868	Intermediate Similarity	NPC18487
0.7868	Intermediate Similarity	NPC476167
0.7843	Intermediate Similarity	NPC310211
0.7843	Intermediate Similarity	NPC308137
0.7837	Intermediate Similarity	NPC174760
0.783	Intermediate Similarity	NPC252251
0.7828	Intermediate Similarity	NPC176538
0.7828	Intermediate Similarity	NPC19872
0.7828	Intermediate Similarity	NPC329747
0.7826	Intermediate Similarity	NPC46561
0.7819	Intermediate Similarity	NPC72980
0.7817	Intermediate Similarity	NPC192315
0.7805	Intermediate Similarity	NPC266931
0.7805	Intermediate Similarity	NPC478074
0.7757	Intermediate Similarity	NPC477531
0.7745	Intermediate Similarity	NPC471304
0.774	Intermediate Similarity	NPC469594
0.7737	Intermediate Similarity	NPC314394
0.7729	Intermediate Similarity	NPC477110
0.7721	Intermediate Similarity	NPC469554
0.771	Intermediate Similarity	NPC209174
0.7708	Intermediate Similarity	NPC473189
0.7708	Intermediate Similarity	NPC314002
0.7707	Intermediate Similarity	NPC9894
0.7701	Intermediate Similarity	NPC34508
0.7681	Intermediate Similarity	NPC116238
0.768	Intermediate Similarity	NPC141353
0.7662	Intermediate Similarity	NPC66815
0.7659	Intermediate Similarity	NPC11464
0.7659	Intermediate Similarity	NPC5145
0.7656	Intermediate Similarity	NPC204717
0.7653	Intermediate Similarity	NPC99666
0.7653	Intermediate Similarity	NPC200888
0.765	Intermediate Similarity	NPC249040
0.7647	Intermediate Similarity	NPC470931
0.7644	Intermediate Similarity	NPC3207
0.7637	Intermediate Similarity	NPC26850
0.7635	Intermediate Similarity	NPC304183
0.763	Intermediate Similarity	NPC280799
0.7629	Intermediate Similarity	NPC66083
0.7619	Intermediate Similarity	NPC292958
0.7612	Intermediate Similarity	NPC232727
0.7608	Intermediate Similarity	NPC169402
0.7604	Intermediate Similarity	NPC220765
0.76	Intermediate Similarity	NPC473188
0.7594	Intermediate Similarity	NPC280272
0.7586	Intermediate Similarity	NPC285558
0.7585	Intermediate Similarity	NPC316981
0.7585	Intermediate Similarity	NPC203168
0.758	Intermediate Similarity	NPC6786
0.7579	Intermediate Similarity	NPC283152
0.7577	Intermediate Similarity	NPC171171
0.7577	Intermediate Similarity	NPC160381
0.7576	Intermediate Similarity	NPC276517
0.7569	Intermediate Similarity	NPC26872
0.7566	Intermediate Similarity	NPC312872
0.7565	Intermediate Similarity	NPC62069
0.7561	Intermediate Similarity	NPC210828
0.7561	Intermediate Similarity	NPC477111
0.7561	Intermediate Similarity	NPC86834
0.756	Intermediate Similarity	NPC288349
0.7558	Intermediate Similarity	NPC101543
0.7547	Intermediate Similarity	NPC198503
0.7539	Intermediate Similarity	NPC270009
0.7538	Intermediate Similarity	NPC13880
0.7536	Intermediate Similarity	NPC213530
0.7536	Intermediate Similarity	NPC193267
0.7536	Intermediate Similarity	NPC23294
0.7534	Intermediate Similarity	NPC473187
0.7525	Intermediate Similarity	NPC79293
0.7525	Intermediate Similarity	NPC279401
0.7523	Intermediate Similarity	NPC180504
0.75	Intermediate Similarity	NPC477533
0.75	Intermediate Similarity	NPC164374
0.75	Intermediate Similarity	NPC86078
0.75	Intermediate Similarity	NPC77555
0.75	Intermediate Similarity	NPC137929
0.7488	Intermediate Similarity	NPC303658
0.7488	Intermediate Similarity	NPC219664
0.7488	Intermediate Similarity	NPC96321
0.7488	Intermediate Similarity	NPC303951
0.7487	Intermediate Similarity	NPC184964
0.7477	Intermediate Similarity	NPC474192
0.7477	Intermediate Similarity	NPC475720
0.7476	Intermediate Similarity	NPC170114
0.7475	Intermediate Similarity	NPC280964
0.7475	Intermediate Similarity	NPC114335
0.7475	Intermediate Similarity	NPC141915
0.7463	Intermediate Similarity	NPC477113
0.7463	Intermediate Similarity	NPC472111
0.7461	Intermediate Similarity	NPC206201
0.7461	Intermediate Similarity	NPC192270
0.7453	Intermediate Similarity	NPC288987
0.7451	Intermediate Similarity	NPC476098
0.7449	Intermediate Similarity	NPC46580
0.7448	Intermediate Similarity	NPC472443
0.744	Intermediate Similarity	NPC469589
0.7437	Intermediate Similarity	NPC230403
0.7435	Intermediate Similarity	NPC288943
0.7429	Intermediate Similarity	NPC470549
0.7423	Intermediate Similarity	NPC472444

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 NPC128823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	694
0.2-0.3	893
0.3-0.4	1365
0.4-0.5	2855
0.5-0.6	2148
0.6-0.7	764
0.7-0.8	119
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8324	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD5164	Discontinued
0.8081	Intermediate Similarity	NPD3003	Approved
0.8073	Intermediate Similarity	NPD1038	Approved
0.806	Intermediate Similarity	NPD4502	Phase 2
0.8051	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD5612	Discontinued
0.7887	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1768	Approved
0.7861	Intermediate Similarity	NPD7452	Approved
0.7861	Intermediate Similarity	NPD7222	Phase 2
0.7861	Intermediate Similarity	NPD7453	Approved
0.7854	Intermediate Similarity	NPD5902	Approved
0.7854	Intermediate Similarity	NPD5903	Approved
0.7784	Intermediate Similarity	NPD1325	Approved
0.7784	Intermediate Similarity	NPD1326	Approved
0.7734	Intermediate Similarity	NPD5658	Approved
0.7707	Intermediate Similarity	NPD5939	Approved
0.7707	Intermediate Similarity	NPD5936	Approved
0.7703	Intermediate Similarity	NPD3875	Discontinued
0.7688	Intermediate Similarity	NPD2175	Phase 3
0.7688	Intermediate Similarity	NPD2177	Approved
0.7688	Intermediate Similarity	NPD2176	Approved
0.7677	Intermediate Similarity	NPD5003	Discontinued
0.7668	Intermediate Similarity	NPD5256	Discontinued
0.7621	Intermediate Similarity	NPD5066	Phase 2
0.7621	Intermediate Similarity	NPD5067	Phase 2
0.7615	Intermediate Similarity	NPD4454	Phase 2
0.7602	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5913	Phase 3
0.76	Intermediate Similarity	NPD3825	Phase 3
0.7598	Intermediate Similarity	NPD1392	Approved
0.7576	Intermediate Similarity	NPD6590	Discontinued
0.7571	Intermediate Similarity	NPD6985	Discontinued
0.7552	Intermediate Similarity	NPD4203	Approved
0.7552	Intermediate Similarity	NPD4204	Approved
0.7551	Intermediate Similarity	NPD2564	Approved
0.7551	Intermediate Similarity	NPD2565	Phase 2
0.7538	Intermediate Similarity	NPD5512	Phase 3
0.7525	Intermediate Similarity	NPD4511	Phase 1
0.7525	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6290	Phase 2
0.7512	Intermediate Similarity	NPD5429	Discontinued
0.7487	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4418	Discontinued
0.7453	Intermediate Similarity	NPD7194	Discontinued
0.7452	Intermediate Similarity	NPD6220	Phase 3
0.7448	Intermediate Similarity	NPD3920	Phase 2
0.7445	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5559	Phase 2
0.7413	Intermediate Similarity	NPD7948	Phase 1
0.7379	Intermediate Similarity	NPD5530	Phase 1
0.7364	Intermediate Similarity	NPD7558	Phase 2
0.7346	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8396	Approved
0.734	Intermediate Similarity	NPD8395	Approved
0.7324	Intermediate Similarity	NPD5632	Approved
0.7308	Intermediate Similarity	NPD2189	Approved
0.7308	Intermediate Similarity	NPD2187	Approved
0.7306	Intermediate Similarity	NPD6159	Phase 2
0.7299	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8403	Phase 1
0.7277	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2383	Phase 1
0.726	Intermediate Similarity	NPD7555	Discontinued
0.7256	Intermediate Similarity	NPD6242	Discontinued
0.7246	Intermediate Similarity	NPD31	Approved
0.7246	Intermediate Similarity	NPD32	Approved
0.7246	Intermediate Similarity	NPD4034	Approved
0.7246	Intermediate Similarity	NPD4122	Approved
0.7246	Intermediate Similarity	NPD4037	Approved
0.7246	Intermediate Similarity	NPD4036	Approved
0.7246	Intermediate Similarity	NPD4039	Approved
0.7246	Intermediate Similarity	NPD4035	Approved
0.7246	Intermediate Similarity	NPD4038	Approved
0.7246	Intermediate Similarity	NPD4033	Approved
0.7243	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6988	Phase 1
0.7228	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD484	Approved
0.7209	Intermediate Similarity	NPD3402	Phase 1
0.7207	Intermediate Similarity	NPD6494	Phase 2
0.7206	Intermediate Similarity	NPD2727	Phase 2
0.7204	Intermediate Similarity	NPD5416	Discontinued
0.7192	Intermediate Similarity	NPD6550	Discontinued
0.7189	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6736	Discontinued
0.7182	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD9705	Discontinued
0.7181	Intermediate Similarity	NPD112	Approved
0.7171	Intermediate Similarity	NPD5999	Phase 2
0.717	Intermediate Similarity	NPD3330	Phase 1
0.7169	Intermediate Similarity	NPD7603	Discontinued
0.7163	Intermediate Similarity	NPD7395	Discontinued
0.7163	Intermediate Similarity	NPD4429	Discontinued
0.715	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6643	Discontinued
0.715	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5022	Discontinued
0.7149	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7726	Phase 1
0.7143	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6569	Phase 2
0.7129	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2920	Discontinued
0.7113	Intermediate Similarity	NPD9690	Approved
0.71	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3746	Discontinued
0.7083	Intermediate Similarity	NPD8363	Approved
0.7083	Intermediate Similarity	NPD8364	Approved
0.7081	Intermediate Similarity	NPD4795	Phase 2
0.7072	Intermediate Similarity	NPD1592	Phase 3
0.7071	Intermediate Similarity	NPD5596	Phase 2
0.7071	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7672	Approved
0.7062	Intermediate Similarity	NPD7671	Approved
0.7062	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6251	Discontinued
0.7056	Intermediate Similarity	NPD3945	Discontinued
0.7053	Intermediate Similarity	NPD1740	Approved
0.7053	Intermediate Similarity	NPD1739	Approved
0.7051	Intermediate Similarity	NPD3258	Approved
0.7048	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3922	Approved
0.7044	Intermediate Similarity	NPD3923	Approved
0.7044	Intermediate Similarity	NPD3921	Approved
0.7044	Intermediate Similarity	NPD3924	Approved
0.704	Intermediate Similarity	NPD1467	Approved
0.704	Intermediate Similarity	NPD1466	Phase 3
0.7033	Intermediate Similarity	NPD6991	Approved
0.7032	Intermediate Similarity	NPD1856	Discontinued
0.7028	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2951	Discontinued
0.7021	Intermediate Similarity	NPD8244	Phase 2
0.7018	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD802	Phase 2
0.7009	Intermediate Similarity	NPD4885	Approved
0.7005	Intermediate Similarity	NPD8386	Phase 2
0.7005	Intermediate Similarity	NPD3354	Phase 2
0.7005	Intermediate Similarity	NPD4548	Discontinued
0.7005	Intermediate Similarity	NPD3814	Phase 1
0.6996	Remote Similarity	NPD5479	Discontinued
0.6995	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3006	Discontinued
0.699	Remote Similarity	NPD2382	Approved
0.699	Remote Similarity	NPD2381	Approved
0.699	Remote Similarity	NPD2380	Approved
0.6989	Remote Similarity	NPD3833	Phase 3
0.6989	Remote Similarity	NPD3835	Phase 3
0.6987	Remote Similarity	NPD6473	Phase 1
0.6987	Remote Similarity	NPD6517	Phase 3
0.6986	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6340	Approved
0.6965	Remote Similarity	NPD6339	Approved
0.6964	Remote Similarity	NPD1867	Approved
0.6964	Remote Similarity	NPD1505	Phase 2
0.6963	Remote Similarity	NPD1685	Approved
0.6963	Remote Similarity	NPD1684	Approved
0.6961	Remote Similarity	NPD3963	Phase 1
0.6959	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7221	Approved
0.6955	Remote Similarity	NPD7219	Approved
0.6944	Remote Similarity	NPD3257	Approved
0.6942	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3477	Phase 2
0.6942	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5065	Approved
0.6935	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2749	Discontinued
0.693	Remote Similarity	NPD4927	Discontinued
0.6927	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4083	Discontinued
0.692	Remote Similarity	NPD7567	Approved
0.6919	Remote Similarity	NPD3397	Phase 2
0.6916	Remote Similarity	NPD7853	Phase 2
0.6912	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1229	Phase 2
0.6905	Remote Similarity	NPD2779	Approved
0.6904	Remote Similarity	NPD4354	Approved
0.6903	Remote Similarity	NPD4080	Discontinued
0.6898	Remote Similarity	NPD4463	Approved
0.6898	Remote Similarity	NPD4462	Approved
0.6892	Remote Similarity	NPD4890	Phase 2
0.6887	Remote Similarity	NPD6150	Discontinued
0.6884	Remote Similarity	NPD7470	Discontinued
0.6884	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6595	Phase 3
0.6883	Remote Similarity	NPD7067	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