NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.05
Volume:	177.592
LogP:	1.925
LogD:	1.422
LogS:	-2.717
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	2.491
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.551
MDCK Permeability:	2.6588280888972804e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.689
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	81.32329559326172%
Volume Distribution (VD):	1.259
Pgp-substrate:	17.675918579101562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.628
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.565
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	7.72
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.722
Carcinogencity:	0.067
Eye Corrosion:	0.451
Eye Irritation:	0.987
Respiratory Toxicity:	0.682

Download Data

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

Natural Product: NPC167504

Natural Product ID:	NPC167504
*Common Name:**	Erythrocentaurin
IUPAC Name:	1-oxo-3,4-dihydroisochromene-5-carbaldehyde
Synonyms:
Standard InCHIKey:	TUADBWMDDLWUME-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O3/c11-6-7-2-1-3-9-8(7)4-5-13-10(9)12/h1-3,6H,4-5H2
SMILES:	O=Cc1cccc2c1CCOC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397161
PubChem CID:	191120
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[16335823]
NPO9686	Lonchocarpus neuroscapha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21158427]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[9397205]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15836	Astragalus peregrinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9686	Lonchocarpus neuroscapha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1297	Doronomyrmex goesswaldi	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22686	Gentiana macrophylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7900	Acamptopappus sphaerocephalus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12842	Fomes annosus	Species	Coriolaceae	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
IC50	3
Others	4

Activity Type	# Activity
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1300000.0	nM	PMID[547064]
NPT27	Others	Unspecified		CC50	=	1760000.0	nM	PMID[547064]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.4	n.a.	PMID[547064]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1140000.0	nM	PMID[547064]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.5	n.a.	PMID[547064]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	760000.0	nM	PMID[547064]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.3	n.a.	PMID[547064]

☑ 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 NPC167504 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	303
0.1-0.2	1514
0.2-0.3	3823
0.3-0.4	10017
0.4-0.5	11249
0.5-0.6	10431
0.6-0.7	4902
0.7-0.8	382
0.8-0.85	50
0.85-0.9	22
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC210089
0.934	High Similarity	NPC79496
0.9083	High Similarity	NPC306740
0.8762	High Similarity	NPC60679
0.8762	High Similarity	NPC89886
0.875	High Similarity	NPC42211
0.8704	High Similarity	NPC83628
0.8704	High Similarity	NPC265407
0.8692	High Similarity	NPC119271
0.8679	High Similarity	NPC114594
0.8673	High Similarity	NPC228318
0.8654	High Similarity	NPC118343
0.8641	High Similarity	NPC92754
0.8641	High Similarity	NPC249912
0.8641	High Similarity	NPC276775
0.8611	High Similarity	NPC56493
0.8598	High Similarity	NPC209632
0.8558	High Similarity	NPC78701
0.8558	High Similarity	NPC35448
0.8558	High Similarity	NPC225060
0.8545	High Similarity	NPC474157
0.8532	High Similarity	NPC17417
0.8532	High Similarity	NPC10251
0.8505	High Similarity	NPC31786
0.8496	Intermediate Similarity	NPC100353
0.8491	Intermediate Similarity	NPC45613
0.8491	Intermediate Similarity	NPC188895
0.8476	Intermediate Similarity	NPC146351
0.8468	Intermediate Similarity	NPC82899
0.8468	Intermediate Similarity	NPC270699
0.8455	Intermediate Similarity	NPC174099
0.8455	Intermediate Similarity	NPC196246
0.8455	Intermediate Similarity	NPC214067
0.8455	Intermediate Similarity	NPC93084
0.8455	Intermediate Similarity	NPC251854
0.8447	Intermediate Similarity	NPC130398
0.8396	Intermediate Similarity	NPC70624
0.8393	Intermediate Similarity	NPC272524
0.839	Intermediate Similarity	NPC223351
0.8378	Intermediate Similarity	NPC1082
0.8378	Intermediate Similarity	NPC305912
0.8378	Intermediate Similarity	NPC260818
0.8364	Intermediate Similarity	NPC99846
0.8364	Intermediate Similarity	NPC269023
0.8349	Intermediate Similarity	NPC30594
0.8349	Intermediate Similarity	NPC37622
0.8333	Intermediate Similarity	NPC135730
0.8319	Intermediate Similarity	NPC228739
0.8319	Intermediate Similarity	NPC308744
0.8319	Intermediate Similarity	NPC307651
0.8304	Intermediate Similarity	NPC321852
0.8257	Intermediate Similarity	NPC269457
0.8246	Intermediate Similarity	NPC210092
0.8246	Intermediate Similarity	NPC474095
0.8246	Intermediate Similarity	NPC474685
0.8241	Intermediate Similarity	NPC474365
0.8241	Intermediate Similarity	NPC301943
0.823	Intermediate Similarity	NPC128368
0.823	Intermediate Similarity	NPC13784
0.8198	Intermediate Similarity	NPC469636
0.8198	Intermediate Similarity	NPC85493
0.8174	Intermediate Similarity	NPC149691
0.8158	Intermediate Similarity	NPC196075
0.8158	Intermediate Similarity	NPC153053
0.8158	Intermediate Similarity	NPC477411
0.8148	Intermediate Similarity	NPC284477
0.8131	Intermediate Similarity	NPC325497
0.8131	Intermediate Similarity	NPC203925
0.8087	Intermediate Similarity	NPC228936
0.8073	Intermediate Similarity	NPC255676
0.8056	Intermediate Similarity	NPC473325
0.8053	Intermediate Similarity	NPC243355
0.8037	Intermediate Similarity	NPC229242
0.8036	Intermediate Similarity	NPC318327
0.8017	Intermediate Similarity	NPC226093
0.8	Intermediate Similarity	NPC237366
0.7982	Intermediate Similarity	NPC212415
0.7982	Intermediate Similarity	NPC158282
0.7963	Intermediate Similarity	NPC228435
0.7961	Intermediate Similarity	NPC173443
0.7951	Intermediate Similarity	NPC295664
0.7946	Intermediate Similarity	NPC470391
0.7944	Intermediate Similarity	NPC270654
0.7917	Intermediate Similarity	NPC144547
0.7917	Intermediate Similarity	NPC50872
0.7899	Intermediate Similarity	NPC204784
0.7876	Intermediate Similarity	NPC474364
0.7843	Intermediate Similarity	NPC318107
0.7833	Intermediate Similarity	NPC988
0.7833	Intermediate Similarity	NPC473243
0.7833	Intermediate Similarity	NPC289432
0.783	Intermediate Similarity	NPC261181
0.7826	Intermediate Similarity	NPC66208
0.781	Intermediate Similarity	NPC119631
0.7797	Intermediate Similarity	NPC158157
0.7778	Intermediate Similarity	NPC82712
0.7767	Intermediate Similarity	NPC89377
0.7759	Intermediate Similarity	NPC474176
0.7739	Intermediate Similarity	NPC476003
0.7727	Intermediate Similarity	NPC282895
0.7692	Intermediate Similarity	NPC196673
0.7686	Intermediate Similarity	NPC77000
0.7686	Intermediate Similarity	NPC232958
0.7686	Intermediate Similarity	NPC238861
0.7672	Intermediate Similarity	NPC474314
0.7661	Intermediate Similarity	NPC107846
0.7658	Intermediate Similarity	NPC304873
0.7652	Intermediate Similarity	NPC273837
0.7636	Intermediate Similarity	NPC472318
0.7636	Intermediate Similarity	NPC217621
0.7636	Intermediate Similarity	NPC98911
0.7627	Intermediate Similarity	NPC476357
0.7627	Intermediate Similarity	NPC470764
0.7627	Intermediate Similarity	NPC186933
0.7619	Intermediate Similarity	NPC325709
0.7619	Intermediate Similarity	NPC220893
0.7612	Intermediate Similarity	NPC470842
0.7611	Intermediate Similarity	NPC105899
0.7607	Intermediate Similarity	NPC161611
0.76	Intermediate Similarity	NPC275576
0.76	Intermediate Similarity	NPC470765
0.76	Intermediate Similarity	NPC476599
0.7586	Intermediate Similarity	NPC291799
0.7583	Intermediate Similarity	NPC45794
0.7581	Intermediate Similarity	NPC51079
0.7581	Intermediate Similarity	NPC85511
0.7573	Intermediate Similarity	NPC58616
0.7573	Intermediate Similarity	NPC294134
0.7547	Intermediate Similarity	NPC240108
0.7547	Intermediate Similarity	NPC213156
0.7547	Intermediate Similarity	NPC62765
0.7542	Intermediate Similarity	NPC474363
0.754	Intermediate Similarity	NPC473220
0.754	Intermediate Similarity	NPC470753
0.754	Intermediate Similarity	NPC169913
0.7524	Intermediate Similarity	NPC153308
0.7524	Intermediate Similarity	NPC304760
0.7521	Intermediate Similarity	NPC280789
0.752	Intermediate Similarity	NPC184219
0.752	Intermediate Similarity	NPC246166
0.75	Intermediate Similarity	NPC190298
0.75	Intermediate Similarity	NPC25458
0.75	Intermediate Similarity	NPC472703
0.748	Intermediate Similarity	NPC51448
0.748	Intermediate Similarity	NPC115797
0.7479	Intermediate Similarity	NPC221275
0.7479	Intermediate Similarity	NPC474408
0.7478	Intermediate Similarity	NPC211439
0.7477	Intermediate Similarity	NPC103346
0.7459	Intermediate Similarity	NPC137710
0.7455	Intermediate Similarity	NPC253423
0.7453	Intermediate Similarity	NPC9822
0.744	Intermediate Similarity	NPC472704
0.7438	Intermediate Similarity	NPC469574
0.7438	Intermediate Similarity	NPC45104
0.7438	Intermediate Similarity	NPC152812
0.7436	Intermediate Similarity	NPC474057
0.7436	Intermediate Similarity	NPC137315
0.7434	Intermediate Similarity	NPC329556
0.7434	Intermediate Similarity	NPC234305
0.7431	Intermediate Similarity	NPC172925
0.7424	Intermediate Similarity	NPC470844
0.7419	Intermediate Similarity	NPC167323
0.7419	Intermediate Similarity	NPC269923
0.7411	Intermediate Similarity	NPC112552
0.7407	Intermediate Similarity	NPC77273
0.7402	Intermediate Similarity	NPC51292
0.7395	Intermediate Similarity	NPC471721
0.7395	Intermediate Similarity	NPC172525
0.7388	Intermediate Similarity	NPC221104
0.7379	Intermediate Similarity	NPC39600
0.7379	Intermediate Similarity	NPC288903
0.7377	Intermediate Similarity	NPC94298
0.7377	Intermediate Similarity	NPC27633
0.7373	Intermediate Similarity	NPC57879
0.7368	Intermediate Similarity	NPC249067
0.7368	Intermediate Similarity	NPC85977
0.7368	Intermediate Similarity	NPC291454
0.7364	Intermediate Similarity	NPC61944
0.7364	Intermediate Similarity	NPC147561
0.736	Intermediate Similarity	NPC67300
0.736	Intermediate Similarity	NPC46634
0.7348	Intermediate Similarity	NPC311339
0.7344	Intermediate Similarity	NPC37512
0.7333	Intermediate Similarity	NPC252004
0.7333	Intermediate Similarity	NPC164526
0.7328	Intermediate Similarity	NPC472656
0.7328	Intermediate Similarity	NPC203732
0.7328	Intermediate Similarity	NPC249811
0.7323	Intermediate Similarity	NPC165556
0.7323	Intermediate Similarity	NPC9180
0.7323	Intermediate Similarity	NPC100402
0.7323	Intermediate Similarity	NPC74612
0.7308	Intermediate Similarity	NPC470278
0.7308	Intermediate Similarity	NPC72915
0.7308	Intermediate Similarity	NPC469519
0.7308	Intermediate Similarity	NPC473271
0.7304	Intermediate Similarity	NPC172483
0.7295	Intermediate Similarity	NPC217423
0.7281	Intermediate Similarity	NPC274443

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 NPC167504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	988
0.2-0.3	1267
0.3-0.4	2858
0.4-0.5	2346
0.5-0.6	1075
0.6-0.7	303
0.7-0.8	33
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD1238	Approved
0.8545	High Similarity	NPD2181	Clinical (unspecified phase)
0.8532	High Similarity	NPD2182	Approved
0.8505	High Similarity	NPD164	Approved
0.7982	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD9257	Approved
0.7843	Intermediate Similarity	NPD9259	Approved
0.783	Intermediate Similarity	NPD1202	Approved
0.7719	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5951	Approved
0.7547	Intermediate Similarity	NPD9256	Approved
0.7547	Intermediate Similarity	NPD9258	Approved
0.75	Intermediate Similarity	NPD7008	Discontinued
0.7434	Intermediate Similarity	NPD1929	Approved
0.7434	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1930	Approved
0.7431	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD1237	Approved
0.7364	Intermediate Similarity	NPD1989	Approved
0.7333	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6287	Discontinued
0.7273	Intermediate Similarity	NPD9260	Approved
0.7258	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD9490	Approved
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1281	Approved
0.7132	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1241	Discontinued
0.7103	Intermediate Similarity	NPD1087	Approved
0.708	Intermediate Similarity	NPD9495	Approved
0.7073	Intermediate Similarity	NPD9493	Approved
0.7069	Intermediate Similarity	NPD5909	Discontinued
0.7068	Intermediate Similarity	NPD3373	Approved
0.7064	Intermediate Similarity	NPD3672	Approved
0.7064	Intermediate Similarity	NPD3673	Approved
0.7059	Intermediate Similarity	NPD2067	Discontinued
0.7048	Intermediate Similarity	NPD9491	Approved
0.7045	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD2066	Phase 3
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD1239	Approved
0.6977	Remote Similarity	NPD1876	Approved
0.6977	Remote Similarity	NPD1283	Approved
0.6977	Remote Similarity	NPD2199	Approved
0.6977	Remote Similarity	NPD2198	Approved
0.6953	Remote Similarity	NPD3972	Approved
0.6953	Remote Similarity	NPD6637	Approved
0.6944	Remote Similarity	NPD650	Approved
0.6917	Remote Similarity	NPD2313	Discontinued
0.6911	Remote Similarity	NPD2629	Approved
0.6909	Remote Similarity	NPD1089	Approved
0.6909	Remote Similarity	NPD1086	Approved
0.6909	Remote Similarity	NPD1090	Approved
0.6906	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5691	Approved
0.6899	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1932	Approved
0.6894	Remote Similarity	NPD6832	Phase 2
0.6893	Remote Similarity	NPD225	Approved
0.6893	Remote Similarity	NPD227	Approved
0.6875	Remote Similarity	NPD1563	Approved
0.686	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.685	Remote Similarity	NPD17	Approved
0.6847	Remote Similarity	NPD7609	Phase 3
0.6846	Remote Similarity	NPD5667	Approved
0.6838	Remote Similarity	NPD9261	Approved
0.6829	Remote Similarity	NPD6010	Discontinued
0.6818	Remote Similarity	NPD800	Approved
0.6815	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD553	Approved
0.6794	Remote Similarity	NPD3266	Approved
0.6794	Remote Similarity	NPD9567	Approved
0.6794	Remote Similarity	NPD3267	Approved
0.6794	Remote Similarity	NPD552	Approved
0.6789	Remote Similarity	NPD1282	Approved
0.6788	Remote Similarity	NPD2567	Approved
0.6788	Remote Similarity	NPD2569	Approved
0.6786	Remote Similarity	NPD7631	Approved
0.6786	Remote Similarity	NPD1088	Approved
0.6783	Remote Similarity	NPD5926	Approved
0.6777	Remote Similarity	NPD1756	Approved
0.6777	Remote Similarity	NPD1752	Approved
0.6777	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1651	Approved
0.6763	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7236	Approved
0.675	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2347	Approved
0.6742	Remote Similarity	NPD1019	Discontinued
0.6741	Remote Similarity	NPD7713	Phase 3
0.6739	Remote Similarity	NPD2799	Discontinued
0.6739	Remote Similarity	NPD3748	Approved
0.6738	Remote Similarity	NPD7003	Approved
0.6726	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2201	Approved
0.6716	Remote Similarity	NPD6039	Approved
0.6712	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD942	Approved
0.6698	Remote Similarity	NPD226	Approved
0.6696	Remote Similarity	NPD1564	Approved
0.6696	Remote Similarity	NPD3495	Discontinued
0.6696	Remote Similarity	NPD1566	Phase 3
0.6696	Remote Similarity	NPD1565	Approved
0.6695	Remote Similarity	NPD6647	Phase 2
0.6693	Remote Similarity	NPD1894	Discontinued
0.6692	Remote Similarity	NPD1608	Approved
0.6692	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD9508	Approved
0.6644	Remote Similarity	NPD7819	Suspended
0.6643	Remote Similarity	NPD1471	Phase 3
0.6639	Remote Similarity	NPD5235	Approved
0.6639	Remote Similarity	NPD5236	Approved
0.6639	Remote Similarity	NPD5240	Approved
0.6639	Remote Similarity	NPD5239	Approved
0.6639	Remote Similarity	NPD5237	Approved
0.6637	Remote Similarity	NPD1508	Approved
0.6621	Remote Similarity	NPD6273	Approved
0.662	Remote Similarity	NPD4628	Phase 3
0.6617	Remote Similarity	NPD2798	Approved
0.6613	Remote Similarity	NPD5277	Phase 2
0.6613	Remote Similarity	NPD7094	Approved
0.6613	Remote Similarity	NPD6858	Approved
0.6612	Remote Similarity	NPD9267	Approved
0.6612	Remote Similarity	NPD1358	Approved
0.6612	Remote Similarity	NPD9263	Approved
0.6612	Remote Similarity	NPD9264	Approved
0.6599	Remote Similarity	NPD3226	Approved
0.6596	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5305	Approved
0.6589	Remote Similarity	NPD5306	Approved
0.6589	Remote Similarity	NPD4626	Approved
0.6587	Remote Similarity	NPD4198	Discontinued
0.6583	Remote Similarity	NPD9697	Approved
0.6575	Remote Similarity	NPD920	Approved
0.6571	Remote Similarity	NPD4476	Approved
0.6571	Remote Similarity	NPD1551	Phase 2
0.6571	Remote Similarity	NPD2438	Suspended
0.6571	Remote Similarity	NPD2935	Discontinued
0.6571	Remote Similarity	NPD2531	Phase 2
0.6571	Remote Similarity	NPD4477	Approved
0.6569	Remote Similarity	NPD3140	Approved
0.6569	Remote Similarity	NPD4307	Phase 2
0.6569	Remote Similarity	NPD3142	Approved
0.6565	Remote Similarity	NPD4878	Approved
0.6557	Remote Similarity	NPD2329	Discontinued
0.6557	Remote Similarity	NPD74	Approved
0.6557	Remote Similarity	NPD9266	Approved
0.6544	Remote Similarity	NPD3268	Approved
0.6541	Remote Similarity	NPD2797	Approved
0.6538	Remote Similarity	NPD4106	Approved
0.6538	Remote Similarity	NPD4135	Approved
0.6538	Remote Similarity	NPD4136	Approved
0.6535	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7239	Suspended
0.6525	Remote Similarity	NPD7611	Approved
0.6522	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1933	Approved
0.6512	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5889	Approved
0.651	Remote Similarity	NPD5890	Approved
0.651	Remote Similarity	NPD7411	Suspended
0.6508	Remote Similarity	NPD4766	Approved
0.6504	Remote Similarity	NPD4234	Approved
0.6504	Remote Similarity	NPD4233	Approved
0.6503	Remote Similarity	NPD3750	Approved
0.65	Remote Similarity	NPD3047	Approved
0.65	Remote Similarity	NPD3046	Approved
0.65	Remote Similarity	NPD3048	Approved
0.6493	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6085	Phase 2
0.6489	Remote Similarity	NPD4806	Approved
0.6489	Remote Similarity	NPD1201	Approved
0.6489	Remote Similarity	NPD4807	Approved
0.6486	Remote Similarity	NPD4793	Discontinued
0.648	Remote Similarity	NPD2607	Approved
0.6479	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1843	Approved
0.6462	Remote Similarity	NPD2345	Approved
0.6458	Remote Similarity	NPD3887	Approved
0.6458	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD9494	Approved
0.6441	Remote Similarity	NPD7798	Approved
0.6434	Remote Similarity	NPD1243	Approved
0.6422	Remote Similarity	NPD3971	Phase 1
0.6418	Remote Similarity	NPD1470	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