NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	180.228
LogP:	1.433
LogD:	1.174
LogS:	-2.133
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.381
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.376
MDCK Permeability:	2.5206614736816846e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.772

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.626
Plasma Protein Binding (PPB):	56.36406707763672%
Volume Distribution (VD):	1.487
Pgp-substrate:	33.788063049316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.351
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.651
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.807
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	9.581
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.379
Carcinogencity:	0.058
Eye Corrosion:	0.007
Eye Irritation:	0.973
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC306740

Natural Product ID:	NPC306740
*Common Name:**	5-(Hydroxymethyl)Isochroman-1-One
IUPAC Name:	5-(hydroxymethyl)-3,4-dihydroisochromen-1-one
Synonyms:
Standard InCHIKey:	DNNSYXUCMMUSNY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O3/c11-6-7-2-1-3-9-8(7)4-5-13-10(9)12/h1-3,11H,4-6H2
SMILES:	OCc1cccc2c1CCOC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397162
PubChem CID:	23725722
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
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	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	=	2700000.0	nM	PMID[495855]
NPT27	Others	Unspecified		CC50	>	3800000.0	nM	PMID[495855]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	1.4	n.a.	PMID[495855]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1460000.0	nM	PMID[495855]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	2.6	n.a.	PMID[495855]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	170000.0	nM	PMID[495855]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	22.4	n.a.	PMID[495855]

☑ 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 NPC306740 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	251
0.1-0.2	1220
0.2-0.3	2825
0.3-0.4	7658
0.4-0.5	12279
0.5-0.6	9563
0.6-0.7	7979
0.7-0.8	838
0.8-0.85	70
0.85-0.9	10
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9217	High Similarity	NPC223351
0.9083	High Similarity	NPC210089
0.9083	High Similarity	NPC167504
0.9	High Similarity	NPC79496
0.8974	High Similarity	NPC228739
0.875	High Similarity	NPC272524
0.8739	High Similarity	NPC260818
0.8661	High Similarity	NPC321852
0.8559	High Similarity	NPC85493
0.8519	High Similarity	NPC284477
0.8509	High Similarity	NPC153053
0.8509	High Similarity	NPC237366
0.8496	Intermediate Similarity	NPC158282
0.844	Intermediate Similarity	NPC60679
0.844	Intermediate Similarity	NPC89886
0.844	Intermediate Similarity	NPC255676
0.8435	Intermediate Similarity	NPC474685
0.8426	Intermediate Similarity	NPC42211
0.8411	Intermediate Similarity	NPC229242
0.8393	Intermediate Similarity	NPC265407
0.8393	Intermediate Similarity	NPC83628
0.8393	Intermediate Similarity	NPC318327
0.8387	Intermediate Similarity	NPC82712
0.8378	Intermediate Similarity	NPC119271
0.8364	Intermediate Similarity	NPC114594
0.8333	Intermediate Similarity	NPC228435
0.8333	Intermediate Similarity	NPC118343
0.8318	Intermediate Similarity	NPC249912
0.8318	Intermediate Similarity	NPC276775
0.8318	Intermediate Similarity	NPC92754
0.8304	Intermediate Similarity	NPC56493
0.8288	Intermediate Similarity	NPC209632
0.8246	Intermediate Similarity	NPC476003
0.8246	Intermediate Similarity	NPC474157
0.8241	Intermediate Similarity	NPC225060
0.8241	Intermediate Similarity	NPC78701
0.8241	Intermediate Similarity	NPC35448
0.823	Intermediate Similarity	NPC17417
0.823	Intermediate Similarity	NPC10251
0.822	Intermediate Similarity	NPC228318
0.8205	Intermediate Similarity	NPC100353
0.8198	Intermediate Similarity	NPC31786
0.819	Intermediate Similarity	NPC196673
0.8182	Intermediate Similarity	NPC45613
0.8174	Intermediate Similarity	NPC66208
0.8174	Intermediate Similarity	NPC82899
0.8174	Intermediate Similarity	NPC270699
0.8165	Intermediate Similarity	NPC146351
0.8158	Intermediate Similarity	NPC196246
0.8158	Intermediate Similarity	NPC174099
0.8158	Intermediate Similarity	NPC214067
0.8158	Intermediate Similarity	NPC93084
0.8158	Intermediate Similarity	NPC251854
0.8131	Intermediate Similarity	NPC130398
0.813	Intermediate Similarity	NPC184219
0.813	Intermediate Similarity	NPC295664
0.8091	Intermediate Similarity	NPC282895
0.8091	Intermediate Similarity	NPC70624
0.8087	Intermediate Similarity	NPC305912
0.8087	Intermediate Similarity	NPC1082
0.8083	Intermediate Similarity	NPC204784
0.807	Intermediate Similarity	NPC269023
0.807	Intermediate Similarity	NPC99846
0.8065	Intermediate Similarity	NPC275576
0.8053	Intermediate Similarity	NPC30594
0.8053	Intermediate Similarity	NPC37622
0.8051	Intermediate Similarity	NPC135730
0.8034	Intermediate Similarity	NPC307651
0.8034	Intermediate Similarity	NPC308744
0.8018	Intermediate Similarity	NPC304873
0.8017	Intermediate Similarity	NPC474314
0.8	Intermediate Similarity	NPC169913
0.8	Intermediate Similarity	NPC217621
0.8	Intermediate Similarity	NPC27633
0.8	Intermediate Similarity	NPC94298
0.7983	Intermediate Similarity	NPC158157
0.7982	Intermediate Similarity	NPC211439
0.7967	Intermediate Similarity	NPC67300
0.7967	Intermediate Similarity	NPC472703
0.7966	Intermediate Similarity	NPC474095
0.7966	Intermediate Similarity	NPC186933
0.7966	Intermediate Similarity	NPC210092
0.7965	Intermediate Similarity	NPC105899
0.7965	Intermediate Similarity	NPC269457
0.7949	Intermediate Similarity	NPC128368
0.7949	Intermediate Similarity	NPC13784
0.7946	Intermediate Similarity	NPC301943
0.7946	Intermediate Similarity	NPC474365
0.7939	Intermediate Similarity	NPC291454
0.7925	Intermediate Similarity	NPC62765
0.7923	Intermediate Similarity	NPC477893
0.7913	Intermediate Similarity	NPC469636
0.7903	Intermediate Similarity	NPC472704
0.7899	Intermediate Similarity	NPC149691
0.7891	Intermediate Similarity	NPC72915
0.7881	Intermediate Similarity	NPC477411
0.7881	Intermediate Similarity	NPC474363
0.7881	Intermediate Similarity	NPC196075
0.7881	Intermediate Similarity	NPC87069
0.7876	Intermediate Similarity	NPC249067
0.7874	Intermediate Similarity	NPC473744
0.7863	Intermediate Similarity	NPC142027
0.7857	Intermediate Similarity	NPC110211
0.7857	Intermediate Similarity	NPC472706
0.7857	Intermediate Similarity	NPC188895
0.7857	Intermediate Similarity	NPC25458
0.784	Intermediate Similarity	NPC246166
0.7838	Intermediate Similarity	NPC203925
0.7838	Intermediate Similarity	NPC325497
0.7833	Intermediate Similarity	NPC131192
0.7829	Intermediate Similarity	NPC470831
0.7829	Intermediate Similarity	NPC214702
0.782	Intermediate Similarity	NPC221104
0.7818	Intermediate Similarity	NPC253423
0.7815	Intermediate Similarity	NPC228936
0.7815	Intermediate Similarity	NPC476357
0.7795	Intermediate Similarity	NPC51448
0.7795	Intermediate Similarity	NPC115797
0.7786	Intermediate Similarity	NPC477896
0.7778	Intermediate Similarity	NPC100402
0.7778	Intermediate Similarity	NPC470842
0.7778	Intermediate Similarity	NPC49938
0.7778	Intermediate Similarity	NPC9180
0.7778	Intermediate Similarity	NPC470765
0.7778	Intermediate Similarity	NPC474057
0.7778	Intermediate Similarity	NPC243355
0.7769	Intermediate Similarity	NPC45794
0.776	Intermediate Similarity	NPC85511
0.7752	Intermediate Similarity	NPC109778
0.775	Intermediate Similarity	NPC226093
0.7731	Intermediate Similarity	NPC172525
0.7727	Intermediate Similarity	NPC472374
0.7727	Intermediate Similarity	NPC472372
0.7727	Intermediate Similarity	NPC61944
0.7727	Intermediate Similarity	NPC27407
0.7719	Intermediate Similarity	NPC171831
0.7719	Intermediate Similarity	NPC242913
0.7719	Intermediate Similarity	NPC280616
0.7717	Intermediate Similarity	NPC473220
0.7717	Intermediate Similarity	NPC204579
0.7717	Intermediate Similarity	NPC253681
0.7717	Intermediate Similarity	NPC470753
0.7712	Intermediate Similarity	NPC212415
0.771	Intermediate Similarity	NPC48929
0.7692	Intermediate Similarity	NPC473777
0.768	Intermediate Similarity	NPC69403
0.768	Intermediate Similarity	NPC46634
0.768	Intermediate Similarity	NPC291189
0.7674	Intermediate Similarity	NPC27712
0.7672	Intermediate Similarity	NPC249811
0.7672	Intermediate Similarity	NPC470391
0.7667	Intermediate Similarity	NPC221275
0.7664	Intermediate Similarity	NPC173443
0.7661	Intermediate Similarity	NPC50872
0.7661	Intermediate Similarity	NPC472981
0.7661	Intermediate Similarity	NPC144547
0.7658	Intermediate Similarity	NPC270654
0.7656	Intermediate Similarity	NPC121104
0.7642	Intermediate Similarity	NPC61779
0.7636	Intermediate Similarity	NPC172925
0.7634	Intermediate Similarity	NPC302844
0.7632	Intermediate Similarity	NPC329556
0.7632	Intermediate Similarity	NPC160382
0.7619	Intermediate Similarity	NPC471466
0.7615	Intermediate Similarity	NPC86774
0.7615	Intermediate Similarity	NPC327457
0.7612	Intermediate Similarity	NPC261292
0.7612	Intermediate Similarity	NPC301915
0.7611	Intermediate Similarity	NPC469481
0.7607	Intermediate Similarity	NPC474364
0.76	Intermediate Similarity	NPC269923
0.76	Intermediate Similarity	NPC167323
0.7597	Intermediate Similarity	NPC2596
0.7597	Intermediate Similarity	NPC2401
0.7597	Intermediate Similarity	NPC301857
0.7591	Intermediate Similarity	NPC471733
0.7589	Intermediate Similarity	NPC160548
0.7589	Intermediate Similarity	NPC210529
0.7589	Intermediate Similarity	NPC175852
0.7586	Intermediate Similarity	NPC37115
0.7586	Intermediate Similarity	NPC475203
0.7586	Intermediate Similarity	NPC472315
0.7586	Intermediate Similarity	NPC136962
0.7586	Intermediate Similarity	NPC472316
0.7586	Intermediate Similarity	NPC474376
0.7581	Intermediate Similarity	NPC289432
0.7581	Intermediate Similarity	NPC473243
0.7581	Intermediate Similarity	NPC233282
0.7581	Intermediate Similarity	NPC988
0.7578	Intermediate Similarity	NPC114096
0.7576	Intermediate Similarity	NPC136608
0.7576	Intermediate Similarity	NPC38420
0.7576	Intermediate Similarity	NPC310662
0.7576	Intermediate Similarity	NPC126516
0.7561	Intermediate Similarity	NPC94637
0.7559	Intermediate Similarity	NPC221798
0.7557	Intermediate Similarity	NPC233692
0.7556	Intermediate Similarity	NPC197666
0.7556	Intermediate Similarity	NPC126739
0.7547	Intermediate Similarity	NPC318107

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 NPC306740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	890
0.2-0.3	1300
0.3-0.4	2641
0.4-0.5	2408
0.5-0.6	1227
0.6-0.7	415
0.7-0.8	44
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD1238	Approved
0.8246	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD2182	Approved
0.8198	Intermediate Similarity	NPD164	Approved
0.807	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9545	Approved
0.7966	Intermediate Similarity	NPD5951	Approved
0.7953	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD9258	Approved
0.7925	Intermediate Similarity	NPD9256	Approved
0.7876	Intermediate Similarity	NPD1237	Approved
0.7857	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7008	Discontinued
0.7712	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1930	Approved
0.7632	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1929	Approved
0.7615	Intermediate Similarity	NPD3764	Approved
0.7589	Intermediate Similarity	NPD9495	Approved
0.7581	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD9259	Approved
0.7547	Intermediate Similarity	NPD9257	Approved
0.7545	Intermediate Similarity	NPD1202	Approved
0.7521	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD9493	Approved
0.7377	Intermediate Similarity	NPD2629	Approved
0.7343	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4628	Phase 3
0.7265	Intermediate Similarity	NPD5909	Discontinued
0.7264	Intermediate Similarity	NPD9491	Approved
0.7227	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD2066	Phase 3
0.7209	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1239	Approved
0.719	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6647	Phase 2
0.7174	Intermediate Similarity	NPD2346	Discontinued
0.7154	Intermediate Similarity	NPD6010	Discontinued
0.7154	Intermediate Similarity	NPD1283	Approved
0.7132	Intermediate Similarity	NPD1608	Approved
0.7117	Intermediate Similarity	NPD1089	Approved
0.7117	Intermediate Similarity	NPD1090	Approved
0.7117	Intermediate Similarity	NPD1086	Approved
0.7105	Intermediate Similarity	NPD1989	Approved
0.7103	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1932	Approved
0.709	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD5048	Discontinued
0.7054	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6287	Discontinued
0.705	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7236	Approved
0.7027	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD800	Approved
0.7021	Intermediate Similarity	NPD3750	Approved
0.7021	Intermediate Similarity	NPD7003	Approved
0.7018	Intermediate Similarity	NPD9260	Approved
0.7007	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9717	Approved
0.6992	Remote Similarity	NPD9508	Approved
0.6991	Remote Similarity	NPD1088	Approved
0.6986	Remote Similarity	NPD3226	Approved
0.697	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD1164	Approved
0.6942	Remote Similarity	NPD9264	Approved
0.6942	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD9267	Approved
0.6935	Remote Similarity	NPD5277	Phase 2
0.6934	Remote Similarity	NPD230	Phase 1
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD1281	Approved
0.6917	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6085	Phase 2
0.6916	Remote Similarity	NPD226	Approved
0.6906	Remote Similarity	NPD2799	Discontinued
0.6899	Remote Similarity	NPD5125	Phase 3
0.6899	Remote Similarity	NPD5305	Approved
0.6899	Remote Similarity	NPD5126	Approved
0.6899	Remote Similarity	NPD5306	Approved
0.6899	Remote Similarity	NPD17	Approved
0.6897	Remote Similarity	NPD6273	Approved
0.6897	Remote Similarity	NPD1564	Approved
0.6897	Remote Similarity	NPD1566	Phase 3
0.6897	Remote Similarity	NPD1565	Approved
0.6892	Remote Similarity	NPD7411	Suspended
0.6887	Remote Similarity	NPD9490	Approved
0.6885	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD9266	Approved
0.688	Remote Similarity	NPD1241	Discontinued
0.6879	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD689	Discontinued
0.6875	Remote Similarity	NPD1894	Discontinued
0.687	Remote Similarity	NPD6637	Approved
0.687	Remote Similarity	NPD1693	Approved
0.687	Remote Similarity	NPD4878	Approved
0.6861	Remote Similarity	NPD3373	Approved
0.6861	Remote Similarity	NPD1240	Approved
0.6857	Remote Similarity	NPD1551	Phase 2
0.6857	Remote Similarity	NPD2935	Discontinued
0.685	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1087	Approved
0.6846	Remote Similarity	NPD4106	Approved
0.6846	Remote Similarity	NPD4135	Approved
0.6846	Remote Similarity	NPD4136	Approved
0.6842	Remote Similarity	NPD1470	Approved
0.6842	Remote Similarity	NPD2797	Approved
0.6829	Remote Similarity	NPD2067	Discontinued
0.6828	Remote Similarity	NPD2533	Approved
0.6828	Remote Similarity	NPD2534	Approved
0.6828	Remote Similarity	NPD2532	Approved
0.6822	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5157	Phase 1
0.6818	Remote Similarity	NPD5159	Phase 2
0.6814	Remote Similarity	NPD3673	Approved
0.6814	Remote Similarity	NPD3672	Approved
0.6809	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7239	Suspended
0.6794	Remote Similarity	NPD4807	Approved
0.6794	Remote Similarity	NPD4806	Approved
0.6786	Remote Similarity	NPD3748	Approved
0.6786	Remote Similarity	NPD1510	Phase 2
0.6783	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4198	Discontinued
0.6769	Remote Similarity	NPD4626	Approved
0.6767	Remote Similarity	NPD2198	Approved
0.6767	Remote Similarity	NPD2199	Approved
0.6767	Remote Similarity	NPD1876	Approved
0.6763	Remote Similarity	NPD1607	Approved
0.6748	Remote Similarity	NPD2329	Discontinued
0.6744	Remote Similarity	NPD7741	Discontinued
0.6742	Remote Similarity	NPD3972	Approved
0.6739	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5405	Approved
0.6738	Remote Similarity	NPD4477	Approved
0.6738	Remote Similarity	NPD4476	Approved
0.6738	Remote Similarity	NPD5406	Approved
0.6738	Remote Similarity	NPD5408	Approved
0.6738	Remote Similarity	NPD5404	Approved
0.6715	Remote Similarity	NPD3268	Approved
0.6711	Remote Similarity	NPD4380	Phase 2
0.6709	Remote Similarity	NPD5844	Phase 1
0.6698	Remote Similarity	NPD9294	Approved
0.6696	Remote Similarity	NPD650	Approved
0.6696	Remote Similarity	NPD4793	Discontinued
0.6692	Remote Similarity	NPD5691	Approved
0.6692	Remote Similarity	NPD4105	Approved
0.6692	Remote Similarity	NPD4102	Approved
0.6691	Remote Similarity	NPD6832	Phase 2
0.669	Remote Similarity	NPD6002	Phase 3
0.669	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6005	Phase 3
0.669	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6004	Phase 3
0.6689	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD4980	Approved
0.6644	Remote Similarity	NPD7458	Discontinued
0.6642	Remote Similarity	NPD5667	Approved
0.6642	Remote Similarity	NPD6966	Discovery
0.6642	Remote Similarity	NPD3225	Approved
0.6641	Remote Similarity	NPD1778	Approved
0.6641	Remote Similarity	NPD2345	Approved
0.6638	Remote Similarity	NPD1563	Approved
0.6636	Remote Similarity	NPD225	Approved
0.6636	Remote Similarity	NPD227	Approved
0.6636	Remote Similarity	NPD3971	Phase 1
0.6623	Remote Similarity	NPD6801	Discontinued
0.6619	Remote Similarity	NPD2979	Phase 3
0.6617	Remote Similarity	NPD1481	Phase 2
0.6612	Remote Similarity	NPD9261	Approved
0.6612	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7609	Phase 3
0.6601	Remote Similarity	NPD7768	Phase 2
0.6599	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2567	Approved
0.6596	Remote Similarity	NPD2569	Approved
0.6594	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD553	Approved
0.6593	Remote Similarity	NPD2625	Approved
0.6593	Remote Similarity	NPD2160	Approved
0.6593	Remote Similarity	NPD2159	Approved
0.6593	Remote Similarity	NPD9567	Approved
0.6593	Remote Similarity	NPD2626	Approved
0.6593	Remote Similarity	NPD552	Approved
0.6593	Remote Similarity	NPD2628	Approved
0.6593	Remote Similarity	NPD2627	Approved
0.6591	Remote Similarity	NPD7457	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