NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.05
Volume:	177.592
LogP:	1.728
LogD:	1.683
LogS:	-2.342
# Rotatable Bonds:	1
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	1.81
Fsp3:	0.1
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:	-4.635
MDCK Permeability:	2.523336479498539e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.462
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.461
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	75.84584045410156%
Volume Distribution (VD):	0.759
Pgp-substrate:	22.299415588378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.634
CYP2C19-substrate:	0.4
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.545
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	11.053
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.358
Rat Oral Acute Toxicity:	0.509
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.203
Carcinogencity:	0.907
Eye Corrosion:	0.556
Eye Irritation:	0.989
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC128633

Natural Product ID:	NPC128633
*Common Name:**	5-Methoxychromen-2-One
IUPAC Name:	5-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	XYFXTIBDEAZMAH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O3/c1-12-8-3-2-4-9-7(8)5-6-10(11)13-9/h2-6H,1H3
SMILES:	COc1cccc2c1ccc(=O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502746
PubChem CID:	10899191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	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
Others	7

Activity Type	# Activity
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1897	Organism	Oryzias latipes	Oryzias latipes	LC50	=	38.0	ppm	PMID[492563]
NPT1897	Organism	Oryzias latipes	Oryzias latipes	LC100	=	50.0	ppm	PMID[492563]
NPT2	Others	Unspecified		Selectivity Index	=	1.5	n.a.	PMID[492563]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	30.0	ppm	PMID[492563]
NPT176	Organism	Artemia salina	Artemia salina	LC100	=	20.0	ppm	PMID[492563]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	MED	=	20.0	ug	PMID[492563]
NPT2	Others	Unspecified		Selectivity Index	=	1.9	n.a.	PMID[492563]

☑ 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 NPC128633 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	489
0.1-0.2	2412
0.2-0.3	5878
0.3-0.4	11803
0.4-0.5	5283
0.5-0.6	5577
0.6-0.7	5705
0.7-0.8	4275
0.8-0.85	946
0.85-0.9	253
0.9-0.95	66
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC265547
0.973	High Similarity	NPC298796
0.973	High Similarity	NPC281356
0.964	High Similarity	NPC96705
0.964	High Similarity	NPC152306
0.9558	High Similarity	NPC180006
0.9558	High Similarity	NPC235190
0.9558	High Similarity	NPC163200
0.9391	High Similarity	NPC96286
0.9391	High Similarity	NPC248429
0.931	High Similarity	NPC472518
0.931	High Similarity	NPC109675
0.931	High Similarity	NPC273772
0.9304	High Similarity	NPC144418
0.9231	High Similarity	NPC73413
0.9231	High Similarity	NPC27671
0.9231	High Similarity	NPC201667
0.9224	High Similarity	NPC257188
0.9224	High Similarity	NPC13007
0.9174	High Similarity	NPC149545
0.9145	High Similarity	NPC154176
0.9145	High Similarity	NPC315807
0.9145	High Similarity	NPC290605
0.9145	High Similarity	NPC173350
0.9138	High Similarity	NPC52247
0.913	High Similarity	NPC247553
0.9076	High Similarity	NPC234109
0.9076	High Similarity	NPC188327
0.9068	High Similarity	NPC111347
0.9052	High Similarity	NPC319378
0.9052	High Similarity	NPC302107
0.9	High Similarity	NPC258567
0.9	High Similarity	NPC121740
0.9	High Similarity	NPC224774
0.8992	High Similarity	NPC471828
0.8992	High Similarity	NPC93219
0.8992	High Similarity	NPC471827
0.8992	High Similarity	NPC244495
0.8981	High Similarity	NPC139891
0.8974	High Similarity	NPC187868
0.8926	High Similarity	NPC469453
0.8926	High Similarity	NPC472519
0.8926	High Similarity	NPC199204
0.8926	High Similarity	NPC185066
0.8919	High Similarity	NPC106141
0.8917	High Similarity	NPC471826
0.8908	High Similarity	NPC291899
0.8852	High Similarity	NPC168710
0.8843	High Similarity	NPC243688
0.8824	High Similarity	NPC50720
0.878	High Similarity	NPC113098
0.878	High Similarity	NPC19242
0.878	High Similarity	NPC240722
0.878	High Similarity	NPC80170
0.878	High Similarity	NPC244799
0.8772	High Similarity	NPC87563
0.877	High Similarity	NPC157212
0.876	High Similarity	NPC101894
0.875	High Similarity	NPC141068
0.8739	High Similarity	NPC150214
0.871	High Similarity	NPC272650
0.871	High Similarity	NPC267336
0.871	High Similarity	NPC29734
0.8699	High Similarity	NPC27239
0.8699	High Similarity	NPC123127
0.8699	High Similarity	NPC474289
0.8678	High Similarity	NPC168259
0.864	High Similarity	NPC194277
0.864	High Similarity	NPC137669
0.864	High Similarity	NPC175159
0.864	High Similarity	NPC14248
0.864	High Similarity	NPC19157
0.8621	High Similarity	NPC33717
0.8571	High Similarity	NPC291837
0.8571	High Similarity	NPC31849
0.8571	High Similarity	NPC296624
0.8571	High Similarity	NPC7526
0.8571	High Similarity	NPC471910
0.8571	High Similarity	NPC207002
0.8571	High Similarity	NPC472524
0.8571	High Similarity	NPC55147
0.8571	High Similarity	NPC167111
0.8571	High Similarity	NPC133956
0.8571	High Similarity	NPC241341
0.8571	High Similarity	NPC233018
0.8571	High Similarity	NPC2363
0.8571	High Similarity	NPC36437
0.8571	High Similarity	NPC222036
0.8571	High Similarity	NPC469449
0.8571	High Similarity	NPC318400
0.8571	High Similarity	NPC163557
0.856	High Similarity	NPC472517
0.8547	High Similarity	NPC471498
0.8547	High Similarity	NPC471503
0.8525	High Similarity	NPC232692
0.8525	High Similarity	NPC202594
0.8512	High Similarity	NPC143725
0.8504	High Similarity	NPC166672
0.8504	High Similarity	NPC253574
0.8504	High Similarity	NPC62366
0.8504	High Similarity	NPC198381
0.8504	High Similarity	NPC260265
0.8504	High Similarity	NPC47163
0.8504	High Similarity	NPC127888
0.8504	High Similarity	NPC326600
0.8504	High Similarity	NPC319859
0.8504	High Similarity	NPC307412
0.8504	High Similarity	NPC204353
0.8504	High Similarity	NPC74655
0.8504	High Similarity	NPC55149
0.8504	High Similarity	NPC195343
0.8504	High Similarity	NPC267412
0.8504	High Similarity	NPC287182
0.8504	High Similarity	NPC84894
0.8504	High Similarity	NPC98179
0.8504	High Similarity	NPC92830
0.8504	High Similarity	NPC50896
0.8504	High Similarity	NPC100986
0.8504	High Similarity	NPC309953
0.8504	High Similarity	NPC164269
0.8504	High Similarity	NPC18804
0.8492	Intermediate Similarity	NPC123954
0.8487	Intermediate Similarity	NPC31314
0.8487	Intermediate Similarity	NPC193193
0.8487	Intermediate Similarity	NPC473290
0.8487	Intermediate Similarity	NPC471504
0.848	Intermediate Similarity	NPC32463
0.8468	Intermediate Similarity	NPC128730
0.8468	Intermediate Similarity	NPC227255
0.8438	Intermediate Similarity	NPC33986
0.8438	Intermediate Similarity	NPC471625
0.8438	Intermediate Similarity	NPC469675
0.8438	Intermediate Similarity	NPC472424
0.8438	Intermediate Similarity	NPC281241
0.8438	Intermediate Similarity	NPC471909
0.8438	Intermediate Similarity	NPC66705
0.8438	Intermediate Similarity	NPC86892
0.8435	Intermediate Similarity	NPC266116
0.8425	Intermediate Similarity	NPC54503
0.8421	Intermediate Similarity	NPC231251
0.8421	Intermediate Similarity	NPC88868
0.8421	Intermediate Similarity	NPC25067
0.8393	Intermediate Similarity	NPC176971
0.8387	Intermediate Similarity	NPC289316
0.8387	Intermediate Similarity	NPC194841
0.8378	Intermediate Similarity	NPC109637
0.8372	Intermediate Similarity	NPC471630
0.8372	Intermediate Similarity	NPC177281
0.8372	Intermediate Similarity	NPC78746
0.8372	Intermediate Similarity	NPC38099
0.8372	Intermediate Similarity	NPC476455
0.8372	Intermediate Similarity	NPC128529
0.8372	Intermediate Similarity	NPC224543
0.8372	Intermediate Similarity	NPC283331
0.8372	Intermediate Similarity	NPC188380
0.8372	Intermediate Similarity	NPC149320
0.8372	Intermediate Similarity	NPC160727
0.8372	Intermediate Similarity	NPC55615
0.8372	Intermediate Similarity	NPC167517
0.8372	Intermediate Similarity	NPC283019
0.8372	Intermediate Similarity	NPC26954
0.8359	Intermediate Similarity	NPC224475
0.8359	Intermediate Similarity	NPC180716
0.8359	Intermediate Similarity	NPC213173
0.8346	Intermediate Similarity	NPC319969
0.8346	Intermediate Similarity	NPC469956
0.8346	Intermediate Similarity	NPC281558
0.8333	Intermediate Similarity	NPC474874
0.8333	Intermediate Similarity	NPC230951
0.832	Intermediate Similarity	NPC139595
0.832	Intermediate Similarity	NPC474616
0.832	Intermediate Similarity	NPC474651
0.832	Intermediate Similarity	NPC60704
0.832	Intermediate Similarity	NPC474623
0.832	Intermediate Similarity	NPC293642
0.8319	Intermediate Similarity	NPC157473
0.8319	Intermediate Similarity	NPC151530
0.8308	Intermediate Similarity	NPC472516
0.8308	Intermediate Similarity	NPC20511
0.8308	Intermediate Similarity	NPC294456
0.8308	Intermediate Similarity	NPC232246
0.8308	Intermediate Similarity	NPC471068
0.8308	Intermediate Similarity	NPC212124
0.8308	Intermediate Similarity	NPC184861
0.8308	Intermediate Similarity	NPC139548
0.8308	Intermediate Similarity	NPC148835
0.8308	Intermediate Similarity	NPC306365
0.8308	Intermediate Similarity	NPC281014
0.8308	Intermediate Similarity	NPC155963
0.8308	Intermediate Similarity	NPC131198
0.8308	Intermediate Similarity	NPC95162
0.8308	Intermediate Similarity	NPC76336
0.8308	Intermediate Similarity	NPC20796
0.8308	Intermediate Similarity	NPC14697
0.8308	Intermediate Similarity	NPC153818
0.8308	Intermediate Similarity	NPC471069
0.8308	Intermediate Similarity	NPC225106
0.8308	Intermediate Similarity	NPC52086
0.8306	Intermediate Similarity	NPC163248
0.8306	Intermediate Similarity	NPC127604

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 NPC128633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	990
0.2-0.3	1767
0.3-0.4	2794
0.4-0.5	1806
0.5-0.6	925
0.6-0.7	286
0.7-0.8	91
0.8-0.85	22
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9138	High Similarity	NPD422	Phase 1
0.8981	High Similarity	NPD9697	Approved
0.8618	High Similarity	NPD1008	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1296	Phase 2
0.8167	Intermediate Similarity	NPD1548	Phase 1
0.8145	Intermediate Similarity	NPD3225	Approved
0.807	Intermediate Similarity	NPD3134	Approved
0.8047	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD1358	Approved
0.8	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1652	Phase 2
0.7984	Intermediate Similarity	NPD9717	Approved
0.7955	Intermediate Similarity	NPD3748	Approved
0.7937	Intermediate Similarity	NPD3267	Approved
0.7937	Intermediate Similarity	NPD2797	Approved
0.7937	Intermediate Similarity	NPD3266	Approved
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7891	Intermediate Similarity	NPD6832	Phase 2
0.7874	Intermediate Similarity	NPD1019	Discontinued
0.7852	Intermediate Similarity	NPD1243	Approved
0.7815	Intermediate Similarity	NPD5535	Approved
0.7795	Intermediate Similarity	NPD1203	Approved
0.7761	Intermediate Similarity	NPD2796	Approved
0.776	Intermediate Similarity	NPD1610	Phase 2
0.775	Intermediate Similarity	NPD1241	Discontinued
0.7742	Intermediate Similarity	NPD1778	Approved
0.7692	Intermediate Similarity	NPD290	Approved
0.7681	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3496	Discontinued
0.7664	Intermediate Similarity	NPD3750	Approved
0.7652	Intermediate Similarity	NPD4307	Phase 2
0.7634	Intermediate Similarity	NPD3268	Approved
0.7626	Intermediate Similarity	NPD6799	Approved
0.76	Intermediate Similarity	NPD17	Approved
0.7594	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD920	Approved
0.7571	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5401	Approved
0.7536	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1653	Approved
0.752	Intermediate Similarity	NPD5691	Approved
0.7519	Intermediate Similarity	NPD1240	Approved
0.7518	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4749	Approved
0.7481	Intermediate Similarity	NPD4908	Phase 1
0.748	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD1611	Approved
0.7465	Intermediate Similarity	NPD5403	Approved
0.7463	Intermediate Similarity	NPD1933	Approved
0.7426	Intermediate Similarity	NPD4308	Phase 3
0.7422	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD9493	Approved
0.7407	Intermediate Similarity	NPD1607	Approved
0.7391	Intermediate Similarity	NPD1549	Phase 2
0.7381	Intermediate Similarity	NPD5585	Approved
0.7368	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD411	Approved
0.7344	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD447	Suspended
0.7323	Intermediate Similarity	NPD4626	Approved
0.7319	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD968	Approved
0.731	Intermediate Similarity	NPD6599	Discontinued
0.7302	Intermediate Similarity	NPD9545	Approved
0.7299	Intermediate Similarity	NPD1510	Phase 2
0.7299	Intermediate Similarity	NPD7033	Discontinued
0.7293	Intermediate Similarity	NPD4625	Phase 3
0.726	Intermediate Similarity	NPD7411	Suspended
0.7254	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6801	Discontinued
0.7206	Intermediate Similarity	NPD4340	Discontinued
0.7203	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD919	Approved
0.719	Intermediate Similarity	NPD2684	Approved
0.7182	Intermediate Similarity	NPD1282	Approved
0.7165	Intermediate Similarity	NPD1894	Discontinued
0.7162	Intermediate Similarity	NPD7819	Suspended
0.7162	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7132	Intermediate Similarity	NPD1613	Approved
0.7132	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD846	Approved
0.7119	Intermediate Similarity	NPD940	Approved
0.7114	Intermediate Similarity	NPD5402	Approved
0.7114	Intermediate Similarity	NPD3817	Phase 2
0.7111	Intermediate Similarity	NPD1048	Approved
0.7111	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD2200	Suspended
0.7099	Intermediate Similarity	NPD4359	Approved
0.7083	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7768	Phase 2
0.7063	Intermediate Similarity	NPD2557	Approved
0.7063	Intermediate Similarity	NPD6671	Approved
0.7059	Intermediate Similarity	NPD9261	Approved
0.7034	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD7075	Discontinued
0.7015	Intermediate Similarity	NPD2237	Approved
0.7014	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6985	Remote Similarity	NPD6798	Discontinued
0.697	Remote Similarity	NPD2982	Phase 2
0.697	Remote Similarity	NPD2983	Phase 2
0.696	Remote Similarity	NPD821	Approved
0.696	Remote Similarity	NPD7843	Approved
0.6957	Remote Similarity	NPD9694	Discovery
0.6957	Remote Similarity	NPD230	Phase 1
0.6953	Remote Similarity	NPD5536	Phase 2
0.6947	Remote Similarity	NPD1535	Discovery
0.694	Remote Similarity	NPD2798	Approved
0.6929	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD4628	Phase 3
0.6918	Remote Similarity	NPD1512	Approved
0.6913	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3749	Approved
0.6905	Remote Similarity	NPD594	Approved
0.6905	Remote Similarity	NPD592	Approved
0.6894	Remote Similarity	NPD1481	Phase 2
0.6884	Remote Similarity	NPD4060	Phase 1
0.688	Remote Similarity	NPD1137	Approved
0.688	Remote Similarity	NPD1139	Approved
0.6879	Remote Similarity	NPD2935	Discontinued
0.6871	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3847	Discontinued
0.6859	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5451	Approved
0.6846	Remote Similarity	NPD3049	Approved
0.6846	Remote Similarity	NPD3443	Approved
0.6846	Remote Similarity	NPD3445	Approved
0.6846	Remote Similarity	NPD3444	Approved
0.6842	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4622	Approved
0.6835	Remote Similarity	NPD4618	Approved
0.6835	Remote Similarity	NPD6355	Discontinued
0.6831	Remote Similarity	NPD5762	Approved
0.6831	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6004	Phase 3
0.6831	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6005	Phase 3
0.6831	Remote Similarity	NPD6002	Phase 3
0.6831	Remote Similarity	NPD5763	Approved
0.6829	Remote Similarity	NPD9264	Approved
0.6829	Remote Similarity	NPD9263	Approved
0.6829	Remote Similarity	NPD9267	Approved
0.6828	Remote Similarity	NPD6666	Approved
0.6828	Remote Similarity	NPD6667	Approved
0.6828	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1138	Approved
0.6822	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7644	Approved
0.6821	Remote Similarity	NPD2801	Approved
0.6818	Remote Similarity	NPD1281	Approved
0.6812	Remote Similarity	NPD6233	Phase 2
0.6807	Remote Similarity	NPD1238	Approved
0.6806	Remote Similarity	NPD7466	Approved
0.6797	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6971	Discontinued
0.6797	Remote Similarity	NPD709	Approved
0.6797	Remote Similarity	NPD7157	Approved
0.6794	Remote Similarity	NPD2554	Approved
0.6794	Remote Similarity	NPD2556	Approved
0.6791	Remote Similarity	NPD8651	Approved
0.6788	Remote Similarity	NPD5163	Phase 2
0.6788	Remote Similarity	NPD3027	Phase 3
0.6786	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD9365	Approved
0.6781	Remote Similarity	NPD7213	Phase 3
0.6781	Remote Similarity	NPD7212	Phase 2
0.6779	Remote Similarity	NPD3226	Approved
0.6774	Remote Similarity	NPD9266	Approved
0.6774	Remote Similarity	NPD74	Approved
0.6769	Remote Similarity	NPD2486	Discontinued
0.6767	Remote Similarity	NPD3972	Approved
0.6765	Remote Similarity	NPD2861	Phase 2
0.6763	Remote Similarity	NPD4140	Approved
0.6755	Remote Similarity	NPD1934	Approved
0.6752	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1242	Phase 1
0.6744	Remote Similarity	NPD3596	Phase 2
0.6741	Remote Similarity	NPD987	Approved
0.6741	Remote Similarity	NPD6362	Approved
0.6739	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5688	Approved
0.6738	Remote Similarity	NPD5689	Approved
0.6736	Remote Similarity	NPD2654	Approved
0.6735	Remote Similarity	NPD7447	Phase 1
0.6735	Remote Similarity	NPD7004	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