NPASS Compound

Structure

NPC66643 OpenBabel07101718182D 23 25 0 0 0 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.05
Volume:	320.859
LogP:	4.033
LogD:	3.549
LogS:	-5.993
# Rotatable Bonds:	4
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	2.038
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	2.891127223847434e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	99.20509338378906%
Volume Distribution (VD):	0.767
Pgp-substrate:	0.7566641569137573%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.911
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.39
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	1.963
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.421
Human Hepatotoxicity (H-HT):	0.667
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.425
Carcinogencity:	0.368
Eye Corrosion:	0.004
Eye Irritation:	0.789
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC66643

Natural Product ID:	NPC66643
*Common Name:**	Ethyl 6-Chloro-2-Oxo-4-Phenylchromene-3-Carboxylate
IUPAC Name:	ethyl 6-chloro-2-oxo-4-phenylchromene-3-carboxylate
Synonyms:
Standard InCHIKey:	IEILXEYYPYUMKW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13ClO4/c1-2-22-17(20)16-15(11-6-4-3-5-7-11)13-10-12(19)8-9-14(13)23-18(16)21/h3-10H,2H2,1H3
SMILES:	CCOC(=O)c1c(c2ccccc2)c2cc(ccc2oc1=O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431776
PubChem CID:	10245979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO10108	Fomitopsis officinalis	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24087924]
NPO10108	Fomitopsis officinalis	Species	Fomitopsidaceae	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	1
Others	9

Activity Type	# Activity
Cell Line	1
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	36.7	ug.mL-1	PMID[544729]
NPT1830	Organism	Mycobacterium marinum	Mycobacterium marinum	MIC90	=	97.1	ug.mL-1	PMID[544729]
NPT2	Others	Unspecified		Selectivity Index	=	0.82	n.a.	PMID[544729]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100.0	ug.mL-1	PMID[544729]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	49.5	ug.mL-1	PMID[544729]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	44.7	ug.mL-1	PMID[544729]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	46.6	ug.mL-1	PMID[544729]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	=	37.1	ug.mL-1	PMID[544729]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	=	44.7	ug.mL-1	PMID[544729]

☑ 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 NPC66643 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	503
0.1-0.2	2196
0.2-0.3	5869
0.3-0.4	12644
0.4-0.5	5614
0.5-0.6	6703
0.6-0.7	6229
0.7-0.8	2843
0.8-0.85	91
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC273984
0.92	High Similarity	NPC151237
0.8605	High Similarity	NPC27198
0.7985	Intermediate Similarity	NPC315807
0.7937	Intermediate Similarity	NPC149545
0.782	Intermediate Similarity	NPC193193
0.782	Intermediate Similarity	NPC31314
0.7744	Intermediate Similarity	NPC98748
0.7692	Intermediate Similarity	NPC66705
0.7676	Intermediate Similarity	NPC2363
0.7652	Intermediate Similarity	NPC33717
0.7643	Intermediate Similarity	NPC238309
0.763	Intermediate Similarity	NPC322569
0.7626	Intermediate Similarity	NPC161322
0.7619	Intermediate Similarity	NPC139891
0.7612	Intermediate Similarity	NPC43435
0.7589	Intermediate Similarity	NPC2989
0.7571	Intermediate Similarity	NPC472519
0.7556	Intermediate Similarity	NPC230951
0.7556	Intermediate Similarity	NPC474874
0.7551	Intermediate Similarity	NPC136095
0.7537	Intermediate Similarity	NPC96705
0.7536	Intermediate Similarity	NPC201667
0.7536	Intermediate Similarity	NPC229113
0.7536	Intermediate Similarity	NPC73413
0.7536	Intermediate Similarity	NPC89630
0.7535	Intermediate Similarity	NPC11173
0.7534	Intermediate Similarity	NPC86087
0.7519	Intermediate Similarity	NPC128633
0.75	Intermediate Similarity	NPC235190
0.75	Intermediate Similarity	NPC180006
0.75	Intermediate Similarity	NPC163200
0.75	Intermediate Similarity	NPC87563
0.7483	Intermediate Similarity	NPC469956
0.7483	Intermediate Similarity	NPC19157
0.7482	Intermediate Similarity	NPC168259
0.7481	Intermediate Similarity	NPC298796
0.7481	Intermediate Similarity	NPC54243
0.7481	Intermediate Similarity	NPC281356
0.7465	Intermediate Similarity	NPC32463
0.7464	Intermediate Similarity	NPC109675
0.7464	Intermediate Similarity	NPC472518
0.7464	Intermediate Similarity	NPC273772
0.7463	Intermediate Similarity	NPC45104
0.7462	Intermediate Similarity	NPC141068
0.7445	Intermediate Similarity	NPC314329
0.7431	Intermediate Similarity	NPC469955
0.7431	Intermediate Similarity	NPC469952
0.7429	Intermediate Similarity	NPC329272
0.7426	Intermediate Similarity	NPC168050
0.7422	Intermediate Similarity	NPC326801
0.7415	Intermediate Similarity	NPC103001
0.741	Intermediate Similarity	NPC27671
0.7407	Intermediate Similarity	NPC265547
0.7407	Intermediate Similarity	NPC32298
0.7407	Intermediate Similarity	NPC152306
0.7402	Intermediate Similarity	NPC109637
0.7402	Intermediate Similarity	NPC283546
0.7391	Intermediate Similarity	NPC248429
0.7391	Intermediate Similarity	NPC90577
0.7391	Intermediate Similarity	NPC96286
0.7383	Intermediate Similarity	NPC182475
0.7379	Intermediate Similarity	NPC287182
0.7379	Intermediate Similarity	NPC198381
0.7379	Intermediate Similarity	NPC267412
0.7379	Intermediate Similarity	NPC18804
0.7379	Intermediate Similarity	NPC127888
0.7379	Intermediate Similarity	NPC195343
0.7379	Intermediate Similarity	NPC260265
0.7379	Intermediate Similarity	NPC319859
0.7379	Intermediate Similarity	NPC74655
0.7379	Intermediate Similarity	NPC100986
0.7379	Intermediate Similarity	NPC166672
0.7379	Intermediate Similarity	NPC84894
0.7379	Intermediate Similarity	NPC164269
0.7379	Intermediate Similarity	NPC47163
0.7376	Intermediate Similarity	NPC264428
0.7376	Intermediate Similarity	NPC41721
0.7364	Intermediate Similarity	NPC151530
0.7364	Intermediate Similarity	NPC157473
0.7357	Intermediate Similarity	NPC2771
0.7357	Intermediate Similarity	NPC4164
0.7357	Intermediate Similarity	NPC471828
0.7357	Intermediate Similarity	NPC471827
0.7353	Intermediate Similarity	NPC201284
0.7353	Intermediate Similarity	NPC35744
0.7353	Intermediate Similarity	NPC264976
0.7344	Intermediate Similarity	NPC473855
0.7344	Intermediate Similarity	NPC128730
0.7343	Intermediate Similarity	NPC228184
0.7338	Intermediate Similarity	NPC154176
0.7338	Intermediate Similarity	NPC290605
0.7338	Intermediate Similarity	NPC173350
0.7333	Intermediate Similarity	NPC263754
0.7333	Intermediate Similarity	NPC183154
0.7333	Intermediate Similarity	NPC217423
0.7329	Intermediate Similarity	NPC281241
0.7329	Intermediate Similarity	NPC234865
0.7329	Intermediate Similarity	NPC471625
0.7329	Intermediate Similarity	NPC471909
0.7329	Intermediate Similarity	NPC472424
0.7329	Intermediate Similarity	NPC86892
0.7328	Intermediate Similarity	NPC473809
0.7328	Intermediate Similarity	NPC88868
0.7328	Intermediate Similarity	NPC231251
0.7328	Intermediate Similarity	NPC25067
0.7324	Intermediate Similarity	NPC199204
0.7324	Intermediate Similarity	NPC125887
0.7319	Intermediate Similarity	NPC144418
0.7319	Intermediate Similarity	NPC14287
0.7315	Intermediate Similarity	NPC472523
0.7313	Intermediate Similarity	NPC296526
0.731	Intermediate Similarity	NPC296624
0.731	Intermediate Similarity	NPC133956
0.731	Intermediate Similarity	NPC207002
0.731	Intermediate Similarity	NPC7526
0.731	Intermediate Similarity	NPC222036
0.731	Intermediate Similarity	NPC471910
0.731	Intermediate Similarity	NPC167111
0.731	Intermediate Similarity	NPC318400
0.7308	Intermediate Similarity	NPC291837
0.7305	Intermediate Similarity	NPC234109
0.7305	Intermediate Similarity	NPC471826
0.7305	Intermediate Similarity	NPC188327
0.7305	Intermediate Similarity	NPC101894
0.7297	Intermediate Similarity	NPC307883
0.7293	Intermediate Similarity	NPC90903
0.7292	Intermediate Similarity	NPC193334
0.7292	Intermediate Similarity	NPC250727
0.7287	Intermediate Similarity	NPC176971
0.7286	Intermediate Similarity	NPC111347
0.7286	Intermediate Similarity	NPC107846
0.7286	Intermediate Similarity	NPC291899
0.7284	Intermediate Similarity	NPC68850
0.7279	Intermediate Similarity	NPC476455
0.7279	Intermediate Similarity	NPC55615
0.7279	Intermediate Similarity	NPC283019
0.7279	Intermediate Similarity	NPC286843
0.7279	Intermediate Similarity	NPC128529
0.7279	Intermediate Similarity	NPC293424
0.7279	Intermediate Similarity	NPC149320
0.7279	Intermediate Similarity	NPC115861
0.7279	Intermediate Similarity	NPC160727
0.7279	Intermediate Similarity	NPC177281
0.7279	Intermediate Similarity	NPC471630
0.7273	Intermediate Similarity	NPC233238
0.7273	Intermediate Similarity	NPC168710
0.7266	Intermediate Similarity	NPC13007
0.7266	Intermediate Similarity	NPC257188
0.7266	Intermediate Similarity	NPC311219
0.726	Intermediate Similarity	NPC131950
0.726	Intermediate Similarity	NPC55149
0.726	Intermediate Similarity	NPC307412
0.7254	Intermediate Similarity	NPC258567
0.7254	Intermediate Similarity	NPC121740
0.7254	Intermediate Similarity	NPC224774
0.7254	Intermediate Similarity	NPC298884
0.7248	Intermediate Similarity	NPC71903
0.7244	Intermediate Similarity	NPC307425
0.7241	Intermediate Similarity	NPC175159
0.7241	Intermediate Similarity	NPC278556
0.7241	Intermediate Similarity	NPC14248
0.7234	Intermediate Similarity	NPC170749
0.7234	Intermediate Similarity	NPC88403
0.723	Intermediate Similarity	NPC306365
0.723	Intermediate Similarity	NPC131198
0.723	Intermediate Similarity	NPC254741
0.723	Intermediate Similarity	NPC474886
0.7226	Intermediate Similarity	NPC172253
0.7226	Intermediate Similarity	NPC59561
0.7222	Intermediate Similarity	NPC80170
0.7222	Intermediate Similarity	NPC30390
0.7222	Intermediate Similarity	NPC113098
0.7219	Intermediate Similarity	NPC119640
0.7219	Intermediate Similarity	NPC183646
0.7219	Intermediate Similarity	NPC24075
0.7218	Intermediate Similarity	NPC280760
0.7218	Intermediate Similarity	NPC266116
0.7214	Intermediate Similarity	NPC50720
0.7214	Intermediate Similarity	NPC320287
0.7214	Intermediate Similarity	NPC248786
0.7209	Intermediate Similarity	NPC227255
0.7205	Intermediate Similarity	NPC472157
0.7203	Intermediate Similarity	NPC293642
0.7203	Intermediate Similarity	NPC157212
0.7203	Intermediate Similarity	NPC219923
0.7203	Intermediate Similarity	NPC139595
0.7203	Intermediate Similarity	NPC60704
0.7203	Intermediate Similarity	NPC185066
0.7203	Intermediate Similarity	NPC469453
0.72	Intermediate Similarity	NPC183642
0.72	Intermediate Similarity	NPC473209
0.72	Intermediate Similarity	NPC170812
0.72	Intermediate Similarity	NPC310370
0.72	Intermediate Similarity	NPC155552
0.7194	Intermediate Similarity	NPC187868
0.7194	Intermediate Similarity	NPC52247
0.7192	Intermediate Similarity	NPC287533
0.7192	Intermediate Similarity	NPC31849
0.7192	Intermediate Similarity	NPC473655

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 NPC66643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	445
0.1-0.2	1046
0.2-0.3	1610
0.3-0.4	2809
0.4-0.5	1995
0.5-0.6	910
0.6-0.7	240
0.7-0.8	88
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8014	Intermediate Similarity	NPD1578	Phase 2
0.7899	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD3267	Approved
0.7868	Intermediate Similarity	NPD3266	Approved
0.7826	Intermediate Similarity	NPD6832	Phase 2
0.7752	Intermediate Similarity	NPD5535	Approved
0.7737	Intermediate Similarity	NPD2797	Approved
0.7632	Intermediate Similarity	NPD4972	Discontinued
0.7619	Intermediate Similarity	NPD9697	Approved
0.7589	Intermediate Similarity	NPD3268	Approved
0.7568	Intermediate Similarity	NPD3887	Approved
0.7552	Intermediate Similarity	NPD1184	Approved
0.7536	Intermediate Similarity	NPD3225	Approved
0.7534	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2353	Approved
0.75	Intermediate Similarity	NPD454	Approved
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7481	Intermediate Similarity	NPD769	Approved
0.7445	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7033	Discontinued
0.7385	Intermediate Similarity	NPD5451	Approved
0.7368	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4534	Discontinued
0.7357	Intermediate Similarity	NPD1203	Approved
0.7343	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD2354	Approved
0.7329	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD1019	Discontinued
0.7279	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9717	Approved
0.7248	Intermediate Similarity	NPD5958	Discontinued
0.7246	Intermediate Similarity	NPD3496	Discontinued
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7214	Intermediate Similarity	NPD4359	Approved
0.7211	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4536	Approved
0.7211	Intermediate Similarity	NPD4538	Approved
0.7194	Intermediate Similarity	NPD422	Phase 1
0.7194	Intermediate Similarity	NPD1611	Approved
0.7174	Intermediate Similarity	NPD6516	Phase 2
0.7174	Intermediate Similarity	NPD5846	Approved
0.7154	Intermediate Similarity	NPD3134	Approved
0.7114	Intermediate Similarity	NPD2796	Approved
0.7114	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5585	Approved
0.7101	Intermediate Similarity	NPD5691	Approved
0.7099	Intermediate Similarity	NPD1358	Approved
0.7083	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2378	Approved
0.7067	Intermediate Similarity	NPD2376	Approved
0.7067	Intermediate Similarity	NPD2377	Approved
0.7063	Intermediate Similarity	NPD2798	Approved
0.7047	Intermediate Similarity	NPD5588	Approved
0.7047	Intermediate Similarity	NPD2799	Discontinued
0.7047	Intermediate Similarity	NPD3748	Approved
0.7047	Intermediate Similarity	NPD5960	Phase 3
0.7037	Intermediate Similarity	NPD1241	Discontinued
0.7029	Intermediate Similarity	NPD1894	Discontinued
0.6986	Remote Similarity	NPD1296	Phase 2
0.6974	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6540	Phase 3
0.6972	Remote Similarity	NPD6543	Approved
0.6972	Remote Similarity	NPD6542	Approved
0.6972	Remote Similarity	NPD6539	Approved
0.6968	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD4622	Approved
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4618	Approved
0.6954	Remote Similarity	NPD2346	Discontinued
0.6948	Remote Similarity	NPD5058	Phase 3
0.6939	Remote Similarity	NPD6233	Phase 2
0.6934	Remote Similarity	NPD2557	Approved
0.6933	Remote Similarity	NPD3260	Discontinued
0.6929	Remote Similarity	NPD17	Approved
0.6928	Remote Similarity	NPD4535	Phase 3
0.6923	Remote Similarity	NPD6538	Approved
0.6923	Remote Similarity	NPD6541	Approved
0.6906	Remote Similarity	NPD1548	Phase 1
0.6903	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6799	Approved
0.6903	Remote Similarity	NPD7041	Phase 2
0.6892	Remote Similarity	NPD4060	Phase 1
0.6887	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD1551	Phase 2
0.6884	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD3847	Discontinued
0.6875	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD987	Approved
0.687	Remote Similarity	NPD9501	Approved
0.6867	Remote Similarity	NPD5689	Approved
0.6867	Remote Similarity	NPD5688	Approved
0.6861	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4340	Discontinued
0.6842	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9552	Approved
0.6842	Remote Similarity	NPD290	Approved
0.6835	Remote Similarity	NPD957	Approved
0.6832	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3750	Approved
0.6813	Remote Similarity	NPD4424	Discontinued
0.6813	Remote Similarity	NPD3274	Phase 2
0.6813	Remote Similarity	NPD5890	Approved
0.6813	Remote Similarity	NPD5889	Approved
0.6813	Remote Similarity	NPD7411	Suspended
0.6809	Remote Similarity	NPD1778	Approved
0.6809	Remote Similarity	NPD4626	Approved
0.6803	Remote Similarity	NPD7095	Approved
0.6797	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1549	Phase 2
0.6791	Remote Similarity	NPD2684	Approved
0.6783	Remote Similarity	NPD1608	Approved
0.6776	Remote Similarity	NPD6032	Approved
0.6772	Remote Similarity	NPD920	Approved
0.677	Remote Similarity	NPD6801	Discontinued
0.6767	Remote Similarity	NPD968	Approved
0.6757	Remote Similarity	NPD411	Approved
0.6755	Remote Similarity	NPD7097	Phase 1
0.6753	Remote Similarity	NPD1652	Phase 2
0.6753	Remote Similarity	NPD1243	Approved
0.6752	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6599	Discontinued
0.6738	Remote Similarity	NPD3444	Approved
0.6738	Remote Similarity	NPD3049	Approved
0.6738	Remote Similarity	NPD3445	Approved
0.6738	Remote Similarity	NPD3443	Approved
0.6735	Remote Similarity	NPD4908	Phase 1
0.6733	Remote Similarity	NPD447	Suspended
0.6732	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7819	Suspended
0.6715	Remote Similarity	NPD7843	Approved
0.6714	Remote Similarity	NPD5536	Phase 2
0.6713	Remote Similarity	NPD1610	Phase 2
0.6713	Remote Similarity	NPD1535	Discovery
0.6711	Remote Similarity	NPD4062	Phase 3
0.6711	Remote Similarity	NPD1510	Phase 2
0.6708	Remote Similarity	NPD958	Approved
0.6691	Remote Similarity	NPD191	Approved
0.6689	Remote Similarity	NPD5163	Phase 2
0.6688	Remote Similarity	NPD2897	Discontinued
0.6687	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3817	Phase 2
0.6687	Remote Similarity	NPD3226	Approved
0.6686	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2203	Discontinued
0.6667	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6581	Approved
0.6667	Remote Similarity	NPD6580	Approved
0.6667	Remote Similarity	NPD2237	Approved
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD2403	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6585	Discontinued
0.6644	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3596	Phase 2
0.6643	Remote Similarity	NPD9493	Approved
0.6624	Remote Similarity	NPD6815	Approved
0.6623	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2344	Approved
0.662	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7075	Discontinued
0.6603	Remote Similarity	NPD4628	Phase 3
0.6603	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8032	Phase 2
0.66	Remote Similarity	NPD4870	Approved
0.6597	Remote Similarity	NPD1281	Approved
0.6585	Remote Similarity	NPD5402	Approved
0.6584	Remote Similarity	NPD3769	Discontinued
0.6584	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1876	Approved
0.6573	Remote Similarity	NPD2556	Approved
0.6573	Remote Similarity	NPD2554	Approved
0.6571	Remote Similarity	NPD7157	Approved
0.6571	Remote Similarity	NPD6387	Discontinued
0.6571	Remote Similarity	NPD6671	Approved
0.6556	Remote Similarity	NPD1240	Approved
0.6556	Remote Similarity	NPD2979	Phase 3
0.6547	Remote Similarity	NPD5283	Phase 1
0.6541	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6362	Approved
0.6519	Remote Similarity	NPD6667	Approved
0.6519	Remote Similarity	NPD6666	Approved
0.6516	Remote Similarity	NPD5762	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