NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.03
Volume:	254.027
LogP:	4.19
LogD:	3.619
LogS:	-6.053
# Rotatable Bonds:	1
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	1.74
Fsp3:	0.0
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:	-4.699
MDCK Permeability:	1.2926578165206593e-05
Pgp-inhibitor:	0.657
Pgp-substrate:	0.342
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	99.5031967163086%
Volume Distribution (VD):	0.825
Pgp-substrate:	1.0442278385162354%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.603
CYP2C19-inhibitor:	0.873
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.395
CYP2D6-substrate:	0.622
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	6.414
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.262
Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.325
Skin Sensitization:	0.176
Carcinogencity:	0.658
Eye Corrosion:	0.026
Eye Irritation:	0.962
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC151237

Natural Product ID:	NPC151237
*Common Name:**	6-Chloro-4-Phenylchromen-2-One
IUPAC Name:	6-chloro-4-phenylchromen-2-one
Synonyms:
Standard InCHIKey:	SBBCYRBHXPXNBP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H9ClO2/c16-11-6-7-14-13(8-11)12(9-15(17)18-14)10-4-2-1-3-5-10/h1-9H
SMILES:	Clc1ccc2c(c1)c(cc(=O)o2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431775
PubChem CID:	46919141
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	7

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100.0	ug.mL-1	PMID[470792]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100.0	ug.mL-1	PMID[470792]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	>	100.0	ug.mL-1	PMID[470792]

☑ 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 NPC151237 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	820
0.1-0.2	2843
0.2-0.3	7684
0.3-0.4	11260
0.4-0.5	5422
0.5-0.6	8605
0.6-0.7	5583
0.7-0.8	466
0.8-0.85	9
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9328	High Similarity	NPC27198
0.92	High Similarity	NPC66643
0.8605	High Similarity	NPC273984
0.8276	Intermediate Similarity	NPC139891
0.8151	Intermediate Similarity	NPC149545
0.7934	Intermediate Similarity	NPC141068
0.7907	Intermediate Similarity	NPC315807
0.7823	Intermediate Similarity	NPC87563
0.7805	Intermediate Similarity	NPC266116
0.7786	Intermediate Similarity	NPC168259
0.7752	Intermediate Similarity	NPC14287
0.7724	Intermediate Similarity	NPC233238
0.7717	Intermediate Similarity	NPC96705
0.7712	Intermediate Similarity	NPC307425
0.771	Intermediate Similarity	NPC107846
0.7704	Intermediate Similarity	NPC11173
0.7698	Intermediate Similarity	NPC33717
0.7698	Intermediate Similarity	NPC128633
0.7669	Intermediate Similarity	NPC161322
0.7667	Intermediate Similarity	NPC475269
0.7661	Intermediate Similarity	NPC280760
0.7638	Intermediate Similarity	NPC183154
0.7638	Intermediate Similarity	NPC263754
0.7627	Intermediate Similarity	NPC107101
0.7603	Intermediate Similarity	NPC326801
0.7597	Intermediate Similarity	NPC474874
0.7583	Intermediate Similarity	NPC109637
0.7578	Intermediate Similarity	NPC32298
0.7578	Intermediate Similarity	NPC152306
0.7578	Intermediate Similarity	NPC265547
0.7576	Intermediate Similarity	NPC229113
0.7576	Intermediate Similarity	NPC89630
0.7576	Intermediate Similarity	NPC111347
0.7559	Intermediate Similarity	NPC163398
0.7557	Intermediate Similarity	NPC96286
0.7557	Intermediate Similarity	NPC248429
0.7557	Intermediate Similarity	NPC13007
0.7557	Intermediate Similarity	NPC257188
0.7521	Intermediate Similarity	NPC128730
0.7521	Intermediate Similarity	NPC227255
0.7521	Intermediate Similarity	NPC473855
0.7519	Intermediate Similarity	NPC98748
0.7519	Intermediate Similarity	NPC54243
0.7519	Intermediate Similarity	NPC35744
0.7519	Intermediate Similarity	NPC281356
0.7519	Intermediate Similarity	NPC264976
0.7519	Intermediate Similarity	NPC298796
0.75	Intermediate Similarity	NPC473809
0.75	Intermediate Similarity	NPC472518
0.75	Intermediate Similarity	NPC32463
0.75	Intermediate Similarity	NPC2989
0.7481	Intermediate Similarity	NPC52247
0.7464	Intermediate Similarity	NPC2363
0.7462	Intermediate Similarity	NPC193193
0.7462	Intermediate Similarity	NPC14177
0.7462	Intermediate Similarity	NPC31314
0.746	Intermediate Similarity	NPC90903
0.7459	Intermediate Similarity	NPC176971
0.7447	Intermediate Similarity	NPC86087
0.7444	Intermediate Similarity	NPC73413
0.7444	Intermediate Similarity	NPC291899
0.7444	Intermediate Similarity	NPC201667
0.7438	Intermediate Similarity	NPC283546
0.7419	Intermediate Similarity	NPC259554
0.7405	Intermediate Similarity	NPC163200
0.7405	Intermediate Similarity	NPC235190
0.7405	Intermediate Similarity	NPC322569
0.7405	Intermediate Similarity	NPC180006
0.7398	Intermediate Similarity	NPC157473
0.7398	Intermediate Similarity	NPC151530
0.7391	Intermediate Similarity	NPC19157
0.7388	Intermediate Similarity	NPC93219
0.7388	Intermediate Similarity	NPC88403
0.7388	Intermediate Similarity	NPC244495
0.7381	Intermediate Similarity	NPC199462
0.7377	Intermediate Similarity	NPC473393
0.7372	Intermediate Similarity	NPC30390
0.7368	Intermediate Similarity	NPC173350
0.7368	Intermediate Similarity	NPC109675
0.7368	Intermediate Similarity	NPC154176
0.7368	Intermediate Similarity	NPC273772
0.7368	Intermediate Similarity	NPC290605
0.7364	Intermediate Similarity	NPC45104
0.736	Intermediate Similarity	NPC25067
0.736	Intermediate Similarity	NPC231251
0.736	Intermediate Similarity	NPC88868
0.7355	Intermediate Similarity	NPC179686
0.7348	Intermediate Similarity	NPC314329
0.7348	Intermediate Similarity	NPC144418
0.7348	Intermediate Similarity	NPC187868
0.7344	Intermediate Similarity	NPC51345
0.7344	Intermediate Similarity	NPC296526
0.7339	Intermediate Similarity	NPC291837
0.7338	Intermediate Similarity	NPC472524
0.7333	Intermediate Similarity	NPC234109
0.7333	Intermediate Similarity	NPC471826
0.7333	Intermediate Similarity	NPC188327
0.7328	Intermediate Similarity	NPC247553
0.7328	Intermediate Similarity	NPC168050
0.7319	Intermediate Similarity	NPC193334
0.7313	Intermediate Similarity	NPC27671
0.7311	Intermediate Similarity	NPC95755
0.7299	Intermediate Similarity	NPC246991
0.7299	Intermediate Similarity	NPC238309
0.7293	Intermediate Similarity	NPC476332
0.7293	Intermediate Similarity	NPC473464
0.7292	Intermediate Similarity	NPC182475
0.7286	Intermediate Similarity	NPC131950
0.7286	Intermediate Similarity	NPC473054
0.7279	Intermediate Similarity	NPC243688
0.7273	Intermediate Similarity	NPC84325
0.7273	Intermediate Similarity	NPC319378
0.7273	Intermediate Similarity	NPC302107
0.7273	Intermediate Similarity	NPC307253
0.7266	Intermediate Similarity	NPC307289
0.7266	Intermediate Similarity	NPC469956
0.7259	Intermediate Similarity	NPC471828
0.7259	Intermediate Similarity	NPC471827
0.7252	Intermediate Similarity	NPC201284
0.7239	Intermediate Similarity	NPC93730
0.7239	Intermediate Similarity	NPC248786
0.7234	Intermediate Similarity	NPC234865
0.7226	Intermediate Similarity	NPC157212
0.7226	Intermediate Similarity	NPC199204
0.7226	Intermediate Similarity	NPC185066
0.7226	Intermediate Similarity	NPC472519
0.7214	Intermediate Similarity	NPC469955
0.7214	Intermediate Similarity	NPC469952
0.7206	Intermediate Similarity	NPC128321
0.7206	Intermediate Similarity	NPC8058
0.7197	Intermediate Similarity	NPC230951
0.7197	Intermediate Similarity	NPC246214
0.7194	Intermediate Similarity	NPC250727
0.7188	Intermediate Similarity	NPC303522
0.7185	Intermediate Similarity	NPC193805
0.7183	Intermediate Similarity	NPC115861
0.7183	Intermediate Similarity	NPC286843
0.7177	Intermediate Similarity	NPC326447
0.7176	Intermediate Similarity	NPC152159
0.7174	Intermediate Similarity	NPC168710
0.7164	Intermediate Similarity	NPC90577
0.7154	Intermediate Similarity	NPC2518
0.7154	Intermediate Similarity	NPC470860
0.7143	Intermediate Similarity	NPC281558
0.7143	Intermediate Similarity	NPC79543
0.7143	Intermediate Similarity	NPC76453
0.7143	Intermediate Similarity	NPC139335
0.7133	Intermediate Similarity	NPC474886
0.7133	Intermediate Similarity	NPC38874
0.7132	Intermediate Similarity	NPC2771
0.7132	Intermediate Similarity	NPC235250
0.7132	Intermediate Similarity	NPC165556
0.7131	Intermediate Similarity	NPC300166
0.7122	Intermediate Similarity	NPC80170
0.7121	Intermediate Similarity	NPC43435
0.7113	Intermediate Similarity	NPC66705
0.7111	Intermediate Similarity	NPC470887
0.7111	Intermediate Similarity	NPC50720
0.7111	Intermediate Similarity	NPC320287
0.7101	Intermediate Similarity	NPC81261
0.7101	Intermediate Similarity	NPC125887
0.7101	Intermediate Similarity	NPC176590
0.7099	Intermediate Similarity	NPC161768
0.7099	Intermediate Similarity	NPC471503
0.7099	Intermediate Similarity	NPC471498
0.7097	Intermediate Similarity	NPC288760
0.7097	Intermediate Similarity	NPC238115
0.7092	Intermediate Similarity	NPC471910
0.7092	Intermediate Similarity	NPC167111
0.7092	Intermediate Similarity	NPC133956
0.7092	Intermediate Similarity	NPC296624
0.7092	Intermediate Similarity	NPC207002
0.7092	Intermediate Similarity	NPC318400
0.7092	Intermediate Similarity	NPC287533
0.7083	Intermediate Similarity	NPC103001
0.708	Intermediate Similarity	NPC101894
0.708	Intermediate Similarity	NPC329272
0.7063	Intermediate Similarity	NPC206341
0.7059	Intermediate Similarity	NPC140521
0.7059	Intermediate Similarity	NPC470008
0.7045	Intermediate Similarity	NPC74821
0.7045	Intermediate Similarity	NPC293424
0.7042	Intermediate Similarity	NPC166672
0.7042	Intermediate Similarity	NPC198381
0.7042	Intermediate Similarity	NPC74655
0.7042	Intermediate Similarity	NPC195343
0.7042	Intermediate Similarity	NPC319859
0.7042	Intermediate Similarity	NPC100986
0.7042	Intermediate Similarity	NPC267412
0.7042	Intermediate Similarity	NPC127888
0.7042	Intermediate Similarity	NPC164269
0.7042	Intermediate Similarity	NPC47163
0.7042	Intermediate Similarity	NPC287182
0.7042	Intermediate Similarity	NPC84894
0.7042	Intermediate Similarity	NPC18804
0.7042	Intermediate Similarity	NPC260265
0.704	Intermediate Similarity	NPC1065
0.7037	Intermediate Similarity	NPC311219
0.7037	Intermediate Similarity	NPC302211
0.7037	Intermediate Similarity	NPC150214

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 NPC151237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	605
0.1-0.2	983
0.2-0.3	1547
0.3-0.4	2833
0.4-0.5	2031
0.5-0.6	886
0.6-0.7	221
0.7-0.8	41
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD9697	Approved
0.7985	Intermediate Similarity	NPD1184	Approved
0.7951	Intermediate Similarity	NPD5535	Approved
0.7786	Intermediate Similarity	NPD2797	Approved
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD1578	Phase 2
0.7669	Intermediate Similarity	NPD454	Approved
0.7576	Intermediate Similarity	NPD3225	Approved
0.7571	Intermediate Similarity	NPD2353	Approved
0.7571	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5451	Approved
0.752	Intermediate Similarity	NPD769	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.7481	Intermediate Similarity	NPD422	Phase 1
0.7481	Intermediate Similarity	NPD1611	Approved
0.7402	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4307	Phase 2
0.7361	Intermediate Similarity	NPD2354	Approved
0.7361	Intermediate Similarity	NPD3887	Approved
0.7348	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5846	Approved
0.7328	Intermediate Similarity	NPD6516	Phase 2
0.7324	Intermediate Similarity	NPD2378	Approved
0.7324	Intermediate Similarity	NPD2377	Approved
0.7324	Intermediate Similarity	NPD2376	Approved
0.7315	Intermediate Similarity	NPD4972	Discontinued
0.7299	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5958	Discontinued
0.7273	Intermediate Similarity	NPD4534	Discontinued
0.7259	Intermediate Similarity	NPD1203	Approved
0.7254	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2313	Discontinued
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7197	Intermediate Similarity	NPD17	Approved
0.7183	Intermediate Similarity	NPD4308	Phase 3
0.7177	Intermediate Similarity	NPD3134	Approved
0.7154	Intermediate Similarity	NPD9501	Approved
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7132	Intermediate Similarity	NPD987	Approved
0.7124	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1296	Phase 2
0.7121	Intermediate Similarity	NPD5691	Approved
0.712	Intermediate Similarity	NPD1358	Approved
0.7113	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4359	Approved
0.7101	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3748	Approved
0.7054	Intermediate Similarity	NPD1241	Discontinued
0.7045	Intermediate Similarity	NPD1894	Discontinued
0.7045	Intermediate Similarity	NPD1548	Phase 1
0.704	Intermediate Similarity	NPD968	Approved
0.7037	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD4536	Approved
0.6993	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4538	Approved
0.6992	Remote Similarity	NPD5585	Approved
0.6985	Remote Similarity	NPD6543	Approved
0.6985	Remote Similarity	NPD6539	Approved
0.6985	Remote Similarity	NPD6542	Approved
0.6985	Remote Similarity	NPD6540	Phase 3
0.6984	Remote Similarity	NPD9552	Approved
0.6963	Remote Similarity	NPD1535	Discovery
0.6957	Remote Similarity	NPD2798	Approved
0.6947	Remote Similarity	NPD2557	Approved
0.6944	Remote Similarity	NPD5588	Approved
0.6944	Remote Similarity	NPD5960	Phase 3
0.694	Remote Similarity	NPD4626	Approved
0.6934	Remote Similarity	NPD6538	Approved
0.6934	Remote Similarity	NPD6541	Approved
0.6928	Remote Similarity	NPD4424	Discontinued
0.6912	Remote Similarity	NPD1481	Phase 2
0.6853	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4622	Approved
0.6853	Remote Similarity	NPD4618	Approved
0.6853	Remote Similarity	NPD4340	Discontinued
0.6853	Remote Similarity	NPD1933	Approved
0.685	Remote Similarity	NPD290	Approved
0.6838	Remote Similarity	NPD1610	Phase 2
0.6835	Remote Similarity	NPD1019	Discontinued
0.6828	Remote Similarity	NPD7033	Discontinued
0.6828	Remote Similarity	NPD2799	Discontinued
0.6828	Remote Similarity	NPD3260	Discontinued
0.6824	Remote Similarity	NPD3750	Approved
0.6818	Remote Similarity	NPD6671	Approved
0.6815	Remote Similarity	NPD1778	Approved
0.6809	Remote Similarity	NPD7095	Approved
0.6803	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2684	Approved
0.6783	Remote Similarity	NPD4060	Phase 1
0.6774	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3847	Discontinued
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5688	Approved
0.6759	Remote Similarity	NPD5689	Approved
0.6757	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3443	Approved
0.6741	Remote Similarity	NPD3445	Approved
0.6741	Remote Similarity	NPD3444	Approved
0.6741	Remote Similarity	NPD3049	Approved
0.6736	Remote Similarity	NPD5124	Phase 1
0.6736	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6355	Discontinued
0.6735	Remote Similarity	NPD2346	Discontinued
0.6733	Remote Similarity	NPD5058	Phase 3
0.6732	Remote Similarity	NPD957	Approved
0.6731	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1281	Approved
0.6713	Remote Similarity	NPD8032	Phase 2
0.6711	Remote Similarity	NPD4535	Phase 3
0.6692	Remote Similarity	NPD709	Approved
0.6692	Remote Similarity	NPD6387	Discontinued
0.6692	Remote Similarity	NPD191	Approved
0.6689	Remote Similarity	NPD7041	Phase 2
0.6689	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD6580	Approved
0.6667	Remote Similarity	NPD2237	Approved
0.6667	Remote Similarity	NPD6581	Approved
0.6667	Remote Similarity	NPD2486	Discontinued
0.6644	Remote Similarity	NPD1243	Approved
0.6644	Remote Similarity	NPD1652	Phase 2
0.6642	Remote Similarity	NPD3596	Phase 2
0.6623	Remote Similarity	NPD6815	Approved
0.6622	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2614	Approved
0.6618	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD958	Approved
0.6603	Remote Similarity	NPD3274	Phase 2
0.6597	Remote Similarity	NPD6233	Phase 2
0.6593	Remote Similarity	NPD7644	Approved
0.6591	Remote Similarity	NPD7843	Approved
0.6577	Remote Similarity	NPD2897	Discontinued
0.6577	Remote Similarity	NPD2808	Discontinued
0.6573	Remote Similarity	NPD5163	Phase 2
0.6571	Remote Similarity	NPD1283	Approved
0.6569	Remote Similarity	NPD2554	Approved
0.6569	Remote Similarity	NPD2556	Approved
0.6554	Remote Similarity	NPD4477	Approved
0.6554	Remote Similarity	NPD6032	Approved
0.6554	Remote Similarity	NPD4476	Approved
0.6554	Remote Similarity	NPD1551	Phase 2
0.6549	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2861	Phase 2
0.6547	Remote Similarity	NPD3972	Approved
0.6541	Remote Similarity	NPD5283	Phase 1
0.6536	Remote Similarity	NPD5401	Approved
0.6531	Remote Similarity	NPD7097	Phase 1
0.6528	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD411	Approved
0.6522	Remote Similarity	NPD915	Approved
0.6522	Remote Similarity	NPD3294	Phase 2
0.6515	Remote Similarity	NPD1139	Approved
0.6515	Remote Similarity	NPD1137	Approved
0.6513	Remote Similarity	NPD643	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD9694	Discovery
0.6507	Remote Similarity	NPD447	Suspended
0.6503	Remote Similarity	NPD4908	Phase 1
0.6503	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6582	Phase 2
0.65	Remote Similarity	NPD6583	Phase 3
0.6496	Remote Similarity	NPD6382	Discontinued
0.6496	Remote Similarity	NPD1651	Approved
0.6484	Remote Similarity	NPD5909	Discontinued
0.6483	Remote Similarity	NPD4062	Phase 3
0.6483	Remote Similarity	NPD4870	Approved
0.6474	Remote Similarity	NPD3226	Approved
0.6471	Remote Similarity	NPD5536	Phase 2
0.6467	Remote Similarity	NPD1549	Phase 2
0.6466	Remote Similarity	NPD1138	Approved
0.6466	Remote Similarity	NPD821	Approved
0.6458	Remote Similarity	NPD4625	Phase 3
0.6454	Remote Similarity	NPD1876	Approved
0.6452	Remote Similarity	NPD5403	Approved
0.6449	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4589	Approved
0.6444	Remote Similarity	NPD7157	Approved
0.6443	Remote Similarity	NPD2935	Discontinued
0.6434	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1157	Approved
0.6429	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1238	Approved
0.6429	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD1182	Approved
0.6418	Remote Similarity	NPD592	Approved
0.6418	Remote Similarity	NPD594	Approved
0.6414	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4098	Discontinued
0.6406	Remote Similarity	NPD9500	Approved
0.6405	Remote Similarity	NPD6666	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