NPASS Compound

Structure

NPC161322 OpenBabel07101719512D 21 23 0 0 0 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -1.7321 -3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -2.0000 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 -0.8660 -1.5000 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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 3 0 0 0 0 2 12 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 14 2 0 0 0 0 6 16 2 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.06
Volume:	291.584
LogP:	3.406
LogD:	2.9
LogS:	-5.006
# Rotatable Bonds:	2
TPSA:	47.28
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	2.458
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.582
MDCK Permeability:	2.0995599697926082e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.399
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	92.01807403564453%
Volume Distribution (VD):	0.998
Pgp-substrate:	2.6470413208007812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.6
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.583
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	1.123
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.717
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.572
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.39
Skin Sensitization:	0.805
Carcinogencity:	0.866
Eye Corrosion:	0.077
Eye Irritation:	0.98
Respiratory Toxicity:	0.623

Download Data

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

Natural Product: NPC161322

Natural Product ID:	NPC161322
*Common Name:**	3-(4-Ethynylphenyl)-2-Oxochromene-4-Carbaldehyde
IUPAC Name:	3-(4-ethynylphenyl)-2-oxochromene-4-carbaldehyde
Synonyms:
Standard InCHIKey:	LXKKGJCJRQEXHO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10O3/c1-2-12-7-9-13(10-8-12)17-15(11-19)14-5-3-4-6-16(14)21-18(17)20/h1,3-11H
SMILES:	O=Cc1c(c2ccc(cc2)C#C)c(=O)oc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956009
PubChem CID:	57345577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002819] Isoflav-3-enes [CHEMONTID:0002820] Isoflav-3-enones

*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
NPO33397	tetramorium sp.	Species	Formicidae	Eukaryota	n.a.	ChangBai Mountain, China	n.a.	PMID[22364815]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	5.0	mm	PMID[557231]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[557231]

☑ 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 NPC161322 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	478
0.1-0.2	2077
0.2-0.3	5476
0.3-0.4	12042
0.4-0.5	5934
0.5-0.6	6651
0.6-0.7	8016
0.7-0.8	1976
0.8-0.85	44
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8231	Intermediate Similarity	NPC107846
0.8195	Intermediate Similarity	NPC238309
0.8189	Intermediate Similarity	NPC54243
0.8175	Intermediate Similarity	NPC45104
0.8168	Intermediate Similarity	NPC88403
0.8148	Intermediate Similarity	NPC175159
0.814	Intermediate Similarity	NPC314329
0.813	Intermediate Similarity	NPC233238
0.8125	Intermediate Similarity	NPC474874
0.8115	Intermediate Similarity	NPC149545
0.811	Intermediate Similarity	NPC32298
0.8095	Intermediate Similarity	NPC316062
0.8092	Intermediate Similarity	NPC89630
0.8074	Intermediate Similarity	NPC472517
0.8047	Intermediate Similarity	NPC98748
0.8047	Intermediate Similarity	NPC201284
0.8047	Intermediate Similarity	NPC35744
0.8047	Intermediate Similarity	NPC264976
0.8	Intermediate Similarity	NPC2989
0.797	Intermediate Similarity	NPC474264
0.7969	Intermediate Similarity	NPC293424
0.7941	Intermediate Similarity	NPC301717
0.7934	Intermediate Similarity	NPC139891
0.7923	Intermediate Similarity	NPC322569
0.791	Intermediate Similarity	NPC298884
0.7907	Intermediate Similarity	NPC137710
0.7895	Intermediate Similarity	NPC2771
0.7883	Intermediate Similarity	NPC307289
0.7879	Intermediate Similarity	NPC315807
0.7874	Intermediate Similarity	NPC51345
0.7852	Intermediate Similarity	NPC125887
0.7846	Intermediate Similarity	NPC193193
0.7846	Intermediate Similarity	NPC31314
0.7846	Intermediate Similarity	NPC168050
0.7846	Intermediate Similarity	NPC230951
0.7842	Intermediate Similarity	NPC66705
0.7829	Intermediate Similarity	NPC206007
0.7823	Intermediate Similarity	NPC259554
0.782	Intermediate Similarity	NPC229113
0.7817	Intermediate Similarity	NPC310370
0.7817	Intermediate Similarity	NPC183642
0.7817	Intermediate Similarity	NPC136095
0.7812	Intermediate Similarity	NPC33717
0.7778	Intermediate Similarity	NPC41721
0.7778	Intermediate Similarity	NPC37512
0.7761	Intermediate Similarity	NPC165556
0.7754	Intermediate Similarity	NPC474340
0.7752	Intermediate Similarity	NPC217423
0.7746	Intermediate Similarity	NPC71903
0.7744	Intermediate Similarity	NPC93730
0.7737	Intermediate Similarity	NPC228184
0.7724	Intermediate Similarity	NPC290038
0.7724	Intermediate Similarity	NPC1065
0.7724	Intermediate Similarity	NPC326801
0.7721	Intermediate Similarity	NPC472519
0.7717	Intermediate Similarity	NPC279916
0.7717	Intermediate Similarity	NPC90903
0.7717	Intermediate Similarity	NPC53953
0.7714	Intermediate Similarity	NPC229128
0.771	Intermediate Similarity	NPC246214
0.7708	Intermediate Similarity	NPC24075
0.7698	Intermediate Similarity	NPC55147
0.7698	Intermediate Similarity	NPC54503
0.7692	Intermediate Similarity	NPC170812
0.7692	Intermediate Similarity	NPC152159
0.7687	Intermediate Similarity	NPC56332
0.7687	Intermediate Similarity	NPC193805
0.7676	Intermediate Similarity	NPC103001
0.7676	Intermediate Similarity	NPC307883
0.7674	Intermediate Similarity	NPC470860
0.7669	Intermediate Similarity	NPC151237
0.7669	Intermediate Similarity	NPC27198
0.766	Intermediate Similarity	NPC223616
0.766	Intermediate Similarity	NPC307401
0.7656	Intermediate Similarity	NPC87563
0.7656	Intermediate Similarity	NPC252004
0.7655	Intermediate Similarity	NPC472840
0.7647	Intermediate Similarity	NPC264428
0.7638	Intermediate Similarity	NPC280760
0.7635	Intermediate Similarity	NPC95526
0.763	Intermediate Similarity	NPC4164
0.7626	Intermediate Similarity	NPC66643
0.7626	Intermediate Similarity	NPC273984
0.7622	Intermediate Similarity	NPC476191
0.7619	Intermediate Similarity	NPC141068
0.7615	Intermediate Similarity	NPC469954
0.7609	Intermediate Similarity	NPC282230
0.7609	Intermediate Similarity	NPC7569
0.7609	Intermediate Similarity	NPC183348
0.7606	Intermediate Similarity	NPC130976
0.7606	Intermediate Similarity	NPC471542
0.7603	Intermediate Similarity	NPC71739
0.7603	Intermediate Similarity	NPC295696
0.7597	Intermediate Similarity	NPC188907
0.7586	Intermediate Similarity	NPC470273
0.7574	Intermediate Similarity	NPC329272
0.7571	Intermediate Similarity	NPC287533
0.7569	Intermediate Similarity	NPC155552
0.7569	Intermediate Similarity	NPC472523
0.7559	Intermediate Similarity	NPC54626
0.7557	Intermediate Similarity	NPC96705
0.7557	Intermediate Similarity	NPC171023
0.7554	Intermediate Similarity	NPC470977
0.7554	Intermediate Similarity	NPC196979
0.7554	Intermediate Similarity	NPC470976
0.7554	Intermediate Similarity	NPC15083
0.7552	Intermediate Similarity	NPC233707
0.7552	Intermediate Similarity	NPC202260
0.7551	Intermediate Similarity	NPC208584
0.755	Intermediate Similarity	NPC24232
0.7541	Intermediate Similarity	NPC84325
0.754	Intermediate Similarity	NPC234639
0.7538	Intermediate Similarity	NPC128249
0.7538	Intermediate Similarity	NPC128633
0.7537	Intermediate Similarity	NPC311219
0.7536	Intermediate Similarity	NPC66246
0.7536	Intermediate Similarity	NPC57552
0.7536	Intermediate Similarity	NPC170546
0.7535	Intermediate Similarity	NPC104796
0.7534	Intermediate Similarity	NPC251372
0.752	Intermediate Similarity	NPC151530
0.752	Intermediate Similarity	NPC157473
0.7519	Intermediate Similarity	NPC235190
0.7519	Intermediate Similarity	NPC180006
0.7518	Intermediate Similarity	NPC22783
0.7518	Intermediate Similarity	NPC265793
0.7518	Intermediate Similarity	NPC274876
0.7518	Intermediate Similarity	NPC292998
0.75	Intermediate Similarity	NPC473855
0.75	Intermediate Similarity	NPC278556
0.75	Intermediate Similarity	NPC266116
0.75	Intermediate Similarity	NPC168259
0.75	Intermediate Similarity	NPC281356
0.75	Intermediate Similarity	NPC43435
0.75	Intermediate Similarity	NPC224657
0.75	Intermediate Similarity	NPC234956
0.75	Intermediate Similarity	NPC170749
0.75	Intermediate Similarity	NPC128730
0.75	Intermediate Similarity	NPC284424
0.75	Intermediate Similarity	NPC60389
0.7483	Intermediate Similarity	NPC472516
0.7483	Intermediate Similarity	NPC471069
0.7483	Intermediate Similarity	NPC471068
0.7483	Intermediate Similarity	NPC254741
0.7482	Intermediate Similarity	NPC469929
0.7482	Intermediate Similarity	NPC115998
0.7482	Intermediate Similarity	NPC86774
0.7482	Intermediate Similarity	NPC327457
0.7482	Intermediate Similarity	NPC245395
0.7482	Intermediate Similarity	NPC475092
0.7482	Intermediate Similarity	NPC278787
0.7482	Intermediate Similarity	NPC39753
0.7481	Intermediate Similarity	NPC11799
0.7481	Intermediate Similarity	NPC141252
0.7481	Intermediate Similarity	NPC183154
0.7481	Intermediate Similarity	NPC263754
0.7481	Intermediate Similarity	NPC473942
0.748	Intermediate Similarity	NPC473809
0.7467	Intermediate Similarity	NPC103116
0.7467	Intermediate Similarity	NPC88445
0.7467	Intermediate Similarity	NPC472298
0.7464	Intermediate Similarity	NPC2596
0.7464	Intermediate Similarity	NPC50583
0.7464	Intermediate Similarity	NPC2401
0.7464	Intermediate Similarity	NPC196034
0.7448	Intermediate Similarity	NPC473209
0.7447	Intermediate Similarity	NPC472524
0.7447	Intermediate Similarity	NPC101294
0.7447	Intermediate Similarity	NPC473655
0.7447	Intermediate Similarity	NPC472591
0.7447	Intermediate Similarity	NPC470871
0.7445	Intermediate Similarity	NPC474476
0.7444	Intermediate Similarity	NPC470092
0.7444	Intermediate Similarity	NPC233282
0.7444	Intermediate Similarity	NPC14177
0.7442	Intermediate Similarity	NPC109241
0.744	Intermediate Similarity	NPC176971
0.7434	Intermediate Similarity	NPC44606
0.7432	Intermediate Similarity	NPC246903
0.7431	Intermediate Similarity	NPC471070
0.7431	Intermediate Similarity	NPC471072
0.7431	Intermediate Similarity	NPC471071
0.7431	Intermediate Similarity	NPC253616
0.7429	Intermediate Similarity	NPC137264
0.7429	Intermediate Similarity	NPC104854
0.7429	Intermediate Similarity	NPC141549
0.7426	Intermediate Similarity	NPC201667
0.7426	Intermediate Similarity	NPC470162
0.7426	Intermediate Similarity	NPC73413
0.7426	Intermediate Similarity	NPC111088
0.7426	Intermediate Similarity	NPC221798
0.7426	Intermediate Similarity	NPC470163
0.7424	Intermediate Similarity	NPC265547
0.7422	Intermediate Similarity	NPC57879
0.7419	Intermediate Similarity	NPC109637
0.7419	Intermediate Similarity	NPC38209
0.7419	Intermediate Similarity	NPC283546
0.7417	Intermediate Similarity	NPC144010
0.7417	Intermediate Similarity	NPC191104
0.7415	Intermediate Similarity	NPC117674

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 NPC161322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	458
0.1-0.2	1004
0.2-0.3	1534
0.3-0.4	2754
0.4-0.5	1983
0.5-0.6	1018
0.6-0.7	313
0.7-0.8	78
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD3267	Approved
0.8308	Intermediate Similarity	NPD3266	Approved
0.8308	Intermediate Similarity	NPD2797	Approved
0.8284	Intermediate Similarity	NPD4307	Phase 2
0.814	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD6832	Phase 2
0.8043	Intermediate Similarity	NPD4308	Phase 3
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD3268	Approved
0.7934	Intermediate Similarity	NPD9697	Approved
0.7857	Intermediate Similarity	NPD1241	Discontinued
0.7829	Intermediate Similarity	NPD1894	Discontinued
0.7826	Intermediate Similarity	NPD4618	Approved
0.7826	Intermediate Similarity	NPD4622	Approved
0.782	Intermediate Similarity	NPD3225	Approved
0.7801	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5535	Approved
0.7761	Intermediate Similarity	NPD1203	Approved
0.7737	Intermediate Similarity	NPD6798	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7714	Intermediate Similarity	NPD5688	Approved
0.7714	Intermediate Similarity	NPD5689	Approved
0.771	Intermediate Similarity	NPD17	Approved
0.7698	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2346	Discontinued
0.766	Intermediate Similarity	NPD3748	Approved
0.7594	Intermediate Similarity	NPD1281	Approved
0.7574	Intermediate Similarity	NPD2798	Approved
0.7574	Intermediate Similarity	NPD1019	Discontinued
0.7571	Intermediate Similarity	NPD1933	Approved
0.7569	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD9717	Approved
0.7537	Intermediate Similarity	NPD3972	Approved
0.7537	Intermediate Similarity	NPD1608	Approved
0.7535	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD5585	Approved
0.7483	Intermediate Similarity	NPD2796	Approved
0.7482	Intermediate Similarity	NPD1296	Phase 2
0.7482	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1611	Approved
0.7447	Intermediate Similarity	NPD6355	Discontinued
0.7444	Intermediate Similarity	NPD1778	Approved
0.7432	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1283	Approved
0.7415	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7033	Discontinued
0.7407	Intermediate Similarity	NPD1481	Phase 2
0.7397	Intermediate Similarity	NPD4628	Phase 3
0.7397	Intermediate Similarity	NPD3750	Approved
0.7379	Intermediate Similarity	NPD2897	Discontinued
0.7376	Intermediate Similarity	NPD2979	Phase 3
0.7361	Intermediate Similarity	NPD4477	Approved
0.7361	Intermediate Similarity	NPD4476	Approved
0.7351	Intermediate Similarity	NPD3226	Approved
0.7351	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD1535	Discovery
0.7315	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5401	Approved
0.731	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6233	Phase 2
0.7305	Intermediate Similarity	NPD8032	Phase 2
0.7302	Intermediate Similarity	NPD3134	Approved
0.7279	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7259	Intermediate Similarity	NPD3496	Discontinued
0.7239	Intermediate Similarity	NPD1651	Approved
0.7236	Intermediate Similarity	NPD1238	Approved
0.7234	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD4359	Approved
0.7219	Intermediate Similarity	NPD5403	Approved
0.7214	Intermediate Similarity	NPD2614	Approved
0.7206	Intermediate Similarity	NPD422	Phase 1
0.7203	Intermediate Similarity	NPD1184	Approved
0.7192	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6599	Discontinued
0.7185	Intermediate Similarity	NPD4626	Approved
0.7183	Intermediate Similarity	NPD4062	Phase 3
0.7174	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7133	Intermediate Similarity	NPD6799	Approved
0.7132	Intermediate Similarity	NPD3847	Discontinued
0.7123	Intermediate Similarity	NPD2438	Suspended
0.7123	Intermediate Similarity	NPD2935	Discontinued
0.7123	Intermediate Similarity	NPD2531	Phase 2
0.7114	Intermediate Similarity	NPD3887	Approved
0.7109	Intermediate Similarity	NPD1358	Approved
0.7095	Intermediate Similarity	NPD1243	Approved
0.7083	Intermediate Similarity	NPD447	Suspended
0.7075	Intermediate Similarity	NPD6004	Phase 3
0.7075	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2344	Approved
0.7075	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6002	Phase 3
0.7075	Intermediate Similarity	NPD2353	Approved
0.7075	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6005	Phase 3
0.7068	Intermediate Similarity	NPD2557	Approved
0.7067	Intermediate Similarity	NPD7440	Discontinued
0.7055	Intermediate Similarity	NPD1510	Phase 2
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1548	Phase 1
0.7034	Intermediate Similarity	NPD1607	Approved
0.7032	Intermediate Similarity	NPD5889	Approved
0.7032	Intermediate Similarity	NPD7411	Suspended
0.7032	Intermediate Similarity	NPD5890	Approved
0.7031	Intermediate Similarity	NPD968	Approved
0.7027	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD454	Approved
0.7021	Intermediate Similarity	NPD2237	Approved
0.7015	Intermediate Similarity	NPD9493	Approved
0.7013	Intermediate Similarity	NPD7458	Discontinued
0.7008	Intermediate Similarity	NPD5909	Discontinued
0.7007	Intermediate Similarity	NPD6032	Approved
0.7006	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5402	Approved
0.6993	Remote Similarity	NPD7427	Discontinued
0.6993	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD6801	Discontinued
0.6986	Remote Similarity	NPD7097	Phase 1
0.6974	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4340	Discontinued
0.6947	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4870	Approved
0.6943	Remote Similarity	NPD7819	Suspended
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6913	Remote Similarity	NPD4534	Discontinued
0.6913	Remote Similarity	NPD5958	Discontinued
0.6912	Remote Similarity	NPD9545	Approved
0.6899	Remote Similarity	NPD3817	Phase 2
0.6897	Remote Similarity	NPD4060	Phase 1
0.6897	Remote Similarity	NPD3142	Approved
0.6897	Remote Similarity	NPD3140	Approved
0.6897	Remote Similarity	NPD4140	Approved
0.6897	Remote Similarity	NPD1240	Approved
0.6894	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2309	Approved
0.6887	Remote Similarity	NPD2354	Approved
0.6883	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD919	Approved
0.687	Remote Similarity	NPD5451	Approved
0.6867	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4662	Approved
0.6863	Remote Similarity	NPD4661	Approved
0.6861	Remote Similarity	NPD3443	Approved
0.6861	Remote Similarity	NPD3445	Approved
0.6861	Remote Similarity	NPD3049	Approved
0.6861	Remote Similarity	NPD3444	Approved
0.6859	Remote Similarity	NPD6585	Discontinued
0.6855	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1989	Approved
0.6849	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5124	Phase 1
0.6846	Remote Similarity	NPD1471	Phase 3
0.6846	Remote Similarity	NPD290	Approved
0.6842	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1610	Phase 2
0.6831	Remote Similarity	NPD5647	Approved
0.6821	Remote Similarity	NPD4110	Phase 3
0.6821	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5049	Phase 3
0.6815	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3749	Approved
0.6813	Remote Similarity	NPD7075	Discontinued
0.6812	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6516	Phase 2
0.6812	Remote Similarity	NPD5846	Approved
0.6806	Remote Similarity	NPD5163	Phase 2
0.6797	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9261	Approved
0.6794	Remote Similarity	NPD2182	Approved
0.6792	Remote Similarity	NPD4288	Approved
0.6788	Remote Similarity	NPD6580	Approved
0.6788	Remote Similarity	NPD6581	Approved
0.6779	Remote Similarity	NPD6100	Approved
0.6779	Remote Similarity	NPD6099	Approved
0.6772	Remote Similarity	NPD6844	Discontinued
0.6765	Remote Similarity	NPD3596	Phase 2
0.6763	Remote Similarity	NPD3294	Phase 2
0.6753	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5844	Phase 1
0.6742	Remote Similarity	NPD2067	Discontinued
0.6739	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8455	Phase 2
0.6716	Remote Similarity	NPD7843	Approved
0.6715	Remote Similarity	NPD5536	Phase 2
0.6715	Remote Similarity	NPD7644	Approved
0.6714	Remote Similarity	NPD6287	Discontinued
0.6708	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6671	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