NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.06
Volume:	194.888
LogP:	1.913
LogD:	1.631
LogS:	-3.426
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	2.825
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	1.6387108189519495e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	60.87864685058594%
Volume Distribution (VD):	0.588
Pgp-substrate:	37.08150863647461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.6
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.256
CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	6.861
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.39
Skin Sensitization:	0.858
Carcinogencity:	0.883
Eye Corrosion:	0.09
Eye Irritation:	0.917
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC473325

Natural Product ID:	NPC473325
*Common Name:**	4-(5-Oxooxolan-3-Yl)Benzaldehyde
IUPAC Name:	4-(5-oxooxolan-3-yl)benzaldehyde
Synonyms:
Standard InCHIKey:	YMBHBGHDXJGHSV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O3/c12-6-8-1-3-9(4-2-8)10-5-11(13)14-7-10/h1-4,6,10H,5,7H2
SMILES:	O=Cc1ccc(cc1)C1COC(=O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400450
PubChem CID:	14863055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000321] Benzoyl 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
NPO32647	sarcodontia crocea	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822300]

☑ 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	6

Activity Type	# Activity
NON-MOLECULAR	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	200.0	ug.mL-1	PMID[550279]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	=	400.0	ug.mL-1	PMID[550279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	200.0	ug.mL-1	PMID[550279]
NPT4113	Organism	Leptosphaeria maculans	Leptosphaeria maculans	MIC	=	400.0	ug.mL-1	PMID[550279]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	800.0	ug.mL-1	PMID[550279]
NPT2920	Organism	Pseudomonas syringae	Pseudomonas syringae	MIC	=	400.0	ug.mL-1	PMID[550279]

☑ 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 NPC473325 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	237
0.1-0.2	1272
0.2-0.3	2961
0.3-0.4	10691
0.4-0.5	16361
0.5-0.6	9198
0.6-0.7	1745
0.7-0.8	228
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8431	Intermediate Similarity	NPC89886
0.8381	Intermediate Similarity	NPC265407
0.8381	Intermediate Similarity	NPC83628
0.8333	Intermediate Similarity	NPC188895
0.8298	Intermediate Similarity	NPC294134
0.8298	Intermediate Similarity	NPC252067
0.8235	Intermediate Similarity	NPC70624
0.8218	Intermediate Similarity	NPC225060
0.8155	Intermediate Similarity	NPC304873
0.8155	Intermediate Similarity	NPC45613
0.8137	Intermediate Similarity	NPC146351
0.8119	Intermediate Similarity	NPC276775
0.8119	Intermediate Similarity	NPC92754
0.8119	Intermediate Similarity	NPC249912
0.8085	Intermediate Similarity	NPC197581
0.8085	Intermediate Similarity	NPC288903
0.8061	Intermediate Similarity	NPC70940
0.8061	Intermediate Similarity	NPC274455
0.8061	Intermediate Similarity	NPC86670
0.8058	Intermediate Similarity	NPC42211
0.8056	Intermediate Similarity	NPC167504
0.8039	Intermediate Similarity	NPC35448
0.8039	Intermediate Similarity	NPC78701
0.8019	Intermediate Similarity	NPC30594
0.8019	Intermediate Similarity	NPC37622
0.8019	Intermediate Similarity	NPC119271
0.8	Intermediate Similarity	NPC307651
0.7982	Intermediate Similarity	NPC270699
0.7982	Intermediate Similarity	NPC82899
0.7963	Intermediate Similarity	NPC214067
0.7963	Intermediate Similarity	NPC196246
0.7961	Intermediate Similarity	NPC203925
0.7961	Intermediate Similarity	NPC118343
0.7961	Intermediate Similarity	NPC217621
0.7959	Intermediate Similarity	NPC9822
0.7944	Intermediate Similarity	NPC56493
0.7941	Intermediate Similarity	NPC270654
0.7938	Intermediate Similarity	NPC322387
0.7921	Intermediate Similarity	NPC130398
0.7909	Intermediate Similarity	NPC128368
0.7895	Intermediate Similarity	NPC270507
0.789	Intermediate Similarity	NPC1082
0.789	Intermediate Similarity	NPC305912
0.7879	Intermediate Similarity	NPC84288
0.7879	Intermediate Similarity	NPC58872
0.7872	Intermediate Similarity	NPC100039
0.787	Intermediate Similarity	NPC10251
0.787	Intermediate Similarity	NPC17417
0.7857	Intermediate Similarity	NPC153308
0.7835	Intermediate Similarity	NPC318107
0.783	Intermediate Similarity	NPC31786
0.781	Intermediate Similarity	NPC25458
0.78	Intermediate Similarity	NPC110704
0.7798	Intermediate Similarity	NPC251854
0.7798	Intermediate Similarity	NPC174099
0.7798	Intermediate Similarity	NPC93084
0.7789	Intermediate Similarity	NPC323103
0.7789	Intermediate Similarity	NPC103387
0.7778	Intermediate Similarity	NPC249811
0.7767	Intermediate Similarity	NPC253423
0.7766	Intermediate Similarity	NPC121800
0.7757	Intermediate Similarity	NPC105899
0.7736	Intermediate Similarity	NPC474365
0.7736	Intermediate Similarity	NPC329556
0.7736	Intermediate Similarity	NPC60679
0.7736	Intermediate Similarity	NPC301943
0.7727	Intermediate Similarity	NPC260818
0.7727	Intermediate Similarity	NPC210089
0.7708	Intermediate Similarity	NPC285773
0.7708	Intermediate Similarity	NPC39600
0.7706	Intermediate Similarity	NPC469636
0.7699	Intermediate Similarity	NPC149691
0.7692	Intermediate Similarity	NPC229242
0.7685	Intermediate Similarity	NPC37914
0.7684	Intermediate Similarity	NPC73978
0.7679	Intermediate Similarity	NPC153053
0.7679	Intermediate Similarity	NPC237366
0.767	Intermediate Similarity	NPC61944
0.7664	Intermediate Similarity	NPC114594
0.766	Intermediate Similarity	NPC170484
0.7658	Intermediate Similarity	NPC321852
0.7658	Intermediate Similarity	NPC79496
0.7653	Intermediate Similarity	NPC164526
0.7647	Intermediate Similarity	NPC261181
0.7624	Intermediate Similarity	NPC103346
0.7619	Intermediate Similarity	NPC325497
0.7593	Intermediate Similarity	NPC209632
0.7593	Intermediate Similarity	NPC269457
0.7589	Intermediate Similarity	NPC474176
0.7586	Intermediate Similarity	NPC137710
0.7579	Intermediate Similarity	NPC157055
0.757	Intermediate Similarity	NPC255676
0.7568	Intermediate Similarity	NPC474157
0.7547	Intermediate Similarity	NPC282895
0.7545	Intermediate Similarity	NPC474364
0.7545	Intermediate Similarity	NPC85493
0.7545	Intermediate Similarity	NPC318327
0.7527	Intermediate Similarity	NPC78500
0.7525	Intermediate Similarity	NPC62765
0.7523	Intermediate Similarity	NPC83409
0.7523	Intermediate Similarity	NPC185763
0.7522	Intermediate Similarity	NPC477411
0.7522	Intermediate Similarity	NPC241851
0.75	Intermediate Similarity	NPC145053
0.75	Intermediate Similarity	NPC280789
0.75	Intermediate Similarity	NPC329282
0.75	Intermediate Similarity	NPC66208
0.75	Intermediate Similarity	NPC329064
0.7477	Intermediate Similarity	NPC284477
0.7456	Intermediate Similarity	NPC470764
0.7456	Intermediate Similarity	NPC306740
0.7456	Intermediate Similarity	NPC210092
0.7447	Intermediate Similarity	NPC298023
0.7436	Intermediate Similarity	NPC202015
0.7434	Intermediate Similarity	NPC272524
0.7429	Intermediate Similarity	NPC226041
0.7426	Intermediate Similarity	NPC325709
0.7426	Intermediate Similarity	NPC173443
0.7423	Intermediate Similarity	NPC230068
0.7417	Intermediate Similarity	NPC318067
0.7417	Intermediate Similarity	NPC328107
0.7414	Intermediate Similarity	NPC94425
0.7411	Intermediate Similarity	NPC137315
0.7396	Intermediate Similarity	NPC127343
0.7396	Intermediate Similarity	NPC190567
0.7391	Intermediate Similarity	NPC226093
0.7391	Intermediate Similarity	NPC135730
0.7387	Intermediate Similarity	NPC99846
0.7387	Intermediate Similarity	NPC269023
0.7383	Intermediate Similarity	NPC112552
0.7368	Intermediate Similarity	NPC137847
0.7368	Intermediate Similarity	NPC471721
0.7368	Intermediate Similarity	NPC76455
0.7368	Intermediate Similarity	NPC308744
0.7368	Intermediate Similarity	NPC196075
0.7353	Intermediate Similarity	NPC213156
0.7353	Intermediate Similarity	NPC240108
0.7347	Intermediate Similarity	NPC44830
0.7345	Intermediate Similarity	NPC158282
0.7345	Intermediate Similarity	NPC474314
0.7339	Intermediate Similarity	NPC19136
0.7333	Intermediate Similarity	NPC472703
0.7312	Intermediate Similarity	NPC208075
0.7311	Intermediate Similarity	NPC144547
0.7311	Intermediate Similarity	NPC50872
0.7304	Intermediate Similarity	NPC186933
0.7304	Intermediate Similarity	NPC217111
0.7304	Intermediate Similarity	NPC474685
0.7304	Intermediate Similarity	NPC474095
0.7304	Intermediate Similarity	NPC476357
0.73	Intermediate Similarity	NPC160339
0.73	Intermediate Similarity	NPC307
0.7297	Intermediate Similarity	NPC112903
0.7297	Intermediate Similarity	NPC470391
0.7292	Intermediate Similarity	NPC300205
0.729	Intermediate Similarity	NPC7435
0.729	Intermediate Similarity	NPC221825
0.729	Intermediate Similarity	NPC228435
0.7288	Intermediate Similarity	NPC204784
0.7288	Intermediate Similarity	NPC472708
0.7282	Intermediate Similarity	NPC317645
0.7282	Intermediate Similarity	NPC133461
0.7281	Intermediate Similarity	NPC13784
0.7281	Intermediate Similarity	NPC161611
0.7273	Intermediate Similarity	NPC472704
0.7273	Intermediate Similarity	NPC172483
0.7265	Intermediate Similarity	NPC61651
0.7265	Intermediate Similarity	NPC228318
0.7265	Intermediate Similarity	NPC152812
0.7263	Intermediate Similarity	NPC245966
0.7263	Intermediate Similarity	NPC329318
0.7257	Intermediate Similarity	NPC476003
0.7257	Intermediate Similarity	NPC474057
0.7255	Intermediate Similarity	NPC220893
0.7248	Intermediate Similarity	NPC247976
0.7248	Intermediate Similarity	NPC274443
0.7241	Intermediate Similarity	NPC100353
0.7238	Intermediate Similarity	NPC172925
0.7232	Intermediate Similarity	NPC192577
0.7228	Intermediate Similarity	NPC89377
0.7228	Intermediate Similarity	NPC69057
0.7227	Intermediate Similarity	NPC473243
0.7227	Intermediate Similarity	NPC988
0.7227	Intermediate Similarity	NPC289432
0.7217	Intermediate Similarity	NPC326664
0.7217	Intermediate Similarity	NPC474363
0.7216	Intermediate Similarity	NPC17408
0.7216	Intermediate Similarity	NPC164086
0.7216	Intermediate Similarity	NPC285716
0.7212	Intermediate Similarity	NPC153885
0.7212	Intermediate Similarity	NPC77273
0.7207	Intermediate Similarity	NPC51174
0.7207	Intermediate Similarity	NPC329705
0.7207	Intermediate Similarity	NPC142326
0.7207	Intermediate Similarity	NPC94751
0.7207	Intermediate Similarity	NPC474111
0.7204	Intermediate Similarity	NPC271437
0.72	Intermediate Similarity	NPC95965
0.7196	Intermediate Similarity	NPC145052
0.7196	Intermediate Similarity	NPC329387

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 NPC473325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	885
0.2-0.3	1401
0.3-0.4	3143
0.4-0.5	2440
0.5-0.6	824
0.6-0.7	192
0.7-0.8	46
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD1087	Approved
0.8224	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1989	Approved
0.8061	Intermediate Similarity	NPD1090	Approved
0.8061	Intermediate Similarity	NPD1089	Approved
0.8061	Intermediate Similarity	NPD1086	Approved
0.7961	Intermediate Similarity	NPD2066	Phase 3
0.7961	Intermediate Similarity	NPD1238	Approved
0.7959	Intermediate Similarity	NPD800	Approved
0.7921	Intermediate Similarity	NPD1693	Approved
0.79	Intermediate Similarity	NPD1088	Approved
0.7879	Intermediate Similarity	NPD3672	Approved
0.7879	Intermediate Similarity	NPD3673	Approved
0.787	Intermediate Similarity	NPD2182	Approved
0.7849	Intermediate Similarity	NPD9490	Approved
0.7835	Intermediate Similarity	NPD9259	Approved
0.7835	Intermediate Similarity	NPD9257	Approved
0.783	Intermediate Similarity	NPD164	Approved
0.7822	Intermediate Similarity	NPD1563	Approved
0.781	Intermediate Similarity	NPD1932	Approved
0.78	Intermediate Similarity	NPD1239	Approved
0.7736	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1930	Approved
0.7736	Intermediate Similarity	NPD1929	Approved
0.7708	Intermediate Similarity	NPD9491	Approved
0.7647	Intermediate Similarity	NPD1202	Approved
0.7596	Intermediate Similarity	NPD1565	Approved
0.7596	Intermediate Similarity	NPD1564	Approved
0.7596	Intermediate Similarity	NPD1566	Phase 3
0.7553	Intermediate Similarity	NPD225	Approved
0.7553	Intermediate Similarity	NPD227	Approved
0.7545	Intermediate Similarity	NPD2329	Discontinued
0.7525	Intermediate Similarity	NPD9258	Approved
0.7525	Intermediate Similarity	NPD9256	Approved
0.7321	Intermediate Similarity	NPD1317	Discontinued
0.7321	Intermediate Similarity	NPD2067	Discontinued
0.732	Intermediate Similarity	NPD226	Approved
0.7308	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1245	Approved
0.7281	Intermediate Similarity	NPD1279	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6647	Phase 2
0.7238	Intermediate Similarity	NPD9260	Approved
0.7238	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1237	Approved
0.7168	Intermediate Similarity	NPD4233	Approved
0.7168	Intermediate Similarity	NPD4234	Approved
0.7167	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5951	Approved
0.7155	Intermediate Similarity	NPD1246	Approved
0.7143	Intermediate Similarity	NPD942	Approved
0.713	Intermediate Similarity	NPD7094	Approved
0.713	Intermediate Similarity	NPD6858	Approved
0.7105	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5347	Phase 2
0.7087	Intermediate Similarity	NPD5346	Phase 2
0.7083	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2652	Approved
0.7069	Intermediate Similarity	NPD2650	Approved
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4793	Discontinued
0.7059	Intermediate Similarity	NPD650	Approved
0.7048	Intermediate Similarity	NPD7631	Approved
0.7048	Intermediate Similarity	NPD1508	Approved
0.7037	Intermediate Similarity	NPD9495	Approved
0.7027	Intermediate Similarity	NPD5909	Discontinued
0.7018	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1752	Approved
0.7018	Intermediate Similarity	NPD1756	Approved
0.7009	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4766	Approved
0.6967	Remote Similarity	NPD6287	Discontinued
0.6952	Remote Similarity	NPD7609	Phase 3
0.6944	Remote Similarity	NPD3495	Discontinued
0.6923	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9508	Approved
0.6852	Remote Similarity	NPD1843	Approved
0.6842	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2607	Approved
0.6822	Remote Similarity	NPD7961	Discontinued
0.6818	Remote Similarity	NPD7798	Approved
0.6803	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9261	Approved
0.6777	Remote Similarity	NPD9545	Approved
0.6754	Remote Similarity	NPD6685	Approved
0.675	Remote Similarity	NPD4574	Approved
0.675	Remote Similarity	NPD4576	Approved
0.6727	Remote Similarity	NPD253	Approved
0.6727	Remote Similarity	NPD5926	Approved
0.6723	Remote Similarity	NPD2629	Approved
0.67	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD2196	Discontinued
0.6694	Remote Similarity	NPD4216	Approved
0.6694	Remote Similarity	NPD2612	Approved
0.6694	Remote Similarity	NPD3132	Approved
0.6694	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2608	Approved
0.6694	Remote Similarity	NPD6065	Approved
0.6694	Remote Similarity	NPD2347	Approved
0.6694	Remote Similarity	NPD3131	Approved
0.6694	Remote Similarity	NPD4218	Approved
0.6694	Remote Similarity	NPD2609	Approved
0.6694	Remote Similarity	NPD4215	Approved
0.6694	Remote Similarity	NPD2610	Approved
0.6694	Remote Similarity	NPD2611	Approved
0.6694	Remote Similarity	NPD4217	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD2345	Approved
0.6639	Remote Similarity	NPD1373	Approved
0.6639	Remote Similarity	NPD1374	Approved
0.6639	Remote Similarity	NPD1370	Approved
0.6639	Remote Similarity	NPD1371	Approved
0.6637	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5765	Approved
0.6615	Remote Similarity	NPD3764	Approved
0.6612	Remote Similarity	NPD9493	Approved
0.6587	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5981	Approved
0.6571	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1282	Approved
0.6557	Remote Similarity	NPD7610	Discontinued
0.6555	Remote Similarity	NPD5277	Phase 2
0.6552	Remote Similarity	NPD9263	Approved
0.6552	Remote Similarity	NPD9267	Approved
0.6552	Remote Similarity	NPD9264	Approved
0.6552	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5306	Approved
0.6532	Remote Similarity	NPD5305	Approved
0.6531	Remote Similarity	NPD9716	Approved
0.6522	Remote Similarity	NPD1677	Discontinued
0.6508	Remote Similarity	NPD3972	Approved
0.6504	Remote Similarity	NPD7009	Phase 2
0.65	Remote Similarity	NPD1241	Discontinued
0.6496	Remote Similarity	NPD74	Approved
0.6496	Remote Similarity	NPD9266	Approved
0.6493	Remote Similarity	NPD2569	Approved
0.6493	Remote Similarity	NPD2567	Approved
0.6471	Remote Similarity	NPD6912	Phase 3
0.6466	Remote Similarity	NPD467	Phase 1
0.6449	Remote Similarity	NPD689	Discontinued
0.6429	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1281	Approved
0.6429	Remote Similarity	NPD4806	Approved
0.6429	Remote Similarity	NPD4807	Approved
0.6406	Remote Similarity	NPD2199	Approved
0.6406	Remote Similarity	NPD2198	Approved
0.6406	Remote Similarity	NPD1876	Approved
0.6404	Remote Similarity	NPD2193	Phase 2
0.6404	Remote Similarity	NPD2648	Phase 3
0.64	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3664	Approved
0.6385	Remote Similarity	NPD3663	Approved
0.6385	Remote Similarity	NPD3661	Approved
0.6385	Remote Similarity	NPD3662	Phase 3
0.6379	Remote Similarity	NPD2197	Approved
0.6379	Remote Similarity	NPD2192	Approved
0.6378	Remote Similarity	NPD6637	Approved
0.6378	Remote Similarity	NPD4878	Approved
0.6372	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3598	Phase 3
0.6364	Remote Similarity	NPD1066	Discontinued
0.6357	Remote Similarity	NPD552	Approved
0.6357	Remote Similarity	NPD553	Approved
0.6357	Remote Similarity	NPD9567	Approved
0.6355	Remote Similarity	NPD1101	Approved
0.635	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4136	Approved
0.6349	Remote Similarity	NPD4106	Approved
0.6349	Remote Similarity	NPD4879	Approved
0.6349	Remote Similarity	NPD1889	Phase 1
0.6349	Remote Similarity	NPD4135	Approved
0.6339	Remote Similarity	NPD9566	Approved
0.6336	Remote Similarity	NPD6832	Phase 2
0.6336	Remote Similarity	NPD2613	Approved
0.6325	Remote Similarity	NPD5704	Approved
0.6325	Remote Similarity	NPD5706	Approved
0.6325	Remote Similarity	NPD5705	Approved
0.6325	Remote Similarity	NPD3134	Approved
0.6316	Remote Similarity	NPD7713	Phase 3
0.6308	Remote Similarity	NPD1019	Discontinued
0.6299	Remote Similarity	NPD7437	Approved
0.6299	Remote Similarity	NPD7436	Approved
0.6299	Remote Similarity	NPD5618	Discontinued
0.6296	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2115	Approved
0.629	Remote Similarity	NPD2116	Approved
0.629	Remote Similarity	NPD2117	Pre-registration
0.6279	Remote Similarity	NPD1283	Approved
0.6277	Remote Similarity	NPD1551	Phase 2
0.627	Remote Similarity	NPD17	Approved
0.6269	Remote Similarity	NPD3373	Approved
0.6269	Remote Similarity	NPD4307	Phase 2
0.6269	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5204	Approved
0.626	Remote Similarity	NPD4198	Discontinued
0.625	Remote Similarity	NPD3644	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