NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.15
Volume:	248.866
LogP:	0.15
LogD:	-0.528
LogS:	-0.861
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	4.099
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	3.8291822420433164e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	22.240615844726562%
Volume Distribution (VD):	1.522
Pgp-substrate:	57.208831787109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.404
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.507
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	5.434
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.334
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.598
Carcinogencity:	0.198
Eye Corrosion:	0.045
Eye Irritation:	0.839
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC322855

Natural Product ID:	NPC322855
*Common Name:**	(5R)-5-[(2R,3R,5R,6S)-3,5-Dihydroxy-6-Methyloxan-2-Yl]Oxyhexan-2-One
IUPAC Name:	(5R)-5-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxyhexan-2-one
Synonyms:
Standard InCHIKey:	KDIFLHQRDPSWHT-IYKVGLELSA-N
Standard InCHI:	InChI=1S/C12H22O5/c1-7(13)4-5-8(2)16-12-11(15)6-10(14)9(3)17-12/h8-12,14-15H,4-6H2,1-3H3/t8-,9+,10-,11-,12-/m1/s1
SMILES:	C[C@@H](O[C@@H]1O[C@@H](C)[C@@H](C[C@H]1O)O)CCC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221888
PubChem CID:	16066475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides [CHEMONTID:0001498] Hexoses

*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
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15690045]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16529801]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17558398]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18650807]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18791072]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19346493]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19549143]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22235948]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22239548]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[222395484]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23163760]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23475189]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23894595]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24411940]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24453122]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	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
EC50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	EC50	=	120.0	nM	PMID[518973]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	EC50	=	460.0	nM	PMID[518973]

☑ 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 NPC322855 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	869
0.1-0.2	6286
0.2-0.3	16691
0.3-0.4	11824
0.4-0.5	5985
0.5-0.6	740
0.6-0.7	200
0.7-0.8	80
0.8-0.85	15
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8704	High Similarity	NPC233726
0.8704	High Similarity	NPC23134
0.8704	High Similarity	NPC124963
0.8667	High Similarity	NPC325773
0.8621	High Similarity	NPC320032
0.8387	Intermediate Similarity	NPC76881
0.8387	Intermediate Similarity	NPC12040
0.8364	Intermediate Similarity	NPC326533
0.8361	Intermediate Similarity	NPC268243
0.8333	Intermediate Similarity	NPC299781
0.8333	Intermediate Similarity	NPC42503
0.8333	Intermediate Similarity	NPC157193
0.8333	Intermediate Similarity	NPC282143
0.8246	Intermediate Similarity	NPC303727
0.8148	Intermediate Similarity	NPC14144
0.8125	Intermediate Similarity	NPC32148
0.8125	Intermediate Similarity	NPC206601
0.807	Intermediate Similarity	NPC145112
0.807	Intermediate Similarity	NPC58629
0.807	Intermediate Similarity	NPC67660
0.807	Intermediate Similarity	NPC107914
0.807	Intermediate Similarity	NPC157514
0.807	Intermediate Similarity	NPC242073
0.807	Intermediate Similarity	NPC165198
0.807	Intermediate Similarity	NPC246558
0.807	Intermediate Similarity	NPC89145
0.807	Intermediate Similarity	NPC269166
0.807	Intermediate Similarity	NPC130683
0.807	Intermediate Similarity	NPC323361
0.8	Intermediate Similarity	NPC50228
0.8	Intermediate Similarity	NPC97736
0.8	Intermediate Similarity	NPC250619
0.7966	Intermediate Similarity	NPC148424
0.7963	Intermediate Similarity	NPC277475
0.7963	Intermediate Similarity	NPC321087
0.7879	Intermediate Similarity	NPC241265
0.7879	Intermediate Similarity	NPC211428
0.7879	Intermediate Similarity	NPC285003
0.7857	Intermediate Similarity	NPC323574
0.7833	Intermediate Similarity	NPC472025
0.7833	Intermediate Similarity	NPC219040
0.7778	Intermediate Similarity	NPC165846
0.7778	Intermediate Similarity	NPC92246
0.7778	Intermediate Similarity	NPC69445
0.7778	Intermediate Similarity	NPC199857
0.7778	Intermediate Similarity	NPC21209
0.7778	Intermediate Similarity	NPC176017
0.7778	Intermediate Similarity	NPC73906
0.7778	Intermediate Similarity	NPC285364
0.7778	Intermediate Similarity	NPC255377
0.7778	Intermediate Similarity	NPC289758
0.7679	Intermediate Similarity	NPC82512
0.7647	Intermediate Similarity	NPC184550
0.7647	Intermediate Similarity	NPC185419
0.7581	Intermediate Similarity	NPC143326
0.7538	Intermediate Similarity	NPC190418
0.7538	Intermediate Similarity	NPC471760
0.7538	Intermediate Similarity	NPC471761
0.7536	Intermediate Similarity	NPC291228
0.7536	Intermediate Similarity	NPC206823
0.7536	Intermediate Similarity	NPC39266
0.7536	Intermediate Similarity	NPC9763
0.7536	Intermediate Similarity	NPC308096
0.7536	Intermediate Similarity	NPC225748
0.7536	Intermediate Similarity	NPC169085
0.7536	Intermediate Similarity	NPC163812
0.75	Intermediate Similarity	NPC317651
0.75	Intermediate Similarity	NPC258690
0.746	Intermediate Similarity	NPC477757
0.746	Intermediate Similarity	NPC477763
0.746	Intermediate Similarity	NPC477755
0.746	Intermediate Similarity	NPC477750
0.746	Intermediate Similarity	NPC472026
0.746	Intermediate Similarity	NPC155457
0.746	Intermediate Similarity	NPC477753
0.746	Intermediate Similarity	NPC477762
0.7419	Intermediate Similarity	NPC34877
0.7419	Intermediate Similarity	NPC317023
0.7419	Intermediate Similarity	NPC290179
0.7407	Intermediate Similarity	NPC70756
0.7407	Intermediate Similarity	NPC320240
0.7361	Intermediate Similarity	NPC476782
0.7361	Intermediate Similarity	NPC476783
0.7361	Intermediate Similarity	NPC476781
0.7361	Intermediate Similarity	NPC216883
0.7321	Intermediate Similarity	NPC230789
0.7321	Intermediate Similarity	NPC252918
0.7231	Intermediate Similarity	NPC277570
0.7222	Intermediate Similarity	NPC298699
0.7222	Intermediate Similarity	NPC86191
0.7222	Intermediate Similarity	NPC317182
0.7222	Intermediate Similarity	NPC134252
0.7222	Intermediate Similarity	NPC477350
0.7222	Intermediate Similarity	NPC213159
0.7222	Intermediate Similarity	NPC291502
0.7206	Intermediate Similarity	NPC67099
0.7123	Intermediate Similarity	NPC110813
0.7121	Intermediate Similarity	NPC31496
0.7121	Intermediate Similarity	NPC294813
0.7121	Intermediate Similarity	NPC13143
0.7027	Intermediate Similarity	NPC146380
0.7027	Intermediate Similarity	NPC477328
0.7027	Intermediate Similarity	NPC477330
0.7027	Intermediate Similarity	NPC475425
0.7027	Intermediate Similarity	NPC113745
0.7027	Intermediate Similarity	NPC477326
0.7027	Intermediate Similarity	NPC477329
0.7027	Intermediate Similarity	NPC477323
0.7027	Intermediate Similarity	NPC109887
0.7027	Intermediate Similarity	NPC281563
0.7027	Intermediate Similarity	NPC477325
0.7027	Intermediate Similarity	NPC133377
0.7027	Intermediate Similarity	NPC477320
0.7015	Intermediate Similarity	NPC147292
0.7	Intermediate Similarity	NPC52268
0.7	Intermediate Similarity	NPC53760
0.6984	Remote Similarity	NPC220922
0.6974	Remote Similarity	NPC280367
0.6933	Remote Similarity	NPC146992
0.6933	Remote Similarity	NPC85759
0.6933	Remote Similarity	NPC477344
0.6933	Remote Similarity	NPC158302
0.6933	Remote Similarity	NPC294748
0.6933	Remote Similarity	NPC477346
0.6933	Remote Similarity	NPC22742
0.6912	Remote Similarity	NPC477756
0.6912	Remote Similarity	NPC477764
0.6912	Remote Similarity	NPC477751
0.6912	Remote Similarity	NPC477752
0.6885	Remote Similarity	NPC314821
0.6885	Remote Similarity	NPC317626
0.6885	Remote Similarity	NPC317501
0.6866	Remote Similarity	NPC6848
0.6852	Remote Similarity	NPC266553
0.6842	Remote Similarity	NPC267592
0.6812	Remote Similarity	NPC477761
0.6812	Remote Similarity	NPC477754
0.6812	Remote Similarity	NPC477758
0.6812	Remote Similarity	NPC477760
0.6812	Remote Similarity	NPC477759
0.6786	Remote Similarity	NPC29721
0.6753	Remote Similarity	NPC27289
0.6753	Remote Similarity	NPC44782
0.6753	Remote Similarity	NPC477318
0.6753	Remote Similarity	NPC307400
0.6753	Remote Similarity	NPC477347
0.6753	Remote Similarity	NPC477331
0.6753	Remote Similarity	NPC169345
0.6753	Remote Similarity	NPC297768
0.6753	Remote Similarity	NPC475667
0.6753	Remote Similarity	NPC476087
0.6753	Remote Similarity	NPC238056
0.6753	Remote Similarity	NPC475270
0.6753	Remote Similarity	NPC115013
0.6753	Remote Similarity	NPC477319
0.6753	Remote Similarity	NPC184915
0.6753	Remote Similarity	NPC472203
0.6753	Remote Similarity	NPC472202
0.6753	Remote Similarity	NPC123204
0.6753	Remote Similarity	NPC475327
0.6753	Remote Similarity	NPC126685
0.6753	Remote Similarity	NPC472200
0.6753	Remote Similarity	NPC290012
0.6753	Remote Similarity	NPC472205
0.6753	Remote Similarity	NPC173328
0.6753	Remote Similarity	NPC472204
0.6753	Remote Similarity	NPC143421
0.6753	Remote Similarity	NPC119583
0.6753	Remote Similarity	NPC186992
0.6753	Remote Similarity	NPC224953
0.6753	Remote Similarity	NPC183888
0.6753	Remote Similarity	NPC89843
0.6753	Remote Similarity	NPC477317
0.6753	Remote Similarity	NPC236649
0.6753	Remote Similarity	NPC259294
0.6753	Remote Similarity	NPC269318
0.6753	Remote Similarity	NPC21693
0.6753	Remote Similarity	NPC472201
0.6709	Remote Similarity	NPC192025
0.6709	Remote Similarity	NPC125253
0.6709	Remote Similarity	NPC253975
0.661	Remote Similarity	NPC172086
0.661	Remote Similarity	NPC247546
0.6607	Remote Similarity	NPC320189
0.6582	Remote Similarity	NPC473500
0.6582	Remote Similarity	NPC38295
0.6582	Remote Similarity	NPC470313
0.6582	Remote Similarity	NPC477332
0.6582	Remote Similarity	NPC156089
0.6582	Remote Similarity	NPC472352
0.6582	Remote Similarity	NPC60849
0.6533	Remote Similarity	NPC326661
0.6528	Remote Similarity	NPC474078
0.6508	Remote Similarity	NPC469937
0.6508	Remote Similarity	NPC23155
0.6508	Remote Similarity	NPC53463
0.6508	Remote Similarity	NPC320588
0.65	Remote Similarity	NPC288471
0.6462	Remote Similarity	NPC293692
0.6447	Remote Similarity	NPC70996

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 NPC322855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1058
0.1-0.2	4880
0.2-0.3	2157
0.3-0.4	668
0.4-0.5	248
0.5-0.6	91
0.6-0.7	20
0.7-0.8	25
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD904	Phase 3
0.8364	Intermediate Similarity	NPD905	Approved
0.8125	Intermediate Similarity	NPD897	Approved
0.8125	Intermediate Similarity	NPD896	Approved
0.8125	Intermediate Similarity	NPD898	Approved
0.807	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD889	Approved
0.807	Intermediate Similarity	NPD888	Phase 3
0.807	Intermediate Similarity	NPD892	Phase 3
0.807	Intermediate Similarity	NPD891	Phase 3
0.807	Intermediate Similarity	NPD895	Approved
0.807	Intermediate Similarity	NPD894	Approved
0.807	Intermediate Similarity	NPD893	Approved
0.807	Intermediate Similarity	NPD887	Approved
0.7895	Intermediate Similarity	NPD2269	Approved
0.7778	Intermediate Similarity	NPD8998	Phase 2
0.7778	Intermediate Similarity	NPD9000	Phase 3
0.7778	Intermediate Similarity	NPD8999	Phase 3
0.7778	Intermediate Similarity	NPD8997	Approved
0.7778	Intermediate Similarity	NPD8993	Phase 1
0.7536	Intermediate Similarity	NPD3181	Approved
0.75	Intermediate Similarity	NPD8965	Approved
0.75	Intermediate Similarity	NPD8961	Approved
0.75	Intermediate Similarity	NPD8966	Approved
0.7377	Intermediate Similarity	NPD2267	Suspended
0.7222	Intermediate Similarity	NPD8788	Approved
0.7188	Intermediate Similarity	NPD6123	Approved
0.7162	Intermediate Similarity	NPD7329	Approved
0.6984	Remote Similarity	NPD8959	Approved
0.697	Remote Similarity	NPD847	Phase 1
0.6885	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9036	Phase 3
0.6786	Remote Similarity	NPD9006	Approved
0.6774	Remote Similarity	NPD7346	Approved
0.6719	Remote Similarity	NPD369	Approved
0.6618	Remote Similarity	NPD1457	Discontinued
0.661	Remote Similarity	NPD9005	Phase 3
0.661	Remote Similarity	NPD9004	Approved
0.661	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3728	Approved
0.6508	Remote Similarity	NPD3730	Approved
0.6379	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD9219	Approved
0.629	Remote Similarity	NPD1400	Approved
0.629	Remote Similarity	NPD1399	Approved
0.6271	Remote Similarity	NPD8994	Approved
0.619	Remote Similarity	NPD9010	Approved
0.619	Remote Similarity	NPD9011	Approved
0.619	Remote Similarity	NPD72	Approved
0.619	Remote Similarity	NPD8960	Approved
0.619	Remote Similarity	NPD9009	Approved
0.619	Remote Similarity	NPD64	Approved
0.619	Remote Similarity	NPD66	Approved
0.619	Remote Similarity	NPD65	Approved
0.619	Remote Similarity	NPD9007	Approved
0.619	Remote Similarity	NPD9008	Approved
0.6154	Remote Similarity	NPD885	Approved
0.6154	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD1447	Phase 3
0.6092	Remote Similarity	NPD1446	Phase 3
0.6081	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8958	Phase 2
0.6034	Remote Similarity	NPD8957	Approved
0.6032	Remote Similarity	NPD9001	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD9002	Approved
0.5974	Remote Similarity	NPD11	Approved
0.5974	Remote Similarity	NPD376	Approved
0.5946	Remote Similarity	NPD9445	Approved
0.5938	Remote Similarity	NPD9049	Discontinued
0.5938	Remote Similarity	NPD9050	Approved
0.5926	Remote Similarity	NPD9053	Approved
0.5926	Remote Similarity	NPD9052	Approved
0.5926	Remote Similarity	NPD9051	Approved
0.5821	Remote Similarity	NPD73	Approved
0.5806	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD3669	Approved
0.5761	Remote Similarity	NPD2255	Approved
0.5753	Remote Similarity	NPD9031	Approved
0.5753	Remote Similarity	NPD9033	Approved
0.5753	Remote Similarity	NPD9032	Approved
0.5753	Remote Similarity	NPD9030	Approved
0.5747	Remote Similarity	NPD3716	Discontinued
0.5745	Remote Similarity	NPD8138	Approved
0.5745	Remote Similarity	NPD8084	Approved
0.5745	Remote Similarity	NPD8083	Approved
0.5745	Remote Similarity	NPD8139	Approved
0.5745	Remote Similarity	NPD8082	Approved
0.5745	Remote Similarity	NPD8086	Approved
0.5745	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD9120	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8964	Approved
0.5714	Remote Similarity	NPD389	Phase 3
0.5714	Remote Similarity	NPD6428	Approved
0.569	Remote Similarity	NPD8996	Phase 3
0.569	Remote Similarity	NPD8995	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD8275	Approved
0.5684	Remote Similarity	NPD8276	Approved
0.5652	Remote Similarity	NPD881	Approved
0.5641	Remote Similarity	NPD1811	Approved
0.5641	Remote Similarity	NPD1810	Approved
0.5632	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8081	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