NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.06
Volume:	156.517
LogP:	-2.047
LogD:	-2.229
LogS:	-0.071
# Rotatable Bonds:	1
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	3.595
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.373
MDCK Permeability:	0.00020486314315348864
Pgp-inhibitor:	0.002
Pgp-substrate:	0.516
Human Intestinal Absorption (HIA):	0.847
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.285
Plasma Protein Binding (PPB):	12.768035888671875%
Volume Distribution (VD):	0.379
Pgp-substrate:	82.40618896484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.573
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.48
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.32
Carcinogencity:	0.023
Eye Corrosion:	0.004
Eye Irritation:	0.685
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC21209

Natural Product ID:	NPC21209
*Common Name:**	Galactose
IUPAC Name:	(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Synonyms:	Galactose
Standard InCHIKey:	WQZGKKKJIJFFOK-PHYPRBDBSA-N
Standard InCHI:	InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1
SMILES:	C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1233058
PubChem CID:	439357
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

☑ 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	4
Kd	1
MIC	1
Others	19
Potency	2

Activity Type	# Activity
Individual Protein	8
Organism	2
Others	3
PHENOTYPE	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1727	Individual Protein	Acrosin	Homo sapiens	Inhibition	=	0.0	%	PMID[477087]
NPT1728	Individual Protein	Galectin-1	Homo sapiens	Activity	=	50.0	mM	PMID[477089]
NPT1729	Individual Protein	Galectin-3	Homo sapiens	Activity	=	50.0	mM	PMID[477089]
NPT1728	Individual Protein	Galectin-1	Homo sapiens	IC50	=	50000000.0	nM	PMID[477090]
NPT1729	Individual Protein	Galectin-3	Homo sapiens	IC50	=	50000000.0	nM	PMID[477090]
NPT1728	Individual Protein	Galectin-1	Homo sapiens	Activity	=	1.0	n.a.	PMID[477090]
NPT1729	Individual Protein	Galectin-3	Homo sapiens	Activity	=	1.0	n.a.	PMID[477090]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[477091]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3500000.0	nM	PMID[477085]
NPT2	Others	Unspecified		IC50	=	57000.0	nM	PMID[477086]
NPT2	Others	Unspecified		Kd	=	40000.0	nM	PMID[477088]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2685.5	nM	PMID[477091]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_bilirubinemia	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholecystitis	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholelithiasis	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cirrhosis	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_elevated liver function tests	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic failure	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic necrosis	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatitis	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatomegaly	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_jaundice	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver disease	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver fatty	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver function tests abnormal	=	0.0	n.a.	PMID[477092]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_Combined Scores	=	0.0	n.a.	PMID[477092]
NPT2	Others	Unspecified		IC50	=	5000000.0	nM	PMID[477093]

☑ 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 NPC21209 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	1313
0.1-0.2	11638
0.2-0.3	17689
0.3-0.4	9563
0.4-0.5	1939
0.5-0.6	374
0.6-0.7	81
0.7-0.8	51
0.8-0.85	14
0.85-0.9	5
0.9-0.95	15
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255377
1.0	High Similarity	NPC69445
1.0	High Similarity	NPC176017
1.0	High Similarity	NPC289758
1.0	High Similarity	NPC92246
1.0	High Similarity	NPC73906
1.0	High Similarity	NPC199857
1.0	High Similarity	NPC285364
1.0	High Similarity	NPC165846
0.9767	High Similarity	NPC321087
0.9767	High Similarity	NPC277475
0.9545	High Similarity	NPC14144
0.9524	High Similarity	NPC70756
0.9524	High Similarity	NPC320240
0.9333	High Similarity	NPC42503
0.9333	High Similarity	NPC157193
0.9333	High Similarity	NPC282143
0.9333	High Similarity	NPC299781
0.9286	High Similarity	NPC317182
0.9286	High Similarity	NPC213159
0.9286	High Similarity	NPC291502
0.9286	High Similarity	NPC134252
0.9286	High Similarity	NPC298699
0.9286	High Similarity	NPC86191
0.913	High Similarity	NPC323574
0.8936	High Similarity	NPC23134
0.8936	High Similarity	NPC326533
0.8936	High Similarity	NPC124963
0.8936	High Similarity	NPC233726
0.881	High Similarity	NPC266553
0.8636	High Similarity	NPC29721
0.8571	High Similarity	NPC89145
0.8571	High Similarity	NPC67660
0.8571	High Similarity	NPC242073
0.8571	High Similarity	NPC314821
0.8571	High Similarity	NPC130683
0.8571	High Similarity	NPC323361
0.8571	High Similarity	NPC246558
0.8571	High Similarity	NPC165198
0.8571	High Similarity	NPC145112
0.8571	High Similarity	NPC107914
0.8571	High Similarity	NPC157514
0.8571	High Similarity	NPC58629
0.8571	High Similarity	NPC317501
0.8571	High Similarity	NPC317626
0.8571	High Similarity	NPC269166
0.8409	Intermediate Similarity	NPC320189
0.84	Intermediate Similarity	NPC303727
0.8085	Intermediate Similarity	NPC252918
0.8085	Intermediate Similarity	NPC230789
0.8077	Intermediate Similarity	NPC148424
0.7925	Intermediate Similarity	NPC472025
0.7925	Intermediate Similarity	NPC219040
0.7778	Intermediate Similarity	NPC320032
0.7778	Intermediate Similarity	NPC290179
0.7778	Intermediate Similarity	NPC322855
0.7778	Intermediate Similarity	NPC34877
0.7778	Intermediate Similarity	NPC317023
0.7755	Intermediate Similarity	NPC82512
0.7636	Intermediate Similarity	NPC143326
0.7619	Intermediate Similarity	NPC86412
0.7619	Intermediate Similarity	NPC293908
0.7619	Intermediate Similarity	NPC192065
0.7619	Intermediate Similarity	NPC325034
0.7619	Intermediate Similarity	NPC66052
0.75	Intermediate Similarity	NPC477763
0.75	Intermediate Similarity	NPC472026
0.75	Intermediate Similarity	NPC477750
0.75	Intermediate Similarity	NPC477762
0.75	Intermediate Similarity	NPC477753
0.75	Intermediate Similarity	NPC477755
0.75	Intermediate Similarity	NPC155457
0.75	Intermediate Similarity	NPC477757
0.7451	Intermediate Similarity	NPC329095
0.7347	Intermediate Similarity	NPC88638
0.7308	Intermediate Similarity	NPC103672
0.7308	Intermediate Similarity	NPC320043
0.7292	Intermediate Similarity	NPC207656
0.7292	Intermediate Similarity	NPC107091
0.7255	Intermediate Similarity	NPC329128
0.7255	Intermediate Similarity	NPC322158
0.7241	Intermediate Similarity	NPC277570
0.7241	Intermediate Similarity	NPC258690
0.7241	Intermediate Similarity	NPC268243
0.7241	Intermediate Similarity	NPC317651
0.7241	Intermediate Similarity	NPC325773
0.7174	Intermediate Similarity	NPC99573
0.7174	Intermediate Similarity	NPC227707
0.7174	Intermediate Similarity	NPC88278
0.7174	Intermediate Similarity	NPC102981
0.7174	Intermediate Similarity	NPC111882
0.7119	Intermediate Similarity	NPC13143
0.7119	Intermediate Similarity	NPC6848
0.7119	Intermediate Similarity	NPC31496
0.7119	Intermediate Similarity	NPC294813
0.7	Intermediate Similarity	NPC147292
0.7	Intermediate Similarity	NPC76881
0.7	Intermediate Similarity	NPC12040
0.7	Intermediate Similarity	NPC471760
0.7	Intermediate Similarity	NPC471761
0.7	Intermediate Similarity	NPC190418
0.6905	Remote Similarity	NPC149070
0.6905	Remote Similarity	NPC197207
0.6905	Remote Similarity	NPC127074
0.6905	Remote Similarity	NPC187058
0.6905	Remote Similarity	NPC182541
0.6885	Remote Similarity	NPC129100
0.6885	Remote Similarity	NPC291650
0.6885	Remote Similarity	NPC477752
0.6885	Remote Similarity	NPC322801
0.6885	Remote Similarity	NPC477751
0.6885	Remote Similarity	NPC477756
0.6885	Remote Similarity	NPC477764
0.6863	Remote Similarity	NPC112363
0.6774	Remote Similarity	NPC477761
0.6774	Remote Similarity	NPC477754
0.6774	Remote Similarity	NPC206601
0.6774	Remote Similarity	NPC477758
0.6774	Remote Similarity	NPC32148
0.6774	Remote Similarity	NPC477759
0.6774	Remote Similarity	NPC477760
0.6667	Remote Similarity	NPC67099
0.6667	Remote Similarity	NPC50228
0.6667	Remote Similarity	NPC97736
0.6667	Remote Similarity	NPC250619
0.6667	Remote Similarity	NPC220922
0.6591	Remote Similarity	NPC227267
0.6562	Remote Similarity	NPC223174
0.6562	Remote Similarity	NPC241265
0.6562	Remote Similarity	NPC327753
0.6562	Remote Similarity	NPC211428
0.6562	Remote Similarity	NPC327486
0.6562	Remote Similarity	NPC285003
0.6462	Remote Similarity	NPC474078
0.6462	Remote Similarity	NPC53760
0.6462	Remote Similarity	NPC471879
0.6462	Remote Similarity	NPC52268
0.6364	Remote Similarity	NPC185419
0.6364	Remote Similarity	NPC184550
0.6346	Remote Similarity	NPC314613
0.6304	Remote Similarity	NPC313405
0.6269	Remote Similarity	NPC308096
0.6269	Remote Similarity	NPC225748
0.6269	Remote Similarity	NPC248427
0.6269	Remote Similarity	NPC132938
0.6269	Remote Similarity	NPC9763
0.6269	Remote Similarity	NPC291228
0.6269	Remote Similarity	NPC163812
0.6269	Remote Similarity	NPC169085
0.6269	Remote Similarity	NPC39266
0.6269	Remote Similarity	NPC206823
0.625	Remote Similarity	NPC179823
0.619	Remote Similarity	NPC33415
0.619	Remote Similarity	NPC301586
0.6176	Remote Similarity	NPC308489
0.6176	Remote Similarity	NPC166250
0.6176	Remote Similarity	NPC472173
0.6176	Remote Similarity	NPC472174
0.6111	Remote Similarity	NPC325822
0.6111	Remote Similarity	NPC61270
0.6102	Remote Similarity	NPC293692
0.6034	Remote Similarity	NPC326557
0.6029	Remote Similarity	NPC470659
0.6029	Remote Similarity	NPC470660
0.6029	Remote Similarity	NPC55652
0.6	Remote Similarity	NPC326661
0.6	Remote Similarity	NPC279575
0.6	Remote Similarity	NPC229655
0.6	Remote Similarity	NPC477350
0.6	Remote Similarity	NPC182903
0.5962	Remote Similarity	NPC62014
0.5952	Remote Similarity	NPC320326
0.5926	Remote Similarity	NPC247546
0.5926	Remote Similarity	NPC172086
0.5915	Remote Similarity	NPC216883
0.5915	Remote Similarity	NPC110813
0.5915	Remote Similarity	NPC188793
0.5915	Remote Similarity	NPC476782
0.5915	Remote Similarity	NPC314772
0.5915	Remote Similarity	NPC314968
0.5915	Remote Similarity	NPC476783
0.5915	Remote Similarity	NPC476781
0.5902	Remote Similarity	NPC174485
0.5862	Remote Similarity	NPC289979
0.5833	Remote Similarity	NPC477330
0.5833	Remote Similarity	NPC133377
0.5833	Remote Similarity	NPC477329
0.5833	Remote Similarity	NPC281563
0.5833	Remote Similarity	NPC477328
0.5833	Remote Similarity	NPC475425
0.5833	Remote Similarity	NPC98750
0.5833	Remote Similarity	NPC109887
0.5833	Remote Similarity	NPC477325
0.5833	Remote Similarity	NPC146380
0.5833	Remote Similarity	NPC477323
0.5833	Remote Similarity	NPC177343
0.5833	Remote Similarity	NPC150557
0.5833	Remote Similarity	NPC477320
0.5833	Remote Similarity	NPC272841
0.5833	Remote Similarity	NPC477326

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 NPC21209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1580
0.1-0.2	5259
0.2-0.3	1656
0.3-0.4	418
0.4-0.5	130
0.5-0.6	47
0.6-0.7	26
0.7-0.8	13
0.8-0.85	8
0.85-0.9	3
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8993	Phase 1
1.0	High Similarity	NPD8998	Phase 2
1.0	High Similarity	NPD8997	Approved
1.0	High Similarity	NPD9000	Phase 3
1.0	High Similarity	NPD8999	Phase 3
0.9545	High Similarity	NPD8965	Approved
0.9545	High Similarity	NPD8966	Approved
0.9286	High Similarity	NPD8788	Approved
0.8936	High Similarity	NPD905	Approved
0.8936	High Similarity	NPD904	Phase 3
0.8636	High Similarity	NPD9006	Approved
0.8571	High Similarity	NPD9036	Phase 3
0.8571	High Similarity	NPD889	Approved
0.8571	High Similarity	NPD893	Approved
0.8571	High Similarity	NPD892	Phase 3
0.8571	High Similarity	NPD887	Approved
0.8571	High Similarity	NPD891	Phase 3
0.8571	High Similarity	NPD9035	Clinical (unspecified phase)
0.8571	High Similarity	NPD888	Phase 3
0.8571	High Similarity	NPD890	Clinical (unspecified phase)
0.8571	High Similarity	NPD895	Approved
0.8571	High Similarity	NPD894	Approved
0.8367	Intermediate Similarity	NPD2269	Approved
0.7872	Intermediate Similarity	NPD8994	Approved
0.7619	Intermediate Similarity	NPD9053	Approved
0.7619	Intermediate Similarity	NPD9052	Approved
0.7619	Intermediate Similarity	NPD9051	Approved
0.7609	Intermediate Similarity	NPD8957	Approved
0.75	Intermediate Similarity	NPD6123	Approved
0.7407	Intermediate Similarity	NPD2267	Suspended
0.7308	Intermediate Similarity	NPD9049	Discontinued
0.7308	Intermediate Similarity	NPD9050	Approved
0.7292	Intermediate Similarity	NPD9218	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9219	Approved
0.7241	Intermediate Similarity	NPD847	Phase 1
0.7241	Intermediate Similarity	NPD8961	Approved
0.7234	Intermediate Similarity	NPD8958	Phase 2
0.7174	Intermediate Similarity	NPD8996	Phase 3
0.7174	Intermediate Similarity	NPD8995	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD369	Approved
0.6905	Remote Similarity	NPD8814	Phase 3
0.6885	Remote Similarity	NPD9031	Approved
0.6885	Remote Similarity	NPD9033	Approved
0.6885	Remote Similarity	NPD9032	Approved
0.6885	Remote Similarity	NPD9030	Approved
0.6863	Remote Similarity	NPD9139	Approved
0.6774	Remote Similarity	NPD897	Approved
0.6774	Remote Similarity	NPD898	Approved
0.6774	Remote Similarity	NPD896	Approved
0.6727	Remote Similarity	NPD7346	Approved
0.6667	Remote Similarity	NPD8959	Approved
0.6562	Remote Similarity	NPD9445	Approved
0.6557	Remote Similarity	NPD1457	Discontinued
0.6327	Remote Similarity	NPD8967	Approved
0.6269	Remote Similarity	NPD67	Phase 2
0.6269	Remote Similarity	NPD389	Phase 3
0.6269	Remote Similarity	NPD9034	Approved
0.6269	Remote Similarity	NPD3181	Approved
0.619	Remote Similarity	NPD8549	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD9061	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8976	Approved
0.6042	Remote Similarity	NPD8977	Phase 3
0.6034	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD885	Approved
0.6	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD9005	Phase 3
0.5926	Remote Similarity	NPD9004	Approved
0.5926	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD9434	Approved
0.5915	Remote Similarity	NPD9435	Approved
0.5893	Remote Similarity	NPD1399	Approved
0.5893	Remote Similarity	NPD1400	Approved
0.5814	Remote Similarity	NPD8988	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD66	Approved
0.5789	Remote Similarity	NPD9008	Approved
0.5789	Remote Similarity	NPD9007	Approved
0.5789	Remote Similarity	NPD65	Approved
0.5789	Remote Similarity	NPD64	Approved
0.5789	Remote Similarity	NPD72	Approved
0.5789	Remote Similarity	NPD9009	Approved
0.5789	Remote Similarity	NPD8960	Approved
0.5789	Remote Similarity	NPD9011	Approved
0.5789	Remote Similarity	NPD9010	Approved
0.5753	Remote Similarity	NPD7329	Approved
0.5735	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.566	Remote Similarity	NPD9110	Approved
0.5614	Remote Similarity	NPD9002	Approved
0.5614	Remote Similarity	NPD9001	Clinical (unspecified phase)

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