NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	442.15
Volume:	418.237
LogP:	-0.28
LogD:	-0.253
LogS:	-1.117
# Rotatable Bonds:	10
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	4.272
Fsp3:	0.45
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.388
MDCK Permeability:	3.822935468633659e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.767
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325
Plasma Protein Binding (PPB):	59.356563568115234%
Volume Distribution (VD):	0.321
Pgp-substrate:	38.882591247558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	1.86
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.634
AMES Toxicity:	0.769
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.943
Carcinogencity:	0.478
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC477293

Natural Product ID:	NPC477293
*Common Name:**	Pubescenoside A
IUPAC Name:	[3-hydroxy-2-methylidene-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	WTKXHULOWFHFAA-GAJPCSOTSA-N
Standard InCHI:	InChI=1S/C20H26O11/c1-10(8-29-16(25)5-3-11-2-4-12(22)13(23)6-11)14(24)9-30-20-19(28)18(27)17(26)15(7-21)31-20/h2-6,14-15,17-24,26-28H,1,7-9H2/b5-3+/t14?,15-,17-,18+,19-,20-/m1/s1
SMILES:	C=C(COC(=O)/C=C/C1=CC(=C(C=C1)O)O)C(CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11236073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787443]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	36.55	%	PMID[15787443]

☑ 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 NPC477293 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	293
0.1-0.2	1362
0.2-0.3	3808
0.3-0.4	8988
0.4-0.5	9463
0.5-0.6	6781
0.6-0.7	8763
0.7-0.8	2692
0.8-0.85	348
0.85-0.9	139
0.9-0.95	49
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477294
1.0	High Similarity	NPC229784
0.9918	High Similarity	NPC232880
0.9839	High Similarity	NPC219677
0.9836	High Similarity	NPC476873
0.976	High Similarity	NPC473924
0.976	High Similarity	NPC473285
0.9683	High Similarity	NPC254398
0.9606	High Similarity	NPC886
0.9606	High Similarity	NPC34293
0.9606	High Similarity	NPC287597
0.9606	High Similarity	NPC471883
0.9531	High Similarity	NPC476870
0.9457	High Similarity	NPC470572
0.9457	High Similarity	NPC157554
0.9426	High Similarity	NPC52097
0.9385	High Similarity	NPC260425
0.9385	High Similarity	NPC78363
0.9385	High Similarity	NPC476376
0.9355	High Similarity	NPC83218
0.9355	High Similarity	NPC126991
0.9344	High Similarity	NPC11724
0.9313	High Similarity	NPC171134
0.9313	High Similarity	NPC205195
0.9313	High Similarity	NPC321638
0.9313	High Similarity	NPC68092
0.9313	High Similarity	NPC220942
0.9313	High Similarity	NPC226005
0.9313	High Similarity	NPC81515
0.9313	High Similarity	NPC89105
0.9313	High Similarity	NPC328273
0.9313	High Similarity	NPC64141
0.9313	High Similarity	NPC476383
0.9313	High Similarity	NPC197316
0.9313	High Similarity	NPC321184
0.9313	High Similarity	NPC472350
0.9313	High Similarity	NPC100389
0.9308	High Similarity	NPC186418
0.928	High Similarity	NPC471157
0.9262	High Similarity	NPC476872
0.9242	High Similarity	NPC202700
0.9173	High Similarity	NPC186406
0.9173	High Similarity	NPC476385
0.9173	High Similarity	NPC47471
0.9173	High Similarity	NPC476377
0.9173	High Similarity	NPC134405
0.916	High Similarity	NPC37468
0.9127	High Similarity	NPC252114
0.9104	High Similarity	NPC157816
0.9104	High Similarity	NPC265648
0.9104	High Similarity	NPC222433
0.9104	High Similarity	NPC140502
0.9098	High Similarity	NPC475530
0.9098	High Similarity	NPC473799
0.9055	High Similarity	NPC106677
0.9055	High Similarity	NPC35288
0.9055	High Similarity	NPC471881
0.9055	High Similarity	NPC288416
0.9055	High Similarity	NPC45224
0.9055	High Similarity	NPC156692
0.9055	High Similarity	NPC471882
0.9055	High Similarity	NPC173150
0.9037	High Similarity	NPC119537
0.9037	High Similarity	NPC247032
0.9037	High Similarity	NPC96795
0.9037	High Similarity	NPC476384
0.9037	High Similarity	NPC105005
0.9037	High Similarity	NPC175214
0.9037	High Similarity	NPC40305
0.9037	High Similarity	NPC478239
0.9037	High Similarity	NPC476397
0.9037	High Similarity	NPC476375
0.9037	High Similarity	NPC476381
0.9037	High Similarity	NPC476378
0.9037	High Similarity	NPC112
0.9037	High Similarity	NPC205864
0.9037	High Similarity	NPC76406
0.9037	High Similarity	NPC476380
0.9037	High Similarity	NPC269141
0.9037	High Similarity	NPC264632
0.9037	High Similarity	NPC298257
0.9032	High Similarity	NPC266045
0.8984	High Similarity	NPC225307
0.8971	High Similarity	NPC300894
0.8971	High Similarity	NPC141455
0.8971	High Similarity	NPC292443
0.8971	High Similarity	NPC476867
0.8971	High Similarity	NPC196063
0.8971	High Similarity	NPC296954
0.8971	High Similarity	NPC297342
0.8971	High Similarity	NPC232228
0.8971	High Similarity	NPC64195
0.8971	High Similarity	NPC110063
0.8963	High Similarity	NPC296643
0.8915	High Similarity	NPC253595
0.8915	High Similarity	NPC307110
0.8905	High Similarity	NPC83743
0.8905	High Similarity	NPC476866
0.8905	High Similarity	NPC100998
0.8905	High Similarity	NPC476382
0.8905	High Similarity	NPC34587
0.8905	High Similarity	NPC476869
0.8905	High Similarity	NPC34927
0.8905	High Similarity	NPC262182
0.8905	High Similarity	NPC476864
0.8905	High Similarity	NPC287615
0.8905	High Similarity	NPC216819
0.8905	High Similarity	NPC476868
0.8905	High Similarity	NPC252292
0.8898	High Similarity	NPC90318
0.8889	High Similarity	NPC224208
0.8889	High Similarity	NPC474275
0.8841	High Similarity	NPC473867
0.8841	High Similarity	NPC476865
0.8841	High Similarity	NPC229505
0.8841	High Similarity	NPC199928
0.8828	High Similarity	NPC61181
0.8797	High Similarity	NPC55040
0.8797	High Similarity	NPC123988
0.8779	High Similarity	NPC235294
0.8779	High Similarity	NPC46137
0.8779	High Similarity	NPC248307
0.8779	High Similarity	NPC254819
0.8779	High Similarity	NPC246869
0.8779	High Similarity	NPC478255
0.8779	High Similarity	NPC138777
0.8779	High Similarity	NPC225384
0.8779	High Similarity	NPC281798
0.8779	High Similarity	NPC65942
0.8777	High Similarity	NPC232992
0.8777	High Similarity	NPC18789
0.876	High Similarity	NPC103533
0.876	High Similarity	NPC108659
0.876	High Similarity	NPC231607
0.876	High Similarity	NPC264900
0.876	High Similarity	NPC79715
0.8731	High Similarity	NPC154485
0.8731	High Similarity	NPC471872
0.873	High Similarity	NPC147654
0.8722	High Similarity	NPC135127
0.8714	High Similarity	NPC300262
0.8714	High Similarity	NPC80732
0.8714	High Similarity	NPC210611
0.8714	High Similarity	NPC199311
0.8714	High Similarity	NPC201148
0.8714	High Similarity	NPC215095
0.8714	High Similarity	NPC478237
0.8714	High Similarity	NPC192763
0.8714	High Similarity	NPC261122
0.8714	High Similarity	NPC3460
0.8714	High Similarity	NPC28651
0.8712	High Similarity	NPC254275
0.8712	High Similarity	NPC252833
0.8699	High Similarity	NPC281277
0.8692	High Similarity	NPC148982
0.8689	High Similarity	NPC313193
0.8689	High Similarity	NPC217472
0.8682	High Similarity	NPC94179
0.8667	High Similarity	NPC302583
0.8667	High Similarity	NPC84789
0.8667	High Similarity	NPC310252
0.8667	High Similarity	NPC100558
0.8657	High Similarity	NPC185778
0.8652	High Similarity	NPC470933
0.8652	High Similarity	NPC94871
0.8652	High Similarity	NPC90896
0.8652	High Similarity	NPC471062
0.8652	High Similarity	NPC306890
0.8652	High Similarity	NPC473427
0.8652	High Similarity	NPC106138
0.8652	High Similarity	NPC259347
0.8652	High Similarity	NPC478242
0.8652	High Similarity	NPC476386
0.8652	High Similarity	NPC283839
0.8652	High Similarity	NPC476398
0.8647	High Similarity	NPC28637
0.8647	High Similarity	NPC6836
0.8647	High Similarity	NPC132895
0.8643	High Similarity	NPC41844
0.8633	High Similarity	NPC108455
0.8626	High Similarity	NPC184092
0.8626	High Similarity	NPC248355
0.8618	High Similarity	NPC233669
0.8593	High Similarity	NPC471665
0.8593	High Similarity	NPC471664
0.8592	High Similarity	NPC257970
0.8592	High Similarity	NPC470934
0.8592	High Similarity	NPC476871
0.8592	High Similarity	NPC69367
0.8592	High Similarity	NPC12006
0.8592	High Similarity	NPC470927
0.8592	High Similarity	NPC188393
0.8582	High Similarity	NPC470881
0.8582	High Similarity	NPC28776
0.8582	High Similarity	NPC35731
0.8582	High Similarity	NPC473138
0.8582	High Similarity	NPC23677
0.8561	High Similarity	NPC229036
0.856	High Similarity	NPC309434
0.8551	High Similarity	NPC145319

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 NPC477293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	786
0.2-0.3	1791
0.3-0.4	3039
0.4-0.5	1772
0.5-0.6	1104
0.6-0.7	384
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9313	High Similarity	NPD7266	Discontinued
0.8521	High Similarity	NPD1653	Approved
0.8227	Intermediate Similarity	NPD6190	Approved
0.7744	Intermediate Similarity	NPD1091	Approved
0.7714	Intermediate Similarity	NPD230	Phase 1
0.7681	Intermediate Similarity	NPD3027	Phase 3
0.763	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7685	Pre-registration
0.7519	Intermediate Similarity	NPD1357	Approved
0.7518	Intermediate Similarity	NPD1613	Approved
0.7518	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3818	Discontinued
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7054	Approved
0.7383	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3705	Approved
0.7346	Intermediate Similarity	NPD7472	Approved
0.7346	Intermediate Similarity	NPD7074	Phase 3
0.7329	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD6234	Discontinued
0.7308	Intermediate Similarity	NPD969	Suspended
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.7266	Intermediate Similarity	NPD1358	Approved
0.7261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7234	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD4967	Phase 2
0.7197	Intermediate Similarity	NPD4965	Approved
0.7185	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD8166	Discontinued
0.7176	Intermediate Similarity	NPD228	Approved
0.7174	Intermediate Similarity	NPD9269	Phase 2
0.7163	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3022	Approved
0.7154	Intermediate Similarity	NPD3021	Approved
0.7123	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6674	Discontinued
0.7111	Intermediate Similarity	NPD5536	Phase 2
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7083	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8455	Phase 2
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7054	Intermediate Similarity	NPD3134	Approved
0.7048	Intermediate Similarity	NPD6559	Discontinued
0.7042	Intermediate Similarity	NPD9494	Approved
0.7032	Intermediate Similarity	NPD3455	Phase 2
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1934	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6988	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9381	Approved
0.6957	Remote Similarity	NPD9384	Approved
0.6918	Remote Similarity	NPD4060	Phase 1
0.6914	Remote Similarity	NPD7199	Phase 2
0.6913	Remote Similarity	NPD9570	Approved
0.6906	Remote Similarity	NPD3496	Discontinued
0.689	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6166	Phase 2
0.6884	Remote Similarity	NPD9268	Approved
0.6879	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD2983	Phase 2
0.6879	Remote Similarity	NPD2982	Phase 2
0.6871	Remote Similarity	NPD4340	Discontinued
0.6864	Remote Similarity	NPD8313	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6859	Remote Similarity	NPD3686	Approved
0.6859	Remote Similarity	NPD3687	Approved
0.6857	Remote Similarity	NPD422	Phase 1
0.6855	Remote Similarity	NPD2977	Approved
0.6855	Remote Similarity	NPD2978	Approved
0.6845	Remote Similarity	NPD7240	Approved
0.6842	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5125	Phase 3
0.6835	Remote Similarity	NPD5126	Approved
0.6824	Remote Similarity	NPD2492	Phase 1
0.6824	Remote Similarity	NPD6653	Approved
0.6813	Remote Similarity	NPD3817	Phase 2
0.6809	Remote Similarity	NPD2981	Phase 2
0.6806	Remote Similarity	NPD2861	Phase 2
0.6803	Remote Similarity	NPD826	Approved
0.6803	Remote Similarity	NPD825	Approved
0.6803	Remote Similarity	NPD3062	Approved
0.6803	Remote Similarity	NPD3059	Approved
0.6803	Remote Similarity	NPD3061	Approved
0.6797	Remote Similarity	NPD1242	Phase 1
0.6781	Remote Similarity	NPD3764	Approved
0.6779	Remote Similarity	NPD7097	Phase 1
0.677	Remote Similarity	NPD3882	Suspended
0.6766	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5844	Phase 1
0.6763	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD9622	Approved
0.6757	Remote Similarity	NPD5124	Phase 1
0.6757	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD447	Suspended
0.6753	Remote Similarity	NPD5058	Phase 3
0.675	Remote Similarity	NPD1465	Phase 2
0.675	Remote Similarity	NPD2801	Approved
0.6741	Remote Similarity	NPD7843	Approved
0.6735	Remote Similarity	NPD6233	Phase 2
0.6732	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7075	Discontinued
0.6727	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7157	Approved
0.6714	Remote Similarity	NPD4626	Approved
0.6711	Remote Similarity	NPD5314	Approved
0.671	Remote Similarity	NPD4357	Discontinued
0.671	Remote Similarity	NPD1511	Approved
0.6708	Remote Similarity	NPD5402	Approved
0.6707	Remote Similarity	NPD8127	Discontinued
0.6705	Remote Similarity	NPD6841	Approved
0.6705	Remote Similarity	NPD6843	Phase 3
0.6705	Remote Similarity	NPD6842	Approved
0.6692	Remote Similarity	NPD2684	Approved
0.6691	Remote Similarity	NPD5283	Phase 1
0.669	Remote Similarity	NPD3018	Phase 2
0.6689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3620	Phase 2
0.6689	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD943	Approved
0.6689	Remote Similarity	NPD2935	Discontinued
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3094	Phase 2
0.6645	Remote Similarity	NPD5762	Approved
0.6645	Remote Similarity	NPD5763	Approved
0.6644	Remote Similarity	NPD1933	Approved
0.6644	Remote Similarity	NPD555	Phase 2
0.6643	Remote Similarity	NPD5691	Approved
0.6624	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1512	Approved
0.6623	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4110	Phase 3
0.6621	Remote Similarity	NPD9620	Approved
0.6621	Remote Similarity	NPD9619	Approved
0.6621	Remote Similarity	NPD9621	Approved
0.6617	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD290	Approved
0.6607	Remote Similarity	NPD3751	Discontinued
0.6605	Remote Similarity	NPD5353	Approved
0.6601	Remote Similarity	NPD2424	Discontinued
0.66	Remote Similarity	NPD817	Approved
0.66	Remote Similarity	NPD823	Approved
0.6599	Remote Similarity	NPD7095	Approved
0.6596	Remote Similarity	NPD1778	Approved
0.6582	Remote Similarity	NPD5403	Approved
0.6577	Remote Similarity	NPD1558	Phase 1
0.6575	Remote Similarity	NPD5736	Approved
0.6566	Remote Similarity	NPD6232	Discontinued
0.6558	Remote Similarity	NPD4236	Phase 3
0.6558	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4237	Approved
0.6558	Remote Similarity	NPD3060	Approved
0.6556	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4536	Approved
0.6556	Remote Similarity	NPD4538	Approved
0.6556	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD597	Approved
0.6554	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD598	Approved
0.6554	Remote Similarity	NPD6798	Discontinued
0.6554	Remote Similarity	NPD601	Approved
0.6547	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD9493	Approved
0.6543	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1375	Discontinued
0.6535	Remote Similarity	NPD2933	Approved
0.6535	Remote Similarity	NPD2934	Approved
0.6533	Remote Similarity	NPD6355	Discontinued
0.6532	Remote Similarity	NPD689	Discontinued
0.6531	Remote Similarity	NPD4908	Phase 1
0.6522	Remote Similarity	NPD6386	Approved
0.6522	Remote Similarity	NPD6385	Approved
0.6516	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5960	Phase 3
0.6513	Remote Similarity	NPD5588	Approved
0.651	Remote Similarity	NPD4062	Phase 3
0.651	Remote Similarity	NPD1130	Approved
0.651	Remote Similarity	NPD259	Phase 1
0.651	Remote Similarity	NPD1132	Approved
0.651	Remote Similarity	NPD1136	Approved
0.6507	Remote Similarity	NPD258	Approved
0.6507	Remote Similarity	NPD257	Approved
0.6503	Remote Similarity	NPD1610	Phase 2
0.6503	Remote Similarity	NPD3092	Approved
0.6503	Remote Similarity	NPD7680	Approved
0.6497	Remote Similarity	NPD6799	Approved
0.6496	Remote Similarity	NPD9377	Approved
0.6496	Remote Similarity	NPD9379	Approved
0.6494	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD291	Approved
0.6484	Remote Similarity	NPD2859	Approved
0.6484	Remote Similarity	NPD2860	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