NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.09
Volume:	264.407
LogP:	1.29
LogD:	1.264
LogS:	-2.147
# Rotatable Bonds:	7
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	2.156
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	2.095322633977048e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	82.27930450439453%
Volume Distribution (VD):	0.504
Pgp-substrate:	12.513029098510742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.825
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.732
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	9.928
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.949
Carcinogencity:	0.299
Eye Corrosion:	0.022
Eye Irritation:	0.234
Respiratory Toxicity:	0.199

Download Data

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

Natural Product: NPC48315

Natural Product ID:	NPC48315
*Common Name:**	2-Hydroxyethyl 3-(4-Hydroxy-3,5-Dimethoxyphenyl)Acrylate
IUPAC Name:	2-hydroxyethyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	DOYRBQFRVWNXCO-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C13H16O6/c1-17-10-7-9(8-11(18-2)13(10)16)3-4-12(15)19-6-5-14/h3-4,7-8,14,16H,5-6H2,1-2H3/b4-3+
SMILES:	COc1cc(/C=C/C(=O)OCCO)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398262
PubChem CID:	23656638
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and 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
NPO33086	bermuda buttercup	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17922549]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	10.0	%	PMID[523595]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	30.0	%	PMID[523595]

☑ 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 NPC48315 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	304
0.1-0.2	1603
0.2-0.3	5313
0.3-0.4	11327
0.4-0.5	6090
0.5-0.6	4525
0.6-0.7	7710
0.7-0.8	4979
0.8-0.85	665
0.85-0.9	156
0.9-0.95	20
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC109275
0.9672	High Similarity	NPC58279
0.9672	High Similarity	NPC27352
0.9672	High Similarity	NPC300326
0.9355	High Similarity	NPC271985
0.935	High Similarity	NPC238810
0.9344	High Similarity	NPC310373
0.9302	High Similarity	NPC111635
0.9268	High Similarity	NPC288238
0.9262	High Similarity	NPC204466
0.9187	High Similarity	NPC70752
0.918	High Similarity	NPC202474
0.918	High Similarity	NPC229401
0.918	High Similarity	NPC222175
0.9154	High Similarity	NPC92830
0.9147	High Similarity	NPC5423
0.9147	High Similarity	NPC245120
0.9032	High Similarity	NPC49341
0.9023	High Similarity	NPC13067
0.9016	High Similarity	NPC164706
0.9016	High Similarity	NPC70744
0.9016	High Similarity	NPC137537
0.9016	High Similarity	NPC272471
0.9016	High Similarity	NPC107588
0.9008	High Similarity	NPC135127
0.8976	High Similarity	NPC127604
0.8971	High Similarity	NPC297342
0.8968	High Similarity	NPC246704
0.8968	High Similarity	NPC20443
0.8968	High Similarity	NPC60517
0.8968	High Similarity	NPC146886
0.8947	High Similarity	NPC95162
0.8947	High Similarity	NPC20511
0.8947	High Similarity	NPC52086
0.8947	High Similarity	NPC76336
0.8947	High Similarity	NPC148835
0.8947	High Similarity	NPC139548
0.8934	High Similarity	NPC259638
0.8931	High Similarity	NPC36490
0.8923	High Similarity	NPC73738
0.8898	High Similarity	NPC289459
0.8889	High Similarity	NPC165375
0.8889	High Similarity	NPC220598
0.8881	High Similarity	NPC164148
0.8881	High Similarity	NPC43500
0.8872	High Similarity	NPC126682
0.8872	High Similarity	NPC82271
0.8872	High Similarity	NPC157554
0.8871	High Similarity	NPC2058
0.8852	High Similarity	NPC193067
0.8832	High Similarity	NPC471763
0.8828	High Similarity	NPC213552
0.8828	High Similarity	NPC120225
0.8815	High Similarity	NPC267291
0.881	High Similarity	NPC262253
0.881	High Similarity	NPC71579
0.881	High Similarity	NPC473411
0.8806	High Similarity	NPC126206
0.88	High Similarity	NPC199023
0.879	High Similarity	NPC37858
0.879	High Similarity	NPC20674
0.8777	High Similarity	NPC476347
0.876	High Similarity	NPC194841
0.875	High Similarity	NPC83375
0.875	High Similarity	NPC224876
0.875	High Similarity	NPC300611
0.8741	High Similarity	NPC100389
0.8741	High Similarity	NPC226005
0.874	High Similarity	NPC108545
0.8731	High Similarity	NPC471719
0.8731	High Similarity	NPC471665
0.8731	High Similarity	NPC186418
0.8731	High Similarity	NPC471664
0.873	High Similarity	NPC470804
0.872	High Similarity	NPC247364
0.872	High Similarity	NPC61516
0.872	High Similarity	NPC10932
0.872	High Similarity	NPC232084
0.8714	High Similarity	NPC187398
0.8714	High Similarity	NPC476348
0.8714	High Similarity	NPC478237
0.871	High Similarity	NPC63083
0.8702	High Similarity	NPC472338
0.8702	High Similarity	NPC19242
0.8692	High Similarity	NPC110313
0.8692	High Similarity	NPC98631
0.8692	High Similarity	NPC186843
0.8692	High Similarity	NPC206615
0.8692	High Similarity	NPC470213
0.8689	High Similarity	NPC328593
0.8689	High Similarity	NPC261453
0.8689	High Similarity	NPC33749
0.8689	High Similarity	NPC294941
0.8689	High Similarity	NPC217472
0.8686	High Similarity	NPC193722
0.8686	High Similarity	NPC278469
0.8672	High Similarity	NPC183446
0.8667	High Similarity	NPC112068
0.8667	High Similarity	NPC25305
0.8667	High Similarity	NPC110899
0.8667	High Similarity	NPC95679
0.8667	High Similarity	NPC125417
0.8652	High Similarity	NPC475250
0.8652	High Similarity	NPC106138
0.8652	High Similarity	NPC283839
0.8652	High Similarity	NPC90896
0.8651	High Similarity	NPC166759
0.8647	High Similarity	NPC26673
0.8647	High Similarity	NPC132895
0.8643	High Similarity	NPC41844
0.8643	High Similarity	NPC178129
0.864	High Similarity	NPC226629
0.8636	High Similarity	NPC472597
0.8636	High Similarity	NPC470095
0.8636	High Similarity	NPC470096
0.8629	High Similarity	NPC39793
0.8626	High Similarity	NPC83062
0.8626	High Similarity	NPC170844
0.8626	High Similarity	NPC476968
0.8623	High Similarity	NPC138212
0.8618	High Similarity	NPC233669
0.8618	High Similarity	NPC474967
0.8615	High Similarity	NPC210355
0.8607	High Similarity	NPC95381
0.8605	High Similarity	NPC173608
0.8605	High Similarity	NPC82483
0.8605	High Similarity	NPC472093
0.8605	High Similarity	NPC17943
0.8605	High Similarity	NPC265483
0.8605	High Similarity	NPC233410
0.8605	High Similarity	NPC116907
0.8605	High Similarity	NPC298757
0.8605	High Similarity	NPC221077
0.8605	High Similarity	NPC193544
0.8605	High Similarity	NPC57490
0.8605	High Similarity	NPC203133
0.8605	High Similarity	NPC251855
0.8605	High Similarity	NPC117214
0.8605	High Similarity	NPC475169
0.8605	High Similarity	NPC299584
0.8605	High Similarity	NPC208950
0.8594	High Similarity	NPC197757
0.8594	High Similarity	NPC228922
0.8594	High Similarity	NPC224208
0.8594	High Similarity	NPC474275
0.8593	High Similarity	NPC37468
0.8592	High Similarity	NPC21184
0.8592	High Similarity	NPC120426
0.8592	High Similarity	NPC294522
0.8592	High Similarity	NPC205727
0.8583	High Similarity	NPC145780
0.8582	High Similarity	NPC237594
0.8582	High Similarity	NPC252402
0.8582	High Similarity	NPC471110
0.8582	High Similarity	NPC476387
0.8582	High Similarity	NPC119060
0.8582	High Similarity	NPC309744
0.8582	High Similarity	NPC249791
0.8582	High Similarity	NPC102934
0.8571	High Similarity	NPC137949
0.8571	High Similarity	NPC253105
0.8571	High Similarity	NPC470270
0.8571	High Similarity	NPC35932
0.8571	High Similarity	NPC184447
0.8571	High Similarity	NPC160991
0.8571	High Similarity	NPC35071
0.8571	High Similarity	NPC474565
0.8571	High Similarity	NPC7903
0.8571	High Similarity	NPC201587
0.8571	High Similarity	NPC137669
0.8571	High Similarity	NPC148615
0.8571	High Similarity	NPC16208
0.8571	High Similarity	NPC177475
0.856	High Similarity	NPC255675
0.856	High Similarity	NPC124916
0.8551	High Similarity	NPC140502
0.8551	High Similarity	NPC157816
0.8551	High Similarity	NPC469564
0.8548	High Similarity	NPC221049
0.8548	High Similarity	NPC281277
0.854	High Similarity	NPC202700
0.854	High Similarity	NPC203351
0.854	High Similarity	NPC210478
0.8538	High Similarity	NPC223136
0.8538	High Similarity	NPC78974
0.8538	High Similarity	NPC28730
0.8538	High Similarity	NPC18924
0.8538	High Similarity	NPC214406
0.8538	High Similarity	NPC103823
0.8538	High Similarity	NPC44748
0.8531	High Similarity	NPC213197
0.8529	High Similarity	NPC474886
0.8521	High Similarity	NPC313334
0.8521	High Similarity	NPC30688
0.8521	High Similarity	NPC176903
0.8521	High Similarity	NPC212670
0.8521	High Similarity	NPC206264
0.8519	High Similarity	NPC274613
0.8519	High Similarity	NPC185778
0.8516	High Similarity	NPC270326

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 NPC48315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	885
0.2-0.3	2072
0.3-0.4	2790
0.4-0.5	1552
0.5-0.6	984
0.6-0.7	504
0.7-0.8	95
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD3027	Phase 3
0.8521	High Similarity	NPD1653	Approved
0.837	Intermediate Similarity	NPD230	Phase 1
0.8308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1613	Approved
0.8145	Intermediate Similarity	NPD228	Approved
0.8115	Intermediate Similarity	NPD1358	Approved
0.8015	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7266	Discontinued
0.7926	Intermediate Similarity	NPD9494	Approved
0.7926	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2983	Phase 2
0.7895	Intermediate Similarity	NPD2982	Phase 2
0.782	Intermediate Similarity	NPD2981	Phase 2
0.7786	Intermediate Similarity	NPD1357	Approved
0.7769	Intermediate Similarity	NPD5536	Phase 2
0.7763	Intermediate Similarity	NPD3882	Suspended
0.7763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3134	Approved
0.774	Intermediate Similarity	NPD4357	Discontinued
0.7724	Intermediate Similarity	NPD6190	Approved
0.7708	Intermediate Similarity	NPD1652	Phase 2
0.7682	Intermediate Similarity	NPD1934	Approved
0.7664	Intermediate Similarity	NPD3018	Phase 2
0.7632	Intermediate Similarity	NPD2801	Approved
0.7589	Intermediate Similarity	NPD447	Suspended
0.7582	Intermediate Similarity	NPD3817	Phase 2
0.7556	Intermediate Similarity	NPD9269	Phase 2
0.7548	Intermediate Similarity	NPD6234	Discontinued
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1511	Approved
0.7481	Intermediate Similarity	NPD3705	Approved
0.7467	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5124	Phase 1
0.7451	Intermediate Similarity	NPD37	Approved
0.7444	Intermediate Similarity	NPD1548	Phase 1
0.7444	Intermediate Similarity	NPD9545	Approved
0.7438	Intermediate Similarity	NPD3818	Discontinued
0.7421	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6166	Phase 2
0.7419	Intermediate Similarity	NPD4967	Phase 2
0.7419	Intermediate Similarity	NPD4966	Approved
0.7419	Intermediate Similarity	NPD4965	Approved
0.7415	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD3496	Discontinued
0.7403	Intermediate Similarity	NPD1465	Phase 2
0.74	Intermediate Similarity	NPD1512	Approved
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD7054	Approved
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7383	Intermediate Similarity	NPD6799	Approved
0.7379	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD2219	Phase 1
0.7357	Intermediate Similarity	NPD4908	Phase 1
0.7353	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD1091	Approved
0.7346	Intermediate Similarity	NPD7472	Approved
0.7346	Intermediate Similarity	NPD7074	Phase 3
0.7344	Intermediate Similarity	NPD2684	Approved
0.7342	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD1778	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7329	Intermediate Similarity	NPD7228	Approved
0.7328	Intermediate Similarity	NPD5283	Phase 1
0.7317	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3686	Approved
0.7303	Intermediate Similarity	NPD3687	Approved
0.7301	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6232	Discontinued
0.728	Intermediate Similarity	NPD291	Approved
0.7273	Intermediate Similarity	NPD1558	Phase 1
0.7267	Intermediate Similarity	NPD5297	Approved
0.7266	Intermediate Similarity	NPD290	Approved
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.7259	Intermediate Similarity	NPD9268	Approved
0.7259	Intermediate Similarity	NPD5691	Approved
0.7254	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7843	Approved
0.7244	Intermediate Similarity	NPD5353	Approved
0.7222	Intermediate Similarity	NPD4340	Discontinued
0.7218	Intermediate Similarity	NPD7157	Approved
0.7213	Intermediate Similarity	NPD9296	Approved
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.72	Intermediate Similarity	NPD1242	Phase 1
0.7195	Intermediate Similarity	NPD6797	Phase 2
0.7192	Intermediate Similarity	NPD1510	Phase 2
0.7181	Intermediate Similarity	NPD3750	Approved
0.7179	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6653	Approved
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7153	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3620	Phase 2
0.7153	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD7251	Discontinued
0.7152	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD3145	Approved
0.7133	Intermediate Similarity	NPD3144	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5403	Approved
0.7122	Intermediate Similarity	NPD4749	Approved
0.7115	Intermediate Similarity	NPD6801	Discontinued
0.7113	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7549	Discontinued
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7107	Intermediate Similarity	NPD919	Approved
0.7105	Intermediate Similarity	NPD2533	Approved
0.7105	Intermediate Similarity	NPD2532	Approved
0.7105	Intermediate Similarity	NPD2534	Approved
0.7097	Intermediate Similarity	NPD4675	Approved
0.7097	Intermediate Similarity	NPD4678	Approved
0.7097	Intermediate Similarity	NPD6599	Discontinued
0.7095	Intermediate Similarity	NPD3540	Phase 1
0.7092	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2674	Phase 3
0.707	Intermediate Similarity	NPD7819	Suspended
0.7067	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4110	Phase 3
0.7067	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1607	Approved
0.7051	Intermediate Similarity	NPD5090	Approved
0.7051	Intermediate Similarity	NPD5089	Approved
0.705	Intermediate Similarity	NPD9717	Approved
0.7047	Intermediate Similarity	NPD1549	Phase 2
0.7044	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5242	Approved
0.7034	Intermediate Similarity	NPD943	Approved
0.7027	Intermediate Similarity	NPD3539	Phase 1
0.7023	Intermediate Similarity	NPD3022	Approved
0.7023	Intermediate Similarity	NPD3021	Approved
0.702	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD846	Approved
0.7008	Intermediate Similarity	NPD940	Approved
0.7	Intermediate Similarity	NPD4237	Approved
0.7	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD3060	Approved
0.6993	Remote Similarity	NPD5401	Approved
0.6982	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7768	Phase 2
0.698	Remote Similarity	NPD5762	Approved
0.698	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1375	Discontinued
0.698	Remote Similarity	NPD5763	Approved
0.6966	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6233	Phase 2
0.695	Remote Similarity	NPD3225	Approved
0.6948	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6559	Discontinued
0.6944	Remote Similarity	NPD4625	Phase 3
0.6943	Remote Similarity	NPD6385	Approved
0.6943	Remote Similarity	NPD7411	Suspended
0.6943	Remote Similarity	NPD6386	Approved
0.6929	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4005	Discontinued
0.6923	Remote Similarity	NPD3111	Phase 1
0.6923	Remote Similarity	NPD3455	Phase 2
0.6918	Remote Similarity	NPD825	Approved
0.6918	Remote Similarity	NPD826	Approved
0.6914	Remote Similarity	NPD8127	Discontinued
0.6912	Remote Similarity	NPD9493	Approved
0.6901	Remote Similarity	NPD1203	Approved
0.6897	Remote Similarity	NPD411	Approved
0.6897	Remote Similarity	NPD1296	Phase 2
0.6897	Remote Similarity	NPD6798	Discontinued
0.6897	Remote Similarity	NPD1048	Approved
0.6894	Remote Similarity	NPD556	Approved
0.6892	Remote Similarity	NPD6111	Discontinued
0.6887	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3146	Approved
0.6883	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD1933	Approved
0.6866	Remote Similarity	NPD5535	Approved
0.6853	Remote Similarity	NPD5647	Approved
0.6852	Remote Similarity	NPD5494	Approved
0.6849	Remote Similarity	NPD4062	Phase 3
0.6846	Remote Similarity	NPD9697	Approved
0.6846	Remote Similarity	NPD3748	Approved
0.6846	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7240	Approved
0.6832	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6971	Discontinued
0.6831	Remote Similarity	NPD8651	Approved
0.6824	Remote Similarity	NPD2653	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