NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.11
Volume:	281.703
LogP:	1.162
LogD:	1.253
LogS:	-2.742
# Rotatable Bonds:	8
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	2.063
Fsp3:	0.357
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:	-4.498
MDCK Permeability:	2.6299565433873795e-05
Pgp-inhibitor:	0.397
Pgp-substrate:	0.497
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	39.516571044921875%
Volume Distribution (VD):	0.451
Pgp-substrate:	17.48552703857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.432
CYP3A4-inhibitor:	0.154
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	8.192
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.872
Carcinogencity:	0.066
Eye Corrosion:	0.096
Eye Irritation:	0.811
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: NPC27352

Natural Product ID:	NPC27352
*Common Name:**	(E)-2-Hydroxyethyl 3-(3,4,5-Trimethoxyphenyl)Acrylate
IUPAC Name:	2-hydroxyethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	ILJWQZPOVCBREW-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C14H18O6/c1-17-11-8-10(4-5-13(16)20-7-6-15)9-12(18-2)14(11)19-3/h4-5,8-9,15H,6-7H2,1-3H3/b5-4+
SMILES:	OCCOC(=O)/C=C/c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252396
PubChem CID:	23656640
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[521303]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	=	30.0	%	PMID[521303]

☑ 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 NPC27352 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	285
0.1-0.2	1482
0.2-0.3	5100
0.3-0.4	11083
0.4-0.5	6640
0.5-0.6	4652
0.6-0.7	8848
0.7-0.8	4076
0.8-0.85	455
0.85-0.9	60
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC48315
0.959	High Similarity	NPC109275
0.958	High Similarity	NPC288238
0.9496	High Similarity	NPC310373
0.9492	High Similarity	NPC222175
0.9344	High Similarity	NPC58279
0.9344	High Similarity	NPC300326
0.9286	High Similarity	NPC5423
0.9268	High Similarity	NPC127604
0.904	High Similarity	NPC194841
0.9032	High Similarity	NPC271985
0.9024	High Similarity	NPC108545
0.9024	High Similarity	NPC238810
0.8992	High Similarity	NPC111635
0.8984	High Similarity	NPC245120
0.8976	High Similarity	NPC19242
0.8934	High Similarity	NPC204466
0.8934	High Similarity	NPC199023
0.8926	High Similarity	NPC37858
0.8872	High Similarity	NPC300611
0.8864	High Similarity	NPC164148
0.8864	High Similarity	NPC43500
0.8862	High Similarity	NPC70752
0.8852	High Similarity	NPC229401
0.8852	High Similarity	NPC202474
0.8846	High Similarity	NPC92830
0.8843	High Similarity	NPC63083
0.8837	High Similarity	NPC137669
0.8824	High Similarity	NPC294941
0.8769	High Similarity	NPC241341
0.8769	High Similarity	NPC233018
0.8769	High Similarity	NPC36437
0.8741	High Similarity	NPC138212
0.873	High Similarity	NPC173608
0.8729	High Similarity	NPC203924
0.8722	High Similarity	NPC13067
0.8712	High Similarity	NPC471719
0.871	High Similarity	NPC49341
0.8702	High Similarity	NPC135127
0.8702	High Similarity	NPC309744
0.8689	High Similarity	NPC277460
0.8689	High Similarity	NPC70744
0.8689	High Similarity	NPC137537
0.8689	High Similarity	NPC124916
0.8689	High Similarity	NPC164706
0.8689	High Similarity	NPC107588
0.8689	High Similarity	NPC272471
0.8682	High Similarity	NPC240722
0.8682	High Similarity	NPC244799
0.8676	High Similarity	NPC297342
0.8672	High Similarity	NPC210674
0.8657	High Similarity	NPC210478
0.8651	High Similarity	NPC146886
0.8651	High Similarity	NPC60517
0.8651	High Similarity	NPC246704
0.8651	High Similarity	NPC20443
0.8647	High Similarity	NPC95162
0.8647	High Similarity	NPC52086
0.8647	High Similarity	NPC148835
0.8647	High Similarity	NPC20511
0.8647	High Similarity	NPC139548
0.8647	High Similarity	NPC76336
0.864	High Similarity	NPC270326
0.8626	High Similarity	NPC36490
0.8626	High Similarity	NPC288743
0.8615	High Similarity	NPC73738
0.8607	High Similarity	NPC259638
0.8605	High Similarity	NPC123127
0.8605	High Similarity	NPC27239
0.8594	High Similarity	NPC474119
0.8583	High Similarity	NPC204120
0.8583	High Similarity	NPC289459
0.8571	High Similarity	NPC37468
0.8571	High Similarity	NPC82271
0.8571	High Similarity	NPC157554
0.8571	High Similarity	NPC220598
0.8571	High Similarity	NPC165375
0.8571	High Similarity	NPC126682
0.8561	High Similarity	NPC309953
0.8559	High Similarity	NPC165386
0.8551	High Similarity	NPC205361
0.855	High Similarity	NPC319969
0.8548	High Similarity	NPC2058
0.854	High Similarity	NPC471763
0.8538	High Similarity	NPC307042
0.8538	High Similarity	NPC476399
0.8538	High Similarity	NPC79184
0.8527	High Similarity	NPC474651
0.8527	High Similarity	NPC474623
0.8525	High Similarity	NPC193067
0.8525	High Similarity	NPC123948
0.8519	High Similarity	NPC267291
0.8516	High Similarity	NPC213552
0.8516	High Similarity	NPC120225
0.8507	High Similarity	NPC126206
0.8492	Intermediate Similarity	NPC71579
0.8492	Intermediate Similarity	NPC473411
0.8492	Intermediate Similarity	NPC262253
0.8489	Intermediate Similarity	NPC15577
0.8489	Intermediate Similarity	NPC476347
0.848	Intermediate Similarity	NPC166759
0.848	Intermediate Similarity	NPC267064
0.8478	Intermediate Similarity	NPC476450
0.8473	Intermediate Similarity	NPC29734
0.8468	Intermediate Similarity	NPC135961
0.8468	Intermediate Similarity	NPC20674
0.8462	Intermediate Similarity	NPC202582
0.8462	Intermediate Similarity	NPC273295
0.8462	Intermediate Similarity	NPC218856
0.8462	Intermediate Similarity	NPC226788
0.8462	Intermediate Similarity	NPC285339
0.8462	Intermediate Similarity	NPC222004
0.8462	Intermediate Similarity	NPC3439
0.8462	Intermediate Similarity	NPC470258
0.8462	Intermediate Similarity	NPC190629
0.8462	Intermediate Similarity	NPC210623
0.8456	Intermediate Similarity	NPC224876
0.8456	Intermediate Similarity	NPC83375
0.8444	Intermediate Similarity	NPC100389
0.8444	Intermediate Similarity	NPC226005
0.8433	Intermediate Similarity	NPC471665
0.8433	Intermediate Similarity	NPC186418
0.8433	Intermediate Similarity	NPC471664
0.8429	Intermediate Similarity	NPC187398
0.8429	Intermediate Similarity	NPC96294
0.8429	Intermediate Similarity	NPC478237
0.8429	Intermediate Similarity	NPC93924
0.8429	Intermediate Similarity	NPC476348
0.8421	Intermediate Similarity	NPC155098
0.8413	Intermediate Similarity	NPC114845
0.8413	Intermediate Similarity	NPC470804
0.8409	Intermediate Similarity	NPC123954
0.8409	Intermediate Similarity	NPC162093
0.84	Intermediate Similarity	NPC61516
0.84	Intermediate Similarity	NPC232084
0.84	Intermediate Similarity	NPC247364
0.84	Intermediate Similarity	NPC10932
0.84	Intermediate Similarity	NPC474565
0.8397	Intermediate Similarity	NPC472338
0.8397	Intermediate Similarity	NPC299010
0.8397	Intermediate Similarity	NPC113098
0.8394	Intermediate Similarity	NPC193722
0.8394	Intermediate Similarity	NPC278469
0.8385	Intermediate Similarity	NPC206615
0.8385	Intermediate Similarity	NPC186843
0.8385	Intermediate Similarity	NPC98631
0.8385	Intermediate Similarity	NPC110313
0.8385	Intermediate Similarity	NPC470213
0.837	Intermediate Similarity	NPC25305
0.837	Intermediate Similarity	NPC125417
0.837	Intermediate Similarity	NPC95679
0.837	Intermediate Similarity	NPC110899
0.837	Intermediate Similarity	NPC112068
0.837	Intermediate Similarity	NPC20796
0.8369	Intermediate Similarity	NPC283839
0.8369	Intermediate Similarity	NPC106138
0.8369	Intermediate Similarity	NPC90896
0.8369	Intermediate Similarity	NPC475250
0.8361	Intermediate Similarity	NPC261453
0.8361	Intermediate Similarity	NPC217472
0.8361	Intermediate Similarity	NPC33749
0.8361	Intermediate Similarity	NPC328593
0.8359	Intermediate Similarity	NPC183446
0.8358	Intermediate Similarity	NPC185778
0.8358	Intermediate Similarity	NPC55040
0.8357	Intermediate Similarity	NPC52740
0.8357	Intermediate Similarity	NPC178129
0.8357	Intermediate Similarity	NPC41844
0.8346	Intermediate Similarity	NPC261661
0.8346	Intermediate Similarity	NPC132895
0.8346	Intermediate Similarity	NPC26673
0.8346	Intermediate Similarity	NPC49074
0.8333	Intermediate Similarity	NPC267336
0.8333	Intermediate Similarity	NPC272650
0.8333	Intermediate Similarity	NPC163200
0.8333	Intermediate Similarity	NPC179309
0.8333	Intermediate Similarity	NPC469625
0.8333	Intermediate Similarity	NPC470096
0.8333	Intermediate Similarity	NPC472597
0.8333	Intermediate Similarity	NPC472596
0.8333	Intermediate Similarity	NPC469613
0.8333	Intermediate Similarity	NPC30043
0.8333	Intermediate Similarity	NPC470095
0.8321	Intermediate Similarity	NPC83062
0.8321	Intermediate Similarity	NPC472520
0.8321	Intermediate Similarity	NPC279851
0.8321	Intermediate Similarity	NPC476968
0.8321	Intermediate Similarity	NPC170844
0.832	Intermediate Similarity	NPC226629
0.832	Intermediate Similarity	NPC57501
0.832	Intermediate Similarity	NPC308217
0.832	Intermediate Similarity	NPC475961
0.832	Intermediate Similarity	NPC69670
0.832	Intermediate Similarity	NPC254625
0.831	Intermediate Similarity	NPC120426
0.831	Intermediate Similarity	NPC21184
0.831	Intermediate Similarity	NPC294522
0.831	Intermediate Similarity	NPC114740
0.831	Intermediate Similarity	NPC205727
0.831	Intermediate Similarity	NPC473091

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 NPC27352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	869
0.2-0.3	2022
0.3-0.4	2764
0.4-0.5	1649
0.5-0.6	971
0.6-0.7	530
0.7-0.8	91
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.839	Intermediate Similarity	NPD1358	Approved
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8239	Intermediate Similarity	NPD1653	Approved
0.814	Intermediate Similarity	NPD2983	Phase 2
0.814	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD230	Phase 1
0.8062	Intermediate Similarity	NPD2981	Phase 2
0.8016	Intermediate Similarity	NPD5536	Phase 2
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3134	Approved
0.7895	Intermediate Similarity	NPD3018	Phase 2
0.7868	Intermediate Similarity	NPD1613	Approved
0.7868	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD422	Phase 1
0.7823	Intermediate Similarity	NPD228	Approved
0.7801	Intermediate Similarity	NPD1652	Phase 2
0.7785	Intermediate Similarity	NPD3817	Phase 2
0.7752	Intermediate Similarity	NPD1357	Approved
0.771	Intermediate Similarity	NPD3705	Approved
0.7708	Intermediate Similarity	NPD4357	Discontinued
0.7704	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7266	Discontinued
0.763	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD9494	Approved
0.7591	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6799	Approved
0.7581	Intermediate Similarity	NPD2684	Approved
0.7559	Intermediate Similarity	NPD5283	Phase 1
0.7554	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD7843	Approved
0.7466	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5297	Approved
0.7448	Intermediate Similarity	NPD6190	Approved
0.7442	Intermediate Similarity	NPD7157	Approved
0.7434	Intermediate Similarity	NPD5353	Approved
0.7429	Intermediate Similarity	NPD5124	Phase 1
0.7429	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4626	Approved
0.7424	Intermediate Similarity	NPD1778	Approved
0.7419	Intermediate Similarity	NPD7199	Phase 2
0.7417	Intermediate Similarity	NPD1934	Approved
0.7417	Intermediate Similarity	NPD37	Approved
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD4965	Approved
0.7379	Intermediate Similarity	NPD4628	Phase 3
0.7377	Intermediate Similarity	NPD291	Approved
0.7368	Intermediate Similarity	NPD2801	Approved
0.7361	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD290	Approved
0.7358	Intermediate Similarity	NPD5844	Phase 1
0.7329	Intermediate Similarity	NPD2219	Phase 1
0.7319	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1091	Approved
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.7292	Intermediate Similarity	NPD3540	Phase 1
0.729	Intermediate Similarity	NPD6234	Discontinued
0.729	Intermediate Similarity	NPD919	Approved
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD3686	Approved
0.7267	Intermediate Similarity	NPD3687	Approved
0.7259	Intermediate Similarity	NPD9269	Phase 2
0.7255	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5089	Approved
0.7237	Intermediate Similarity	NPD5090	Approved
0.7234	Intermediate Similarity	NPD4060	Phase 1
0.723	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD1551	Phase 2
0.7222	Intermediate Similarity	NPD3539	Phase 1
0.7218	Intermediate Similarity	NPD9268	Approved
0.7215	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5242	Approved
0.7211	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5402	Approved
0.72	Intermediate Similarity	NPD5403	Approved
0.7194	Intermediate Similarity	NPD4908	Phase 1
0.719	Intermediate Similarity	NPD6801	Discontinued
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7185	Intermediate Similarity	NPD1610	Phase 2
0.7181	Intermediate Similarity	NPD5401	Approved
0.7172	Intermediate Similarity	NPD1375	Discontinued
0.717	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6166	Phase 2
0.717	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6653	Approved
0.7133	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1512	Approved
0.7124	Intermediate Similarity	NPD6386	Approved
0.7124	Intermediate Similarity	NPD6385	Approved
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7109	Intermediate Similarity	NPD556	Approved
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1296	Phase 2
0.7083	Intermediate Similarity	NPD6111	Discontinued
0.7081	Intermediate Similarity	NPD7228	Approved
0.7077	Intermediate Similarity	NPD5535	Approved
0.7075	Intermediate Similarity	NPD4236	Phase 3
0.7075	Intermediate Similarity	NPD4237	Approved
0.7073	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7549	Discontinued
0.7067	Intermediate Similarity	NPD3146	Approved
0.7067	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD9697	Approved
0.7059	Intermediate Similarity	NPD4675	Approved
0.7059	Intermediate Similarity	NPD4678	Approved
0.7059	Intermediate Similarity	NPD4380	Phase 2
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5762	Approved
0.705	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.7034	Intermediate Similarity	NPD1510	Phase 2
0.7034	Intermediate Similarity	NPD3748	Approved
0.7029	Intermediate Similarity	NPD8651	Approved
0.7027	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD5494	Approved
0.7023	Intermediate Similarity	NPD1241	Discontinued
0.7019	Intermediate Similarity	NPD7473	Discontinued
0.7016	Intermediate Similarity	NPD1242	Phase 1
0.7014	Intermediate Similarity	NPD2653	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD9717	Approved
0.6993	Remote Similarity	NPD1240	Approved
0.6993	Remote Similarity	NPD1558	Phase 1
0.6993	Remote Similarity	NPD4005	Discontinued
0.6986	Remote Similarity	NPD2796	Approved
0.6986	Remote Similarity	NPD2935	Discontinued
0.6981	Remote Similarity	NPD8127	Discontinued
0.6972	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6798	Discontinued
0.697	Remote Similarity	NPD7808	Phase 3
0.6963	Remote Similarity	NPD5585	Approved
0.6957	Remote Similarity	NPD4749	Approved
0.6954	Remote Similarity	NPD2533	Approved
0.6954	Remote Similarity	NPD2532	Approved
0.6954	Remote Similarity	NPD2534	Approved
0.6951	Remote Similarity	NPD6797	Phase 2
0.6944	Remote Similarity	NPD6355	Discontinued
0.694	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7124	Phase 2
0.6923	Remote Similarity	NPD4585	Approved
0.6923	Remote Similarity	NPD4062	Phase 3
0.6918	Remote Similarity	NPD5677	Discontinued
0.6917	Remote Similarity	NPD9365	Approved
0.6912	Remote Similarity	NPD17	Approved
0.6909	Remote Similarity	NPD7251	Discontinued
0.6909	Remote Similarity	NPD7685	Pre-registration
0.6909	Remote Similarity	NPD7240	Approved
0.6906	Remote Similarity	NPD3225	Approved
0.6903	Remote Similarity	NPD7411	Suspended
0.6901	Remote Similarity	NPD3180	Approved
0.6901	Remote Similarity	NPD3179	Approved
0.6899	Remote Similarity	NPD6971	Discontinued
0.6899	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1607	Approved
0.6897	Remote Similarity	NPD2492	Phase 1
0.6892	Remote Similarity	NPD1549	Phase 2
0.6892	Remote Similarity	NPD2424	Discontinued
0.6889	Remote Similarity	NPD7533	Approved
0.6889	Remote Similarity	NPD7534	Approved
0.6885	Remote Similarity	NPD9296	Approved
0.6879	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD1247	Approved
0.6875	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3620	Phase 2
0.6861	Remote Similarity	NPD3847	Discontinued
0.6857	Remote Similarity	NPD987	Approved
0.6853	Remote Similarity	NPD3144	Approved
0.6853	Remote Similarity	NPD411	Approved
0.6853	Remote Similarity	NPD1048	Approved
0.6853	Remote Similarity	NPD3145	Approved
0.6846	Remote Similarity	NPD3060	Approved
0.6846	Remote Similarity	NPD6674	Discontinued
0.6846	Remote Similarity	NPD4162	Approved
0.6846	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7768	Phase 2

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