NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.0
Volume:	213.732
LogP:	-0.33
LogD:	-0.192
LogS:	-1.8
# Rotatable Bonds:	4
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	2.082
Fsp3:	0.0
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:	-5.269
MDCK Permeability:	9.038515599968378e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.528
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	92.73616027832031%
Volume Distribution (VD):	0.285
Pgp-substrate:	3.216489791870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.12
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.931
Carcinogencity:	0.1
Eye Corrosion:	0.891
Eye Irritation:	0.988
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC140619

Natural Product ID:	NPC140619
*Common Name:**	P-Sulfoxycinnamic Acid
IUPAC Name:	(E)-3-(4-sulfooxyphenyl)prop-2-enoic acid
Synonyms:	P-Sulfoxycinnamic Acid
Standard InCHIKey:	OYDCCWNLILCHDJ-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C9H8O6S/c10-9(11)6-3-7-1-4-8(5-2-7)15-16(12,13)14/h1-6H,(H,10,11)(H,12,13,14)/b6-3+
SMILES:	c1cc(ccc1/C=C/C(=O)O)OS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575429
PubChem CID:	6070438
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002504] Cinnamic acids

*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
NPO16749	Zostera marina	Species	Zosteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16749	Zostera marina	Species	Zosteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1
Others	5

Activity Type	# Activity
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1724	Organism	Dengue virus	Dengue virus	IC50	=	2000000.0	nM	PMID[553461]
NPT2	Others	Unspecified		Drug metabolism	=	100.0	%	PMID[553462]
NPT2	Others	Unspecified		Km	=	262000.0	nM	PMID[553462]
NPT2	Others	Unspecified		Vmax	=	0.02	microM/s	PMID[553462]
NPT2	Others	Unspecified		Kcat	=	2.35	10'5/s	PMID[553462]
NPT2	Others	Unspecified		Activity	=	898.0	/s/microM	PMID[553462]

☑ 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 NPC140619 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	275
0.1-0.2	2789
0.2-0.3	6718
0.3-0.4	12309
0.4-0.5	7167
0.5-0.6	10258
0.6-0.7	2722
0.7-0.8	415
0.8-0.85	33
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC81010
0.9247	High Similarity	NPC32977
0.8776	High Similarity	NPC253746
0.875	High Similarity	NPC257182
0.875	High Similarity	NPC246679
0.8737	High Similarity	NPC181709
0.86	High Similarity	NPC470202
0.86	High Similarity	NPC304638
0.8557	High Similarity	NPC286006
0.8529	High Similarity	NPC1786
0.8529	High Similarity	NPC1075
0.8529	High Similarity	NPC294902
0.8515	High Similarity	NPC2518
0.8485	Intermediate Similarity	NPC130193
0.8431	Intermediate Similarity	NPC303141
0.8431	Intermediate Similarity	NPC127676
0.8384	Intermediate Similarity	NPC201967
0.8333	Intermediate Similarity	NPC93831
0.8317	Intermediate Similarity	NPC94343
0.83	Intermediate Similarity	NPC171843
0.83	Intermediate Similarity	NPC245561
0.828	Intermediate Similarity	NPC265146
0.8269	Intermediate Similarity	NPC260952
0.8252	Intermediate Similarity	NPC243677
0.8235	Intermediate Similarity	NPC68269
0.8218	Intermediate Similarity	NPC52472
0.8208	Intermediate Similarity	NPC183700
0.8191	Intermediate Similarity	NPC175313
0.8191	Intermediate Similarity	NPC248817
0.819	Intermediate Similarity	NPC206341
0.8131	Intermediate Similarity	NPC226250
0.8125	Intermediate Similarity	NPC104216
0.8113	Intermediate Similarity	NPC75272
0.8113	Intermediate Similarity	NPC79543
0.8113	Intermediate Similarity	NPC471954
0.8105	Intermediate Similarity	NPC197783
0.81	Intermediate Similarity	NPC283711
0.8085	Intermediate Similarity	NPC124436
0.8077	Intermediate Similarity	NPC227255
0.8077	Intermediate Similarity	NPC13495
0.8077	Intermediate Similarity	NPC288760
0.8058	Intermediate Similarity	NPC135784
0.8058	Intermediate Similarity	NPC179686
0.8021	Intermediate Similarity	NPC184169
0.8021	Intermediate Similarity	NPC23167
0.8019	Intermediate Similarity	NPC470039
0.8	Intermediate Similarity	NPC184658
0.7982	Intermediate Similarity	NPC95381
0.7981	Intermediate Similarity	NPC109637
0.7981	Intermediate Similarity	NPC79672
0.7981	Intermediate Similarity	NPC52087
0.7963	Intermediate Similarity	NPC139946
0.7961	Intermediate Similarity	NPC472585
0.7959	Intermediate Similarity	NPC300017
0.7938	Intermediate Similarity	NPC113460
0.7938	Intermediate Similarity	NPC25493
0.7925	Intermediate Similarity	NPC29883
0.7909	Intermediate Similarity	NPC294941
0.7909	Intermediate Similarity	NPC328593
0.7909	Intermediate Similarity	NPC33749
0.7909	Intermediate Similarity	NPC217472
0.7909	Intermediate Similarity	NPC261453
0.7905	Intermediate Similarity	NPC128730
0.789	Intermediate Similarity	NPC17693
0.789	Intermediate Similarity	NPC199462
0.789	Intermediate Similarity	NPC131530
0.7885	Intermediate Similarity	NPC477802
0.7885	Intermediate Similarity	NPC477801
0.7879	Intermediate Similarity	NPC45040
0.7879	Intermediate Similarity	NPC270547
0.7857	Intermediate Similarity	NPC123273
0.7857	Intermediate Similarity	NPC258219
0.7857	Intermediate Similarity	NPC242240
0.7857	Intermediate Similarity	NPC177420
0.7857	Intermediate Similarity	NPC318325
0.7857	Intermediate Similarity	NPC280347
0.7857	Intermediate Similarity	NPC98772
0.7843	Intermediate Similarity	NPC260000
0.7843	Intermediate Similarity	NPC175298
0.7838	Intermediate Similarity	NPC233669
0.7838	Intermediate Similarity	NPC474967
0.783	Intermediate Similarity	NPC6984
0.783	Intermediate Similarity	NPC19149
0.783	Intermediate Similarity	NPC29989
0.783	Intermediate Similarity	NPC70843
0.783	Intermediate Similarity	NPC176971
0.783	Intermediate Similarity	NPC95178
0.783	Intermediate Similarity	NPC326447
0.783	Intermediate Similarity	NPC69332
0.78	Intermediate Similarity	NPC138117
0.78	Intermediate Similarity	NPC325292
0.7798	Intermediate Similarity	NPC228609
0.7778	Intermediate Similarity	NPC88141
0.7778	Intermediate Similarity	NPC326187
0.7778	Intermediate Similarity	NPC300478
0.7778	Intermediate Similarity	NPC55561
0.7768	Intermediate Similarity	NPC281277
0.7767	Intermediate Similarity	NPC280869
0.7757	Intermediate Similarity	NPC157473
0.7757	Intermediate Similarity	NPC151530
0.7757	Intermediate Similarity	NPC226699
0.7732	Intermediate Similarity	NPC155393
0.7723	Intermediate Similarity	NPC151715
0.7723	Intermediate Similarity	NPC128062
0.7714	Intermediate Similarity	NPC13426
0.7706	Intermediate Similarity	NPC222084
0.7706	Intermediate Similarity	NPC222905
0.7706	Intermediate Similarity	NPC63345
0.77	Intermediate Similarity	NPC155908
0.77	Intermediate Similarity	NPC204210
0.77	Intermediate Similarity	NPC304541
0.7699	Intermediate Similarity	NPC278652
0.7699	Intermediate Similarity	NPC65791
0.7699	Intermediate Similarity	NPC122117
0.7692	Intermediate Similarity	NPC107101
0.7692	Intermediate Similarity	NPC13755
0.7685	Intermediate Similarity	NPC31274
0.7685	Intermediate Similarity	NPC17525
0.7679	Intermediate Similarity	NPC296526
0.7664	Intermediate Similarity	NPC187913
0.7653	Intermediate Similarity	NPC407
0.7653	Intermediate Similarity	NPC307235
0.7647	Intermediate Similarity	NPC313650
0.7647	Intermediate Similarity	NPC26244
0.7647	Intermediate Similarity	NPC274678
0.7642	Intermediate Similarity	NPC283546
0.7636	Intermediate Similarity	NPC470355
0.7636	Intermediate Similarity	NPC297657
0.7632	Intermediate Similarity	NPC203124
0.7632	Intermediate Similarity	NPC275519
0.7632	Intermediate Similarity	NPC107588
0.7632	Intermediate Similarity	NPC309434
0.7632	Intermediate Similarity	NPC164706
0.7632	Intermediate Similarity	NPC272471
0.7632	Intermediate Similarity	NPC124916
0.7632	Intermediate Similarity	NPC137537
0.7632	Intermediate Similarity	NPC70744
0.7629	Intermediate Similarity	NPC286904
0.7629	Intermediate Similarity	NPC150837
0.7619	Intermediate Similarity	NPC307425
0.7615	Intermediate Similarity	NPC95172
0.7611	Intermediate Similarity	NPC128249
0.7611	Intermediate Similarity	NPC471936
0.7611	Intermediate Similarity	NPC131192
0.7596	Intermediate Similarity	NPC275104
0.7589	Intermediate Similarity	NPC197513
0.7586	Intermediate Similarity	NPC319378
0.7582	Intermediate Similarity	NPC32203
0.7582	Intermediate Similarity	NPC206800
0.7576	Intermediate Similarity	NPC27974
0.7573	Intermediate Similarity	NPC292730
0.7573	Intermediate Similarity	NPC216520
0.7573	Intermediate Similarity	NPC132271
0.7573	Intermediate Similarity	NPC473388
0.7573	Intermediate Similarity	NPC82664
0.757	Intermediate Similarity	NPC219913
0.7568	Intermediate Similarity	NPC51698
0.7568	Intermediate Similarity	NPC48525
0.7565	Intermediate Similarity	NPC263386
0.7565	Intermediate Similarity	NPC264976
0.7565	Intermediate Similarity	NPC141791
0.7565	Intermediate Similarity	NPC57501
0.7565	Intermediate Similarity	NPC37858
0.7549	Intermediate Similarity	NPC27323
0.7549	Intermediate Similarity	NPC316301
0.7545	Intermediate Similarity	NPC116842
0.7545	Intermediate Similarity	NPC21162
0.7545	Intermediate Similarity	NPC473809
0.7524	Intermediate Similarity	NPC223393
0.7523	Intermediate Similarity	NPC100551
0.75	Intermediate Similarity	NPC264558
0.75	Intermediate Similarity	NPC70436
0.75	Intermediate Similarity	NPC317592
0.75	Intermediate Similarity	NPC148969
0.75	Intermediate Similarity	NPC309808
0.75	Intermediate Similarity	NPC109955
0.75	Intermediate Similarity	NPC188677
0.75	Intermediate Similarity	NPC107619
0.75	Intermediate Similarity	NPC202474
0.7478	Intermediate Similarity	NPC273282
0.7478	Intermediate Similarity	NPC311091
0.7478	Intermediate Similarity	NPC471033
0.7478	Intermediate Similarity	NPC27633
0.7478	Intermediate Similarity	NPC94298
0.7478	Intermediate Similarity	NPC474890
0.7478	Intermediate Similarity	NPC161943
0.7477	Intermediate Similarity	NPC8931
0.7477	Intermediate Similarity	NPC120693
0.7477	Intermediate Similarity	NPC212718
0.7477	Intermediate Similarity	NPC114682
0.7477	Intermediate Similarity	NPC268388
0.7477	Intermediate Similarity	NPC261573
0.7476	Intermediate Similarity	NPC8392
0.7476	Intermediate Similarity	NPC107522
0.7455	Intermediate Similarity	NPC234639
0.7453	Intermediate Similarity	NPC7686
0.7453	Intermediate Similarity	NPC91461
0.7453	Intermediate Similarity	NPC40258
0.7436	Intermediate Similarity	NPC476872
0.7436	Intermediate Similarity	NPC204466

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 NPC140619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1147
0.2-0.3	1463
0.3-0.4	3088
0.4-0.5	1980
0.5-0.6	982
0.6-0.7	231
0.7-0.8	36
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8085	Intermediate Similarity	NPD111	Approved
0.7925	Intermediate Similarity	NPD1358	Approved
0.7925	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD3134	Approved
0.7723	Intermediate Similarity	NPD2933	Approved
0.7723	Intermediate Similarity	NPD2934	Approved
0.7647	Intermediate Similarity	NPD2859	Approved
0.7647	Intermediate Similarity	NPD2860	Approved
0.7593	Intermediate Similarity	NPD9264	Approved
0.7593	Intermediate Similarity	NPD9263	Approved
0.7593	Intermediate Similarity	NPD9267	Approved
0.7582	Intermediate Similarity	NPD9716	Approved
0.7549	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD9266	Approved
0.7523	Intermediate Similarity	NPD74	Approved
0.7478	Intermediate Similarity	NPD9545	Approved
0.7429	Intermediate Similarity	NPD3020	Approved
0.7407	Intermediate Similarity	NPD9697	Approved
0.7383	Intermediate Similarity	NPD9261	Approved
0.7358	Intermediate Similarity	NPD1242	Phase 1
0.7327	Intermediate Similarity	NPD9258	Approved
0.7327	Intermediate Similarity	NPD9256	Approved
0.7304	Intermediate Similarity	NPD9493	Approved
0.729	Intermediate Similarity	NPD846	Approved
0.729	Intermediate Similarity	NPD940	Approved
0.7281	Intermediate Similarity	NPD9281	Approved
0.7217	Intermediate Similarity	NPD255	Approved
0.7217	Intermediate Similarity	NPD256	Approved
0.7203	Intermediate Similarity	NPD4626	Approved
0.7196	Intermediate Similarity	NPD3028	Approved
0.7155	Intermediate Similarity	NPD9568	Approved
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD1809	Phase 2
0.7115	Intermediate Similarity	NPD845	Approved
0.7115	Intermediate Similarity	NPD1202	Approved
0.7105	Intermediate Similarity	NPD5535	Approved
0.71	Intermediate Similarity	NPD9257	Approved
0.71	Intermediate Similarity	NPD9259	Approved
0.7097	Intermediate Similarity	NPD9087	Approved
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7075	Intermediate Similarity	NPD288	Approved
0.7037	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD9610	Approved
0.7	Intermediate Similarity	NPD9608	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6992	Remote Similarity	NPD1164	Approved
0.6991	Remote Similarity	NPD3021	Approved
0.6991	Remote Similarity	NPD3022	Approved
0.6983	Remote Similarity	NPD475	Phase 2
0.6979	Remote Similarity	NPD9088	Approved
0.6975	Remote Similarity	NPD9268	Approved
0.6949	Remote Similarity	NPD1758	Phase 1
0.6942	Remote Similarity	NPD1535	Discovery
0.6897	Remote Similarity	NPD1241	Discontinued
0.6891	Remote Similarity	NPD1759	Phase 1
0.6885	Remote Similarity	NPD9269	Phase 2
0.6885	Remote Similarity	NPD1481	Phase 2
0.6875	Remote Similarity	NPD9294	Approved
0.686	Remote Similarity	NPD3847	Discontinued
0.686	Remote Similarity	NPD3026	Approved
0.686	Remote Similarity	NPD3023	Approved
0.6855	Remote Similarity	NPD1203	Approved
0.6852	Remote Similarity	NPD9273	Approved
0.6852	Remote Similarity	NPD9495	Approved
0.685	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5691	Approved
0.6829	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5536	Phase 2
0.68	Remote Similarity	NPD9491	Approved
0.68	Remote Similarity	NPD3971	Phase 1
0.6774	Remote Similarity	NPD3225	Approved
0.6754	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2684	Approved
0.675	Remote Similarity	NPD1894	Discontinued
0.6729	Remote Similarity	NPD9260	Approved
0.6726	Remote Similarity	NPD968	Approved
0.6724	Remote Similarity	NPD228	Approved
0.6723	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1296	Phase 2
0.67	Remote Similarity	NPD9089	Approved
0.6699	Remote Similarity	NPD1282	Approved
0.6695	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3025	Approved
0.6694	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3024	Approved
0.6692	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD9377	Approved
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD9379	Approved
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6639	Remote Similarity	NPD3095	Discontinued
0.6638	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD9712	Approved
0.6636	Remote Similarity	NPD1238	Approved
0.6614	Remote Similarity	NPD9569	Approved
0.661	Remote Similarity	NPD2228	Approved
0.661	Remote Similarity	NPD2234	Approved
0.661	Remote Similarity	NPD2229	Approved
0.6607	Remote Similarity	NPD6647	Phase 2
0.6607	Remote Similarity	NPD9500	Approved
0.66	Remote Similarity	NPD226	Approved
0.66	Remote Similarity	NPD9093	Approved
0.6587	Remote Similarity	NPD2797	Approved
0.6581	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD969	Suspended
0.6579	Remote Similarity	NPD1445	Approved
0.6579	Remote Similarity	NPD1444	Approved
0.6571	Remote Similarity	NPD689	Discontinued
0.6566	Remote Similarity	NPD9490	Approved
0.6565	Remote Similarity	NPD230	Phase 1
0.6549	Remote Similarity	NPD1237	Approved
0.6549	Remote Similarity	NPD164	Approved
0.6545	Remote Similarity	NPD9710	Approved
0.6545	Remote Similarity	NPD9095	Approved
0.6545	Remote Similarity	NPD9096	Approved
0.6545	Remote Similarity	NPD68	Approved
0.6545	Remote Similarity	NPD9711	Approved
0.6545	Remote Similarity	NPD9097	Approved
0.6538	Remote Similarity	NPD520	Approved
0.6525	Remote Similarity	NPD5277	Phase 2
0.6525	Remote Similarity	NPD821	Approved
0.6522	Remote Similarity	NPD290	Approved
0.6512	Remote Similarity	NPD3136	Phase 2
0.6508	Remote Similarity	NPD196	Phase 1
0.6508	Remote Similarity	NPD1283	Approved
0.6504	Remote Similarity	NPD1778	Approved
0.6504	Remote Similarity	NPD2932	Approved
0.6504	Remote Similarity	NPD3019	Approved
0.65	Remote Similarity	NPD7157	Approved
0.6493	Remote Similarity	NPD2935	Discontinued
0.6489	Remote Similarity	NPD468	Phase 1
0.6486	Remote Similarity	NPD2066	Phase 3
0.6484	Remote Similarity	NPD9494	Approved
0.6484	Remote Similarity	NPD5736	Approved
0.6481	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD227	Approved
0.6465	Remote Similarity	NPD225	Approved
0.6462	Remote Similarity	NPD411	Approved
0.6462	Remote Similarity	NPD3268	Approved
0.6457	Remote Similarity	NPD1470	Approved
0.6457	Remote Similarity	NPD987	Approved
0.6457	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7266	Discontinued
0.6441	Remote Similarity	NPD9508	Approved
0.6439	Remote Similarity	NPD447	Suspended
0.6434	Remote Similarity	NPD2614	Approved
0.6423	Remote Similarity	NPD1357	Approved
0.6418	Remote Similarity	NPD2799	Discontinued
0.6415	Remote Similarity	NPD800	Approved
0.6415	Remote Similarity	NPD9295	Approved
0.6412	Remote Similarity	NPD259	Phase 1
0.6412	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1792	Phase 2
0.641	Remote Similarity	NPD5451	Approved
0.641	Remote Similarity	NPD4750	Phase 3
0.6406	Remote Similarity	NPD1019	Discontinued
0.6404	Remote Similarity	NPD5909	Discontinued
0.64	Remote Similarity	NPD1201	Approved
0.64	Remote Similarity	NPD1281	Approved
0.6393	Remote Similarity	NPD856	Approved
0.6393	Remote Similarity	NPD16	Approved
0.6393	Remote Similarity	NPD317	Approved
0.6393	Remote Similarity	NPD318	Approved
0.6389	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7095	Approved
0.6385	Remote Similarity	NPD9537	Phase 1
0.6385	Remote Similarity	NPD9536	Phase 1
0.6379	Remote Similarity	NPD2342	Discontinued
0.6371	Remote Similarity	NPD1104	Approved
0.637	Remote Similarity	NPD5405	Approved
0.637	Remote Similarity	NPD5404	Approved
0.637	Remote Similarity	NPD5408	Approved
0.637	Remote Similarity	NPD5406	Approved
0.6364	Remote Similarity	NPD6387	Discontinued
0.6364	Remote Similarity	NPD826	Approved
0.6364	Remote Similarity	NPD825	Approved
0.6364	Remote Similarity	NPD943	Approved
0.6364	Remote Similarity	NPD4060	Phase 1
0.6357	Remote Similarity	NPD454	Approved
0.6357	Remote Similarity	NPD4212	Discontinued
0.6355	Remote Similarity	NPD1089	Approved
0.6355	Remote Similarity	NPD1090	Approved
0.6355	Remote Similarity	NPD1086	Approved
0.635	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD1608	Approved
0.6349	Remote Similarity	NPD3972	Approved
0.6346	Remote Similarity	NPD9073	Approved
0.6341	Remote Similarity	NPD1548	Phase 1
0.6341	Remote Similarity	NPD3091	Approved
0.6336	Remote Similarity	NPD6798	Discontinued
0.6336	Remote Similarity	NPD6859	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