NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	287.288
LogP:	4.1
LogD:	3.713
LogS:	-5.218
# Rotatable Bonds:	6
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	2.257
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.532
MDCK Permeability:	2.155448055418674e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	92.54938507080078%
Volume Distribution (VD):	2.069
Pgp-substrate:	8.150190353393555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.593
CYP2D6-substrate:	0.776
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	11.871
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.939
Carcinogencity:	0.196
Eye Corrosion:	0.02
Eye Irritation:	0.529
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC473809

Natural Product ID:	NPC473809
*Common Name:**	Palicatin B Methyl Ether
IUPAC Name:	methyl (E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoate
Synonyms:	palicatin B methyl ether
Standard InCHIKey:	PPFGVSIVQVZNNN-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-12(2)5-8-14-11-13(6-9-15(14)18-3)7-10-16(17)19-4/h5-7,9-11H,8H2,1-4H3/b10-7+
SMILES:	COC(=O)/C=C/c1ccc(c(c1)CC=C(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452480
PubChem CID:	10706469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO32851	brazilian green propolis	Species	n.a.	n.a.	n.a.	Brazilian green propolis	n.a.	PMID[21865046]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	37600.0	nM	PMID[550689]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	13.2	%	PMID[550688]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	21.5	%	PMID[550688]
NPT2	Others	Unspecified		Ratio	=	1.17	n.a.	PMID[550689]

☑ 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 NPC473809 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	267
0.1-0.2	1702
0.2-0.3	4667
0.3-0.4	12230
0.4-0.5	5882
0.5-0.6	7496
0.6-0.7	8914
0.7-0.8	1435
0.8-0.85	77
0.85-0.9	19
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC199462
0.9048	High Similarity	NPC326447
0.9009	High Similarity	NPC183154
0.9009	High Similarity	NPC263754
0.8972	High Similarity	NPC75272
0.8972	High Similarity	NPC471954
0.8962	High Similarity	NPC157473
0.8962	High Similarity	NPC151530
0.8952	High Similarity	NPC227255
0.8942	High Similarity	NPC179686
0.8868	High Similarity	NPC176971
0.8857	High Similarity	NPC2518
0.8774	High Similarity	NPC128730
0.8774	High Similarity	NPC473855
0.8738	High Similarity	NPC175298
0.8718	High Similarity	NPC201667
0.8718	High Similarity	NPC73413
0.8707	High Similarity	NPC248429
0.8707	High Similarity	NPC96286
0.8679	High Similarity	NPC109637
0.8667	High Similarity	NPC84325
0.8649	High Similarity	NPC90903
0.8632	High Similarity	NPC472518
0.8632	High Similarity	NPC109675
0.8632	High Similarity	NPC273772
0.8598	High Similarity	NPC243677
0.8598	High Similarity	NPC303141
0.8571	High Similarity	NPC13755
0.8559	High Similarity	NPC89630
0.8559	High Similarity	NPC27671
0.8534	High Similarity	NPC131868
0.8522	High Similarity	NPC98748
0.8519	High Similarity	NPC1065
0.8491	Intermediate Similarity	NPC307425
0.8487	Intermediate Similarity	NPC471828
0.8487	Intermediate Similarity	NPC471827
0.8462	Intermediate Similarity	NPC251259
0.8431	Intermediate Similarity	NPC321956
0.843	Intermediate Similarity	NPC472519
0.8426	Intermediate Similarity	NPC139891
0.8426	Intermediate Similarity	NPC473393
0.8426	Intermediate Similarity	NPC288760
0.8426	Intermediate Similarity	NPC238115
0.8411	Intermediate Similarity	NPC470202
0.8403	Intermediate Similarity	NPC291899
0.8396	Intermediate Similarity	NPC107101
0.8376	Intermediate Similarity	NPC235190
0.8376	Intermediate Similarity	NPC322569
0.8376	Intermediate Similarity	NPC180006
0.8364	Intermediate Similarity	NPC470039
0.8347	Intermediate Similarity	NPC473993
0.8347	Intermediate Similarity	NPC293387
0.8347	Intermediate Similarity	NPC37512
0.8347	Intermediate Similarity	NPC243688
0.8347	Intermediate Similarity	NPC121104
0.8333	Intermediate Similarity	NPC296526
0.8333	Intermediate Similarity	NPC283546
0.8333	Intermediate Similarity	NPC71853
0.8319	Intermediate Similarity	NPC35344
0.8319	Intermediate Similarity	NPC141003
0.8305	Intermediate Similarity	NPC144418
0.8293	Intermediate Similarity	NPC183348
0.8293	Intermediate Similarity	NPC282230
0.8288	Intermediate Similarity	NPC234639
0.8288	Intermediate Similarity	NPC149545
0.8279	Intermediate Similarity	NPC185066
0.8279	Intermediate Similarity	NPC478215
0.8276	Intermediate Similarity	NPC96705
0.8276	Intermediate Similarity	NPC265547
0.8276	Intermediate Similarity	NPC293424
0.8269	Intermediate Similarity	NPC471581
0.8264	Intermediate Similarity	NPC188327
0.8264	Intermediate Similarity	NPC234109
0.8264	Intermediate Similarity	NPC471826
0.825	Intermediate Similarity	NPC111347
0.8246	Intermediate Similarity	NPC87563
0.8241	Intermediate Similarity	NPC298224
0.8235	Intermediate Similarity	NPC257188
0.8235	Intermediate Similarity	NPC13007
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC259134
0.823	Intermediate Similarity	NPC280760
0.8226	Intermediate Similarity	NPC196979
0.8226	Intermediate Similarity	NPC15083
0.8226	Intermediate Similarity	NPC470977
0.8226	Intermediate Similarity	NPC470976
0.8224	Intermediate Similarity	NPC253746
0.822	Intermediate Similarity	NPC163200
0.8214	Intermediate Similarity	NPC88868
0.8214	Intermediate Similarity	NPC231251
0.8214	Intermediate Similarity	NPC25067
0.8211	Intermediate Similarity	NPC168710
0.8211	Intermediate Similarity	NPC66246
0.8211	Intermediate Similarity	NPC170546
0.8208	Intermediate Similarity	NPC470161
0.8205	Intermediate Similarity	NPC281356
0.8205	Intermediate Similarity	NPC298796
0.8198	Intermediate Similarity	NPC291837
0.819	Intermediate Similarity	NPC469954
0.8182	Intermediate Similarity	NPC244495
0.8182	Intermediate Similarity	NPC113457
0.8182	Intermediate Similarity	NPC165556
0.8182	Intermediate Similarity	NPC93219
0.8174	Intermediate Similarity	NPC220540
0.8174	Intermediate Similarity	NPC188907
0.8167	Intermediate Similarity	NPC290605
0.8167	Intermediate Similarity	NPC154176
0.8167	Intermediate Similarity	NPC50720
0.8167	Intermediate Similarity	NPC173350
0.8167	Intermediate Similarity	NPC315807
0.8165	Intermediate Similarity	NPC38209
0.816	Intermediate Similarity	NPC14248
0.8158	Intermediate Similarity	NPC109241
0.8148	Intermediate Similarity	NPC300166
0.8145	Intermediate Similarity	NPC80170
0.8142	Intermediate Similarity	NPC470723
0.8142	Intermediate Similarity	NPC139946
0.8142	Intermediate Similarity	NPC23332
0.8131	Intermediate Similarity	NPC100870
0.813	Intermediate Similarity	NPC157212
0.813	Intermediate Similarity	NPC199204
0.8125	Intermediate Similarity	NPC259554
0.812	Intermediate Similarity	NPC277460
0.812	Intermediate Similarity	NPC152306
0.8103	Intermediate Similarity	NPC33717
0.8103	Intermediate Similarity	NPC19290
0.8103	Intermediate Similarity	NPC128633
0.8095	Intermediate Similarity	NPC133956
0.8095	Intermediate Similarity	NPC222036
0.8095	Intermediate Similarity	NPC296624
0.8095	Intermediate Similarity	NPC31849
0.8095	Intermediate Similarity	NPC167111
0.8095	Intermediate Similarity	NPC318400
0.8095	Intermediate Similarity	NPC207002
0.8095	Intermediate Similarity	NPC7526
0.8095	Intermediate Similarity	NPC471910
0.8091	Intermediate Similarity	NPC470393
0.8087	Intermediate Similarity	NPC114144
0.8087	Intermediate Similarity	NPC294941
0.8083	Intermediate Similarity	NPC150214
0.8083	Intermediate Similarity	NPC67300
0.8073	Intermediate Similarity	NPC304638
0.8073	Intermediate Similarity	NPC12870
0.8073	Intermediate Similarity	NPC24327
0.8053	Intermediate Similarity	NPC183700
0.8053	Intermediate Similarity	NPC183648
0.8051	Intermediate Similarity	NPC264976
0.8051	Intermediate Similarity	NPC69670
0.8036	Intermediate Similarity	NPC206341
0.8034	Intermediate Similarity	NPC45104
0.8034	Intermediate Similarity	NPC217423
0.8033	Intermediate Similarity	NPC470858
0.8033	Intermediate Similarity	NPC232387
0.8031	Intermediate Similarity	NPC307412
0.8031	Intermediate Similarity	NPC55149
0.8031	Intermediate Similarity	NPC84894
0.8031	Intermediate Similarity	NPC100986
0.8031	Intermediate Similarity	NPC319859
0.8031	Intermediate Similarity	NPC195343
0.8031	Intermediate Similarity	NPC267412
0.8031	Intermediate Similarity	NPC74655
0.8031	Intermediate Similarity	NPC166672
0.8031	Intermediate Similarity	NPC198381
0.8031	Intermediate Similarity	NPC260265
0.8031	Intermediate Similarity	NPC287182
0.8031	Intermediate Similarity	NPC47163
0.8031	Intermediate Similarity	NPC18804
0.8031	Intermediate Similarity	NPC164269
0.8031	Intermediate Similarity	NPC127888
0.8017	Intermediate Similarity	NPC141252
0.8017	Intermediate Similarity	NPC11799
0.8016	Intermediate Similarity	NPC19157
0.8	Intermediate Similarity	NPC303522
0.8	Intermediate Similarity	NPC38079
0.8	Intermediate Similarity	NPC327457
0.8	Intermediate Similarity	NPC108875
0.8	Intermediate Similarity	NPC86774
0.8	Intermediate Similarity	NPC32463
0.7984	Intermediate Similarity	NPC219923
0.7983	Intermediate Similarity	NPC31314
0.7983	Intermediate Similarity	NPC474874
0.7983	Intermediate Similarity	NPC193193
0.7969	Intermediate Similarity	NPC86892
0.7969	Intermediate Similarity	NPC469675
0.7969	Intermediate Similarity	NPC472424
0.7969	Intermediate Similarity	NPC471625
0.7969	Intermediate Similarity	NPC471909
0.7969	Intermediate Similarity	NPC281241
0.7967	Intermediate Similarity	NPC329272
0.7966	Intermediate Similarity	NPC131118
0.7965	Intermediate Similarity	NPC474272
0.7963	Intermediate Similarity	NPC471576
0.7953	Intermediate Similarity	NPC54503
0.7953	Intermediate Similarity	NPC55147
0.7951	Intermediate Similarity	NPC60517
0.7951	Intermediate Similarity	NPC470163
0.7951	Intermediate Similarity	NPC184219
0.7951	Intermediate Similarity	NPC470162

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 NPC473809 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	1075
0.2-0.3	1339
0.3-0.4	2673
0.4-0.5	1912
0.5-0.6	1166
0.6-0.7	608
0.7-0.8	108
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD3134	Approved
0.9018	High Similarity	NPD5691	Approved
0.8938	High Similarity	NPD4626	Approved
0.8785	High Similarity	NPD1358	Approved
0.8426	Intermediate Similarity	NPD9697	Approved
0.8393	Intermediate Similarity	NPD5535	Approved
0.8067	Intermediate Similarity	NPD3496	Discontinued
0.8036	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD1241	Discontinued
0.7982	Intermediate Similarity	NPD1139	Approved
0.7982	Intermediate Similarity	NPD1137	Approved
0.7965	Intermediate Similarity	NPD5451	Approved
0.7917	Intermediate Similarity	NPD3847	Discontinued
0.7913	Intermediate Similarity	NPD1138	Approved
0.7851	Intermediate Similarity	NPD1281	Approved
0.7851	Intermediate Similarity	NPD422	Phase 1
0.7846	Intermediate Similarity	NPD2935	Discontinued
0.7787	Intermediate Similarity	NPD3972	Approved
0.7769	Intermediate Similarity	NPD2799	Discontinued
0.7759	Intermediate Similarity	NPD7843	Approved
0.775	Intermediate Similarity	NPD1651	Approved
0.7742	Intermediate Similarity	NPD2797	Approved
0.7734	Intermediate Similarity	NPD4060	Phase 1
0.7731	Intermediate Similarity	NPD5536	Phase 2
0.7712	Intermediate Similarity	NPD6387	Discontinued
0.7705	Intermediate Similarity	NPD1611	Approved
0.7698	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD5283	Phase 1
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1283	Approved
0.7612	Intermediate Similarity	NPD7003	Approved
0.76	Intermediate Similarity	NPD3266	Approved
0.76	Intermediate Similarity	NPD3267	Approved
0.7581	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6798	Discontinued
0.7563	Intermediate Similarity	NPD7157	Approved
0.7541	Intermediate Similarity	NPD1778	Approved
0.754	Intermediate Similarity	NPD2798	Approved
0.7538	Intermediate Similarity	NPD5124	Phase 1
0.7538	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1894	Discontinued
0.752	Intermediate Similarity	NPD1876	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7478	Intermediate Similarity	NPD290	Approved
0.7462	Intermediate Similarity	NPD2979	Phase 3
0.7459	Intermediate Similarity	NPD5585	Approved
0.7458	Intermediate Similarity	NPD821	Approved
0.7444	Intermediate Similarity	NPD4476	Approved
0.7444	Intermediate Similarity	NPD4477	Approved
0.7442	Intermediate Similarity	NPD2313	Discontinued
0.7442	Intermediate Similarity	NPD3268	Approved
0.7442	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6671	Approved
0.7417	Intermediate Similarity	NPD2557	Approved
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7402	Intermediate Similarity	NPD1019	Discontinued
0.7402	Intermediate Similarity	NPD3690	Phase 2
0.7402	Intermediate Similarity	NPD3691	Phase 2
0.7395	Intermediate Similarity	NPD594	Approved
0.7395	Intermediate Similarity	NPD592	Approved
0.7377	Intermediate Similarity	NPD9545	Approved
0.7373	Intermediate Similarity	NPD228	Approved
0.7364	Intermediate Similarity	NPD2860	Approved
0.7364	Intermediate Similarity	NPD1809	Phase 2
0.7364	Intermediate Similarity	NPD2859	Approved
0.7355	Intermediate Similarity	NPD3596	Phase 2
0.7344	Intermediate Similarity	NPD2237	Approved
0.7339	Intermediate Similarity	NPD845	Approved
0.7328	Intermediate Similarity	NPD4140	Approved
0.7328	Intermediate Similarity	NPD4307	Phase 2
0.7328	Intermediate Similarity	NPD2203	Discontinued
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7302	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7644	Approved
0.7293	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD2934	Approved
0.7259	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2667	Approved
0.7258	Intermediate Similarity	NPD2668	Approved
0.7258	Intermediate Similarity	NPD17	Approved
0.7252	Intermediate Similarity	NPD8032	Phase 2
0.7244	Intermediate Similarity	NPD3225	Approved
0.7244	Intermediate Similarity	NPD8651	Approved
0.7239	Intermediate Similarity	NPD3748	Approved
0.7236	Intermediate Similarity	NPD6580	Approved
0.7236	Intermediate Similarity	NPD6581	Approved
0.7231	Intermediate Similarity	NPD5746	Approved
0.7231	Intermediate Similarity	NPD5163	Phase 2
0.7231	Intermediate Similarity	NPD7095	Approved
0.7218	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2424	Discontinued
0.7197	Intermediate Similarity	NPD1240	Approved
0.7193	Intermediate Similarity	NPD846	Approved
0.7193	Intermediate Similarity	NPD940	Approved
0.719	Intermediate Similarity	NPD593	Approved
0.719	Intermediate Similarity	NPD595	Approved
0.7188	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD987	Approved
0.7185	Intermediate Similarity	NPD2531	Phase 2
0.7185	Intermediate Similarity	NPD2796	Approved
0.7185	Intermediate Similarity	NPD2438	Suspended
0.7183	Intermediate Similarity	NPD7458	Discontinued
0.7177	Intermediate Similarity	NPD3443	Approved
0.7177	Intermediate Similarity	NPD3049	Approved
0.7177	Intermediate Similarity	NPD3444	Approved
0.7177	Intermediate Similarity	NPD3445	Approved
0.7177	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3020	Approved
0.7165	Intermediate Similarity	NPD4359	Approved
0.7165	Intermediate Similarity	NPD5327	Phase 3
0.7165	Intermediate Similarity	NPD3685	Discontinued
0.7165	Intermediate Similarity	NPD1669	Approved
0.7153	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4618	Approved
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD4622	Approved
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2346	Discontinued
0.7131	Intermediate Similarity	NPD709	Approved
0.713	Intermediate Similarity	NPD9261	Approved
0.7122	Intermediate Similarity	NPD6667	Approved
0.7122	Intermediate Similarity	NPD6666	Approved
0.7121	Intermediate Similarity	NPD5745	Approved
0.7121	Intermediate Similarity	NPD6233	Phase 2
0.7121	Intermediate Similarity	NPD4062	Phase 3
0.712	Intermediate Similarity	NPD5846	Approved
0.712	Intermediate Similarity	NPD6516	Phase 2
0.7117	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4308	Phase 3
0.7109	Intermediate Similarity	NPD196	Phase 1
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7094	Intermediate Similarity	NPD968	Approved
0.7092	Intermediate Similarity	NPD5049	Phase 3
0.709	Intermediate Similarity	NPD1607	Approved
0.7087	Intermediate Similarity	NPD1481	Phase 2
0.7087	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7071	Intermediate Similarity	NPD6799	Approved
0.7068	Intermediate Similarity	NPD3142	Approved
0.7068	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD2862	Discontinued
0.7054	Intermediate Similarity	NPD844	Approved
0.705	Intermediate Similarity	NPD3887	Approved
0.704	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5688	Approved
0.7037	Intermediate Similarity	NPD5689	Approved
0.7031	Intermediate Similarity	NPD6582	Phase 2
0.7031	Intermediate Similarity	NPD6583	Phase 3
0.7029	Intermediate Similarity	NPD1652	Phase 2
0.7023	Intermediate Similarity	NPD4908	Phase 1
0.7023	Intermediate Similarity	NPD2614	Approved
0.7008	Intermediate Similarity	NPD1610	Phase 2
0.7008	Intermediate Similarity	NPD3705	Approved
0.7007	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6002	Phase 3
0.7007	Intermediate Similarity	NPD6005	Phase 3
0.7007	Intermediate Similarity	NPD2353	Approved
0.7007	Intermediate Similarity	NPD5763	Approved
0.7007	Intermediate Similarity	NPD5762	Approved
0.7007	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4624	Approved
0.6986	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7033	Discontinued
0.6984	Remote Similarity	NPD2554	Approved
0.6984	Remote Similarity	NPD2556	Approved
0.6978	Remote Similarity	NPD3750	Approved
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2182	Approved
0.6972	Remote Similarity	NPD6273	Approved
0.6972	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2157	Approved
0.6963	Remote Similarity	NPD4097	Suspended
0.696	Remote Similarity	NPD2486	Discontinued
0.6957	Remote Similarity	NPD3028	Approved
0.6953	Remote Similarity	NPD2230	Approved
0.6953	Remote Similarity	NPD2233	Approved
0.6953	Remote Similarity	NPD2232	Approved
0.6947	Remote Similarity	NPD454	Approved
0.6947	Remote Similarity	NPD2861	Phase 2
0.6944	Remote Similarity	NPD1282	Approved
0.6942	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD6362	Approved
0.6923	Remote Similarity	NPD164	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