NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.13
Volume:	246.542
LogP:	3.352
LogD:	2.986
LogS:	-3.091
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	2.564
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.598
MDCK Permeability:	2.5319590349681675e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	95.9462661743164%
Volume Distribution (VD):	3.732
Pgp-substrate:	4.580868244171143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.299
CYP2C19-inhibitor:	0.334
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.445
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	16.039
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.668
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.947
Carcinogencity:	0.372
Eye Corrosion:	0.05
Eye Irritation:	0.967
Respiratory Toxicity:	0.31

Download Data

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

Natural Product: NPC128723

Natural Product ID:	NPC128723
*Common Name:**	4-Hydroxy-3-(3-Methyl-2-Butenyl)Cinnamyl Alcohol
IUPAC Name:	4-[(E)-3-hydroxyprop-1-enyl]-2-(3-methylbut-2-enyl)phenol
Synonyms:
Standard InCHIKey:	UJHVAGVJXNRBBS-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C14H18O2/c1-11(2)5-7-13-10-12(4-3-9-15)6-8-14(13)16/h3-6,8,10,15-16H,7,9H2,1-2H3/b4-3+
SMILES:	OC/C=C/c1ccc(c(c1)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252311
PubChem CID:	6440309
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		IC50	=	75140.0	nM	PMID[526258]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	20.2	%	PMID[526259]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	27.1	%	PMID[526259]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	36.8	%	PMID[526259]

☑ 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 NPC128723 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	209
0.1-0.2	1400
0.2-0.3	4519
0.3-0.4	13327
0.4-0.5	6640
0.5-0.6	9443
0.6-0.7	5512
0.7-0.8	1298
0.8-0.85	226
0.85-0.9	107
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC204210
0.9263	High Similarity	NPC77492
0.9255	High Similarity	NPC8392
0.9247	High Similarity	NPC138117
0.9247	High Similarity	NPC325292
0.9239	High Similarity	NPC300017
0.9167	High Similarity	NPC122005
0.9167	High Similarity	NPC252821
0.913	High Similarity	NPC242240
0.913	High Similarity	NPC70436
0.913	High Similarity	NPC123273
0.913	High Similarity	NPC318325
0.9072	High Similarity	NPC225506
0.9053	High Similarity	NPC313650
0.9053	High Similarity	NPC144682
0.9022	High Similarity	NPC25493
0.9022	High Similarity	NPC104216
0.9022	High Similarity	NPC113460
0.901	High Similarity	NPC262365
0.8969	High Similarity	NPC51333
0.8969	High Similarity	NPC78119
0.8969	High Similarity	NPC216468
0.8969	High Similarity	NPC132078
0.8947	High Similarity	NPC128062
0.8947	High Similarity	NPC289769
0.8925	High Similarity	NPC258219
0.8925	High Similarity	NPC280347
0.8925	High Similarity	NPC177420
0.8913	High Similarity	NPC407
0.8913	High Similarity	NPC307235
0.8913	High Similarity	NPC23167
0.89	High Similarity	NPC303141
0.89	High Similarity	NPC138942
0.8889	High Similarity	NPC235762
0.8889	High Similarity	NPC471228
0.8889	High Similarity	NPC168829
0.8878	High Similarity	NPC213730
0.8878	High Similarity	NPC174911
0.8866	High Similarity	NPC474073
0.8854	High Similarity	NPC26244
0.8846	High Similarity	NPC228425
0.8835	High Similarity	NPC44732
0.883	High Similarity	NPC47950
0.883	High Similarity	NPC300478
0.883	High Similarity	NPC55561
0.8804	High Similarity	NPC155393
0.8804	High Similarity	NPC197783
0.88	High Similarity	NPC475225
0.88	High Similarity	NPC288411
0.8788	High Similarity	NPC91461
0.8788	High Similarity	NPC7686
0.8788	High Similarity	NPC40258
0.8763	High Similarity	NPC473388
0.875	High Similarity	NPC27323
0.875	High Similarity	NPC308689
0.875	High Similarity	NPC316301
0.875	High Similarity	NPC152415
0.875	High Similarity	NPC151715
0.8738	High Similarity	NPC75272
0.8738	High Similarity	NPC471954
0.8737	High Similarity	NPC45040
0.8737	High Similarity	NPC304541
0.8737	High Similarity	NPC306074
0.8725	High Similarity	NPC228737
0.8713	High Similarity	NPC154899
0.8713	High Similarity	NPC243677
0.8713	High Similarity	NPC233396
0.871	High Similarity	NPC184169
0.87	High Similarity	NPC470202
0.87	High Similarity	NPC108497
0.8696	High Similarity	NPC286904
0.8696	High Similarity	NPC175313
0.8696	High Similarity	NPC248817
0.8679	High Similarity	NPC12656
0.8641	High Similarity	NPC63698
0.8641	High Similarity	NPC61885
0.8627	High Similarity	NPC92623
0.8627	High Similarity	NPC135464
0.8627	High Similarity	NPC271274
0.86	High Similarity	NPC471578
0.86	High Similarity	NPC101025
0.8598	High Similarity	NPC474486
0.8587	High Similarity	NPC265146
0.8587	High Similarity	NPC124436
0.8586	High Similarity	NPC80027
0.8586	High Similarity	NPC92730
0.8544	High Similarity	NPC66834
0.8542	High Similarity	NPC155908
0.8542	High Similarity	NPC270547
0.8529	High Similarity	NPC99557
0.8529	High Similarity	NPC219286
0.8526	High Similarity	NPC98772
0.8515	High Similarity	NPC269212
0.8505	High Similarity	NPC473137
0.8505	High Similarity	NPC268160
0.85	High Similarity	NPC130103
0.85	High Similarity	NPC48730
0.85	High Similarity	NPC72729
0.85	High Similarity	NPC294741
0.85	High Similarity	NPC129373
0.85	High Similarity	NPC211885
0.85	High Similarity	NPC248396
0.8491	Intermediate Similarity	NPC228988
0.8491	Intermediate Similarity	NPC302371
0.8485	Intermediate Similarity	NPC6597
0.8485	Intermediate Similarity	NPC152097
0.8485	Intermediate Similarity	NPC79241
0.8485	Intermediate Similarity	NPC225464
0.8476	Intermediate Similarity	NPC296683
0.8476	Intermediate Similarity	NPC132720
0.8476	Intermediate Similarity	NPC475018
0.8469	Intermediate Similarity	NPC274678
0.8469	Intermediate Similarity	NPC222146
0.8462	Intermediate Similarity	NPC470039
0.8462	Intermediate Similarity	NPC317305
0.8454	Intermediate Similarity	NPC271440
0.8454	Intermediate Similarity	NPC306884
0.8454	Intermediate Similarity	NPC94139
0.8454	Intermediate Similarity	NPC3358
0.8454	Intermediate Similarity	NPC210497
0.8454	Intermediate Similarity	NPC147284
0.8454	Intermediate Similarity	NPC162314
0.8447	Intermediate Similarity	NPC21594
0.8447	Intermediate Similarity	NPC54765
0.844	Intermediate Similarity	NPC477136
0.8438	Intermediate Similarity	NPC312304
0.8438	Intermediate Similarity	NPC192
0.8431	Intermediate Similarity	NPC119860
0.8426	Intermediate Similarity	NPC192948
0.8426	Intermediate Similarity	NPC35797
0.8426	Intermediate Similarity	NPC147179
0.8421	Intermediate Similarity	NPC19680
0.8421	Intermediate Similarity	NPC27974
0.8416	Intermediate Similarity	NPC110764
0.8416	Intermediate Similarity	NPC51015
0.8411	Intermediate Similarity	NPC35344
0.8411	Intermediate Similarity	NPC141003
0.84	Intermediate Similarity	NPC33675
0.84	Intermediate Similarity	NPC299762
0.84	Intermediate Similarity	NPC100870
0.84	Intermediate Similarity	NPC260775
0.8396	Intermediate Similarity	NPC95716
0.8396	Intermediate Similarity	NPC225679
0.8396	Intermediate Similarity	NPC165770
0.8396	Intermediate Similarity	NPC4493
0.8396	Intermediate Similarity	NPC476632
0.8384	Intermediate Similarity	NPC259512
0.8384	Intermediate Similarity	NPC292730
0.8384	Intermediate Similarity	NPC132271
0.8384	Intermediate Similarity	NPC82664
0.8384	Intermediate Similarity	NPC216520
0.8384	Intermediate Similarity	NPC283711
0.8384	Intermediate Similarity	NPC312132
0.8381	Intermediate Similarity	NPC58865
0.8381	Intermediate Similarity	NPC473524
0.8367	Intermediate Similarity	NPC245187
0.8365	Intermediate Similarity	NPC151477
0.8351	Intermediate Similarity	NPC231150
0.835	Intermediate Similarity	NPC474839
0.835	Intermediate Similarity	NPC471350
0.8349	Intermediate Similarity	NPC477137
0.8349	Intermediate Similarity	NPC38893
0.8349	Intermediate Similarity	NPC308828
0.8349	Intermediate Similarity	NPC219112
0.8349	Intermediate Similarity	NPC308311
0.8333	Intermediate Similarity	NPC62351
0.8318	Intermediate Similarity	NPC43525
0.8318	Intermediate Similarity	NPC473521
0.8318	Intermediate Similarity	NPC46940
0.8317	Intermediate Similarity	NPC12931
0.8317	Intermediate Similarity	NPC70677
0.8317	Intermediate Similarity	NPC130756
0.8302	Intermediate Similarity	NPC13482
0.8302	Intermediate Similarity	NPC63345
0.83	Intermediate Similarity	NPC475078
0.83	Intermediate Similarity	NPC88420
0.83	Intermediate Similarity	NPC260000
0.8288	Intermediate Similarity	NPC473767
0.8288	Intermediate Similarity	NPC151197
0.8286	Intermediate Similarity	NPC95344
0.8283	Intermediate Similarity	NPC286006
0.828	Intermediate Similarity	NPC304538
0.8273	Intermediate Similarity	NPC304510
0.8273	Intermediate Similarity	NPC172219
0.8269	Intermediate Similarity	NPC113457
0.8269	Intermediate Similarity	NPC469913
0.8265	Intermediate Similarity	NPC55903
0.8265	Intermediate Similarity	NPC29373
0.8265	Intermediate Similarity	NPC181709
0.8252	Intermediate Similarity	NPC108875
0.8252	Intermediate Similarity	NPC12278
0.8252	Intermediate Similarity	NPC323810
0.8252	Intermediate Similarity	NPC272029
0.8252	Intermediate Similarity	NPC38079
0.8241	Intermediate Similarity	NPC242136
0.8241	Intermediate Similarity	NPC117846
0.8241	Intermediate Similarity	NPC28784
0.8241	Intermediate Similarity	NPC296144
0.8235	Intermediate Similarity	NPC252105
0.8235	Intermediate Similarity	NPC477685

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 NPC128723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1005
0.2-0.3	1386
0.3-0.4	2826
0.4-0.5	1971
0.5-0.6	1145
0.6-0.7	503
0.7-0.8	93
0.8-0.85	5
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9053	High Similarity	NPD1809	Phase 2
0.9043	High Similarity	NPD845	Approved
0.8854	High Similarity	NPD2859	Approved
0.8854	High Similarity	NPD2860	Approved
0.8788	High Similarity	NPD846	Approved
0.8788	High Similarity	NPD940	Approved
0.875	High Similarity	NPD1432	Clinical (unspecified phase)
0.875	High Similarity	NPD2934	Approved
0.875	High Similarity	NPD2933	Approved
0.866	High Similarity	NPD844	Approved
0.8587	High Similarity	NPD111	Approved
0.8586	High Similarity	NPD3020	Approved
0.8396	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8384	Intermediate Similarity	NPD288	Approved
0.8317	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD2684	Approved
0.7876	Intermediate Similarity	NPD3091	Approved
0.787	Intermediate Similarity	NPD3021	Approved
0.787	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3022	Approved
0.7818	Intermediate Similarity	NPD7635	Approved
0.7797	Intermediate Similarity	NPD1131	Approved
0.7797	Intermediate Similarity	NPD1133	Approved
0.7797	Intermediate Similarity	NPD1129	Approved
0.7797	Intermediate Similarity	NPD1135	Approved
0.7797	Intermediate Similarity	NPD1134	Approved
0.7736	Intermediate Similarity	NPD9610	Approved
0.7736	Intermediate Similarity	NPD9608	Approved
0.7719	Intermediate Similarity	NPD5303	Approved
0.7719	Intermediate Similarity	NPD5304	Approved
0.7717	Intermediate Similarity	NPD9294	Approved
0.7706	Intermediate Similarity	NPD4750	Phase 3
0.7685	Intermediate Similarity	NPD2342	Discontinued
0.7685	Intermediate Similarity	NPD290	Approved
0.7658	Intermediate Similarity	NPD7843	Approved
0.7632	Intermediate Similarity	NPD16	Approved
0.7632	Intermediate Similarity	NPD856	Approved
0.7627	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3028	Approved
0.7619	Intermediate Similarity	NPD1242	Phase 1
0.7607	Intermediate Similarity	NPD3092	Approved
0.7596	Intermediate Similarity	NPD9273	Approved
0.7593	Intermediate Similarity	NPD1445	Approved
0.7593	Intermediate Similarity	NPD1444	Approved
0.7589	Intermediate Similarity	NPD2229	Approved
0.7589	Intermediate Similarity	NPD2228	Approved
0.7589	Intermediate Similarity	NPD2234	Approved
0.7586	Intermediate Similarity	NPD4626	Approved
0.7586	Intermediate Similarity	NPD4589	Approved
0.7586	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD821	Approved
0.75	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD318	Approved
0.7478	Intermediate Similarity	NPD317	Approved
0.7477	Intermediate Similarity	NPD9500	Approved
0.7456	Intermediate Similarity	NPD6671	Approved
0.7456	Intermediate Similarity	NPD7157	Approved
0.7438	Intermediate Similarity	NPD3690	Phase 2
0.7438	Intermediate Similarity	NPD3691	Phase 2
0.7436	Intermediate Similarity	NPD3095	Discontinued
0.7431	Intermediate Similarity	NPD968	Approved
0.7414	Intermediate Similarity	NPD1548	Phase 1
0.7391	Intermediate Similarity	NPD9087	Approved
0.7387	Intermediate Similarity	NPD1792	Phase 2
0.7373	Intermediate Similarity	NPD3143	Discontinued
0.7368	Intermediate Similarity	NPD9618	Approved
0.7368	Intermediate Similarity	NPD9614	Approved
0.7355	Intermediate Similarity	NPD3094	Phase 2
0.735	Intermediate Similarity	NPD5691	Approved
0.7345	Intermediate Similarity	NPD1138	Approved
0.7339	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4659	Approved
0.7315	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1610	Phase 2
0.7304	Intermediate Similarity	NPD256	Approved
0.7304	Intermediate Similarity	NPD255	Approved
0.7288	Intermediate Similarity	NPD3019	Approved
0.7288	Intermediate Similarity	NPD2932	Approved
0.7288	Intermediate Similarity	NPD4059	Approved
0.728	Intermediate Similarity	NPD6407	Approved
0.728	Intermediate Similarity	NPD6405	Approved
0.7265	Intermediate Similarity	NPD7330	Discontinued
0.7263	Intermediate Similarity	NPD9088	Approved
0.7257	Intermediate Similarity	NPD1139	Approved
0.7257	Intermediate Similarity	NPD1137	Approved
0.725	Intermediate Similarity	NPD3070	Discontinued
0.725	Intermediate Similarity	NPD2561	Approved
0.725	Intermediate Similarity	NPD2562	Approved
0.7241	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4208	Discontinued
0.7232	Intermediate Similarity	NPD5451	Approved
0.7227	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7217	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4103	Phase 2
0.7203	Intermediate Similarity	NPD4093	Discontinued
0.7193	Intermediate Similarity	NPD9379	Approved
0.7193	Intermediate Similarity	NPD9377	Approved
0.719	Intermediate Similarity	NPD6583	Phase 3
0.719	Intermediate Similarity	NPD6582	Phase 2
0.7188	Intermediate Similarity	NPD3553	Approved
0.7188	Intermediate Similarity	NPD3552	Approved
0.7188	Intermediate Similarity	NPD3554	Approved
0.7188	Intermediate Similarity	NPD3555	Approved
0.7179	Intermediate Similarity	NPD9613	Approved
0.7179	Intermediate Similarity	NPD9615	Approved
0.7179	Intermediate Similarity	NPD9616	Approved
0.7177	Intermediate Similarity	NPD4908	Phase 1
0.7167	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9384	Approved
0.7143	Intermediate Similarity	NPD2286	Discontinued
0.7143	Intermediate Similarity	NPD9381	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7131	Intermediate Similarity	NPD8651	Approved
0.7119	Intermediate Similarity	NPD9545	Approved
0.7119	Intermediate Similarity	NPD316	Approved
0.7117	Intermediate Similarity	NPD3134	Approved
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7097	Intermediate Similarity	NPD5736	Approved
0.7094	Intermediate Similarity	NPD7636	Approved
0.7094	Intermediate Similarity	NPD9493	Approved
0.7083	Intermediate Similarity	NPD3421	Phase 3
0.7073	Intermediate Similarity	NPD1164	Approved
0.7069	Intermediate Similarity	NPD1793	Approved
0.7069	Intermediate Similarity	NPD475	Phase 2
0.7069	Intermediate Similarity	NPD497	Approved
0.7069	Intermediate Similarity	NPD1791	Approved
0.7059	Intermediate Similarity	NPD1357	Approved
0.7054	Intermediate Similarity	NPD1358	Approved
0.7054	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3685	Discontinued
0.7049	Intermediate Similarity	NPD9622	Approved
0.704	Intermediate Similarity	NPD4207	Discontinued
0.7025	Intermediate Similarity	NPD422	Phase 1
0.7016	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD2667	Approved
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD5846	Approved
0.6991	Remote Similarity	NPD74	Approved
0.6991	Remote Similarity	NPD9266	Approved
0.699	Remote Similarity	NPD9295	Approved
0.6984	Remote Similarity	NPD3027	Phase 3
0.6983	Remote Similarity	NPD498	Approved
0.6983	Remote Similarity	NPD495	Approved
0.6983	Remote Similarity	NPD496	Approved
0.6983	Remote Similarity	NPD594	Approved
0.6983	Remote Similarity	NPD592	Approved
0.6983	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1759	Phase 1
0.697	Remote Similarity	NPD9089	Approved
0.696	Remote Similarity	NPD4212	Discontinued
0.6952	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD9568	Approved
0.6944	Remote Similarity	NPD9611	Approved
0.6944	Remote Similarity	NPD9612	Approved
0.6944	Remote Similarity	NPD9495	Approved
0.6944	Remote Similarity	NPD9609	Approved
0.6942	Remote Similarity	NPD3496	Discontinued
0.6942	Remote Similarity	NPD3847	Discontinued
0.6929	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1651	Approved
0.6911	Remote Similarity	NPD1669	Approved
0.6909	Remote Similarity	NPD854	Approved
0.6909	Remote Similarity	NPD855	Approved
0.6903	Remote Similarity	NPD9267	Approved
0.6903	Remote Similarity	NPD9264	Approved
0.6903	Remote Similarity	NPD9263	Approved
0.6897	Remote Similarity	NPD5535	Approved
0.6891	Remote Similarity	NPD1758	Phase 1
0.6885	Remote Similarity	NPD1201	Approved
0.6885	Remote Similarity	NPD1091	Approved
0.688	Remote Similarity	NPD9621	Approved
0.688	Remote Similarity	NPD9620	Approved
0.688	Remote Similarity	NPD9619	Approved
0.6875	Remote Similarity	NPD6663	Approved
0.687	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9093	Approved
0.6864	Remote Similarity	NPD6387	Discontinued
0.6864	Remote Similarity	NPD2557	Approved
0.686	Remote Similarity	NPD1778	Approved
0.6855	Remote Similarity	NPD1283	Approved
0.6855	Remote Similarity	NPD6696	Suspended
0.685	Remote Similarity	NPD3136	Phase 2
0.685	Remote Similarity	NPD4625	Phase 3
0.6846	Remote Similarity	NPD4097	Suspended
0.6846	Remote Similarity	NPD2157	Approved
0.6838	Remote Similarity	NPD1398	Phase 1
0.6838	Remote Similarity	NPD1241	Discontinued
0.6829	Remote Similarity	NPD2230	Approved
0.6829	Remote Similarity	NPD2233	Approved
0.6829	Remote Similarity	NPD2232	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