NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.12
Volume:	281.964
LogP:	3.781
LogD:	3.545
LogS:	-2.951
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	2.92
Fsp3:	0.059
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:	-4.722
MDCK Permeability:	1.4058059605304152e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	99.51065826416016%
Volume Distribution (VD):	0.547
Pgp-substrate:	0.7881879806518555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.698
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	6.44
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.154
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.57
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.838
Carcinogencity:	0.138
Eye Corrosion:	0.004
Eye Irritation:	0.286
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC292730

Natural Product ID:	NPC292730
*Common Name:**	Nyasol
IUPAC Name:	4-[(1Z,3R)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenol
Synonyms:
Standard InCHIKey:	VEAUNWQYYMXIRB-JHAQOBCDSA-N
Standard InCHI:	InChI=1S/C17H16O2/c1-2-14(15-7-11-17(19)12-8-15)6-3-13-4-9-16(18)10-5-13/h2-12,14,18-19H,1H2/b6-3-/t14-/m1/s1
SMILES:	C=C[C@H](/C=Cc1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451713
PubChem CID:	6915833
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO15006	Asparagus africanus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358645]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15006	Asparagus africanus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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	12
Others	4

Activity Type	# Activity
Cell Line	6
Organism	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[491859]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[491859]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[491859]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[491859]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[491859]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	>	100000.0	nM	PMID[491861]
NPT27	Others	Unspecified		CC50	=	58100.0	nM	PMID[491859]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	46400.0	nM	PMID[491859]
NPT2	Others	Unspecified		Ratio IC50	=	16.7	n.a.	PMID[491860]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	12000.0	nM	PMID[491860]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12000.0	nM	PMID[491860]
NPT2	Others	Unspecified		Ratio IC50	=	4.1	n.a.	PMID[491860]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	49000.0	nM	PMID[491860]
NPT27	Others	Unspecified		IC50	=	200000.0	nM	PMID[491860]

☑ 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 NPC292730 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	258
0.1-0.2	1977
0.2-0.3	5193
0.3-0.4	13177
0.4-0.5	6291
0.5-0.6	9634
0.6-0.7	4669
0.7-0.8	1184
0.8-0.85	201
0.85-0.9	86
0.9-0.95	20
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132271
1.0	High Similarity	NPC82664
1.0	High Similarity	NPC216520
0.9565	High Similarity	NPC473388
0.956	High Similarity	NPC151715
0.9457	High Similarity	NPC26244
0.9362	High Similarity	NPC92730
0.9341	High Similarity	NPC45040
0.9271	High Similarity	NPC168829
0.9255	High Similarity	NPC225464
0.9247	High Similarity	NPC274678
0.9175	High Similarity	NPC288411
0.9158	High Similarity	NPC216468
0.9158	High Similarity	NPC78119
0.9158	High Similarity	NPC51333
0.9158	High Similarity	NPC132078
0.914	High Similarity	NPC128062
0.914	High Similarity	NPC76938
0.913	High Similarity	NPC304541
0.9082	High Similarity	NPC138942
0.9062	High Similarity	NPC213730
0.9043	High Similarity	NPC32714
0.9	High Similarity	NPC11554
0.9	High Similarity	NPC201959
0.899	High Similarity	NPC271274
0.898	High Similarity	NPC323810
0.8969	High Similarity	NPC40258
0.8969	High Similarity	NPC7686
0.8969	High Similarity	NPC91461
0.8936	High Similarity	NPC316301
0.8936	High Similarity	NPC27323
0.8925	High Similarity	NPC155908
0.8913	High Similarity	NPC318325
0.8913	High Similarity	NPC258219
0.8913	High Similarity	NPC280347
0.8913	High Similarity	NPC242240
0.8913	High Similarity	NPC177420
0.8913	High Similarity	NPC123273
0.8911	High Similarity	NPC228343
0.8911	High Similarity	NPC254833
0.8889	High Similarity	NPC175313
0.8889	High Similarity	NPC239291
0.8866	High Similarity	NPC294741
0.8854	High Similarity	NPC77492
0.8854	High Similarity	NPC32674
0.8854	High Similarity	NPC201967
0.883	High Similarity	NPC271440
0.8824	High Similarity	NPC296683
0.8817	High Similarity	NPC55561
0.8817	High Similarity	NPC192
0.8812	High Similarity	NPC262365
0.8804	High Similarity	NPC25493
0.8804	High Similarity	NPC113460
0.88	High Similarity	NPC248904
0.8791	High Similarity	NPC197783
0.8788	High Similarity	NPC120693
0.8788	High Similarity	NPC261573
0.8788	High Similarity	NPC8931
0.8778	High Similarity	NPC265146
0.8776	High Similarity	NPC12221
0.8763	High Similarity	NPC130193
0.8723	High Similarity	NPC270547
0.871	High Similarity	NPC98772
0.87	High Similarity	NPC154899
0.87	High Similarity	NPC233396
0.87	High Similarity	NPC474839
0.8696	High Similarity	NPC184169
0.8696	High Similarity	NPC23167
0.8687	High Similarity	NPC135784
0.8681	High Similarity	NPC248817
0.8673	High Similarity	NPC225506
0.8646	High Similarity	NPC8392
0.8641	High Similarity	NPC44732
0.8632	High Similarity	NPC210497
0.8632	High Similarity	NPC94139
0.8632	High Similarity	NPC3358
0.8632	High Similarity	NPC306884
0.8632	High Similarity	NPC147284
0.8632	High Similarity	NPC162314
0.8617	High Similarity	NPC300017
0.8614	High Similarity	NPC54765
0.8614	High Similarity	NPC188677
0.8614	High Similarity	NPC113457
0.8614	High Similarity	NPC92623
0.8614	High Similarity	NPC135464
0.8602	High Similarity	NPC104216
0.86	High Similarity	NPC119860
0.86	High Similarity	NPC241891
0.86	High Similarity	NPC327811
0.86	High Similarity	NPC471511
0.86	High Similarity	NPC254965
0.86	High Similarity	NPC30506
0.8586	High Similarity	NPC51015
0.8571	High Similarity	NPC124436
0.8571	High Similarity	NPC176730
0.8571	High Similarity	NPC252821
0.8571	High Similarity	NPC122005
0.8571	High Similarity	NPC123175
0.8558	High Similarity	NPC308689
0.8558	High Similarity	NPC95716
0.8544	High Similarity	NPC55617
0.8544	High Similarity	NPC58865
0.8544	High Similarity	NPC62258
0.8542	High Similarity	NPC152415
0.8529	High Similarity	NPC320439
0.8529	High Similarity	NPC151477
0.8515	High Similarity	NPC99557
0.8515	High Similarity	NPC219286
0.8515	High Similarity	NPC134829
0.85	High Similarity	NPC68269
0.8491	Intermediate Similarity	NPC120280
0.8485	Intermediate Similarity	NPC72729
0.8485	Intermediate Similarity	NPC223393
0.8485	Intermediate Similarity	NPC161571
0.8485	Intermediate Similarity	NPC275053
0.8485	Intermediate Similarity	NPC248573
0.8476	Intermediate Similarity	NPC46940
0.8476	Intermediate Similarity	NPC228425
0.8476	Intermediate Similarity	NPC228988
0.8476	Intermediate Similarity	NPC286222
0.8469	Intermediate Similarity	NPC79241
0.8469	Intermediate Similarity	NPC6597
0.8469	Intermediate Similarity	NPC156313
0.8462	Intermediate Similarity	NPC174096
0.8462	Intermediate Similarity	NPC147634
0.8462	Intermediate Similarity	NPC226401
0.8462	Intermediate Similarity	NPC120982
0.8462	Intermediate Similarity	NPC13482
0.8462	Intermediate Similarity	NPC79793
0.8447	Intermediate Similarity	NPC95344
0.8447	Intermediate Similarity	NPC61885
0.8447	Intermediate Similarity	NPC63698
0.8447	Intermediate Similarity	NPC75440
0.8438	Intermediate Similarity	NPC325292
0.8438	Intermediate Similarity	NPC138117
0.8438	Intermediate Similarity	NPC55903
0.8431	Intermediate Similarity	NPC95178
0.8431	Intermediate Similarity	NPC302681
0.8431	Intermediate Similarity	NPC39097
0.8431	Intermediate Similarity	NPC69332
0.8431	Intermediate Similarity	NPC477814
0.8431	Intermediate Similarity	NPC70843
0.8431	Intermediate Similarity	NPC39664
0.8431	Intermediate Similarity	NPC109691
0.8431	Intermediate Similarity	NPC118286
0.8431	Intermediate Similarity	NPC29989
0.8431	Intermediate Similarity	NPC470700
0.8411	Intermediate Similarity	NPC322197
0.8404	Intermediate Similarity	NPC27974
0.84	Intermediate Similarity	NPC100340
0.84	Intermediate Similarity	NPC143659
0.84	Intermediate Similarity	NPC101025
0.84	Intermediate Similarity	NPC471578
0.8396	Intermediate Similarity	NPC715
0.8396	Intermediate Similarity	NPC141003
0.8396	Intermediate Similarity	NPC35344
0.8387	Intermediate Similarity	NPC155393
0.8384	Intermediate Similarity	NPC128723
0.8384	Intermediate Similarity	NPC275104
0.8381	Intermediate Similarity	NPC322753
0.8381	Intermediate Similarity	NPC257430
0.8381	Intermediate Similarity	NPC476632
0.8381	Intermediate Similarity	NPC151537
0.8381	Intermediate Similarity	NPC225679
0.8381	Intermediate Similarity	NPC165770
0.8381	Intermediate Similarity	NPC187583
0.8381	Intermediate Similarity	NPC224527
0.8381	Intermediate Similarity	NPC4493
0.8381	Intermediate Similarity	NPC179002
0.8367	Intermediate Similarity	NPC312132
0.8367	Intermediate Similarity	NPC259512
0.8367	Intermediate Similarity	NPC202986
0.8365	Intermediate Similarity	NPC306045
0.8365	Intermediate Similarity	NPC88141
0.8365	Intermediate Similarity	NPC265211
0.835	Intermediate Similarity	NPC54844
0.8333	Intermediate Similarity	NPC246056
0.8333	Intermediate Similarity	NPC306074
0.8333	Intermediate Similarity	NPC117115
0.8333	Intermediate Similarity	NPC204210
0.8318	Intermediate Similarity	NPC195922
0.8318	Intermediate Similarity	NPC473137
0.8318	Intermediate Similarity	NPC107240
0.8318	Intermediate Similarity	NPC12656
0.8317	Intermediate Similarity	NPC62351
0.8317	Intermediate Similarity	NPC196479
0.8317	Intermediate Similarity	NPC233827
0.8317	Intermediate Similarity	NPC168393
0.8302	Intermediate Similarity	NPC250323
0.8302	Intermediate Similarity	NPC166995
0.8302	Intermediate Similarity	NPC43525
0.83	Intermediate Similarity	NPC10588
0.83	Intermediate Similarity	NPC48730
0.83	Intermediate Similarity	NPC248396
0.83	Intermediate Similarity	NPC129373
0.83	Intermediate Similarity	NPC211885
0.8298	Intermediate Similarity	NPC307235
0.8298	Intermediate Similarity	NPC407
0.8286	Intermediate Similarity	NPC252544
0.8286	Intermediate Similarity	NPC321252

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 NPC292730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	1081
0.2-0.3	1068
0.3-0.4	2911
0.4-0.5	2009
0.5-0.6	1213
0.6-0.7	474
0.7-0.8	90
0.8-0.85	8
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9783	High Similarity	NPD3020	Approved
0.9457	High Similarity	NPD2860	Approved
0.9457	High Similarity	NPD2859	Approved
0.9348	High Similarity	NPD2934	Approved
0.9348	High Similarity	NPD2933	Approved
0.8936	High Similarity	NPD1432	Clinical (unspecified phase)
0.8911	High Similarity	NPD3021	Approved
0.8911	High Similarity	NPD3022	Approved
0.8571	High Similarity	NPD111	Approved
0.8485	Intermediate Similarity	NPD1242	Phase 1
0.8438	Intermediate Similarity	NPD845	Approved
0.8396	Intermediate Similarity	NPD2234	Approved
0.8396	Intermediate Similarity	NPD2228	Approved
0.8396	Intermediate Similarity	NPD2229	Approved
0.8367	Intermediate Similarity	NPD288	Approved
0.8265	Intermediate Similarity	NPD1809	Phase 2
0.8265	Intermediate Similarity	NPD844	Approved
0.8218	Intermediate Similarity	NPD940	Approved
0.8218	Intermediate Similarity	NPD846	Approved
0.8131	Intermediate Similarity	NPD7635	Approved
0.8119	Intermediate Similarity	NPD3028	Approved
0.8119	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD1792	Phase 2
0.8019	Intermediate Similarity	NPD4750	Phase 3
0.8018	Intermediate Similarity	NPD3091	Approved
0.8	Intermediate Similarity	NPD2342	Discontinued
0.7946	Intermediate Similarity	NPD4093	Discontinued
0.7905	Intermediate Similarity	NPD1444	Approved
0.7905	Intermediate Similarity	NPD1445	Approved
0.7876	Intermediate Similarity	NPD4059	Approved
0.7876	Intermediate Similarity	NPD3019	Approved
0.7876	Intermediate Similarity	NPD2932	Approved
0.7857	Intermediate Similarity	NPD5303	Approved
0.7857	Intermediate Similarity	NPD5304	Approved
0.7759	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD3092	Approved
0.7727	Intermediate Similarity	NPD5283	Phase 1
0.7719	Intermediate Similarity	NPD4589	Approved
0.7719	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2286	Discontinued
0.7658	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.757	Intermediate Similarity	NPD968	Approved
0.7565	Intermediate Similarity	NPD2668	Approved
0.7565	Intermediate Similarity	NPD3095	Discontinued
0.7565	Intermediate Similarity	NPD2667	Approved
0.7565	Intermediate Similarity	NPD1751	Approved
0.7556	Intermediate Similarity	NPD9087	Approved
0.7547	Intermediate Similarity	NPD9608	Approved
0.7547	Intermediate Similarity	NPD9610	Approved
0.7545	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD5451	Approved
0.7522	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7479	Intermediate Similarity	NPD3094	Phase 2
0.7479	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4659	Approved
0.7453	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4908	Phase 1
0.7436	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6671	Approved
0.7431	Intermediate Similarity	NPD2684	Approved
0.7419	Intermediate Similarity	NPD9088	Approved
0.7411	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD228	Approved
0.7364	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5736	Approved
0.735	Intermediate Similarity	NPD3421	Phase 3
0.7345	Intermediate Similarity	NPD475	Phase 2
0.7333	Intermediate Similarity	NPD4103	Phase 2
0.7333	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD9379	Approved
0.7321	Intermediate Similarity	NPD5535	Approved
0.7321	Intermediate Similarity	NPD9377	Approved
0.7317	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6583	Phase 3
0.7311	Intermediate Similarity	NPD6582	Phase 2
0.729	Intermediate Similarity	NPD9500	Approved
0.7281	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD6584	Phase 3
0.7273	Intermediate Similarity	NPD2195	Approved
0.7273	Intermediate Similarity	NPD2194	Approved
0.725	Intermediate Similarity	NPD5311	Approved
0.725	Intermediate Similarity	NPD5310	Approved
0.7241	Intermediate Similarity	NPD7330	Discontinued
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7241	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD9273	Approved
0.7236	Intermediate Similarity	NPD5155	Approved
0.7236	Intermediate Similarity	NPD5156	Approved
0.7227	Intermediate Similarity	NPD2230	Approved
0.7227	Intermediate Similarity	NPD2233	Approved
0.7227	Intermediate Similarity	NPD2561	Approved
0.7227	Intermediate Similarity	NPD2562	Approved
0.7227	Intermediate Similarity	NPD2232	Approved
0.7213	Intermediate Similarity	NPD3636	Approved
0.7213	Intermediate Similarity	NPD3635	Approved
0.7213	Intermediate Similarity	NPD3637	Approved
0.7203	Intermediate Similarity	NPD3847	Discontinued
0.7203	Intermediate Similarity	NPD3023	Approved
0.7203	Intermediate Similarity	NPD3026	Approved
0.72	Intermediate Similarity	NPD4060	Phase 1
0.7196	Intermediate Similarity	NPD4817	Approved
0.7196	Intermediate Similarity	NPD4818	Approved
0.7193	Intermediate Similarity	NPD1791	Approved
0.7193	Intermediate Similarity	NPD1793	Approved
0.719	Intermediate Similarity	NPD3055	Approved
0.719	Intermediate Similarity	NPD1164	Approved
0.719	Intermediate Similarity	NPD3053	Approved
0.7179	Intermediate Similarity	NPD3025	Approved
0.7179	Intermediate Similarity	NPD3024	Approved
0.7168	Intermediate Similarity	NPD7843	Approved
0.7167	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2606	Approved
0.7154	Intermediate Similarity	NPD3594	Approved
0.7154	Intermediate Similarity	NPD3595	Approved
0.7154	Intermediate Similarity	NPD2605	Approved
0.7143	Intermediate Similarity	NPD1201	Approved
0.7131	Intermediate Similarity	NPD4624	Approved
0.713	Intermediate Similarity	NPD4656	Approved
0.713	Intermediate Similarity	NPD256	Approved
0.713	Intermediate Similarity	NPD255	Approved
0.713	Intermediate Similarity	NPD4229	Approved
0.713	Intermediate Similarity	NPD4231	Approved
0.713	Intermediate Similarity	NPD3680	Approved
0.713	Intermediate Similarity	NPD3682	Approved
0.713	Intermediate Similarity	NPD4658	Approved
0.7128	Intermediate Similarity	NPD9294	Approved
0.712	Intermediate Similarity	NPD6663	Approved
0.7119	Intermediate Similarity	NPD4626	Approved
0.7119	Intermediate Similarity	NPD6516	Phase 2
0.7119	Intermediate Similarity	NPD5846	Approved
0.7113	Intermediate Similarity	NPD9089	Approved
0.7107	Intermediate Similarity	NPD1283	Approved
0.7103	Intermediate Similarity	NPD1616	Discontinued
0.7097	Intermediate Similarity	NPD3027	Phase 3
0.7091	Intermediate Similarity	NPD3134	Approved
0.7083	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2797	Approved
0.7043	Intermediate Similarity	NPD497	Approved
0.704	Intermediate Similarity	NPD3764	Approved
0.7034	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1651	Approved
0.7034	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1669	Approved
0.7025	Intermediate Similarity	NPD4749	Approved
0.7018	Intermediate Similarity	NPD821	Approved
0.701	Intermediate Similarity	NPD9093	Approved
0.7009	Intermediate Similarity	NPD16	Approved
0.7009	Intermediate Similarity	NPD856	Approved
0.7	Intermediate Similarity	NPD1535	Discovery
0.6992	Remote Similarity	NPD7451	Discontinued
0.6991	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6405	Approved
0.6984	Remote Similarity	NPD6407	Approved
0.6983	Remote Similarity	NPD6387	Discontinued
0.6983	Remote Similarity	NPD709	Approved
0.6972	Remote Similarity	NPD3681	Approved
0.6972	Remote Similarity	NPD3683	Approved
0.696	Remote Similarity	NPD4625	Phase 3
0.696	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD496	Approved
0.6957	Remote Similarity	NPD498	Approved
0.6957	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD495	Approved
0.6949	Remote Similarity	NPD1894	Discontinued
0.6942	Remote Similarity	NPD1481	Phase 2
0.6942	Remote Similarity	NPD2235	Phase 2
0.6942	Remote Similarity	NPD1608	Approved
0.6942	Remote Similarity	NPD2231	Phase 2
0.6929	Remote Similarity	NPD3620	Phase 2
0.6929	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6346	Approved
0.6923	Remote Similarity	NPD9568	Approved
0.6923	Remote Similarity	NPD3596	Phase 2
0.6923	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1981	Approved
0.6917	Remote Similarity	NPD1983	Approved
0.6917	Remote Similarity	NPD3143	Discontinued
0.6917	Remote Similarity	NPD1980	Approved
0.6911	Remote Similarity	NPD1470	Approved
0.6897	Remote Similarity	NPD9614	Approved
0.6897	Remote Similarity	NPD9618	Approved
0.6885	Remote Similarity	NPD5327	Phase 3
0.6885	Remote Similarity	NPD1755	Approved
0.688	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6355	Discontinued
0.6864	Remote Similarity	NPD317	Approved
0.6864	Remote Similarity	NPD5536	Phase 2
0.6864	Remote Similarity	NPD318	Approved
0.686	Remote Similarity	NPD1281	Approved
0.6855	Remote Similarity	NPD2798	Approved
0.6846	Remote Similarity	NPD7742	Approved
0.6846	Remote Similarity	NPD7743	Approved
0.6833	Remote Similarity	NPD9381	Approved
0.6833	Remote Similarity	NPD9384	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