NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	441.19
Volume:	479.058
LogP:	3.969
LogD:	3.823
LogS:	-5.386
# Rotatable Bonds:	11
TPSA:	64.63
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	2.786
Fsp3:	0.143
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:	-5.014
MDCK Permeability:	1.1279366844973993e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.624
Plasma Protein Binding (PPB):	100.0363540649414%
Volume Distribution (VD):	0.612
Pgp-substrate:	0.37060362100601196%

ADMET: Metabolism

CYP1A2-inhibitor:	0.381
CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.505
CYP2C9-inhibitor:	0.943
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.31
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.719

ADMET: Excretion

Clearance (CL):	3.503
Half-life (T1/2):	0.283

ADMET: Toxicity

hERG Blockers:	0.297
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.295
Skin Sensitization:	0.88
Carcinogencity:	0.707
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.283

Download Data

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

Natural Product: NPC478189

Natural Product ID:	NPC478189
*Common Name:**	(E)-N-[(E,2R)-2-(3,4-dimethoxyphenyl)-3-oxo-5-phenylpent-4-enyl]-3-phenylprop-2-enamide
IUPAC Name:	(E)-N-[(E,2R)-2-(3,4-dimethoxyphenyl)-3-oxo-5-phenylpent-4-enyl]-3-phenylprop-2-enamide
Synonyms:
Standard InCHIKey:	AMILGQDSXRGLMA-YDSPNMOESA-N
Standard InCHI:	InChI=1S/C28H27NO4/c1-32-26-17-15-23(19-27(26)33-2)24(25(30)16-13-21-9-5-3-6-10-21)20-29-28(31)18-14-22-11-7-4-8-12-22/h3-19,24H,20H2,1-2H3,(H,29,31)/b16-13+,18-14+/t24-/m0/s1
SMILES:	COC1=C(C=C(C=C1)[C@H](CNC(=O)/C=C/C2=CC=CC=C2)C(=O)/C=C/C3=CC=CC=C3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559210
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002810] Cinnamic acid amides

*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
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	PMID[14738394]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124784]
NPO27680	Zanthoxylum syncarpum	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4200	nM	PMID[16124784]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6100	nM	PMID[16124784]

☑ 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 NPC478189 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	222
0.1-0.2	1197
0.2-0.3	4109
0.3-0.4	12058
0.4-0.5	5018
0.5-0.6	7274
0.6-0.7	11698
0.7-0.8	1096
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC153644
0.8808	High Similarity	NPC58661
0.844	Intermediate Similarity	NPC301713
0.8366	Intermediate Similarity	NPC182119
0.8276	Intermediate Similarity	NPC214869
0.8176	Intermediate Similarity	NPC88065
0.8176	Intermediate Similarity	NPC95485
0.8176	Intermediate Similarity	NPC89504
0.817	Intermediate Similarity	NPC290404
0.8158	Intermediate Similarity	NPC141817
0.8158	Intermediate Similarity	NPC176030
0.8158	Intermediate Similarity	NPC192597
0.8158	Intermediate Similarity	NPC169214
0.8158	Intermediate Similarity	NPC229218
0.8146	Intermediate Similarity	NPC908
0.8146	Intermediate Similarity	NPC138438
0.8138	Intermediate Similarity	NPC35961
0.8138	Intermediate Similarity	NPC52029
0.8138	Intermediate Similarity	NPC195749
0.8121	Intermediate Similarity	NPC471316
0.8082	Intermediate Similarity	NPC114102
0.8069	Intermediate Similarity	NPC155838
0.8026	Intermediate Similarity	NPC28398
0.8014	Intermediate Similarity	NPC304622
0.8	Intermediate Similarity	NPC123228
0.8	Intermediate Similarity	NPC5018
0.8	Intermediate Similarity	NPC123722
0.8	Intermediate Similarity	NPC153990
0.8	Intermediate Similarity	NPC251571
0.8	Intermediate Similarity	NPC151167
0.8	Intermediate Similarity	NPC276466
0.7987	Intermediate Similarity	NPC5462
0.7974	Intermediate Similarity	NPC472410
0.7964	Intermediate Similarity	NPC207721
0.7959	Intermediate Similarity	NPC66905
0.7949	Intermediate Similarity	NPC470019
0.7931	Intermediate Similarity	NPC276014
0.7931	Intermediate Similarity	NPC179777
0.7931	Intermediate Similarity	NPC303680
0.7931	Intermediate Similarity	NPC84076
0.7931	Intermediate Similarity	NPC90128
0.7898	Intermediate Similarity	NPC469540
0.7898	Intermediate Similarity	NPC469539
0.7881	Intermediate Similarity	NPC312770
0.7881	Intermediate Similarity	NPC41473
0.7881	Intermediate Similarity	NPC160607
0.7881	Intermediate Similarity	NPC204848
0.7881	Intermediate Similarity	NPC14600
0.7877	Intermediate Similarity	NPC186898
0.7871	Intermediate Similarity	NPC46880
0.7871	Intermediate Similarity	NPC239608
0.7871	Intermediate Similarity	NPC46161
0.7862	Intermediate Similarity	NPC53305
0.7862	Intermediate Similarity	NPC257589
0.7853	Intermediate Similarity	NPC153631
0.7852	Intermediate Similarity	NPC239302
0.7847	Intermediate Similarity	NPC474691
0.7834	Intermediate Similarity	NPC161544
0.7829	Intermediate Similarity	NPC299583
0.7808	Intermediate Similarity	NPC92207
0.7808	Intermediate Similarity	NPC127937
0.7806	Intermediate Similarity	NPC137920
0.7806	Intermediate Similarity	NPC86455
0.7806	Intermediate Similarity	NPC80928
0.7806	Intermediate Similarity	NPC125134
0.78	Intermediate Similarity	NPC218530
0.78	Intermediate Similarity	NPC327410
0.78	Intermediate Similarity	NPC473463
0.7792	Intermediate Similarity	NPC222039
0.7792	Intermediate Similarity	NPC100478
0.7778	Intermediate Similarity	NPC284409
0.775	Intermediate Similarity	NPC58310
0.775	Intermediate Similarity	NPC295977
0.773	Intermediate Similarity	NPC280001
0.7727	Intermediate Similarity	NPC474784
0.7727	Intermediate Similarity	NPC223336
0.7724	Intermediate Similarity	NPC242372
0.7724	Intermediate Similarity	NPC164778
0.7724	Intermediate Similarity	NPC4181
0.7724	Intermediate Similarity	NPC257976
0.7722	Intermediate Similarity	NPC470935
0.7722	Intermediate Similarity	NPC471032
0.7718	Intermediate Similarity	NPC172673
0.7712	Intermediate Similarity	NPC296898
0.7707	Intermediate Similarity	NPC472836
0.7707	Intermediate Similarity	NPC300603
0.7707	Intermediate Similarity	NPC91694
0.7703	Intermediate Similarity	NPC147247
0.7703	Intermediate Similarity	NPC246974
0.7703	Intermediate Similarity	NPC226661
0.7702	Intermediate Similarity	NPC472838
0.7702	Intermediate Similarity	NPC306011
0.7702	Intermediate Similarity	NPC267091
0.7701	Intermediate Similarity	NPC124626
0.7688	Intermediate Similarity	NPC127402
0.7688	Intermediate Similarity	NPC52475
0.7677	Intermediate Similarity	NPC78987
0.7677	Intermediate Similarity	NPC82336
0.7671	Intermediate Similarity	NPC30216
0.7671	Intermediate Similarity	NPC312404
0.7671	Intermediate Similarity	NPC273686
0.7667	Intermediate Similarity	NPC130595
0.7667	Intermediate Similarity	NPC93882
0.7662	Intermediate Similarity	NPC470962
0.7658	Intermediate Similarity	NPC73416
0.7658	Intermediate Similarity	NPC160777
0.7658	Intermediate Similarity	NPC30890
0.7655	Intermediate Similarity	NPC114298
0.7647	Intermediate Similarity	NPC90431
0.7643	Intermediate Similarity	NPC50954
0.7643	Intermediate Similarity	NPC469978
0.764	Intermediate Similarity	NPC18614
0.764	Intermediate Similarity	NPC243891
0.7639	Intermediate Similarity	NPC225245
0.7635	Intermediate Similarity	NPC32163
0.7635	Intermediate Similarity	NPC16651
0.7635	Intermediate Similarity	NPC99798
0.7635	Intermediate Similarity	NPC157740
0.7625	Intermediate Similarity	NPC474556
0.7625	Intermediate Similarity	NPC474903
0.7616	Intermediate Similarity	NPC6854
0.7616	Intermediate Similarity	NPC313737
0.7616	Intermediate Similarity	NPC285078
0.7616	Intermediate Similarity	NPC153453
0.761	Intermediate Similarity	NPC39361
0.7606	Intermediate Similarity	NPC185738
0.7605	Intermediate Similarity	NPC3906
0.7603	Intermediate Similarity	NPC18984
0.7603	Intermediate Similarity	NPC163083
0.7603	Intermediate Similarity	NPC160900
0.7603	Intermediate Similarity	NPC229084
0.7603	Intermediate Similarity	NPC106659
0.76	Intermediate Similarity	NPC65935
0.76	Intermediate Similarity	NPC255550
0.76	Intermediate Similarity	NPC215941
0.76	Intermediate Similarity	NPC244246
0.76	Intermediate Similarity	NPC275724
0.76	Intermediate Similarity	NPC123196
0.76	Intermediate Similarity	NPC311419
0.76	Intermediate Similarity	NPC308885
0.76	Intermediate Similarity	NPC474009
0.76	Intermediate Similarity	NPC137427
0.76	Intermediate Similarity	NPC319282
0.7595	Intermediate Similarity	NPC196941
0.7595	Intermediate Similarity	NPC309169
0.7595	Intermediate Similarity	NPC207732
0.7586	Intermediate Similarity	NPC201777
0.7578	Intermediate Similarity	NPC237441
0.7574	Intermediate Similarity	NPC164608
0.7572	Intermediate Similarity	NPC298339
0.7568	Intermediate Similarity	NPC251466
0.7568	Intermediate Similarity	NPC156944
0.7562	Intermediate Similarity	NPC470088
0.7562	Intermediate Similarity	NPC52692
0.7548	Intermediate Similarity	NPC33011
0.7547	Intermediate Similarity	NPC115144
0.7547	Intermediate Similarity	NPC157133
0.7547	Intermediate Similarity	NPC277857
0.7546	Intermediate Similarity	NPC164912
0.7546	Intermediate Similarity	NPC107602
0.7533	Intermediate Similarity	NPC470706
0.7532	Intermediate Similarity	NPC224884
0.7532	Intermediate Similarity	NPC119663
0.7532	Intermediate Similarity	NPC209085
0.7532	Intermediate Similarity	NPC324929
0.7532	Intermediate Similarity	NPC120852
0.7531	Intermediate Similarity	NPC475718
0.7531	Intermediate Similarity	NPC275027
0.7529	Intermediate Similarity	NPC227683
0.7529	Intermediate Similarity	NPC67978
0.7529	Intermediate Similarity	NPC303581
0.7517	Intermediate Similarity	NPC291449
0.7517	Intermediate Similarity	NPC189844
0.7517	Intermediate Similarity	NPC158949
0.7517	Intermediate Similarity	NPC269843
0.7517	Intermediate Similarity	NPC41331
0.7517	Intermediate Similarity	NPC60962
0.7517	Intermediate Similarity	NPC14007
0.7517	Intermediate Similarity	NPC223807
0.7517	Intermediate Similarity	NPC109083
0.7517	Intermediate Similarity	NPC224814
0.7516	Intermediate Similarity	NPC5310
0.7516	Intermediate Similarity	NPC6913
0.7516	Intermediate Similarity	NPC110419
0.7516	Intermediate Similarity	NPC300776
0.7516	Intermediate Similarity	NPC176814
0.7516	Intermediate Similarity	NPC4982
0.7516	Intermediate Similarity	NPC68779
0.7515	Intermediate Similarity	NPC213401
0.7515	Intermediate Similarity	NPC86469
0.75	Intermediate Similarity	NPC12377
0.75	Intermediate Similarity	NPC182147
0.75	Intermediate Similarity	NPC170583
0.75	Intermediate Similarity	NPC152186
0.75	Intermediate Similarity	NPC3221
0.75	Intermediate Similarity	NPC71105
0.75	Intermediate Similarity	NPC207541
0.75	Intermediate Similarity	NPC246133
0.75	Intermediate Similarity	NPC50763
0.75	Intermediate Similarity	NPC32064

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 NPC478189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	713
0.2-0.3	956
0.3-0.4	1905
0.4-0.5	2516
0.5-0.6	1845
0.6-0.7	931
0.7-0.8	106
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD5977	Approved
0.8	Intermediate Similarity	NPD5978	Approved
0.7857	Intermediate Similarity	NPD6331	Phase 2
0.7812	Intermediate Similarity	NPD7110	Phase 1
0.7812	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6873	Phase 2
0.7785	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2821	Approved
0.775	Intermediate Similarity	NPD6876	Approved
0.775	Intermediate Similarity	NPD6875	Approved
0.7742	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6386	Approved
0.7702	Intermediate Similarity	NPD6385	Approved
0.7667	Intermediate Similarity	NPD2674	Phase 3
0.7613	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5536	Phase 2
0.7603	Intermediate Similarity	NPD1669	Approved
0.7603	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3145	Approved
0.76	Intermediate Similarity	NPD3144	Approved
0.7597	Intermediate Similarity	NPD2161	Phase 2
0.7572	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3640	Phase 3
0.7562	Intermediate Similarity	NPD3639	Approved
0.7562	Intermediate Similarity	NPD3641	Approved
0.7546	Intermediate Similarity	NPD7577	Discontinued
0.7546	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6502	Phase 2
0.7484	Intermediate Similarity	NPD4357	Discontinued
0.7469	Intermediate Similarity	NPD824	Approved
0.7468	Intermediate Similarity	NPD6896	Approved
0.7468	Intermediate Similarity	NPD6895	Approved
0.7457	Intermediate Similarity	NPD7039	Approved
0.7457	Intermediate Similarity	NPD7038	Approved
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5283	Phase 1
0.7399	Intermediate Similarity	NPD3823	Discontinued
0.7386	Intermediate Similarity	NPD3140	Approved
0.7386	Intermediate Similarity	NPD3142	Approved
0.7378	Intermediate Similarity	NPD5089	Approved
0.7378	Intermediate Similarity	NPD5090	Approved
0.7368	Intermediate Similarity	NPD5110	Phase 2
0.7368	Intermediate Similarity	NPD5718	Phase 2
0.7368	Intermediate Similarity	NPD5109	Approved
0.7368	Intermediate Similarity	NPD5111	Phase 2
0.7362	Intermediate Similarity	NPD4005	Discontinued
0.7362	Intermediate Similarity	NPD3455	Phase 2
0.7358	Intermediate Similarity	NPD5241	Discontinued
0.7353	Intermediate Similarity	NPD5242	Approved
0.7351	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4123	Phase 3
0.7315	Intermediate Similarity	NPD2922	Phase 1
0.7308	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7291	Discontinued
0.7297	Intermediate Similarity	NPD3972	Approved
0.7296	Intermediate Similarity	NPD4110	Phase 3
0.7296	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9494	Approved
0.7278	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3060	Approved
0.7215	Intermediate Similarity	NPD1375	Discontinued
0.7212	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2667	Approved
0.7211	Intermediate Similarity	NPD2668	Approved
0.7198	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4108	Discontinued
0.7179	Intermediate Similarity	NPD2653	Approved
0.7179	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7526	Approved
0.7178	Intermediate Similarity	NPD52	Approved
0.7178	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6746	Phase 2
0.7176	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7153	Discontinued
0.7168	Intermediate Similarity	NPD7473	Discontinued
0.7167	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4466	Phase 1
0.7143	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6618	Phase 2
0.7133	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1934	Approved
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5177	Phase 3
0.7125	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4162	Approved
0.7118	Intermediate Similarity	NPD6862	Phase 2
0.7117	Intermediate Similarity	NPD4739	Approved
0.711	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4678	Approved
0.7108	Intermediate Similarity	NPD4675	Approved
0.7105	Intermediate Similarity	NPD2798	Approved
0.7105	Intermediate Similarity	NPD6584	Phase 3
0.7099	Intermediate Similarity	NPD7124	Phase 2
0.7097	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7093	Intermediate Similarity	NPD7315	Approved
0.7086	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD2801	Approved
0.7083	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7067	Intermediate Similarity	NPD2233	Approved
0.7067	Intermediate Similarity	NPD2230	Approved
0.7067	Intermediate Similarity	NPD2232	Approved
0.7065	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD4055	Discovery
0.7048	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5967	Approved
0.7033	Intermediate Similarity	NPD2488	Approved
0.7033	Intermediate Similarity	NPD2490	Approved
0.703	Intermediate Similarity	NPD7427	Discontinued
0.7027	Intermediate Similarity	NPD1651	Approved
0.7013	Intermediate Similarity	NPD2614	Approved
0.7012	Intermediate Similarity	NPD3146	Approved
0.7012	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4584	Approved
0.7011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD7028	Phase 2
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3882	Suspended
0.6995	Remote Similarity	NPD3819	Phase 2
0.6994	Remote Similarity	NPD6747	Phase 1
0.6994	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3965	Phase 1
0.6989	Remote Similarity	NPD5844	Phase 1
0.6987	Remote Similarity	NPD7477	Discontinued
0.6983	Remote Similarity	NPD2968	Approved
0.6983	Remote Similarity	NPD7280	Phase 3
0.6983	Remote Similarity	NPD2971	Approved
0.6983	Remote Similarity	NPD7281	Phase 3
0.6983	Remote Similarity	NPD7546	Discontinued
0.6982	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5494	Approved
0.6975	Remote Similarity	NPD8166	Discontinued
0.6975	Remote Similarity	NPD7003	Approved
0.6974	Remote Similarity	NPD1283	Approved
0.6971	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7833	Phase 2
0.6959	Remote Similarity	NPD7831	Phase 2
0.6954	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1608	Approved
0.6949	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2325	Approved
0.6946	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5914	Approved
0.6941	Remote Similarity	NPD3817	Phase 2
0.6941	Remote Similarity	NPD5353	Approved
0.6937	Remote Similarity	NPD4477	Approved
0.6937	Remote Similarity	NPD2935	Discontinued
0.6937	Remote Similarity	NPD4476	Approved
0.6933	Remote Similarity	NPD3847	Discontinued
0.6928	Remote Similarity	NPD7131	Phase 3
0.6928	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7549	Discontinued
0.6923	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6844	Discontinued
0.6923	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2898	Approved
0.6914	Remote Similarity	NPD6894	Phase 1
0.691	Remote Similarity	NPD6297	Approved
0.6908	Remote Similarity	NPD6583	Phase 3
0.6908	Remote Similarity	NPD1755	Approved
0.6908	Remote Similarity	NPD6582	Phase 2
0.6901	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2344	Approved
0.6887	Remote Similarity	NPD1281	Approved
0.6886	Remote Similarity	NPD3687	Approved
0.6886	Remote Similarity	NPD3686	Approved
0.6882	Remote Similarity	NPD5772	Approved
0.6882	Remote Similarity	NPD7972	Discontinued
0.6882	Remote Similarity	NPD5773	Approved
0.6875	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD1510	Phase 2
0.6867	Remote Similarity	NPD17	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