NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	267.13
Volume:	292.961
LogP:	2.87
LogD:	3.329
LogS:	-3.558
# Rotatable Bonds:	6
TPSA:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.818
Synthetic Accessibility Score:	1.748
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.811
MDCK Permeability:	1.478082594985608e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	95.34967041015625%
Volume Distribution (VD):	0.87
Pgp-substrate:	2.612807035446167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	10.771
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.315
AMES Toxicity:	0.5
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.91
Carcinogencity:	0.424
Eye Corrosion:	0.005
Eye Irritation:	0.64
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC96224

Natural Product ID:	NPC96224
*Common Name:**	N-(4-Hydroxyphenethyl)Cinnamamide
IUPAC Name:	(E)-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enamide
Synonyms:
Standard InCHIKey:	KGOYCHSKGXJDND-DHZHZOJOSA-N
Standard InCHI:	InChI=1S/C17H17NO2/c19-16-9-6-15(7-10-16)12-13-18-17(20)11-8-14-4-2-1-3-5-14/h1-11,19H,12-13H2,(H,18,20)/b11-8+
SMILES:	c1ccc(cc1)/C=C/C(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL417389
PubChem CID:	5315911
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
NPO24670	Casearia lucida	Species	Salicaceae	Eukaryota	Barks	n.a.	n.a.	PMID[11858738]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	amniotic fluid	n.a.	Database[Article]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24764	Amphius huxleyi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22909	Echinogorgia flora	Species	Paramuriceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24579	Rhamnus procumbens	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24961	Teucrium lucidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24670	Casearia lucida	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17037	Dichapetalum toxicarium	Species	Dichapetalaceae	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	7

Activity Type	# Activity
Others	4
Protein Complex	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	300000.0	nM	PMID[561852]
NPT2	Others	Unspecified		IC50	=	680.0	nM	PMID[561852]
NPT1837	Protein Complex	Glutamate NMDA receptor; Grin1/Grin2a	Rattus norvegicus	IC50	>	100000.0	nM	PMID[561853]
NPT1838	Protein Complex	Glutamate NMDA receptor; Grin1/Grin2b	Rattus norvegicus	IC50	=	680.0	nM	PMID[561853]
NPT1839	Protein Complex	Glutamate NMDA receptor; Grin1/Grin2c	Rattus norvegicus	IC50	>	100000.0	nM	PMID[561853]
NPT2	Others	Unspecified		IC50	=	215250.0	nM	PMID[561854]

☑ 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 NPC96224 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	165
0.1-0.2	2308
0.2-0.3	10208
0.3-0.4	7772
0.4-0.5	10356
0.5-0.6	8934
0.6-0.7	2365
0.7-0.8	521
0.8-0.85	48
0.85-0.9	9
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24101
0.951	High Similarity	NPC142297
0.9417	High Similarity	NPC153690
0.9412	High Similarity	NPC231705
0.9307	High Similarity	NPC178902
0.9174	High Similarity	NPC283468
0.9143	High Similarity	NPC258056
0.9091	High Similarity	NPC122009
0.9083	High Similarity	NPC82963
0.9057	High Similarity	NPC474149
0.9	High Similarity	NPC38458
0.9	High Similarity	NPC311737
0.8839	High Similarity	NPC268572
0.8727	High Similarity	NPC118202
0.8673	High Similarity	NPC43275
0.8649	High Similarity	NPC317254
0.8596	High Similarity	NPC263835
0.8558	High Similarity	NPC155847
0.8558	High Similarity	NPC289381
0.8482	Intermediate Similarity	NPC37302
0.8462	Intermediate Similarity	NPC125732
0.8431	Intermediate Similarity	NPC151715
0.8393	Intermediate Similarity	NPC142599
0.839	Intermediate Similarity	NPC62101
0.839	Intermediate Similarity	NPC95733
0.8365	Intermediate Similarity	NPC107619
0.8362	Intermediate Similarity	NPC284078
0.835	Intermediate Similarity	NPC26244
0.8348	Intermediate Similarity	NPC283760
0.8333	Intermediate Similarity	NPC251571
0.8319	Intermediate Similarity	NPC303370
0.8305	Intermediate Similarity	NPC211218
0.8291	Intermediate Similarity	NPC474862
0.8288	Intermediate Similarity	NPC166837
0.8269	Intermediate Similarity	NPC132271
0.8269	Intermediate Similarity	NPC292730
0.8269	Intermediate Similarity	NPC216520
0.8269	Intermediate Similarity	NPC82664
0.8269	Intermediate Similarity	NPC473388
0.8269	Intermediate Similarity	NPC33168
0.8264	Intermediate Similarity	NPC155838
0.8235	Intermediate Similarity	NPC45040
0.8197	Intermediate Similarity	NPC35961
0.8197	Intermediate Similarity	NPC52029
0.8197	Intermediate Similarity	NPC195749
0.8167	Intermediate Similarity	NPC29477
0.8115	Intermediate Similarity	NPC325651
0.8113	Intermediate Similarity	NPC51333
0.8113	Intermediate Similarity	NPC78119
0.8113	Intermediate Similarity	NPC132078
0.8113	Intermediate Similarity	NPC216468
0.8099	Intermediate Similarity	NPC301713
0.8077	Intermediate Similarity	NPC128062
0.8073	Intermediate Similarity	NPC211551
0.8065	Intermediate Similarity	NPC214869
0.8051	Intermediate Similarity	NPC83279
0.8049	Intermediate Similarity	NPC474091
0.8039	Intermediate Similarity	NPC280347
0.8039	Intermediate Similarity	NPC177420
0.8037	Intermediate Similarity	NPC29601
0.8037	Intermediate Similarity	NPC213730
0.8034	Intermediate Similarity	NPC256369
0.8034	Intermediate Similarity	NPC319950
0.8019	Intermediate Similarity	NPC201967
0.8	Intermediate Similarity	NPC175313
0.8	Intermediate Similarity	NPC274678
0.8	Intermediate Similarity	NPC203076
0.7984	Intermediate Similarity	NPC473724
0.7984	Intermediate Similarity	NPC45191
0.7984	Intermediate Similarity	NPC326966
0.7984	Intermediate Similarity	NPC114102
0.7963	Intermediate Similarity	NPC7686
0.7963	Intermediate Similarity	NPC91461
0.7963	Intermediate Similarity	NPC40258
0.7961	Intermediate Similarity	NPC55561
0.7946	Intermediate Similarity	NPC145638
0.7946	Intermediate Similarity	NPC290566
0.7944	Intermediate Similarity	NPC92730
0.7944	Intermediate Similarity	NPC130193
0.7941	Intermediate Similarity	NPC25493
0.7941	Intermediate Similarity	NPC113460
0.7921	Intermediate Similarity	NPC197783
0.792	Intermediate Similarity	NPC244866
0.7917	Intermediate Similarity	NPC471314
0.7917	Intermediate Similarity	NPC471315
0.7905	Intermediate Similarity	NPC76938
0.79	Intermediate Similarity	NPC265146
0.789	Intermediate Similarity	NPC68055
0.789	Intermediate Similarity	NPC168829
0.7886	Intermediate Similarity	NPC153990
0.7886	Intermediate Similarity	NPC296712
0.7886	Intermediate Similarity	NPC186898
0.7885	Intermediate Similarity	NPC270547
0.7874	Intermediate Similarity	NPC6913
0.7864	Intermediate Similarity	NPC318325
0.7864	Intermediate Similarity	NPC172128
0.7864	Intermediate Similarity	NPC98772
0.7864	Intermediate Similarity	NPC123273
0.7864	Intermediate Similarity	NPC242240
0.7857	Intermediate Similarity	NPC267237
0.7851	Intermediate Similarity	NPC307020
0.785	Intermediate Similarity	NPC225464
0.7843	Intermediate Similarity	NPC23167
0.7843	Intermediate Similarity	NPC184169
0.784	Intermediate Similarity	NPC475735
0.7833	Intermediate Similarity	NPC27581
0.783	Intermediate Similarity	NPC32714
0.7823	Intermediate Similarity	NPC271808
0.7822	Intermediate Similarity	NPC248817
0.7818	Intermediate Similarity	NPC288411
0.7818	Intermediate Similarity	NPC8931
0.7818	Intermediate Similarity	NPC261573
0.7818	Intermediate Similarity	NPC120693
0.7788	Intermediate Similarity	NPC300017
0.7767	Intermediate Similarity	NPC104216
0.7752	Intermediate Similarity	NPC41473
0.7752	Intermediate Similarity	NPC160607
0.7752	Intermediate Similarity	NPC204848
0.7752	Intermediate Similarity	NPC14600
0.7752	Intermediate Similarity	NPC312770
0.7748	Intermediate Similarity	NPC474839
0.7748	Intermediate Similarity	NPC138942
0.7748	Intermediate Similarity	NPC154899
0.7748	Intermediate Similarity	NPC233396
0.7739	Intermediate Similarity	NPC146422
0.7727	Intermediate Similarity	NPC68269
0.7727	Intermediate Similarity	NPC135784
0.7723	Intermediate Similarity	NPC124436
0.7706	Intermediate Similarity	NPC294741
0.7692	Intermediate Similarity	NPC258219
0.7692	Intermediate Similarity	NPC299583
0.7692	Intermediate Similarity	NPC10286
0.7692	Intermediate Similarity	NPC296898
0.7692	Intermediate Similarity	NPC213
0.7686	Intermediate Similarity	NPC142577
0.7685	Intermediate Similarity	NPC32674
0.768	Intermediate Similarity	NPC478147
0.7679	Intermediate Similarity	NPC92623
0.7679	Intermediate Similarity	NPC95178
0.7679	Intermediate Similarity	NPC70843
0.7679	Intermediate Similarity	NPC135464
0.7679	Intermediate Similarity	NPC69332
0.7679	Intermediate Similarity	NPC29989
0.7679	Intermediate Similarity	NPC188677
0.7679	Intermediate Similarity	NPC113457
0.7667	Intermediate Similarity	NPC160120
0.7667	Intermediate Similarity	NPC321133
0.7667	Intermediate Similarity	NPC41801
0.7667	Intermediate Similarity	NPC289330
0.7667	Intermediate Similarity	NPC252817
0.7667	Intermediate Similarity	NPC53596
0.7667	Intermediate Similarity	NPC17388
0.7667	Intermediate Similarity	NPC471308
0.7661	Intermediate Similarity	NPC218323
0.7658	Intermediate Similarity	NPC119860
0.7652	Intermediate Similarity	NPC163674
0.7652	Intermediate Similarity	NPC227553
0.7642	Intermediate Similarity	NPC271440
0.7642	Intermediate Similarity	NPC325292
0.7642	Intermediate Similarity	NPC138117
0.7619	Intermediate Similarity	NPC192
0.7619	Intermediate Similarity	NPC151764
0.7615	Intermediate Similarity	NPC214988
0.7615	Intermediate Similarity	NPC275104
0.7603	Intermediate Similarity	NPC318357
0.76	Intermediate Similarity	NPC477839
0.7581	Intermediate Similarity	NPC318965
0.7573	Intermediate Similarity	NPC155393
0.757	Intermediate Similarity	NPC316301
0.757	Intermediate Similarity	NPC27323
0.7557	Intermediate Similarity	NPC476989
0.7547	Intermediate Similarity	NPC304541
0.7547	Intermediate Similarity	NPC155908
0.7545	Intermediate Similarity	NPC248573
0.7545	Intermediate Similarity	NPC275053
0.7545	Intermediate Similarity	NPC223393
0.7545	Intermediate Similarity	NPC161571
0.7544	Intermediate Similarity	NPC61885
0.7544	Intermediate Similarity	NPC262365
0.7544	Intermediate Similarity	NPC201959
0.7544	Intermediate Similarity	NPC63698
0.7544	Intermediate Similarity	NPC11554
0.7523	Intermediate Similarity	NPC315921
0.7522	Intermediate Similarity	NPC271274
0.7521	Intermediate Similarity	NPC59387
0.752	Intermediate Similarity	NPC476353
0.75	Intermediate Similarity	NPC30506
0.75	Intermediate Similarity	NPC328070
0.75	Intermediate Similarity	NPC130595
0.75	Intermediate Similarity	NPC93882
0.75	Intermediate Similarity	NPC471511
0.75	Intermediate Similarity	NPC85276
0.75	Intermediate Similarity	NPC241891
0.75	Intermediate Similarity	NPC323810
0.75	Intermediate Similarity	NPC313650
0.75	Intermediate Similarity	NPC407
0.75	Intermediate Similarity	NPC471953
0.75	Intermediate Similarity	NPC168861
0.75	Intermediate Similarity	NPC307235
0.748	Intermediate Similarity	NPC470706

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 NPC96224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	761
0.2-0.3	1035
0.3-0.4	1820
0.4-0.5	2879
0.5-0.6	1818
0.6-0.7	592
0.7-0.8	109
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD2229	Approved
0.8468	Intermediate Similarity	NPD2234	Approved
0.8468	Intermediate Similarity	NPD2228	Approved
0.8431	Intermediate Similarity	NPD2934	Approved
0.8431	Intermediate Similarity	NPD2933	Approved
0.835	Intermediate Similarity	NPD2859	Approved
0.835	Intermediate Similarity	NPD2860	Approved
0.825	Intermediate Similarity	NPD7451	Discontinued
0.822	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3421	Phase 3
0.8148	Intermediate Similarity	NPD9610	Approved
0.8148	Intermediate Similarity	NPD9608	Approved
0.8113	Intermediate Similarity	NPD3020	Approved
0.8034	Intermediate Similarity	NPD4093	Discontinued
0.7966	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5304	Approved
0.7949	Intermediate Similarity	NPD5303	Approved
0.7946	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD1792	Phase 2
0.7917	Intermediate Similarity	NPD2561	Approved
0.7917	Intermediate Similarity	NPD2562	Approved
0.7851	Intermediate Similarity	NPD4659	Approved
0.7851	Intermediate Similarity	NPD1669	Approved
0.7838	Intermediate Similarity	NPD1444	Approved
0.7838	Intermediate Similarity	NPD1445	Approved
0.7797	Intermediate Similarity	NPD1759	Phase 1
0.7787	Intermediate Similarity	NPD5310	Approved
0.7787	Intermediate Similarity	NPD5311	Approved
0.7739	Intermediate Similarity	NPD9379	Approved
0.7739	Intermediate Similarity	NPD9377	Approved
0.7724	Intermediate Similarity	NPD3055	Approved
0.7724	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4103	Phase 2
0.7724	Intermediate Similarity	NPD3053	Approved
0.7723	Intermediate Similarity	NPD111	Approved
0.7712	Intermediate Similarity	NPD16	Approved
0.7712	Intermediate Similarity	NPD856	Approved
0.7712	Intermediate Similarity	NPD1758	Phase 1
0.7705	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2668	Approved
0.7667	Intermediate Similarity	NPD2667	Approved
0.7647	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3136	Phase 2
0.7619	Intermediate Similarity	NPD2372	Approved
0.7615	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD317	Approved
0.7563	Intermediate Similarity	NPD318	Approved
0.7557	Intermediate Similarity	NPD7450	Phase 2
0.7545	Intermediate Similarity	NPD1242	Phase 1
0.7538	Intermediate Similarity	NPD3552	Approved
0.7538	Intermediate Similarity	NPD3554	Approved
0.7538	Intermediate Similarity	NPD3555	Approved
0.7538	Intermediate Similarity	NPD3553	Approved
0.7523	Intermediate Similarity	NPD9273	Approved
0.7521	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2674	Phase 3
0.7479	Intermediate Similarity	NPD9568	Approved
0.7478	Intermediate Similarity	NPD3021	Approved
0.7478	Intermediate Similarity	NPD3022	Approved
0.7459	Intermediate Similarity	NPD1980	Approved
0.7459	Intermediate Similarity	NPD1983	Approved
0.7459	Intermediate Similarity	NPD1981	Approved
0.7458	Intermediate Similarity	NPD1793	Approved
0.7458	Intermediate Similarity	NPD1791	Approved
0.7442	Intermediate Similarity	NPD6346	Approved
0.7422	Intermediate Similarity	NPD3145	Approved
0.7422	Intermediate Similarity	NPD3144	Approved
0.7422	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6583	Phase 3
0.7419	Intermediate Similarity	NPD6582	Phase 2
0.7411	Intermediate Similarity	NPD4656	Approved
0.7411	Intermediate Similarity	NPD4658	Approved
0.7398	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3028	Approved
0.7364	Intermediate Similarity	NPD7477	Discontinued
0.7364	Intermediate Similarity	NPD6405	Approved
0.7364	Intermediate Similarity	NPD6407	Approved
0.7345	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5155	Approved
0.7344	Intermediate Similarity	NPD5156	Approved
0.7333	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4993	Discontinued
0.7323	Intermediate Similarity	NPD3635	Approved
0.7323	Intermediate Similarity	NPD3637	Approved
0.7323	Intermediate Similarity	NPD3636	Approved
0.7321	Intermediate Similarity	NPD4818	Approved
0.7321	Intermediate Similarity	NPD4817	Approved
0.7321	Intermediate Similarity	NPD940	Approved
0.7321	Intermediate Similarity	NPD846	Approved
0.7317	Intermediate Similarity	NPD1671	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3143	Discontinued
0.7311	Intermediate Similarity	NPD9618	Approved
0.7311	Intermediate Similarity	NPD9614	Approved
0.7308	Intermediate Similarity	NPD3062	Approved
0.7308	Intermediate Similarity	NPD3061	Approved
0.7308	Intermediate Similarity	NPD3059	Approved
0.7304	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD821	Approved
0.7273	Intermediate Similarity	NPD9613	Approved
0.7273	Intermediate Similarity	NPD9616	Approved
0.7273	Intermediate Similarity	NPD9615	Approved
0.7266	Intermediate Similarity	NPD2605	Approved
0.7266	Intermediate Similarity	NPD2606	Approved
0.7266	Intermediate Similarity	NPD3595	Approved
0.7266	Intermediate Similarity	NPD3594	Approved
0.7257	Intermediate Similarity	NPD4231	Approved
0.7257	Intermediate Similarity	NPD3682	Approved
0.7257	Intermediate Similarity	NPD4229	Approved
0.7257	Intermediate Similarity	NPD3680	Approved
0.725	Intermediate Similarity	NPD256	Approved
0.725	Intermediate Similarity	NPD255	Approved
0.7244	Intermediate Similarity	NPD2194	Approved
0.7244	Intermediate Similarity	NPD2195	Approved
0.7244	Intermediate Similarity	NPD6584	Phase 3
0.7236	Intermediate Similarity	NPD9381	Approved
0.7236	Intermediate Similarity	NPD9384	Approved
0.7213	Intermediate Similarity	NPD316	Approved
0.72	Intermediate Similarity	NPD2232	Approved
0.72	Intermediate Similarity	NPD2233	Approved
0.72	Intermediate Similarity	NPD2230	Approved
0.7197	Intermediate Similarity	NPD3052	Approved
0.7197	Intermediate Similarity	NPD5314	Approved
0.7197	Intermediate Similarity	NPD2568	Approved
0.7197	Intermediate Similarity	NPD3054	Approved
0.719	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD844	Approved
0.7182	Intermediate Similarity	NPD1809	Phase 2
0.7177	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1134	Approved
0.7165	Intermediate Similarity	NPD1131	Approved
0.7165	Intermediate Similarity	NPD1129	Approved
0.7165	Intermediate Similarity	NPD1135	Approved
0.7165	Intermediate Similarity	NPD1133	Approved
0.7156	Intermediate Similarity	NPD845	Approved
0.7119	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7978	Discontinued
0.7105	Intermediate Similarity	NPD3681	Approved
0.7105	Intermediate Similarity	NPD3683	Approved
0.7097	Intermediate Similarity	NPD2286	Discontinued
0.7087	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3400	Discontinued
0.708	Intermediate Similarity	NPD6331	Phase 2
0.7077	Intermediate Similarity	NPD1024	Discontinued
0.7073	Intermediate Similarity	NPD2486	Discontinued
0.7071	Intermediate Similarity	NPD7303	Discontinued
0.7064	Intermediate Similarity	NPD6690	Approved
0.7063	Intermediate Similarity	NPD2235	Phase 2
0.7063	Intermediate Similarity	NPD2231	Phase 2
0.7063	Intermediate Similarity	NPD3070	Discontinued
0.7049	Intermediate Similarity	NPD3596	Phase 2
0.7045	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD475	Phase 2
0.7023	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD854	Approved
0.7018	Intermediate Similarity	NPD855	Approved
0.7016	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9507	Approved
0.7008	Intermediate Similarity	NPD9622	Approved
0.7008	Intermediate Similarity	NPD4129	Approved
0.7008	Intermediate Similarity	NPD1755	Approved
0.7008	Intermediate Similarity	NPD3685	Discontinued
0.6991	Remote Similarity	NPD9712	Approved
0.6977	Remote Similarity	NPD9619	Approved
0.6977	Remote Similarity	NPD9620	Approved
0.6977	Remote Similarity	NPD9621	Approved
0.6975	Remote Similarity	NPD4253	Approved
0.6975	Remote Similarity	NPD4254	Approved
0.697	Remote Similarity	NPD839	Approved
0.697	Remote Similarity	NPD840	Approved
0.6967	Remote Similarity	NPD709	Approved
0.6964	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD4108	Discontinued
0.6957	Remote Similarity	NPD5103	Approved
0.6953	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2157	Approved
0.6935	Remote Similarity	NPD6581	Approved
0.6935	Remote Similarity	NPD6580	Approved
0.693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD1712	Approved
0.6917	Remote Similarity	NPD2500	Approved
0.6917	Remote Similarity	NPD2499	Approved
0.6912	Remote Similarity	NPD2161	Phase 2
0.6909	Remote Similarity	NPD1812	Approved
0.6909	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1814	Approved
0.6905	Remote Similarity	NPD3294	Phase 2
0.6905	Remote Similarity	NPD3847	Discontinued
0.6903	Remote Similarity	NPD9711	Approved
0.6903	Remote Similarity	NPD9611	Approved
0.6903	Remote Similarity	NPD9609	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