NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	373.19
Volume:	391.152
LogP:	1.449
LogD:	0.554
LogS:	-3.463
# Rotatable Bonds:	10
TPSA:	103.7
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	3.477
Fsp3:	0.476
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:	-5.487
MDCK Permeability:	1.6043579307734035e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.747

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.71411895751953%
Volume Distribution (VD):	0.21
Pgp-substrate:	7.498764991760254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.648
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	11.578
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.448
Skin Sensitization:	0.117
Carcinogencity:	0.328
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC478147

Natural Product ID:	NPC478147
*Common Name:**	(2S)-3-(4-hydroxyphenyl)-2-[[2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
IUPAC Name:	(2S)-3-(4-hydroxyphenyl)-2-[[2-[3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]propanoic acid
Synonyms:
Standard InCHIKey:	SLWSWKGGZQCLDU-ZRUKUQQCSA-N
Standard InCHI:	InChI=1S/C21H27NO5/c1-2-3-4-5-17-15(8-11-19(17)24)13-20(25)22-18(21(26)27)12-14-6-9-16(23)10-7-14/h3-4,6-7,9-10,15,17-18,23H,2,5,8,11-13H2,1H3,(H,22,25)(H,26,27)/b4-3-/t15?,17?,18-/m0/s1
SMILES:	CC/C=C\CC1C(CCC1=O)CC(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004319] Tyrosine and derivatives

*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
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16180811]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23510	Vicia faba	Species	Fabaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Activity	=	2318	n.a.	PMID[16180811]

☑ 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 NPC478147 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	147
0.1-0.2	791
0.2-0.3	3217
0.3-0.4	11340
0.4-0.5	10335
0.5-0.6	13883
0.6-0.7	2667
0.7-0.8	280
0.8-0.85	28
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9174	High Similarity	NPC319950
0.8976	High Similarity	NPC296712
0.88	High Similarity	NPC142577
0.88	High Similarity	NPC474862
0.88	High Similarity	NPC27581
0.876	High Similarity	NPC325651
0.8702	High Similarity	NPC244866
0.8626	High Similarity	NPC326966
0.8605	High Similarity	NPC476353
0.8485	Intermediate Similarity	NPC45191
0.8421	Intermediate Similarity	NPC328070
0.8387	Intermediate Similarity	NPC317254
0.837	Intermediate Similarity	NPC6570
0.832	Intermediate Similarity	NPC188867
0.832	Intermediate Similarity	NPC281686
0.832	Intermediate Similarity	NPC106551
0.8309	Intermediate Similarity	NPC473052
0.8309	Intermediate Similarity	NPC473055
0.8284	Intermediate Similarity	NPC470392
0.8248	Intermediate Similarity	NPC322526
0.8235	Intermediate Similarity	NPC6913
0.816	Intermediate Similarity	NPC118202
0.813	Intermediate Similarity	NPC474149
0.8129	Intermediate Similarity	NPC91953
0.8125	Intermediate Similarity	NPC239697
0.8125	Intermediate Similarity	NPC283760
0.8116	Intermediate Similarity	NPC471201
0.8099	Intermediate Similarity	NPC231705
0.808	Intermediate Similarity	NPC309808
0.8058	Intermediate Similarity	NPC197921
0.8049	Intermediate Similarity	NPC258056
0.8	Intermediate Similarity	NPC56634
0.8	Intermediate Similarity	NPC469360
0.7969	Intermediate Similarity	NPC311737
0.7969	Intermediate Similarity	NPC38458
0.7907	Intermediate Similarity	NPC317784
0.7907	Intermediate Similarity	NPC142638
0.7902	Intermediate Similarity	NPC16188
0.7891	Intermediate Similarity	NPC82963
0.7886	Intermediate Similarity	NPC142297
0.7863	Intermediate Similarity	NPC326079
0.7857	Intermediate Similarity	NPC48202
0.7851	Intermediate Similarity	NPC178902
0.7832	Intermediate Similarity	NPC81026
0.7823	Intermediate Similarity	NPC39431
0.7786	Intermediate Similarity	NPC242159
0.7786	Intermediate Similarity	NPC313694
0.7762	Intermediate Similarity	NPC266741
0.7721	Intermediate Similarity	NPC16031
0.7721	Intermediate Similarity	NPC145888
0.7721	Intermediate Similarity	NPC161593
0.7687	Intermediate Similarity	NPC233702
0.768	Intermediate Similarity	NPC24101
0.768	Intermediate Similarity	NPC96224
0.7652	Intermediate Similarity	NPC80150
0.7652	Intermediate Similarity	NPC190663
0.7651	Intermediate Similarity	NPC473580
0.7638	Intermediate Similarity	NPC227553
0.7638	Intermediate Similarity	NPC163674
0.7635	Intermediate Similarity	NPC202198
0.763	Intermediate Similarity	NPC4974
0.7626	Intermediate Similarity	NPC88667
0.7615	Intermediate Similarity	NPC471924
0.7615	Intermediate Similarity	NPC471928
0.7615	Intermediate Similarity	NPC471925
0.7603	Intermediate Similarity	NPC12730
0.7603	Intermediate Similarity	NPC245561
0.7594	Intermediate Similarity	NPC473050
0.7594	Intermediate Similarity	NPC473051
0.7581	Intermediate Similarity	NPC13495
0.7578	Intermediate Similarity	NPC474584
0.7566	Intermediate Similarity	NPC469243
0.7557	Intermediate Similarity	NPC471926
0.7554	Intermediate Similarity	NPC257390
0.7552	Intermediate Similarity	NPC476989
0.7551	Intermediate Similarity	NPC132771
0.755	Intermediate Similarity	NPC56635
0.7541	Intermediate Similarity	NPC52472
0.754	Intermediate Similarity	NPC31274
0.754	Intermediate Similarity	NPC153690
0.7537	Intermediate Similarity	NPC160493
0.7521	Intermediate Similarity	NPC260000
0.7518	Intermediate Similarity	NPC321561
0.7518	Intermediate Similarity	NPC305717
0.7465	Intermediate Similarity	NPC109580
0.746	Intermediate Similarity	NPC228737
0.7459	Intermediate Similarity	NPC280869
0.7451	Intermediate Similarity	NPC475544
0.7444	Intermediate Similarity	NPC268572
0.7442	Intermediate Similarity	NPC17693
0.7429	Intermediate Similarity	NPC48909
0.7424	Intermediate Similarity	NPC169328
0.7419	Intermediate Similarity	NPC63931
0.7419	Intermediate Similarity	NPC223207
0.74	Intermediate Similarity	NPC262166
0.74	Intermediate Similarity	NPC56685
0.74	Intermediate Similarity	NPC261934
0.74	Intermediate Similarity	NPC5194
0.7383	Intermediate Similarity	NPC324081
0.7381	Intermediate Similarity	NPC188677
0.7381	Intermediate Similarity	NPC274089
0.7381	Intermediate Similarity	NPC327481
0.7381	Intermediate Similarity	NPC191215
0.7381	Intermediate Similarity	NPC70843
0.7372	Intermediate Similarity	NPC61004
0.7372	Intermediate Similarity	NPC304074
0.7372	Intermediate Similarity	NPC471771
0.7372	Intermediate Similarity	NPC290755
0.7368	Intermediate Similarity	NPC310467
0.736	Intermediate Similarity	NPC120693
0.736	Intermediate Similarity	NPC261573
0.736	Intermediate Similarity	NPC8931
0.7358	Intermediate Similarity	NPC137627
0.7338	Intermediate Similarity	NPC476194
0.7328	Intermediate Similarity	NPC142599
0.7324	Intermediate Similarity	NPC243404
0.7313	Intermediate Similarity	NPC31296
0.7313	Intermediate Similarity	NPC473974
0.7313	Intermediate Similarity	NPC258366
0.7313	Intermediate Similarity	NPC79933
0.7305	Intermediate Similarity	NPC246913
0.7305	Intermediate Similarity	NPC275538
0.7296	Intermediate Similarity	NPC89831
0.729	Intermediate Similarity	NPC241794
0.7287	Intermediate Similarity	NPC319579
0.728	Intermediate Similarity	NPC471317
0.728	Intermediate Similarity	NPC164859
0.7279	Intermediate Similarity	NPC268348
0.7267	Intermediate Similarity	NPC473491
0.7266	Intermediate Similarity	NPC317305
0.7266	Intermediate Similarity	NPC210950
0.7266	Intermediate Similarity	NPC199738
0.726	Intermediate Similarity	NPC33011
0.7259	Intermediate Similarity	NPC190501
0.7259	Intermediate Similarity	NPC318552
0.7258	Intermediate Similarity	NPC289381
0.7258	Intermediate Similarity	NPC155847
0.725	Intermediate Similarity	NPC306804
0.7246	Intermediate Similarity	NPC471927
0.7246	Intermediate Similarity	NPC47667
0.7244	Intermediate Similarity	NPC69332
0.7244	Intermediate Similarity	NPC95178
0.7244	Intermediate Similarity	NPC29989
0.7241	Intermediate Similarity	NPC471283
0.7239	Intermediate Similarity	NPC122009
0.7236	Intermediate Similarity	NPC107619
0.7233	Intermediate Similarity	NPC475204
0.7233	Intermediate Similarity	NPC475123
0.7233	Intermediate Similarity	NPC198254
0.7233	Intermediate Similarity	NPC274198
0.7231	Intermediate Similarity	NPC329011
0.723	Intermediate Similarity	NPC473804
0.7215	Intermediate Similarity	NPC107938
0.7215	Intermediate Similarity	NPC294516
0.7215	Intermediate Similarity	NPC209463
0.7211	Intermediate Similarity	NPC66518
0.7209	Intermediate Similarity	NPC88141
0.7209	Intermediate Similarity	NPC95172
0.7209	Intermediate Similarity	NPC326187
0.7208	Intermediate Similarity	NPC207675
0.7208	Intermediate Similarity	NPC212699
0.7206	Intermediate Similarity	NPC164852
0.7205	Intermediate Similarity	NPC155506
0.7205	Intermediate Similarity	NPC26108
0.7205	Intermediate Similarity	NPC279871
0.7205	Intermediate Similarity	NPC159767
0.7203	Intermediate Similarity	NPC169766
0.72	Intermediate Similarity	NPC318154
0.72	Intermediate Similarity	NPC476444
0.7194	Intermediate Similarity	NPC124776
0.7192	Intermediate Similarity	NPC328137
0.7192	Intermediate Similarity	NPC282087
0.7192	Intermediate Similarity	NPC150712
0.7192	Intermediate Similarity	NPC317741
0.7192	Intermediate Similarity	NPC318984
0.7192	Intermediate Similarity	NPC241086
0.7192	Intermediate Similarity	NPC318028
0.7192	Intermediate Similarity	NPC259800
0.719	Intermediate Similarity	NPC476268
0.7188	Intermediate Similarity	NPC226699
0.7185	Intermediate Similarity	NPC43275
0.7185	Intermediate Similarity	NPC42657
0.7181	Intermediate Similarity	NPC119569
0.7176	Intermediate Similarity	NPC48525
0.7172	Intermediate Similarity	NPC236795
0.7164	Intermediate Similarity	NPC76308
0.7164	Intermediate Similarity	NPC325295
0.7164	Intermediate Similarity	NPC283468
0.7154	Intermediate Similarity	NPC222084
0.7153	Intermediate Similarity	NPC470441
0.7143	Intermediate Similarity	NPC322197
0.7143	Intermediate Similarity	NPC13426
0.7143	Intermediate Similarity	NPC471929
0.7143	Intermediate Similarity	NPC471935
0.7143	Intermediate Similarity	NPC197470
0.7143	Intermediate Similarity	NPC471930
0.7143	Intermediate Similarity	NPC251439
0.7133	Intermediate Similarity	NPC474753
0.7133	Intermediate Similarity	NPC17760
0.7132	Intermediate Similarity	NPC478014

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 NPC478147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	450
0.2-0.3	821
0.3-0.4	1939
0.4-0.5	2961
0.5-0.6	2135
0.6-0.7	660
0.7-0.8	52
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8692	High Similarity	NPD3136	Phase 2
0.8421	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD9568	Approved
0.8189	Intermediate Similarity	NPD1759	Phase 1
0.8169	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1758	Phase 1
0.8095	Intermediate Similarity	NPD256	Approved
0.8095	Intermediate Similarity	NPD255	Approved
0.7986	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6390	Discontinued
0.7929	Intermediate Similarity	NPD7450	Phase 2
0.7877	Intermediate Similarity	NPD7523	Phase 3
0.7872	Intermediate Similarity	NPD7978	Discontinued
0.7721	Intermediate Similarity	NPD9569	Approved
0.7708	Intermediate Similarity	NPD3400	Discontinued
0.7698	Intermediate Similarity	NPD3644	Approved
0.7698	Intermediate Similarity	NPD3642	Approved
0.7698	Intermediate Similarity	NPD3643	Approved
0.7682	Intermediate Similarity	NPD7972	Discontinued
0.7626	Intermediate Similarity	NPD259	Phase 1
0.7616	Intermediate Similarity	NPD7495	Discontinued
0.7571	Intermediate Similarity	NPD6346	Approved
0.7569	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD258	Approved
0.7518	Intermediate Similarity	NPD555	Phase 2
0.7518	Intermediate Similarity	NPD257	Approved
0.7518	Intermediate Similarity	NPD7451	Discontinued
0.75	Intermediate Similarity	NPD8019	Approved
0.75	Intermediate Similarity	NPD196	Phase 1
0.7482	Intermediate Similarity	NPD9536	Phase 1
0.7482	Intermediate Similarity	NPD9537	Phase 1
0.7481	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2234	Approved
0.7385	Intermediate Similarity	NPD2229	Approved
0.7385	Intermediate Similarity	NPD2228	Approved
0.736	Intermediate Similarity	NPD9610	Approved
0.736	Intermediate Similarity	NPD9608	Approved
0.7324	Intermediate Similarity	NPD825	Approved
0.7324	Intermediate Similarity	NPD826	Approved
0.732	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1040	Phase 2
0.7299	Intermediate Similarity	NPD1755	Approved
0.7261	Intermediate Similarity	NPD8303	Discontinued
0.7259	Intermediate Similarity	NPD3019	Approved
0.7259	Intermediate Similarity	NPD2932	Approved
0.7234	Intermediate Similarity	NPD4738	Phase 2
0.7234	Intermediate Similarity	NPD9718	Approved
0.7192	Intermediate Similarity	NPD1519	Approved
0.7192	Intermediate Similarity	NPD1537	Approved
0.7192	Intermediate Similarity	NPD1538	Phase 1
0.7192	Intermediate Similarity	NPD9570	Approved
0.7163	Intermediate Similarity	NPD2614	Approved
0.7153	Intermediate Similarity	NPD274	Approved
0.7153	Intermediate Similarity	NPD275	Approved
0.7152	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1348	Approved
0.7125	Intermediate Similarity	NPD7315	Approved
0.7122	Intermediate Similarity	NPD6325	Discontinued
0.7111	Intermediate Similarity	NPD4479	Discontinued
0.7111	Intermediate Similarity	NPD5304	Approved
0.7111	Intermediate Similarity	NPD5303	Approved
0.7111	Intermediate Similarity	NPD2218	Phase 2
0.7111	Intermediate Similarity	NPD2217	Approved
0.7109	Intermediate Similarity	NPD1444	Approved
0.7109	Intermediate Similarity	NPD1445	Approved
0.7105	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6624	Discontinued
0.7089	Intermediate Similarity	NPD2098	Approved
0.7075	Intermediate Similarity	NPD1522	Approved
0.7075	Intermediate Similarity	NPD1523	Approved
0.7059	Intermediate Similarity	NPD5981	Approved
0.7059	Intermediate Similarity	NPD7131	Phase 3
0.7055	Intermediate Similarity	NPD1536	Approved
0.705	Intermediate Similarity	NPD4659	Approved
0.7037	Intermediate Similarity	NPD317	Approved
0.7037	Intermediate Similarity	NPD318	Approved
0.7032	Intermediate Similarity	NPD6502	Phase 2
0.7019	Intermediate Similarity	NPD7608	Discontinued
0.7014	Intermediate Similarity	NPD5745	Approved
0.7	Intermediate Similarity	NPD3125	Approved
0.7	Intermediate Similarity	NPD3098	Discontinued
0.698	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2562	Approved
0.6978	Remote Similarity	NPD2561	Approved
0.6968	Remote Similarity	NPD3455	Phase 2
0.6966	Remote Similarity	NPD468	Phase 1
0.6962	Remote Similarity	NPD2097	Approved
0.6957	Remote Similarity	NPD3421	Phase 3
0.6954	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4103	Phase 2
0.695	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1792	Phase 2
0.6939	Remote Similarity	NPD1520	Approved
0.6939	Remote Similarity	NPD1521	Approved
0.6934	Remote Similarity	NPD4093	Discontinued
0.6934	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4652	Approved
0.6913	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD856	Approved
0.6912	Remote Similarity	NPD16	Approved
0.6908	Remote Similarity	NPD7554	Discontinued
0.6906	Remote Similarity	NPD5618	Discontinued
0.6905	Remote Similarity	NPD3020	Approved
0.6905	Remote Similarity	NPD9712	Approved
0.6897	Remote Similarity	NPD6663	Approved
0.6894	Remote Similarity	NPD6746	Phase 2
0.6887	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7303	Discontinued
0.688	Remote Similarity	NPD9566	Approved
0.6875	Remote Similarity	NPD5746	Approved
0.6871	Remote Similarity	NPD2157	Approved
0.6861	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2933	Approved
0.6855	Remote Similarity	NPD2934	Approved
0.6853	Remote Similarity	NPD5736	Approved
0.685	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2240	Approved
0.6846	Remote Similarity	NPD2239	Approved
0.6838	Remote Similarity	NPD3123	Discovery
0.6835	Remote Similarity	NPD5355	Approved
0.6835	Remote Similarity	NPD5356	Approved
0.6835	Remote Similarity	NPD3026	Approved
0.6835	Remote Similarity	NPD3847	Discontinued
0.6835	Remote Similarity	NPD3143	Discontinued
0.6835	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3023	Approved
0.6825	Remote Similarity	NPD9710	Approved
0.6825	Remote Similarity	NPD9711	Approved
0.6815	Remote Similarity	NPD9618	Approved
0.6815	Remote Similarity	NPD9614	Approved
0.6812	Remote Similarity	NPD3025	Approved
0.6812	Remote Similarity	NPD3024	Approved
0.6809	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4125	Approved
0.68	Remote Similarity	NPD2859	Approved
0.68	Remote Similarity	NPD2860	Approved
0.6794	Remote Similarity	NPD6406	Approved
0.6781	Remote Similarity	NPD2674	Phase 3
0.6769	Remote Similarity	NPD999	Phase 2
0.6766	Remote Similarity	NPD5557	Phase 1
0.6763	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2668	Approved
0.6763	Remote Similarity	NPD2667	Approved
0.6759	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2017	Approved
0.6748	Remote Similarity	NPD2890	Approved
0.6748	Remote Similarity	NPD2889	Approved
0.6748	Remote Similarity	NPD2888	Approved
0.6747	Remote Similarity	NPD3909	Discontinued
0.6741	Remote Similarity	NPD2652	Approved
0.6741	Remote Similarity	NPD2650	Approved
0.6739	Remote Similarity	NPD9545	Approved
0.6738	Remote Similarity	NPD2584	Suspended
0.6736	Remote Similarity	NPD3663	Approved
0.6736	Remote Similarity	NPD3661	Approved
0.6736	Remote Similarity	NPD3662	Phase 3
0.6736	Remote Similarity	NPD3637	Approved
0.6736	Remote Similarity	NPD3664	Approved
0.6736	Remote Similarity	NPD3636	Approved
0.6736	Remote Similarity	NPD3635	Approved
0.6733	Remote Similarity	NPD2161	Phase 2
0.6731	Remote Similarity	NPD1670	Discontinued
0.673	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1693	Approved
0.6713	Remote Similarity	NPD3055	Approved
0.6713	Remote Similarity	NPD2159	Approved
0.6713	Remote Similarity	NPD2160	Approved
0.6713	Remote Similarity	NPD2627	Approved
0.6713	Remote Similarity	NPD2625	Approved
0.6713	Remote Similarity	NPD2626	Approved
0.6713	Remote Similarity	NPD2628	Approved
0.6713	Remote Similarity	NPD3053	Approved
0.6712	Remote Similarity	NPD3144	Approved
0.6712	Remote Similarity	NPD3145	Approved
0.6712	Remote Similarity	NPD4621	Approved
0.6712	Remote Similarity	NPD4619	Approved
0.6711	Remote Similarity	NPD3555	Approved
0.6711	Remote Similarity	NPD3554	Approved
0.6711	Remote Similarity	NPD3552	Approved
0.6711	Remote Similarity	NPD3553	Approved
0.671	Remote Similarity	NPD4739	Approved
0.6707	Remote Similarity	NPD3965	Phase 1
0.6691	Remote Similarity	NPD1793	Approved
0.6691	Remote Similarity	NPD4102	Approved
0.6691	Remote Similarity	NPD1791	Approved
0.6691	Remote Similarity	NPD4105	Approved
0.6691	Remote Similarity	NPD475	Phase 2
0.6691	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1669	Approved
0.669	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3685	Discontinued
0.669	Remote Similarity	NPD2605	Approved
0.669	Remote Similarity	NPD2606	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