NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	253.11
Volume:	245.225
LogP:	-2.411
LogD:	-0.401
LogS:	-2.317
# Rotatable Bonds:	7
TPSA:	124.68
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	2.613
Fsp3:	0.273
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:	-5.707
MDCK Permeability:	0.00019235718355048448
Pgp-inhibitor:	0.001
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.481
Plasma Protein Binding (PPB):	28.934934616088867%
Volume Distribution (VD):	0.262
Pgp-substrate:	69.6125717163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	13.925
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.856
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.693
Carcinogencity:	0.56
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC122542

Natural Product ID:	NPC122542
*Common Name:**	L-Glutamic Acid 5-[(2-Hydroxyphenyl)-Hydrazide]
IUPAC Name:	(2S)-2-amino-5-[2-(2-hydroxyphenyl)hydrazinyl]-5-oxopentanoic acid
Synonyms:
Standard InCHIKey:	CRSVHQICRXRCEP-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C11H15N3O4/c12-7(11(17)18)5-6-10(16)14-13-8-3-1-2-4-9(8)15/h1-4,7,13,15H,5-6,12H2,(H,14,16)(H,17,18)/t7-/m0/s1
SMILES:	OC(=O)[C@H](CCC(=NNc1ccccc1O)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1210425
PubChem CID:	46911433
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:0004315] Glutamine 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
NPO14642	Lichina pygmaea	Species	Lichinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20570625]
NPO14642	Lichina pygmaea	Species	Lichinaceae	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	5
Others	6

Activity Type	# Activity
Cell Line	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1083	Cell Line	A-375	Homo sapiens	IC50	>	50000.0	nM	PMID[555802]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	11.0	%	PMID[555802]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	19.0	%	PMID[555802]
NPT319	Cell Line	B16	Mus musculus	IC50	=	20000.0	nM	PMID[555802]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	100.0	%	PMID[555802]
NPT319	Cell Line	B16	Mus musculus	IC50	=	14000.0	nM	PMID[555802]
NPT35	Others	n.a.		Ratio IC50	=	2.0	n.a.	PMID[555803]
NPT35	Others	n.a.		Stability	=	45.71	%	PMID[555803]
NPT35	Others	n.a.		IC50	=	8.67	ug.mL-1	PMID[555803]

☑ 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 NPC122542 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	229
0.1-0.2	4279
0.2-0.3	12904
0.3-0.4	11696
0.4-0.5	12112
0.5-0.6	1334
0.6-0.7	129
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC91615
0.9248	High Similarity	NPC469828
0.7538	Intermediate Similarity	NPC255721
0.748	Intermediate Similarity	NPC311660
0.7365	Intermediate Similarity	NPC469829
0.7248	Intermediate Similarity	NPC47986
0.7161	Intermediate Similarity	NPC241392
0.7133	Intermediate Similarity	NPC314252
0.7121	Intermediate Similarity	NPC76327
0.7101	Intermediate Similarity	NPC469831
0.7078	Intermediate Similarity	NPC259678
0.7054	Intermediate Similarity	NPC70201
0.6972	Remote Similarity	NPC27581
0.6936	Remote Similarity	NPC469830
0.6871	Remote Similarity	NPC325651
0.6842	Remote Similarity	NPC181527
0.6838	Remote Similarity	NPC9336
0.6815	Remote Similarity	NPC315829
0.6797	Remote Similarity	NPC181526
0.6786	Remote Similarity	NPC188867
0.6786	Remote Similarity	NPC281686
0.6786	Remote Similarity	NPC106551
0.6779	Remote Similarity	NPC326966
0.6767	Remote Similarity	NPC256838
0.6761	Remote Similarity	NPC321869
0.6667	Remote Similarity	NPC313466
0.6643	Remote Similarity	NPC239697
0.6643	Remote Similarity	NPC319950
0.6629	Remote Similarity	NPC477391
0.6627	Remote Similarity	NPC83241
0.6558	Remote Similarity	NPC43218
0.655	Remote Similarity	NPC95412
0.6538	Remote Similarity	NPC314113
0.6519	Remote Similarity	NPC323798
0.6516	Remote Similarity	NPC48202
0.6496	Remote Similarity	NPC44836
0.6484	Remote Similarity	NPC92689
0.6479	Remote Similarity	NPC222982
0.6458	Remote Similarity	NPC317784
0.6458	Remote Similarity	NPC142638
0.6454	Remote Similarity	NPC264782
0.6452	Remote Similarity	NPC316574
0.6438	Remote Similarity	NPC326079
0.6433	Remote Similarity	NPC91953
0.6424	Remote Similarity	NPC478147
0.6405	Remote Similarity	NPC208022
0.6403	Remote Similarity	NPC172046
0.6384	Remote Similarity	NPC477392
0.6384	Remote Similarity	NPC315934
0.6369	Remote Similarity	NPC197921
0.6369	Remote Similarity	NPC204156
0.6364	Remote Similarity	NPC297584
0.6358	Remote Similarity	NPC145888
0.6358	Remote Similarity	NPC16031
0.6358	Remote Similarity	NPC161593
0.6329	Remote Similarity	NPC469360
0.6301	Remote Similarity	NPC283760
0.6299	Remote Similarity	NPC244866
0.6286	Remote Similarity	NPC315631
0.6284	Remote Similarity	NPC142577
0.6284	Remote Similarity	NPC474862
0.6272	Remote Similarity	NPC191863
0.6272	Remote Similarity	NPC133470
0.6272	Remote Similarity	NPC289776
0.625	Remote Similarity	NPC296712
0.6233	Remote Similarity	NPC229353
0.6216	Remote Similarity	NPC108847
0.62	Remote Similarity	NPC315632
0.6194	Remote Similarity	NPC88667
0.619	Remote Similarity	NPC116573
0.6188	Remote Similarity	NPC301702
0.6178	Remote Similarity	NPC6570
0.6176	Remote Similarity	NPC475983
0.6163	Remote Similarity	NPC127362
0.6163	Remote Similarity	NPC314861
0.6159	Remote Similarity	NPC257142
0.6158	Remote Similarity	NPC474815
0.6143	Remote Similarity	NPC37584
0.6139	Remote Similarity	NPC287358
0.6131	Remote Similarity	NPC477889
0.6129	Remote Similarity	NPC48909
0.6125	Remote Similarity	NPC43477
0.6111	Remote Similarity	NPC309808
0.6101	Remote Similarity	NPC238412
0.6101	Remote Similarity	NPC476475
0.6092	Remote Similarity	NPC471778
0.6087	Remote Similarity	NPC13696
0.6084	Remote Similarity	NPC163674
0.6084	Remote Similarity	NPC227553
0.6078	Remote Similarity	NPC58827
0.6078	Remote Similarity	NPC476353
0.6078	Remote Similarity	NPC307437
0.6078	Remote Similarity	NPC72473
0.6065	Remote Similarity	NPC473987
0.6058	Remote Similarity	NPC29601
0.6053	Remote Similarity	NPC205946
0.6048	Remote Similarity	NPC284348
0.6047	Remote Similarity	NPC189116
0.6045	Remote Similarity	NPC8467
0.604	Remote Similarity	NPC130931
0.604	Remote Similarity	NPC150323
0.6038	Remote Similarity	NPC166667
0.6037	Remote Similarity	NPC146370
0.6034	Remote Similarity	NPC39822
0.6027	Remote Similarity	NPC317254
0.6026	Remote Similarity	NPC45191
0.6023	Remote Similarity	NPC19023
0.6023	Remote Similarity	NPC231862
0.6014	Remote Similarity	NPC226914
0.6014	Remote Similarity	NPC329358
0.6	Remote Similarity	NPC322735
0.5989	Remote Similarity	NPC132751
0.5988	Remote Similarity	NPC57105
0.5985	Remote Similarity	NPC125732
0.5976	Remote Similarity	NPC119569
0.5975	Remote Similarity	NPC6913
0.5974	Remote Similarity	NPC321561
0.5969	Remote Similarity	NPC214368
0.5966	Remote Similarity	NPC253810
0.5963	Remote Similarity	NPC282087
0.5963	Remote Similarity	NPC259800
0.5963	Remote Similarity	NPC317741
0.5963	Remote Similarity	NPC328137
0.5963	Remote Similarity	NPC318984
0.5963	Remote Similarity	NPC318028
0.5963	Remote Similarity	NPC241086
0.5959	Remote Similarity	NPC118202
0.5959	Remote Similarity	NPC329190
0.5957	Remote Similarity	NPC327481
0.5949	Remote Similarity	NPC253476
0.5946	Remote Similarity	NPC311737
0.5946	Remote Similarity	NPC38458
0.5944	Remote Similarity	NPC290566
0.5944	Remote Similarity	NPC145638
0.5939	Remote Similarity	NPC17760
0.5939	Remote Similarity	NPC478039
0.5939	Remote Similarity	NPC473769
0.5938	Remote Similarity	NPC126637
0.5932	Remote Similarity	NPC225381
0.592	Remote Similarity	NPC61004
0.5917	Remote Similarity	NPC473580
0.5916	Remote Similarity	NPC45459
0.5916	Remote Similarity	NPC315491
0.5915	Remote Similarity	NPC473804
0.5912	Remote Similarity	NPC470441
0.5909	Remote Similarity	NPC46009
0.5906	Remote Similarity	NPC70549
0.5896	Remote Similarity	NPC199737
0.5894	Remote Similarity	NPC56634
0.589	Remote Similarity	NPC66518
0.5886	Remote Similarity	NPC470392
0.5885	Remote Similarity	NPC472330
0.5885	Remote Similarity	NPC472329
0.5878	Remote Similarity	NPC82963
0.5872	Remote Similarity	NPC469243
0.587	Remote Similarity	NPC288854
0.5864	Remote Similarity	NPC197239
0.5864	Remote Similarity	NPC326860
0.5862	Remote Similarity	NPC329011
0.5857	Remote Similarity	NPC164859
0.5857	Remote Similarity	NPC178902
0.5857	Remote Similarity	NPC68055
0.5852	Remote Similarity	NPC476483
0.5852	Remote Similarity	NPC315388
0.5845	Remote Similarity	NPC231705
0.5843	Remote Similarity	NPC470395
0.5839	Remote Similarity	NPC473055
0.5839	Remote Similarity	NPC473052
0.5829	Remote Similarity	NPC70340
0.5829	Remote Similarity	NPC92803
0.5825	Remote Similarity	NPC476098
0.5822	Remote Similarity	NPC474584
0.5818	Remote Similarity	NPC470403
0.5818	Remote Similarity	NPC81026
0.5818	Remote Similarity	NPC470404
0.5818	Remote Similarity	NPC470394
0.5818	Remote Similarity	NPC260601
0.5812	Remote Similarity	NPC306376
0.5811	Remote Similarity	NPC160179
0.5808	Remote Similarity	NPC254798
0.5808	Remote Similarity	NPC220523
0.5806	Remote Similarity	NPC18890
0.5802	Remote Similarity	NPC322526
0.5801	Remote Similarity	NPC269750
0.5801	Remote Similarity	NPC194671
0.5797	Remote Similarity	NPC107619
0.5793	Remote Similarity	NPC319579
0.5792	Remote Similarity	NPC272375
0.5789	Remote Similarity	NPC473051
0.5789	Remote Similarity	NPC473050
0.5786	Remote Similarity	NPC328070
0.578	Remote Similarity	NPC475544
0.578	Remote Similarity	NPC103250
0.5779	Remote Similarity	NPC317758
0.5775	Remote Similarity	NPC144381
0.5771	Remote Similarity	NPC223207
0.5771	Remote Similarity	NPC139506
0.5771	Remote Similarity	NPC292143
0.5769	Remote Similarity	NPC98416
0.5765	Remote Similarity	NPC39431

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 NPC122542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	643
0.2-0.3	1220
0.3-0.4	2270
0.4-0.5	3912
0.5-0.6	894
0.6-0.7	75
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7333	Intermediate Similarity	NPD9342	Approved
0.7121	Intermediate Similarity	NPD9507	Approved
0.6943	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3136	Phase 2
0.6815	Remote Similarity	NPD2114	Discontinued
0.6806	Remote Similarity	NPD522	Approved
0.6786	Remote Similarity	NPD9568	Approved
0.6689	Remote Similarity	NPD1393	Approved
0.6594	Remote Similarity	NPD9376	Approved
0.6579	Remote Similarity	NPD756	Suspended
0.6534	Remote Similarity	NPD6045	Phase 3
0.6478	Remote Similarity	NPD302	Approved
0.6463	Remote Similarity	NPD3684	Discontinued
0.6452	Remote Similarity	NPD9279	Approved
0.6448	Remote Similarity	NPD6161	Approved
0.6448	Remote Similarity	NPD6162	Approved
0.6415	Remote Similarity	NPD1196	Approved
0.641	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3556	Approved
0.6407	Remote Similarity	NPD3558	Approved
0.6407	Remote Similarity	NPD3557	Approved
0.6407	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3560	Approved
0.6369	Remote Similarity	NPD3391	Approved
0.6369	Remote Similarity	NPD1422	Approved
0.6364	Remote Similarity	NPD256	Approved
0.6364	Remote Similarity	NPD255	Approved
0.6358	Remote Similarity	NPD9569	Approved
0.6352	Remote Similarity	NPD1195	Approved
0.6347	Remote Similarity	NPD6283	Phase 2
0.6346	Remote Similarity	NPD3096	Phase 2
0.6329	Remote Similarity	NPD7978	Discontinued
0.6296	Remote Similarity	NPD1543	Discontinued
0.6296	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD313	Approved
0.6276	Remote Similarity	NPD254	Approved
0.6265	Remote Similarity	NPD948	Phase 3
0.6258	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD1040	Phase 2
0.6218	Remote Similarity	NPD274	Approved
0.6218	Remote Similarity	NPD275	Approved
0.6215	Remote Similarity	NPD5445	Approved
0.6213	Remote Similarity	NPD3241	Phase 2
0.6209	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD259	Phase 1
0.6194	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD75	Approved
0.6188	Remote Similarity	NPD9277	Approved
0.6184	Remote Similarity	NPD9723	Approved
0.6169	Remote Similarity	NPD9537	Phase 1
0.6169	Remote Similarity	NPD9536	Phase 1
0.6164	Remote Similarity	NPD7450	Phase 2
0.6159	Remote Similarity	NPD196	Phase 1
0.6136	Remote Similarity	NPD2361	Approved
0.6127	Remote Similarity	NPD2249	Approved
0.6127	Remote Similarity	NPD2247	Approved
0.6125	Remote Similarity	NPD9275	Approved
0.6125	Remote Similarity	NPD9278	Suspended
0.6125	Remote Similarity	NPD9274	Approved
0.6125	Remote Similarity	NPD9276	Approved
0.6122	Remote Similarity	NPD1759	Phase 1
0.6115	Remote Similarity	NPD555	Phase 2
0.6114	Remote Similarity	NPD3951	Phase 3
0.6114	Remote Similarity	NPD3952	Approved
0.6114	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD2360	Approved
0.6092	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7523	Phase 3
0.6084	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.608	Remote Similarity	NPD2359	Approved
0.6074	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD9570	Approved
0.6062	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7883	Discontinued
0.6054	Remote Similarity	NPD1758	Phase 1
0.6047	Remote Similarity	NPD863	Approved
0.6047	Remote Similarity	NPD861	Approved
0.6047	Remote Similarity	NPD862	Approved
0.6043	Remote Similarity	NPD9608	Approved
0.6043	Remote Similarity	NPD9610	Approved
0.6042	Remote Similarity	NPD181	Approved
0.604	Remote Similarity	NPD9272	Approved
0.6038	Remote Similarity	NPD6636	Phase 3
0.6036	Remote Similarity	NPD2672	Discontinued
0.6025	Remote Similarity	NPD9477	Approved
0.6011	Remote Similarity	NPD3965	Phase 1
0.6	Remote Similarity	NPD5871	Discontinued
0.6	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1839	Phase 1
0.6	Remote Similarity	NPD822	Approved
0.5989	Remote Similarity	NPD927	Approved
0.5974	Remote Similarity	NPD7451	Discontinued
0.5974	Remote Similarity	NPD257	Approved
0.5974	Remote Similarity	NPD258	Approved
0.5972	Remote Similarity	NPD308	Approved
0.5966	Remote Similarity	NPD1913	Phase 1
0.5963	Remote Similarity	NPD1537	Approved
0.5963	Remote Similarity	NPD1538	Phase 1
0.5963	Remote Similarity	NPD1519	Approved
0.5962	Remote Similarity	NPD9718	Approved
0.5959	Remote Similarity	NPD286	Approved
0.5948	Remote Similarity	NPD9587	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7617	Discontinued
0.5944	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD484	Approved
0.5906	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7495	Discontinued
0.5906	Remote Similarity	NPD8019	Approved
0.5901	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD711	Discontinued
0.5892	Remote Similarity	NPD1898	Discontinued
0.5892	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD935	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3154	Approved
0.587	Remote Similarity	NPD3153	Approved
0.5864	Remote Similarity	NPD1523	Approved
0.5864	Remote Similarity	NPD1522	Approved
0.5862	Remote Similarity	NPD2098	Approved
0.586	Remote Similarity	NPD1070	Approved
0.586	Remote Similarity	NPD1069	Approved
0.5858	Remote Similarity	NPD4003	Phase 3
0.5858	Remote Similarity	NPD950	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD2681	Approved
0.5852	Remote Similarity	NPD1394	Approved
0.5852	Remote Similarity	NPD2889	Approved
0.5852	Remote Similarity	NPD2890	Approved
0.5852	Remote Similarity	NPD2017	Approved
0.5852	Remote Similarity	NPD2680	Approved
0.5852	Remote Similarity	NPD2888	Approved
0.585	Remote Similarity	NPD9614	Approved
0.585	Remote Similarity	NPD9618	Approved
0.5848	Remote Similarity	NPD7105	Phase 1
0.5848	Remote Similarity	NPD1187	Discontinued
0.5848	Remote Similarity	NPD2366	Approved
0.5839	Remote Similarity	NPD317	Approved
0.5839	Remote Similarity	NPD1536	Approved
0.5839	Remote Similarity	NPD318	Approved
0.5838	Remote Similarity	NPD1012	Discontinued
0.5833	Remote Similarity	NPD662	Approved
0.5833	Remote Similarity	NPD663	Approved
0.5833	Remote Similarity	NPD659	Approved
0.5833	Remote Similarity	NPD6519	Phase 2
0.5833	Remote Similarity	NPD658	Approved
0.5833	Remote Similarity	NPD656	Approved
0.5819	Remote Similarity	NPD4652	Approved
0.5818	Remote Similarity	NPD5819	Phase 2
0.5818	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.581	Remote Similarity	NPD158	Discontinued
0.5792	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9692	Approved
0.5789	Remote Similarity	NPD1236	Phase 3
0.5789	Remote Similarity	NPD9693	Approved
0.5787	Remote Similarity	NPD4083	Discontinued
0.5779	Remote Similarity	NPD182	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD1544	Phase 1
0.5774	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD955	Approved
0.5769	Remote Similarity	NPD849	Approved
0.5769	Remote Similarity	NPD850	Approved
0.5769	Remote Similarity	NPD848	Approved
0.5765	Remote Similarity	NPD1633	Approved
0.5761	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD2789	Approved
0.5756	Remote Similarity	NPD2468	Approved
0.5756	Remote Similarity	NPD6913	Approved
0.5756	Remote Similarity	NPD3778	Approved
0.5756	Remote Similarity	NPD2469	Approved
0.5753	Remote Similarity	NPD9508	Approved
0.575	Remote Similarity	NPD825	Approved
0.575	Remote Similarity	NPD826	Approved
0.5749	Remote Similarity	NPD7554	Discontinued
0.5747	Remote Similarity	NPD2097	Approved
0.5741	Remote Similarity	NPD1520	Approved
0.5741	Remote Similarity	NPD1521	Approved
0.5739	Remote Similarity	NPD8303	Discontinued
0.5733	Remote Similarity	NPD9247	Phase 3
0.5732	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.5731	Remote Similarity	NPD1634	Approved
0.5731	Remote Similarity	NPD5811	Approved
0.5731	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD9566	Approved
0.5724	Remote Similarity	NPD1108	Approved
0.5724	Remote Similarity	NPD1107	Approved
0.5723	Remote Similarity	NPD864	Approved
0.5723	Remote Similarity	NPD865	Approved
0.5723	Remote Similarity	NPD3400	Discontinued
0.5714	Remote Similarity	NPD964	Approved
0.5714	Remote Similarity	NPD738	Approved
0.5714	Remote Similarity	NPD9694	Discovery
0.5706	Remote Similarity	NPD6864	Phase 2
0.5706	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD6865	Phase 2

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