NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.1
Volume:	234.228
LogP:	-1.28
LogD:	-0.909
LogS:	-1.486
# Rotatable Bonds:	6
TPSA:	112.65
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	2.284
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:	-6.238
MDCK Permeability:	0.0005415023770183325
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.199
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	19.510284423828125%
Volume Distribution (VD):	0.357
Pgp-substrate:	77.31930541992188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	3.029
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.226
Carcinogencity:	0.108
Eye Corrosion:	0.004
Eye Irritation:	0.057
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC27581

Natural Product ID:	NPC27581
*Common Name:**	Gy
IUPAC Name:	(2S)-2-[(2-azaniumylacetyl)amino]-3-(4-hydroxyphenyl)propanoate
Synonyms:	Gly-Tyr
Standard InCHIKey:	XBGGUPMXALFZOT-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C11H14N2O4/c12-6-10(15)13-9(11(16)17)5-7-1-3-8(14)4-2-7/h1-4,9,14H,5-6,12H2,(H,13,15)(H,16,17)/t9-/m0/s1
SMILES:	c1cc(ccc1C[C@@H](C(=O)O)N=C(CN)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL53400
PubChem CID:	6994980 92829
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:0000348] Peptides

*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

☑ 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
EC50	1
IC50	2
Ki	2
Others	6

Activity Type	# Activity
Individual Protein	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	IC50	=	208929.61	nM	PMID[484990]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	EC50	=	140000.0	nM	PMID[484992]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	max activation	=	125.0	%	PMID[484992]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	IC50	=	120000.0	nM	PMID[484992]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	Ratio	=	870.0	n.a.	PMID[484992]
NPT1241	Individual Protein	Oligopeptide transporter, kidney isoform	Rattus norvegicus	Ki	=	14000.0	nM	PMID[484993]
NPT1240	Individual Protein	Solute carrier family 15 member 1	Rattus norvegicus	Ki	=	210000.0	nM	PMID[484993]
NPT1166	Individual Protein	Angiotensin-converting enzyme	Homo sapiens	logIC50	=	2.32	n.a.	PMID[484994]
NPT2	Others	Unspecified		Log 1/T	=	1.77	n.a.	PMID[484989]
NPT35	Others	n.a.		LogP	=	3.12	n.a.	PMID[484989]
NPT2	Others	Unspecified		Log 1/T	=	1.77	n.a.	PMID[484991]

☑ 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 NPC27581 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	152
0.1-0.2	1379
0.2-0.3	5742
0.3-0.4	11517
0.4-0.5	10038
0.5-0.6	11242
0.6-0.7	2256
0.7-0.8	310
0.8-0.85	37
0.85-0.9	16
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC319950
0.9421	High Similarity	NPC325651
0.9304	High Similarity	NPC281686
0.9304	High Similarity	NPC106551
0.9304	High Similarity	NPC188867
0.9068	High Similarity	NPC239697
0.9	High Similarity	NPC142577
0.896	High Similarity	NPC326966
0.8871	High Similarity	NPC296712
0.8824	High Similarity	NPC317784
0.8824	High Similarity	NPC142638
0.88	High Similarity	NPC478147
0.876	High Similarity	NPC326079
0.874	High Similarity	NPC244866
0.8689	High Similarity	NPC474862
0.864	High Similarity	NPC476353
0.8571	High Similarity	NPC161593
0.8571	High Similarity	NPC145888
0.8571	High Similarity	NPC16031
0.855	High Similarity	NPC48202
0.8516	High Similarity	NPC45191
0.8443	Intermediate Similarity	NPC283760
0.8403	Intermediate Similarity	NPC309808
0.8397	Intermediate Similarity	NPC6913
0.8333	Intermediate Similarity	NPC164859
0.8308	Intermediate Similarity	NPC470392
0.8308	Intermediate Similarity	NPC88667
0.8306	Intermediate Similarity	NPC56634
0.8284	Intermediate Similarity	NPC91953
0.8264	Intermediate Similarity	NPC317254
0.8258	Intermediate Similarity	NPC6570
0.8231	Intermediate Similarity	NPC48909
0.8209	Intermediate Similarity	NPC197921
0.8182	Intermediate Similarity	NPC118202
0.8174	Intermediate Similarity	NPC178902
0.8148	Intermediate Similarity	NPC469360
0.813	Intermediate Similarity	NPC38458
0.813	Intermediate Similarity	NPC311737
0.807	Intermediate Similarity	NPC245561
0.8062	Intermediate Similarity	NPC321561
0.8049	Intermediate Similarity	NPC82963
0.8	Intermediate Similarity	NPC52472
0.7966	Intermediate Similarity	NPC231705
0.7941	Intermediate Similarity	NPC328137
0.7941	Intermediate Similarity	NPC318028
0.7941	Intermediate Similarity	NPC241086
0.7941	Intermediate Similarity	NPC282087
0.7941	Intermediate Similarity	NPC318984
0.7941	Intermediate Similarity	NPC317741
0.7941	Intermediate Similarity	NPC259800
0.7934	Intermediate Similarity	NPC329011
0.7934	Intermediate Similarity	NPC227553
0.7934	Intermediate Similarity	NPC163674
0.7926	Intermediate Similarity	NPC313694
0.7926	Intermediate Similarity	NPC242159
0.7917	Intermediate Similarity	NPC258056
0.7913	Intermediate Similarity	NPC125732
0.7913	Intermediate Similarity	NPC12730
0.7902	Intermediate Similarity	NPC473580
0.7899	Intermediate Similarity	NPC142297
0.7895	Intermediate Similarity	NPC328070
0.7881	Intermediate Similarity	NPC13495
0.7869	Intermediate Similarity	NPC474584
0.7851	Intermediate Similarity	NPC474149
0.7851	Intermediate Similarity	NPC319579
0.7833	Intermediate Similarity	NPC153690
0.7833	Intermediate Similarity	NPC24101
0.7833	Intermediate Similarity	NPC96224
0.7826	Intermediate Similarity	NPC107619
0.7826	Intermediate Similarity	NPC66518
0.7826	Intermediate Similarity	NPC13696
0.7815	Intermediate Similarity	NPC327481
0.781	Intermediate Similarity	NPC326860
0.781	Intermediate Similarity	NPC197239
0.7808	Intermediate Similarity	NPC469243
0.7794	Intermediate Similarity	NPC473055
0.7794	Intermediate Similarity	NPC473052
0.7769	Intermediate Similarity	NPC145638
0.7769	Intermediate Similarity	NPC290566
0.7739	Intermediate Similarity	NPC10781
0.7739	Intermediate Similarity	NPC122493
0.7739	Intermediate Similarity	NPC293628
0.7737	Intermediate Similarity	NPC322526
0.7714	Intermediate Similarity	NPC81026
0.7687	Intermediate Similarity	NPC475544
0.7687	Intermediate Similarity	NPC257390
0.768	Intermediate Similarity	NPC197470
0.7672	Intermediate Similarity	NPC260000
0.766	Intermediate Similarity	NPC16188
0.7651	Intermediate Similarity	NPC223207
0.7643	Intermediate Similarity	NPC266741
0.7634	Intermediate Similarity	NPC4974
0.7623	Intermediate Similarity	NPC326187
0.7609	Intermediate Similarity	NPC238412
0.7609	Intermediate Similarity	NPC471201
0.7607	Intermediate Similarity	NPC280869
0.7606	Intermediate Similarity	NPC17760
0.76	Intermediate Similarity	NPC304074
0.76	Intermediate Similarity	NPC290755
0.76	Intermediate Similarity	NPC471771
0.76	Intermediate Similarity	NPC142599
0.7586	Intermediate Similarity	NPC324569
0.7574	Intermediate Similarity	NPC267237
0.7574	Intermediate Similarity	NPC243404
0.7563	Intermediate Similarity	NPC13426
0.7563	Intermediate Similarity	NPC68055
0.7561	Intermediate Similarity	NPC222084
0.7551	Intermediate Similarity	NPC56635
0.7542	Intermediate Similarity	NPC155847
0.7542	Intermediate Similarity	NPC289381
0.7542	Intermediate Similarity	NPC29601
0.7541	Intermediate Similarity	NPC31274
0.754	Intermediate Similarity	NPC213
0.754	Intermediate Similarity	NPC10286
0.7533	Intermediate Similarity	NPC63931
0.7466	Intermediate Similarity	NPC39431
0.7464	Intermediate Similarity	NPC109580
0.7451	Intermediate Similarity	NPC198254
0.7451	Intermediate Similarity	NPC274198
0.7448	Intermediate Similarity	NPC233702
0.7442	Intermediate Similarity	NPC268572
0.744	Intermediate Similarity	NPC17693
0.744	Intermediate Similarity	NPC48525
0.744	Intermediate Similarity	NPC146422
0.7438	Intermediate Similarity	NPC67043
0.7434	Intermediate Similarity	NPC209463
0.7431	Intermediate Similarity	NPC132771
0.7426	Intermediate Similarity	NPC275538
0.7397	Intermediate Similarity	NPC202198
0.7397	Intermediate Similarity	NPC56685
0.7391	Intermediate Similarity	NPC470441
0.7388	Intermediate Similarity	NPC305717
0.7388	Intermediate Similarity	NPC210950
0.7388	Intermediate Similarity	NPC199738
0.7385	Intermediate Similarity	NPC80150
0.7385	Intermediate Similarity	NPC190663
0.7381	Intermediate Similarity	NPC148969
0.7379	Intermediate Similarity	NPC324081
0.7377	Intermediate Similarity	NPC70843
0.7377	Intermediate Similarity	NPC188677
0.7377	Intermediate Similarity	NPC317592
0.7372	Intermediate Similarity	NPC474753
0.7368	Intermediate Similarity	NPC61004
0.7364	Intermediate Similarity	NPC122009
0.7364	Intermediate Similarity	NPC314992
0.7357	Intermediate Similarity	NPC214988
0.7355	Intermediate Similarity	NPC120693
0.7355	Intermediate Similarity	NPC8931
0.7355	Intermediate Similarity	NPC261573
0.735	Intermediate Similarity	NPC3371
0.7348	Intermediate Similarity	NPC35996
0.7344	Intermediate Similarity	NPC2265
0.7343	Intermediate Similarity	NPC473804
0.7338	Intermediate Similarity	NPC64205
0.7338	Intermediate Similarity	NPC276506
0.7329	Intermediate Similarity	NPC241392
0.7323	Intermediate Similarity	NPC221870
0.7313	Intermediate Similarity	NPC124776
0.7305	Intermediate Similarity	NPC476989
0.7292	Intermediate Similarity	NPC119569
0.729	Intermediate Similarity	NPC89831
0.7287	Intermediate Similarity	NPC169328
0.7287	Intermediate Similarity	NPC283468
0.7285	Intermediate Similarity	NPC241794
0.7273	Intermediate Similarity	NPC268348
0.7273	Intermediate Similarity	NPC160493
0.7266	Intermediate Similarity	NPC4665
0.7266	Intermediate Similarity	NPC160179
0.7265	Intermediate Similarity	NPC81010
0.7265	Intermediate Similarity	NPC32977
0.7261	Intermediate Similarity	NPC196243
0.7254	Intermediate Similarity	NPC168861
0.7244	Intermediate Similarity	NPC306804
0.7236	Intermediate Similarity	NPC69332
0.7236	Intermediate Similarity	NPC95178
0.7236	Intermediate Similarity	NPC29989
0.7231	Intermediate Similarity	NPC310467
0.7231	Intermediate Similarity	NPC85276
0.7226	Intermediate Similarity	NPC46009
0.7217	Intermediate Similarity	NPC258627
0.7209	Intermediate Similarity	NPC128249
0.7208	Intermediate Similarity	NPC328649
0.72	Intermediate Similarity	NPC234639
0.72	Intermediate Similarity	NPC88141
0.7197	Intermediate Similarity	NPC284078
0.7197	Intermediate Similarity	NPC324702
0.719	Intermediate Similarity	NPC318154
0.7181	Intermediate Similarity	NPC476268
0.7177	Intermediate Similarity	NPC29883
0.7177	Intermediate Similarity	NPC228737
0.7177	Intermediate Similarity	NPC226699
0.7162	Intermediate Similarity	NPC5194
0.7162	Intermediate Similarity	NPC261934
0.7162	Intermediate Similarity	NPC262166
0.7154	Intermediate Similarity	NPC137096
0.7153	Intermediate Similarity	NPC271808
0.7152	Intermediate Similarity	NPC319320
0.7152	Intermediate Similarity	NPC287757
0.7143	Intermediate Similarity	NPC21162
0.7133	Intermediate Similarity	NPC251439

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 NPC27581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	485
0.2-0.3	910
0.3-0.4	2006
0.4-0.5	2804
0.5-0.6	2069
0.6-0.7	648
0.7-0.8	94
0.8-0.85	16
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9304	High Similarity	NPD9568	Approved
0.9032	High Similarity	NPD3136	Phase 2
0.8729	High Similarity	NPD255	Approved
0.8729	High Similarity	NPD256	Approved
0.8571	High Similarity	NPD9569	Approved
0.8409	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD1759	Phase 1
0.8346	Intermediate Similarity	NPD7450	Phase 2
0.8333	Intermediate Similarity	NPD196	Phase 1
0.8321	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD259	Phase 1
0.8308	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD9537	Phase 1
0.8295	Intermediate Similarity	NPD9536	Phase 1
0.8284	Intermediate Similarity	NPD7978	Discontinued
0.8279	Intermediate Similarity	NPD1758	Phase 1
0.8182	Intermediate Similarity	NPD555	Phase 2
0.8143	Intermediate Similarity	NPD7523	Phase 3
0.8103	Intermediate Similarity	NPD9608	Approved
0.8103	Intermediate Similarity	NPD9610	Approved
0.8062	Intermediate Similarity	NPD257	Approved
0.8062	Intermediate Similarity	NPD258	Approved
0.8015	Intermediate Similarity	NPD9718	Approved
0.7941	Intermediate Similarity	NPD9570	Approved
0.7941	Intermediate Similarity	NPD1519	Approved
0.7941	Intermediate Similarity	NPD1538	Phase 1
0.7941	Intermediate Similarity	NPD1537	Approved
0.7923	Intermediate Similarity	NPD7451	Discontinued
0.7881	Intermediate Similarity	NPD1040	Phase 2
0.7862	Intermediate Similarity	NPD8019	Approved
0.7862	Intermediate Similarity	NPD7495	Discontinued
0.7842	Intermediate Similarity	NPD3400	Discontinued
0.781	Intermediate Similarity	NPD1523	Approved
0.781	Intermediate Similarity	NPD1522	Approved
0.7794	Intermediate Similarity	NPD1536	Approved
0.7778	Intermediate Similarity	NPD275	Approved
0.7778	Intermediate Similarity	NPD274	Approved
0.7769	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD9566	Approved
0.7704	Intermediate Similarity	NPD826	Approved
0.7704	Intermediate Similarity	NPD825	Approved
0.7698	Intermediate Similarity	NPD318	Approved
0.7698	Intermediate Similarity	NPD317	Approved
0.768	Intermediate Similarity	NPD1348	Approved
0.7664	Intermediate Similarity	NPD1521	Approved
0.7664	Intermediate Similarity	NPD1520	Approved
0.7571	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6390	Discontinued
0.7537	Intermediate Similarity	NPD2614	Approved
0.75	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9614	Approved
0.746	Intermediate Similarity	NPD9618	Approved
0.7442	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD9379	Approved
0.744	Intermediate Similarity	NPD9377	Approved
0.7432	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD16	Approved
0.7422	Intermediate Similarity	NPD856	Approved
0.7394	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8303	Discontinued
0.7364	Intermediate Similarity	NPD2218	Phase 2
0.7364	Intermediate Similarity	NPD2217	Approved
0.7348	Intermediate Similarity	NPD2562	Approved
0.7348	Intermediate Similarity	NPD2561	Approved
0.7348	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6346	Approved
0.7303	Intermediate Similarity	NPD2098	Approved
0.7297	Intermediate Similarity	NPD3455	Phase 2
0.7293	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3644	Approved
0.728	Intermediate Similarity	NPD3643	Approved
0.728	Intermediate Similarity	NPD3642	Approved
0.7241	Intermediate Similarity	NPD7554	Discontinued
0.7222	Intermediate Similarity	NPD9508	Approved
0.7211	Intermediate Similarity	NPD7303	Discontinued
0.7211	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2240	Approved
0.7183	Intermediate Similarity	NPD2239	Approved
0.7177	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2097	Approved
0.7167	Intermediate Similarity	NPD9712	Approved
0.7164	Intermediate Similarity	NPD9622	Approved
0.7154	Intermediate Similarity	NPD9615	Approved
0.7154	Intermediate Similarity	NPD9616	Approved
0.7154	Intermediate Similarity	NPD9613	Approved
0.7152	Intermediate Similarity	NPD5355	Approved
0.7152	Intermediate Similarity	NPD5356	Approved
0.7133	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5745	Approved
0.7121	Intermediate Similarity	NPD9381	Approved
0.7121	Intermediate Similarity	NPD9384	Approved
0.7115	Intermediate Similarity	NPD7608	Discontinued
0.7115	Intermediate Similarity	NPD4652	Approved
0.7109	Intermediate Similarity	NPD2228	Approved
0.7109	Intermediate Similarity	NPD2234	Approved
0.7109	Intermediate Similarity	NPD2229	Approved
0.7105	Intermediate Similarity	NPD7972	Discontinued
0.7099	Intermediate Similarity	NPD316	Approved
0.7086	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9611	Approved
0.7083	Intermediate Similarity	NPD253	Approved
0.7083	Intermediate Similarity	NPD9711	Approved
0.7083	Intermediate Similarity	NPD9710	Approved
0.7083	Intermediate Similarity	NPD9609	Approved
0.7083	Intermediate Similarity	NPD9612	Approved
0.7068	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD1135	Approved
0.7059	Intermediate Similarity	NPD1133	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7059	Intermediate Similarity	NPD1129	Approved
0.7059	Intermediate Similarity	NPD1134	Approved
0.7059	Intermediate Similarity	NPD1131	Approved
0.7051	Intermediate Similarity	NPD2888	Approved
0.7051	Intermediate Similarity	NPD2889	Approved
0.7051	Intermediate Similarity	NPD2017	Approved
0.7051	Intermediate Similarity	NPD2890	Approved
0.705	Intermediate Similarity	NPD1330	Phase 2
0.705	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7131	Phase 3
0.7042	Intermediate Similarity	NPD3555	Approved
0.7042	Intermediate Similarity	NPD3554	Approved
0.7042	Intermediate Similarity	NPD3552	Approved
0.7042	Intermediate Similarity	NPD3553	Approved
0.7037	Intermediate Similarity	NPD1755	Approved
0.7016	Intermediate Similarity	NPD999	Phase 2
0.7	Intermediate Similarity	NPD839	Approved
0.7	Intermediate Similarity	NPD840	Approved
0.6986	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5310	Approved
0.6985	Remote Similarity	NPD5311	Approved
0.6978	Remote Similarity	NPD5746	Approved
0.6963	Remote Similarity	NPD6624	Discontinued
0.696	Remote Similarity	NPD1444	Approved
0.696	Remote Similarity	NPD1445	Approved
0.6957	Remote Similarity	NPD7828	Discontinued
0.695	Remote Similarity	NPD468	Phase 1
0.6949	Remote Similarity	NPD1814	Approved
0.6949	Remote Similarity	NPD1812	Approved
0.6942	Remote Similarity	NPD9273	Approved
0.694	Remote Similarity	NPD3421	Phase 3
0.6935	Remote Similarity	NPD10	Approved
0.6935	Remote Similarity	NPD309	Approved
0.6935	Remote Similarity	NPD314	Approved
0.6935	Remote Similarity	NPD311	Approved
0.6935	Remote Similarity	NPD315	Approved
0.6935	Remote Similarity	NPD310	Approved
0.6934	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD597	Approved
0.6929	Remote Similarity	NPD598	Approved
0.6929	Remote Similarity	NPD601	Approved
0.6913	Remote Similarity	NPD3536	Discontinued
0.6912	Remote Similarity	NPD4659	Approved
0.6889	Remote Similarity	NPD1535	Discovery
0.6884	Remote Similarity	NPD9621	Approved
0.6884	Remote Similarity	NPD9619	Approved
0.6884	Remote Similarity	NPD9620	Approved
0.6879	Remote Similarity	NPD1136	Approved
0.6879	Remote Similarity	NPD1130	Approved
0.6879	Remote Similarity	NPD1132	Approved
0.6879	Remote Similarity	NPD520	Approved
0.6861	Remote Similarity	NPD3098	Discontinued
0.6861	Remote Similarity	NPD3125	Approved
0.6857	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4738	Phase 2
0.6853	Remote Similarity	NPD2568	Approved
0.685	Remote Similarity	NPD74	Approved
0.685	Remote Similarity	NPD9266	Approved
0.6842	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD5303	Approved
0.6842	Remote Similarity	NPD5304	Approved
0.6838	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1481	Phase 2
0.6833	Remote Similarity	NPD2934	Approved
0.6833	Remote Similarity	NPD2933	Approved
0.6818	Remote Similarity	NPD3123	Discovery
0.6815	Remote Similarity	NPD3847	Discontinued
0.6812	Remote Similarity	NPD4103	Phase 2
0.6812	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5445	Approved
0.6809	Remote Similarity	NPD5299	Approved
0.6797	Remote Similarity	NPD6502	Phase 2
0.6797	Remote Similarity	NPD1792	Phase 2
0.6794	Remote Similarity	NPD747	Discontinued
0.6783	Remote Similarity	NPD111	Approved
0.6777	Remote Similarity	NPD2860	Approved
0.6777	Remote Similarity	NPD2859	Approved
0.6772	Remote Similarity	NPD9264	Approved
0.6772	Remote Similarity	NPD9263	Approved
0.6772	Remote Similarity	NPD9267	Approved
0.6769	Remote Similarity	NPD181	Approved
0.6763	Remote Similarity	NPD599	Approved
0.6763	Remote Similarity	NPD2195	Approved
0.6763	Remote Similarity	NPD2194	Approved
0.6763	Remote Similarity	NPD602	Approved
0.6761	Remote Similarity	NPD6405	Approved
0.6761	Remote Similarity	NPD6407	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