NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	195.05
Volume:	182.719
LogP:	0.999
LogD:	0.985
LogS:	-2.111
# Rotatable Bonds:	1
TPSA:	67.79
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	3.084
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	1.3959253010398243e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.253
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.799
Plasma Protein Binding (PPB):	62.784202575683594%
Volume Distribution (VD):	0.679
Pgp-substrate:	42.28998947143555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.473
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.368
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.479
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	7.031
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.249
Skin Sensitization:	0.749
Carcinogencity:	0.02
Eye Corrosion:	0.017
Eye Irritation:	0.614
Respiratory Toxicity:	0.539

Download Data

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

Natural Product: NPC473769

Natural Product ID:	NPC473769
*Common Name:**	2-Hydroxy-7-Methoxy-4H-1,4-Benzoxazin-3-One
IUPAC Name:	2-hydroxy-7-methoxy-4H-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	NDEPTLCFICMYLH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H9NO4/c1-13-5-2-3-6-7(4-5)14-9(12)8(11)10-6/h2-4,9,12H,1H3,(H,10,11)
SMILES:	COC1=CC2=C(C=C1)NC(=O)C(O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451316
PubChem CID:	152213
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001396] Benzoxazines [CHEMONTID:0001437] Benzoxazinones

*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
NPO33369.1	coix lachryma-jobi	Under-species	n.a.	n.a.	Roots	n.a.	n.a.	PMID[2453615]

☑ 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
MIC	1
Others	4

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	91.3	%	PMID[526441]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	85.5	%	PMID[526441]
NPT1136	Cell Line	mast cells	Mus musculus	ID50	=	6.0	10'-5M	PMID[526441]
NPT2528	Organism	Rhopalosiphum padi	Rhopalosiphum padi	Activity	=	35.0	%	PMID[526442]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5123600.0	nM	PMID[526443]

☑ 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 NPC473769 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	366
0.1-0.2	4426
0.2-0.3	12520
0.3-0.4	6190
0.4-0.5	13565
0.5-0.6	5400
0.6-0.7	212
0.7-0.8	11
0.8-0.85	2
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC112766
0.9247	High Similarity	NPC70549
0.8971	High Similarity	NPC473987
0.8529	High Similarity	NPC315632
0.8188	Intermediate Similarity	NPC473874
0.8121	Intermediate Similarity	NPC260601
0.7987	Intermediate Similarity	NPC476462
0.7866	Intermediate Similarity	NPC290069
0.7818	Intermediate Similarity	NPC220560
0.7799	Intermediate Similarity	NPC19023
0.7721	Intermediate Similarity	NPC264782
0.7635	Intermediate Similarity	NPC297584
0.7578	Intermediate Similarity	NPC306366
0.7531	Intermediate Similarity	NPC57105
0.7469	Intermediate Similarity	NPC231862
0.7333	Intermediate Similarity	NPC208022
0.7333	Intermediate Similarity	NPC204179
0.7289	Intermediate Similarity	NPC314861
0.7251	Intermediate Similarity	NPC316161
0.7244	Intermediate Similarity	NPC168750
0.7127	Intermediate Similarity	NPC478049
0.7127	Intermediate Similarity	NPC314948
0.7073	Intermediate Similarity	NPC10730
0.7073	Intermediate Similarity	NPC10875
0.7039	Intermediate Similarity	NPC313466
0.7006	Intermediate Similarity	NPC314113
0.6943	Remote Similarity	NPC36434
0.6929	Remote Similarity	NPC255721
0.6906	Remote Similarity	NPC76327
0.6899	Remote Similarity	NPC298821
0.6855	Remote Similarity	NPC123761
0.6845	Remote Similarity	NPC235628
0.68	Remote Similarity	NPC315631
0.676	Remote Similarity	NPC313886
0.6728	Remote Similarity	NPC136951
0.6728	Remote Similarity	NPC97004
0.6728	Remote Similarity	NPC161155
0.6711	Remote Similarity	NPC276195
0.6687	Remote Similarity	NPC97282
0.6667	Remote Similarity	NPC63628
0.6667	Remote Similarity	NPC178466
0.6648	Remote Similarity	NPC168153
0.6646	Remote Similarity	NPC195814
0.6645	Remote Similarity	NPC25817
0.6645	Remote Similarity	NPC221090
0.6623	Remote Similarity	NPC152722
0.659	Remote Similarity	NPC127362
0.658	Remote Similarity	NPC308392
0.6579	Remote Similarity	NPC192810
0.6579	Remote Similarity	NPC217854
0.6575	Remote Similarity	NPC142319
0.6558	Remote Similarity	NPC298845
0.6519	Remote Similarity	NPC469829
0.6516	Remote Similarity	NPC37074
0.6497	Remote Similarity	NPC474491
0.6494	Remote Similarity	NPC12308
0.6488	Remote Similarity	NPC184161
0.6479	Remote Similarity	NPC41594
0.6477	Remote Similarity	NPC471736
0.6474	Remote Similarity	NPC247146
0.6467	Remote Similarity	NPC217294
0.6464	Remote Similarity	NPC469831
0.6452	Remote Similarity	NPC469622
0.6452	Remote Similarity	NPC189589
0.6452	Remote Similarity	NPC171533
0.6443	Remote Similarity	NPC9248
0.6441	Remote Similarity	NPC225381
0.6429	Remote Similarity	NPC114659
0.6429	Remote Similarity	NPC139699
0.6414	Remote Similarity	NPC9336
0.6414	Remote Similarity	NPC226914
0.641	Remote Similarity	NPC198798
0.64	Remote Similarity	NPC228907
0.6392	Remote Similarity	NPC60756
0.6378	Remote Similarity	NPC295287
0.6358	Remote Similarity	NPC476475
0.6354	Remote Similarity	NPC214368
0.6352	Remote Similarity	NPC287780
0.6343	Remote Similarity	NPC70172
0.634	Remote Similarity	NPC226712
0.6335	Remote Similarity	NPC220408
0.6329	Remote Similarity	NPC218003
0.6328	Remote Similarity	NPC198741
0.6321	Remote Similarity	NPC311357
0.6316	Remote Similarity	NPC60589
0.6316	Remote Similarity	NPC469708
0.6312	Remote Similarity	NPC162093
0.6307	Remote Similarity	NPC19555
0.6306	Remote Similarity	NPC469621
0.6296	Remote Similarity	NPC126637
0.6294	Remote Similarity	NPC219383
0.6292	Remote Similarity	NPC310894
0.6289	Remote Similarity	NPC208769
0.6289	Remote Similarity	NPC262606
0.6284	Remote Similarity	NPC98197
0.6279	Remote Similarity	NPC187028
0.6279	Remote Similarity	NPC10221
0.6279	Remote Similarity	NPC18249
0.6279	Remote Similarity	NPC140915
0.6279	Remote Similarity	NPC197741
0.6279	Remote Similarity	NPC305700
0.6275	Remote Similarity	NPC269242
0.6275	Remote Similarity	NPC469412
0.6275	Remote Similarity	NPC198734
0.6273	Remote Similarity	NPC60982
0.6273	Remote Similarity	NPC49074
0.6273	Remote Similarity	NPC115022
0.6273	Remote Similarity	NPC294166
0.6263	Remote Similarity	NPC108847
0.625	Remote Similarity	NPC318429
0.625	Remote Similarity	NPC121376
0.625	Remote Similarity	NPC473653
0.6243	Remote Similarity	NPC79293
0.6243	Remote Similarity	NPC279401
0.6234	Remote Similarity	NPC57751
0.623	Remote Similarity	NPC314025
0.622	Remote Similarity	NPC296898
0.6211	Remote Similarity	NPC85799
0.6211	Remote Similarity	NPC26080
0.6211	Remote Similarity	NPC165686
0.6211	Remote Similarity	NPC303422
0.6211	Remote Similarity	NPC299144
0.6207	Remote Similarity	NPC291359
0.6196	Remote Similarity	NPC314656
0.6196	Remote Similarity	NPC314213
0.6196	Remote Similarity	NPC470236
0.6196	Remote Similarity	NPC185778
0.6196	Remote Similarity	NPC238243
0.6185	Remote Similarity	NPC315257
0.6181	Remote Similarity	NPC307875
0.6176	Remote Similarity	NPC302546
0.6176	Remote Similarity	NPC108826
0.6174	Remote Similarity	NPC322735
0.6173	Remote Similarity	NPC69513
0.6173	Remote Similarity	NPC215833
0.6171	Remote Similarity	NPC320064
0.6167	Remote Similarity	NPC182257
0.6163	Remote Similarity	NPC474560
0.6162	Remote Similarity	NPC315913
0.6159	Remote Similarity	NPC258992
0.6159	Remote Similarity	NPC104167
0.6159	Remote Similarity	NPC197723
0.6159	Remote Similarity	NPC164857
0.6159	Remote Similarity	NPC165482
0.6159	Remote Similarity	NPC103409
0.6159	Remote Similarity	NPC138350
0.6159	Remote Similarity	NPC40664
0.6159	Remote Similarity	NPC3293
0.6154	Remote Similarity	NPC110374
0.6154	Remote Similarity	NPC311660
0.6154	Remote Similarity	NPC289743
0.6154	Remote Similarity	NPC211218
0.6154	Remote Similarity	NPC228040
0.615	Remote Similarity	NPC469830
0.6149	Remote Similarity	NPC475067
0.6149	Remote Similarity	NPC471953
0.6146	Remote Similarity	NPC272706
0.6135	Remote Similarity	NPC264956
0.6135	Remote Similarity	NPC188555
0.6135	Remote Similarity	NPC13745
0.6135	Remote Similarity	NPC130496
0.6135	Remote Similarity	NPC48863
0.6135	Remote Similarity	NPC251981
0.6133	Remote Similarity	NPC329190
0.6131	Remote Similarity	NPC168250
0.6127	Remote Similarity	NPC70201
0.6126	Remote Similarity	NPC29472
0.6125	Remote Similarity	NPC295970
0.6122	Remote Similarity	NPC159101
0.6121	Remote Similarity	NPC134260
0.6121	Remote Similarity	NPC262328
0.6121	Remote Similarity	NPC87777
0.6121	Remote Similarity	NPC124149
0.6117	Remote Similarity	NPC475919
0.6117	Remote Similarity	NPC474661
0.6115	Remote Similarity	NPC16649
0.6115	Remote Similarity	NPC62101
0.6115	Remote Similarity	NPC95733
0.6115	Remote Similarity	NPC287429
0.6108	Remote Similarity	NPC288349
0.6105	Remote Similarity	NPC294244
0.6104	Remote Similarity	NPC263835
0.6103	Remote Similarity	NPC47422
0.6099	Remote Similarity	NPC8467
0.6095	Remote Similarity	NPC313414
0.609	Remote Similarity	NPC476142
0.6089	Remote Similarity	NPC54125
0.6089	Remote Similarity	NPC89199
0.6087	Remote Similarity	NPC115343
0.6087	Remote Similarity	NPC1291
0.6084	Remote Similarity	NPC98777
0.6084	Remote Similarity	NPC189724
0.6084	Remote Similarity	NPC212770
0.6084	Remote Similarity	NPC212850
0.6084	Remote Similarity	NPC83289
0.6076	Remote Similarity	NPC470510
0.6074	Remote Similarity	NPC132895
0.6074	Remote Similarity	NPC469449
0.6065	Remote Similarity	NPC199023
0.6064	Remote Similarity	NPC219170

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 NPC473769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	977
0.2-0.3	1238
0.3-0.4	2893
0.4-0.5	2740
0.5-0.6	988
0.6-0.7	93
0.7-0.8	10
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
0.8015	Intermediate Similarity	NPD254	Approved
0.78	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1422	Approved
0.74	Intermediate Similarity	NPD756	Suspended
0.732	Intermediate Similarity	NPD204	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1393	Approved
0.7284	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3778	Approved
0.7202	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2241	Approved
0.694	Remote Similarity	NPD6034	Phase 2
0.6906	Remote Similarity	NPD9507	Approved
0.6899	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4255	Phase 1
0.6763	Remote Similarity	NPD2216	Approved
0.6763	Remote Similarity	NPD2215	Approved
0.6759	Remote Similarity	NPD9342	Approved
0.674	Remote Similarity	NPD1898	Discontinued
0.6707	Remote Similarity	NPD3296	Phase 1
0.6667	Remote Similarity	NPD2366	Approved
0.6667	Remote Similarity	NPD822	Approved
0.6667	Remote Similarity	NPD1440	Discontinued
0.663	Remote Similarity	NPD4325	Phase 2
0.663	Remote Similarity	NPD4324	Phase 2
0.6629	Remote Similarity	NPD6184	Discontinued
0.6623	Remote Similarity	NPD522	Approved
0.659	Remote Similarity	NPD4944	Phase 2
0.659	Remote Similarity	NPD4943	Phase 2
0.6587	Remote Similarity	NPD4003	Phase 3
0.6578	Remote Similarity	NPD4605	Approved
0.6578	Remote Similarity	NPD4604	Approved
0.6573	Remote Similarity	NPD556	Approved
0.6568	Remote Similarity	NPD3236	Phase 3
0.6568	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3538	Suspended
0.6505	Remote Similarity	NPD7125	Discontinued
0.65	Remote Similarity	NPD6104	Discontinued
0.6474	Remote Similarity	NPD3453	Discontinued
0.6453	Remote Similarity	NPD3558	Approved
0.6453	Remote Similarity	NPD3557	Approved
0.6453	Remote Similarity	NPD3556	Approved
0.6453	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3560	Approved
0.6453	Remote Similarity	NPD6063	Approved
0.6446	Remote Similarity	NPD2114	Discontinued
0.6438	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4678	Approved
0.6412	Remote Similarity	NPD4675	Approved
0.64	Remote Similarity	NPD7533	Approved
0.64	Remote Similarity	NPD7534	Approved
0.6391	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3656	Approved
0.6364	Remote Similarity	NPD1158	Phase 2
0.6341	Remote Similarity	NPD5719	Approved
0.634	Remote Similarity	NPD1091	Approved
0.6331	Remote Similarity	NPD3627	Approved
0.633	Remote Similarity	NPD5150	Phase 2
0.6306	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD965	Approved
0.6282	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5811	Approved
0.6257	Remote Similarity	NPD789	Phase 2
0.625	Remote Similarity	NPD9365	Approved
0.6242	Remote Similarity	NPD4597	Approved
0.6242	Remote Similarity	NPD4598	Approved
0.6242	Remote Similarity	NPD1160	Phase 2
0.623	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD1191	Discontinued
0.6222	Remote Similarity	NPD5938	Phase 3
0.6213	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4993	Discontinued
0.6203	Remote Similarity	NPD2250	Discontinued
0.62	Remote Similarity	NPD191	Approved
0.6197	Remote Similarity	NPD291	Approved
0.6193	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.619	Remote Similarity	NPD9376	Approved
0.6188	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3153	Approved
0.6183	Remote Similarity	NPD3154	Approved
0.6182	Remote Similarity	NPD1375	Discontinued
0.618	Remote Similarity	NPD2247	Approved
0.618	Remote Similarity	NPD2249	Approved
0.6175	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD9694	Discovery
0.617	Remote Similarity	NPD2845	Phase 2
0.617	Remote Similarity	NPD2843	Phase 2
0.6164	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD286	Approved
0.6131	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6045	Phase 3
0.6121	Remote Similarity	NPD3454	Phase 3
0.6118	Remote Similarity	NPD4123	Phase 3
0.6111	Remote Similarity	NPD7263	Phase 2
0.6098	Remote Similarity	NPD2200	Suspended
0.6095	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6072	Discontinued
0.6089	Remote Similarity	NPD6379	Discontinued
0.6087	Remote Similarity	NPD7007	Discovery
0.6077	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.607	Remote Similarity	NPD4206	Approved
0.6069	Remote Similarity	NPD4005	Discontinued
0.6066	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3965	Phase 1
0.6064	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4587	Phase 3
0.6057	Remote Similarity	NPD1769	Discontinued
0.6051	Remote Similarity	NPD3685	Discontinued
0.6049	Remote Similarity	NPD7477	Discontinued
0.6048	Remote Similarity	NPD7153	Discontinued
0.6038	Remote Similarity	NPD849	Approved
0.6038	Remote Similarity	NPD848	Approved
0.6038	Remote Similarity	NPD850	Approved
0.6034	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2341	Discontinued
0.6034	Remote Similarity	NPD1557	Discontinued
0.6026	Remote Similarity	NPD776	Approved
0.6022	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7476	Discontinued
0.6	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1048	Approved
0.5968	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD5847	Phase 1
0.5959	Remote Similarity	NPD7256	Discontinued
0.5957	Remote Similarity	NPD4586	Phase 3
0.595	Remote Similarity	NPD6296	Discontinued
0.5949	Remote Similarity	NPD6877	Discontinued
0.5938	Remote Similarity	NPD3634	Approved
0.5938	Remote Similarity	NPD3633	Approved
0.5936	Remote Similarity	NPD2802	Phase 3
0.5935	Remote Similarity	NPD2595	Approved
0.5935	Remote Similarity	NPD1798	Approved
0.5935	Remote Similarity	NPD2594	Approved
0.5935	Remote Similarity	NPD1797	Approved
0.5934	Remote Similarity	NPD4083	Discontinued
0.593	Remote Similarity	NPD7499	Phase 1
0.593	Remote Similarity	NPD7498	Phase 1
0.5928	Remote Similarity	NPD5582	Discontinued
0.5926	Remote Similarity	NPD3179	Approved
0.5926	Remote Similarity	NPD3180	Approved
0.5922	Remote Similarity	NPD4055	Discovery
0.5916	Remote Similarity	NPD4258	Approved
0.5916	Remote Similarity	NPD4259	Approved
0.5914	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD2821	Approved
0.5909	Remote Similarity	NPD4205	Phase 3
0.5904	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD696	Discontinued
0.5904	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD1212	Approved
0.589	Remote Similarity	NPD3145	Approved
0.589	Remote Similarity	NPD3144	Approved
0.5879	Remote Similarity	NPD654	Phase 3
0.5879	Remote Similarity	NPD6669	Phase 2
0.5878	Remote Similarity	NPD290	Approved
0.5878	Remote Similarity	NPD5374	Approved
0.5878	Remote Similarity	NPD5373	Approved
0.5876	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7212	Phase 2
0.5872	Remote Similarity	NPD7213	Phase 3
0.5871	Remote Similarity	NPD1548	Phase 1
0.5871	Remote Similarity	NPD7583	Approved
0.587	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4108	Discontinued
0.5866	Remote Similarity	NPD19	Approved
0.5866	Remote Similarity	NPD1743	Approved
0.5866	Remote Similarity	NPD1742	Approved
0.5864	Remote Similarity	NPD6842	Approved
0.5864	Remote Similarity	NPD6841	Approved
0.5864	Remote Similarity	NPD6843	Phase 3
0.586	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.586	Remote Similarity	NPD795	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7129	Suspended
0.5854	Remote Similarity	NPD840	Approved
0.5854	Remote Similarity	NPD2674	Phase 3
0.5854	Remote Similarity	NPD839	Approved
0.5846	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7585	Approved
0.5838	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD7447	Phase 1
0.5833	Remote Similarity	NPD6136	Phase 2
0.5829	Remote Similarity	NPD5267	Discontinued
0.5829	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD2680	Approved
0.5824	Remote Similarity	NPD3983	Phase 3
0.5824	Remote Similarity	NPD2681	Approved
0.5824	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3511	Discontinued

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