NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	165.04
Volume:	156.633
LogP:	0.714
LogD:	0.852
LogS:	-2.225
# Rotatable Bonds:	0
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	2.893
Fsp3:	0.125
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:	-5.02
MDCK Permeability:	7.118701432773378e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.43

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	46.2587776184082%
Volume Distribution (VD):	0.767
Pgp-substrate:	47.07595443725586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.405
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.659
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	2.373
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.372
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.757
Carcinogencity:	0.307
Eye Corrosion:	0.007
Eye Irritation:	0.395
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC473987

Natural Product ID:	NPC473987
*Common Name:**	2-Hydroxy-4H-1,4-Benzoxazin-3-One
IUPAC Name:	2-hydroxy-4H-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	VMQBFYRBJKDACN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO3/c10-7-8(11)12-6-4-2-1-3-5(6)9-7/h1-4,8,11H,(H,9,10)
SMILES:	C1=CC=C2C(=C1)NC(=O)C(O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457386
PubChem CID:	322636
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
Others	3

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	52.5	%	PMID[483716]
NPT1136	Cell Line	mast cells	Mus musculus	Inhibition	=	65.8	%	PMID[483716]
NPT2528	Organism	Rhopalosiphum padi	Rhopalosiphum padi	Activity	=	38.0	%	PMID[483717]

☑ 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 NPC473987 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	351
0.1-0.2	4942
0.2-0.3	12385
0.3-0.4	6376
0.4-0.5	15062
0.5-0.6	3363
0.6-0.7	203
0.7-0.8	8
0.8-0.85	3
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9508	High Similarity	NPC315632
0.9037	High Similarity	NPC473874
0.8971	High Similarity	NPC473769
0.8472	Intermediate Similarity	NPC112766
0.8414	Intermediate Similarity	NPC70549
0.8162	Intermediate Similarity	NPC297584
0.7956	Intermediate Similarity	NPC208022
0.7874	Intermediate Similarity	NPC264782
0.7832	Intermediate Similarity	NPC168750
0.7532	Intermediate Similarity	NPC57105
0.7422	Intermediate Similarity	NPC255721
0.7355	Intermediate Similarity	NPC231862
0.7355	Intermediate Similarity	NPC19023
0.7181	Intermediate Similarity	NPC260601
0.717	Intermediate Similarity	NPC314861
0.7134	Intermediate Similarity	NPC316161
0.7047	Intermediate Similarity	NPC476462
0.7014	Intermediate Similarity	NPC313466
0.7012	Intermediate Similarity	NPC290069
0.7	Intermediate Similarity	NPC76327
0.697	Remote Similarity	NPC220560
0.6959	Remote Similarity	NPC476475
0.6957	Remote Similarity	NPC127362
0.6923	Remote Similarity	NPC41594
0.6867	Remote Similarity	NPC314113
0.6842	Remote Similarity	NPC9336
0.6842	Remote Similarity	NPC226914
0.6835	Remote Similarity	NPC10730
0.6835	Remote Similarity	NPC10875
0.6829	Remote Similarity	NPC318429
0.6822	Remote Similarity	NPC311660
0.68	Remote Similarity	NPC36434
0.6755	Remote Similarity	NPC298821
0.6711	Remote Similarity	NPC123761
0.6708	Remote Similarity	NPC306366
0.6667	Remote Similarity	NPC315631
0.6628	Remote Similarity	NPC313886
0.6581	Remote Similarity	NPC136951
0.6581	Remote Similarity	NPC161155
0.6581	Remote Similarity	NPC97004
0.657	Remote Similarity	NPC469829
0.6547	Remote Similarity	NPC258992
0.6538	Remote Similarity	NPC97282
0.6522	Remote Similarity	NPC471736
0.6522	Remote Similarity	NPC315257
0.6522	Remote Similarity	NPC142319
0.6516	Remote Similarity	NPC178466
0.6516	Remote Similarity	NPC63628
0.6494	Remote Similarity	NPC195814
0.6485	Remote Similarity	NPC204179
0.6479	Remote Similarity	NPC263835
0.6462	Remote Similarity	NPC132725
0.6452	Remote Similarity	NPC308392
0.6444	Remote Similarity	NPC478049
0.6412	Remote Similarity	NPC8467
0.6412	Remote Similarity	NPC70201
0.6408	Remote Similarity	NPC256369
0.6385	Remote Similarity	NPC313918
0.6383	Remote Similarity	NPC9248
0.6354	Remote Similarity	NPC314948
0.6338	Remote Similarity	NPC228907
0.6336	Remote Similarity	NPC314803
0.6335	Remote Similarity	NPC219383
0.6322	Remote Similarity	NPC469831
0.6316	Remote Similarity	NPC168153
0.6304	Remote Similarity	NPC214368
0.6291	Remote Similarity	NPC471953
0.6273	Remote Similarity	NPC114659
0.6273	Remote Similarity	NPC139699
0.6269	Remote Similarity	NPC256838
0.6268	Remote Similarity	NPC323948
0.6267	Remote Similarity	NPC470706
0.6264	Remote Similarity	NPC118776
0.6259	Remote Similarity	NPC325013
0.625	Remote Similarity	NPC289330
0.625	Remote Similarity	NPC160120
0.625	Remote Similarity	NPC60589
0.625	Remote Similarity	NPC44836
0.625	Remote Similarity	NPC17388
0.625	Remote Similarity	NPC469708
0.625	Remote Similarity	NPC471308
0.625	Remote Similarity	NPC53596
0.6242	Remote Similarity	NPC198798
0.6242	Remote Similarity	NPC197680
0.6242	Remote Similarity	NPC259098
0.6236	Remote Similarity	NPC110741
0.6235	Remote Similarity	NPC310894
0.6235	Remote Similarity	NPC184161
0.6233	Remote Similarity	NPC471314
0.6233	Remote Similarity	NPC471315
0.6228	Remote Similarity	NPC118511
0.6222	Remote Similarity	NPC17537
0.6221	Remote Similarity	NPC286195
0.6218	Remote Similarity	NPC189724
0.6218	Remote Similarity	NPC83289
0.6218	Remote Similarity	NPC212850
0.6207	Remote Similarity	NPC83279
0.6207	Remote Similarity	NPC469412
0.6207	Remote Similarity	NPC269242
0.6207	Remote Similarity	NPC198734
0.6205	Remote Similarity	NPC235628
0.6204	Remote Similarity	NPC146530
0.62	Remote Similarity	NPC469977
0.619	Remote Similarity	NPC211218
0.6184	Remote Similarity	NPC274732
0.6184	Remote Similarity	NPC470392
0.6183	Remote Similarity	NPC311357
0.6181	Remote Similarity	NPC321869
0.618	Remote Similarity	NPC469830
0.6164	Remote Similarity	NPC57751
0.6164	Remote Similarity	NPC226712
0.6149	Remote Similarity	NPC95733
0.6149	Remote Similarity	NPC62101
0.6138	Remote Similarity	NPC41801
0.6133	Remote Similarity	NPC101372
0.6131	Remote Similarity	NPC194034
0.6127	Remote Similarity	NPC303370
0.6121	Remote Similarity	NPC10221
0.6121	Remote Similarity	NPC140915
0.6121	Remote Similarity	NPC305700
0.6121	Remote Similarity	NPC18249
0.6121	Remote Similarity	NPC187028
0.6121	Remote Similarity	NPC197741
0.612	Remote Similarity	NPC108847
0.6118	Remote Similarity	NPC255550
0.6118	Remote Similarity	NPC1527
0.6118	Remote Similarity	NPC308885
0.6115	Remote Similarity	NPC95977
0.6105	Remote Similarity	NPC225381
0.6099	Remote Similarity	NPC322735
0.6096	Remote Similarity	NPC276195
0.6095	Remote Similarity	NPC70172
0.6089	Remote Similarity	NPC232872
0.6087	Remote Similarity	NPC245974
0.6082	Remote Similarity	NPC477888
0.608	Remote Similarity	NPC125306
0.6078	Remote Similarity	NPC97870
0.6078	Remote Similarity	NPC130595
0.6078	Remote Similarity	NPC247018
0.6078	Remote Similarity	NPC307123
0.6078	Remote Similarity	NPC93882
0.6067	Remote Similarity	NPC251466
0.6065	Remote Similarity	NPC122542
0.6062	Remote Similarity	NPC247298
0.6059	Remote Similarity	NPC19555
0.6056	Remote Similarity	NPC329190
0.6051	Remote Similarity	NPC288349
0.604	Remote Similarity	NPC25817
0.604	Remote Similarity	NPC287429
0.604	Remote Similarity	NPC300955
0.604	Remote Similarity	NPC221090
0.6039	Remote Similarity	NPC313737
0.6039	Remote Similarity	NPC285078
0.6039	Remote Similarity	NPC6854
0.6034	Remote Similarity	NPC262725
0.6024	Remote Similarity	NPC56635
0.6014	Remote Similarity	NPC152722
0.6012	Remote Similarity	NPC320064
0.6	Remote Similarity	NPC320242
0.6	Remote Similarity	NPC136112
0.6	Remote Similarity	NPC329358
0.6	Remote Similarity	NPC141739
0.6	Remote Similarity	NPC71105
0.6	Remote Similarity	NPC282477
0.6	Remote Similarity	NPC284855
0.6	Remote Similarity	NPC51633
0.6	Remote Similarity	NPC207541
0.6	Remote Similarity	NPC46844
0.6	Remote Similarity	NPC170583
0.6	Remote Similarity	NPC470510
0.6	Remote Similarity	NPC218530
0.6	Remote Similarity	NPC182147
0.6	Remote Similarity	NPC246133
0.6	Remote Similarity	NPC152186
0.6	Remote Similarity	NPC29477
0.5987	Remote Similarity	NPC160607
0.5987	Remote Similarity	NPC155838
0.5987	Remote Similarity	NPC41473
0.5987	Remote Similarity	NPC204848
0.5987	Remote Similarity	NPC14600
0.5987	Remote Similarity	NPC312770
0.5979	Remote Similarity	NPC159101
0.5978	Remote Similarity	NPC42591
0.5976	Remote Similarity	NPC72291
0.5973	Remote Similarity	NPC192810
0.5973	Remote Similarity	NPC217854
0.5972	Remote Similarity	NPC154256
0.5972	Remote Similarity	NPC290470
0.5966	Remote Similarity	NPC287152
0.596	Remote Similarity	NPC233559
0.596	Remote Similarity	NPC156944
0.596	Remote Similarity	NPC298845
0.596	Remote Similarity	NPC301713
0.5959	Remote Similarity	NPC14950
0.5959	Remote Similarity	NPC43275
0.5957	Remote Similarity	NPC166837
0.5956	Remote Similarity	NPC192596
0.5952	Remote Similarity	NPC301163
0.5952	Remote Similarity	NPC291359
0.5951	Remote Similarity	NPC277857

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 NPC473987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	971
0.2-0.3	1118
0.3-0.4	2649
0.4-0.5	2895
0.5-0.6	1166
0.6-0.7	135
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8189	Intermediate Similarity	NPD254	Approved
0.7733	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD204	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1422	Approved
0.7569	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1393	Approved
0.7394	Intermediate Similarity	NPD756	Suspended
0.7386	Intermediate Similarity	NPD3778	Approved
0.7152	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8330	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9342	Approved
0.705	Intermediate Similarity	NPD522	Approved
0.7	Intermediate Similarity	NPD9507	Approved
0.698	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4003	Phase 3
0.6842	Remote Similarity	NPD2241	Approved
0.6835	Remote Similarity	NPD4255	Phase 1
0.6835	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3236	Phase 3
0.6829	Remote Similarity	NPD2216	Approved
0.6829	Remote Similarity	NPD9365	Approved
0.6829	Remote Similarity	NPD2215	Approved
0.6772	Remote Similarity	NPD3296	Phase 1
0.6767	Remote Similarity	NPD556	Approved
0.6752	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD822	Approved
0.6709	Remote Similarity	NPD789	Phase 2
0.6708	Remote Similarity	NPD6063	Approved
0.6667	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4944	Phase 2
0.6646	Remote Similarity	NPD4943	Phase 2
0.6645	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4597	Approved
0.6601	Remote Similarity	NPD4598	Approved
0.6599	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4325	Phase 2
0.6591	Remote Similarity	NPD4324	Phase 2
0.6575	Remote Similarity	NPD4993	Discontinued
0.6575	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD965	Approved
0.6548	Remote Similarity	NPD5938	Phase 3
0.6543	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4604	Approved
0.6536	Remote Similarity	NPD4605	Approved
0.6536	Remote Similarity	NPD3656	Approved
0.6528	Remote Similarity	NPD1158	Phase 2
0.6509	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD191	Approved
0.6463	Remote Similarity	NPD2250	Discontinued
0.6438	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD9694	Discovery
0.6424	Remote Similarity	NPD3453	Discontinued
0.642	Remote Similarity	NPD2366	Approved
0.642	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3556	Approved
0.6402	Remote Similarity	NPD3557	Approved
0.6402	Remote Similarity	NPD3558	Approved
0.6402	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3560	Approved
0.64	Remote Similarity	NPD7477	Discontinued
0.6398	Remote Similarity	NPD5811	Approved
0.6395	Remote Similarity	NPD849	Approved
0.6395	Remote Similarity	NPD850	Approved
0.6395	Remote Similarity	NPD848	Approved
0.6395	Remote Similarity	NPD6184	Discontinued
0.6395	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1160	Phase 2
0.6392	Remote Similarity	NPD2114	Discontinued
0.6389	Remote Similarity	NPD776	Approved
0.6387	Remote Similarity	NPD5719	Approved
0.638	Remote Similarity	NPD1769	Discontinued
0.6364	Remote Similarity	NPD291	Approved
0.6352	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD654	Phase 3
0.6301	Remote Similarity	NPD3685	Discontinued
0.6294	Remote Similarity	NPD2594	Approved
0.6294	Remote Similarity	NPD2595	Approved
0.6294	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1798	Approved
0.6294	Remote Similarity	NPD1797	Approved
0.6286	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7153	Discontinued
0.6273	Remote Similarity	NPD3627	Approved
0.6269	Remote Similarity	NPD9501	Approved
0.625	Remote Similarity	NPD5374	Approved
0.625	Remote Similarity	NPD5373	Approved
0.6234	Remote Similarity	NPD696	Discontinued
0.6232	Remote Similarity	NPD9376	Approved
0.622	Remote Similarity	NPD4205	Phase 3
0.6218	Remote Similarity	NPD9245	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD1012	Discontinued
0.6194	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5150	Phase 2
0.6185	Remote Similarity	NPD3965	Phase 1
0.6175	Remote Similarity	NPD6034	Phase 2
0.6168	Remote Similarity	NPD1191	Discontinued
0.6164	Remote Similarity	NPD1091	Approved
0.6163	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1557	Discontinued
0.6149	Remote Similarity	NPD7498	Phase 1
0.6149	Remote Similarity	NPD7499	Phase 1
0.6145	Remote Similarity	NPD1898	Discontinued
0.6143	Remote Similarity	NPD821	Approved
0.6135	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD290	Approved
0.6131	Remote Similarity	NPD9552	Approved
0.6127	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD3154	Approved
0.6124	Remote Similarity	NPD3153	Approved
0.6118	Remote Similarity	NPD3145	Approved
0.6118	Remote Similarity	NPD6379	Discontinued
0.6118	Remote Similarity	NPD2821	Approved
0.6118	Remote Similarity	NPD2681	Approved
0.6118	Remote Similarity	NPD2249	Approved
0.6118	Remote Similarity	NPD2680	Approved
0.6118	Remote Similarity	NPD2247	Approved
0.6118	Remote Similarity	NPD3144	Approved
0.6115	Remote Similarity	NPD1375	Discontinued
0.6115	Remote Similarity	NPD2673	Approved
0.6115	Remote Similarity	NPD2671	Approved
0.6105	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2684	Approved
0.6084	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5847	Phase 1
0.6081	Remote Similarity	NPD4129	Approved
0.6078	Remote Similarity	NPD2674	Phase 3
0.6078	Remote Similarity	NPD1423	Approved
0.6069	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD2990	Approved
0.6067	Remote Similarity	NPD2987	Approved
0.6062	Remote Similarity	NPD5160	Discontinued
0.6059	Remote Similarity	NPD2341	Discontinued
0.6057	Remote Similarity	NPD3580	Discontinued
0.6057	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD286	Approved
0.6051	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4123	Phase 3
0.6047	Remote Similarity	NPD4083	Discontinued
0.6042	Remote Similarity	NPD1102	Approved
0.6042	Remote Similarity	NPD1103	Approved
0.6042	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD3463	Discontinued
0.6038	Remote Similarity	NPD2459	Approved
0.6038	Remote Similarity	NPD2460	Phase 3
0.6038	Remote Similarity	NPD2458	Approved
0.6037	Remote Similarity	NPD5267	Discontinued
0.6037	Remote Similarity	NPD2883	Discontinued
0.6023	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2843	Phase 2
0.6022	Remote Similarity	NPD2845	Phase 2
0.6014	Remote Similarity	NPD9624	Approved
0.6013	Remote Similarity	NPD7752	Approved
0.6013	Remote Similarity	NPD1048	Approved
0.6013	Remote Similarity	NPD7753	Approved
0.6013	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7318	Phase 3
0.6012	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD5858	Discontinued
0.6012	Remote Similarity	NPD3951	Phase 3
0.6012	Remote Similarity	NPD3952	Approved
0.6	Remote Similarity	NPD1817	Approved
0.6	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1819	Approved
0.6	Remote Similarity	NPD6331	Phase 2
0.6	Remote Similarity	NPD1818	Approved
0.6	Remote Similarity	NPD1794	Approved
0.6	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3568	Approved
0.6	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3567	Approved
0.6	Remote Similarity	NPD1820	Approved
0.5989	Remote Similarity	NPD6104	Discontinued
0.5989	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD155	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD481	Phase 3
0.5973	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6877	Discontinued
0.5964	Remote Similarity	NPD3538	Suspended
0.5962	Remote Similarity	NPD2224	Approved
0.5962	Remote Similarity	NPD2223	Approved
0.5957	Remote Similarity	NPD308	Approved
0.5955	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6738	Phase 2
0.5952	Remote Similarity	NPD6737	Phase 2
0.5949	Remote Similarity	NPD729	Discontinued
0.5946	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3369	Phase 2
0.5936	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD313	Approved
0.5926	Remote Similarity	NPD5756	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