NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	181.04
Volume:	165.423
LogP:	0.159
LogD:	-0.003
LogS:	-1.097
# Rotatable Bonds:	0
TPSA:	70.0
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	3.096
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.255
MDCK Permeability:	1.9382734535611235e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.624

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	10.2951078414917%
Volume Distribution (VD):	0.647
Pgp-substrate:	69.05606079101562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.229
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.432
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	4.344
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.509
Carcinogencity:	0.698
Eye Corrosion:	0.02
Eye Irritation:	0.455
Respiratory Toxicity:	0.216

Download Data

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

Natural Product: NPC168750

Natural Product ID:	NPC168750
*Common Name:**	2,4-Dihydroxy-1,4-Benzoxazin-3-One
IUPAC Name:	2,4-dihydroxy-1,4-benzoxazin-3-one
Synonyms:
Standard InCHIKey:	COVOPZQGJGUPEY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H
SMILES:	O=C1C(O)Oc2c(N1O)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483002
PubChem CID:	28495
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
NPO20789	Acanthus ilicifolius	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20789	Acanthus ilicifolius	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	4
Others	9

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	0.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	6.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	40.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	59.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	72.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	82.0	%	PMID[515981]
NPT522	Organism	Abutilon theophrasti	Abutilon theophrasti	Activity	=	97.0	%	PMID[515981]
NPT2528	Organism	Rhopalosiphum padi	Rhopalosiphum padi	Activity	=	92.3	%	PMID[515982]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2760200.0	nM	PMID[515983]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3676600.0	nM	PMID[515983]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	6900500.0	nM	PMID[515983]

☑ 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 NPC168750 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	354
0.1-0.2	4984
0.2-0.3	12620
0.3-0.4	6747
0.4-0.5	16119
0.5-0.6	1807
0.6-0.7	57
0.7-0.8	5
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8471	Intermediate Similarity	NPC290069
0.8451	Intermediate Similarity	NPC476475
0.8418	Intermediate Similarity	NPC220560
0.7832	Intermediate Similarity	NPC473987
0.7566	Intermediate Similarity	NPC260601
0.7434	Intermediate Similarity	NPC476462
0.7413	Intermediate Similarity	NPC315632
0.7244	Intermediate Similarity	NPC473769
0.7179	Intermediate Similarity	NPC473874
0.6994	Remote Similarity	NPC112766
0.6974	Remote Similarity	NPC297584
0.6951	Remote Similarity	NPC70549
0.6867	Remote Similarity	NPC19023
0.6797	Remote Similarity	NPC208022
0.6761	Remote Similarity	NPC264782
0.6687	Remote Similarity	NPC315257
0.6607	Remote Similarity	NPC301163
0.6595	Remote Similarity	NPC314948
0.6595	Remote Similarity	NPC478049
0.6471	Remote Similarity	NPC231862
0.6457	Remote Similarity	NPC73280
0.6433	Remote Similarity	NPC57105
0.6404	Remote Similarity	NPC287152
0.6374	Remote Similarity	NPC320064
0.6374	Remote Similarity	NPC262725
0.6364	Remote Similarity	NPC255721
0.6335	Remote Similarity	NPC47986
0.6322	Remote Similarity	NPC314861
0.6321	Remote Similarity	NPC471736
0.6319	Remote Similarity	NPC226914
0.6299	Remote Similarity	NPC250476
0.6292	Remote Similarity	NPC286195
0.6286	Remote Similarity	NPC311660
0.6256	Remote Similarity	NPC308392
0.6243	Remote Similarity	NPC116096
0.6243	Remote Similarity	NPC118776
0.6229	Remote Similarity	NPC127362
0.6216	Remote Similarity	NPC110741
0.6215	Remote Similarity	NPC471648
0.6207	Remote Similarity	NPC118511
0.6207	Remote Similarity	NPC292143
0.6207	Remote Similarity	NPC95977
0.6207	Remote Similarity	NPC139506
0.6187	Remote Similarity	NPC132725
0.6159	Remote Similarity	NPC321869
0.6149	Remote Similarity	NPC257763
0.6139	Remote Similarity	NPC231382
0.6125	Remote Similarity	NPC132308
0.6111	Remote Similarity	NPC44836
0.6102	Remote Similarity	NPC1527
0.6101	Remote Similarity	NPC313466
0.6098	Remote Similarity	NPC314113
0.6092	Remote Similarity	NPC306366
0.6087	Remote Similarity	NPC469829
0.6084	Remote Similarity	NPC17537
0.6082	Remote Similarity	NPC311357
0.6081	Remote Similarity	NPC322735
0.608	Remote Similarity	NPC70172
0.608	Remote Similarity	NPC24954
0.6073	Remote Similarity	NPC472191
0.6057	Remote Similarity	NPC177404
0.6049	Remote Similarity	NPC196708
0.6048	Remote Similarity	NPC161155
0.6048	Remote Similarity	NPC97004
0.6048	Remote Similarity	NPC136951
0.6045	Remote Similarity	NPC471652
0.6042	Remote Similarity	NPC112937
0.604	Remote Similarity	NPC329190
0.6037	Remote Similarity	NPC204156
0.6037	Remote Similarity	NPC36434
0.6032	Remote Similarity	NPC473004
0.6012	Remote Similarity	NPC469808
0.6012	Remote Similarity	NPC97282
0.6	Remote Similarity	NPC313918
0.6	Remote Similarity	NPC298821
0.6	Remote Similarity	NPC76327
0.5986	Remote Similarity	NPC329358
0.598	Remote Similarity	NPC477160
0.5978	Remote Similarity	NPC288305
0.5978	Remote Similarity	NPC472163
0.5969	Remote Similarity	NPC230313
0.5968	Remote Similarity	NPC42591
0.5964	Remote Similarity	NPC123761
0.5964	Remote Similarity	NPC325857
0.5934	Remote Similarity	NPC473432
0.5933	Remote Similarity	NPC142319
0.5931	Remote Similarity	NPC41594
0.5915	Remote Similarity	NPC70201
0.5915	Remote Similarity	NPC106606
0.5912	Remote Similarity	NPC318429
0.5902	Remote Similarity	NPC283152
0.5902	Remote Similarity	NPC315631
0.5899	Remote Similarity	NPC204179
0.5896	Remote Similarity	NPC26872
0.5894	Remote Similarity	NPC99724
0.5893	Remote Similarity	NPC470403
0.5893	Remote Similarity	NPC470404
0.5893	Remote Similarity	NPC470394
0.5892	Remote Similarity	NPC197335
0.5885	Remote Similarity	NPC243626
0.5882	Remote Similarity	NPC313886
0.5878	Remote Similarity	NPC9336
0.5876	Remote Similarity	NPC230942
0.5876	Remote Similarity	NPC315498
0.587	Remote Similarity	NPC316161
0.5867	Remote Similarity	NPC470586
0.5865	Remote Similarity	NPC148124
0.5864	Remote Similarity	NPC469961
0.586	Remote Similarity	NPC314659
0.586	Remote Similarity	NPC469831
0.5859	Remote Similarity	NPC14339
0.5846	Remote Similarity	NPC220408
0.5842	Remote Similarity	NPC45389
0.5838	Remote Similarity	NPC166169
0.5838	Remote Similarity	NPC284348
0.5833	Remote Similarity	NPC254957
0.5833	Remote Similarity	NPC471825
0.5829	Remote Similarity	NPC320394
0.5825	Remote Similarity	NPC197141
0.5824	Remote Similarity	NPC470395
0.5819	Remote Similarity	NPC93653
0.5817	Remote Similarity	NPC46259
0.5817	Remote Similarity	NPC9248
0.5815	Remote Similarity	NPC127082
0.5808	Remote Similarity	NPC207971
0.5806	Remote Similarity	NPC266551
0.5806	Remote Similarity	NPC270301
0.5806	Remote Similarity	NPC219963
0.5805	Remote Similarity	NPC288349
0.5798	Remote Similarity	NPC20249
0.5795	Remote Similarity	NPC26850
0.5793	Remote Similarity	NPC167096
0.5793	Remote Similarity	NPC256838
0.5782	Remote Similarity	NPC26928
0.5779	Remote Similarity	NPC470484
0.5779	Remote Similarity	NPC228907
0.5779	Remote Similarity	NPC268077
0.5769	Remote Similarity	NPC14651
0.5769	Remote Similarity	NPC121658
0.5767	Remote Similarity	NPC87391
0.5764	Remote Similarity	NPC471532
0.5761	Remote Similarity	NPC288943
0.5761	Remote Similarity	NPC8467
0.5759	Remote Similarity	NPC473008
0.5758	Remote Similarity	NPC255817
0.5758	Remote Similarity	NPC73883
0.5758	Remote Similarity	NPC136330
0.5758	Remote Similarity	NPC196609
0.5758	Remote Similarity	NPC205178
0.5758	Remote Similarity	NPC251454
0.5758	Remote Similarity	NPC230698
0.5758	Remote Similarity	NPC277042
0.5755	Remote Similarity	NPC248903
0.5753	Remote Similarity	NPC85613
0.5753	Remote Similarity	NPC283810
0.5753	Remote Similarity	NPC5167
0.575	Remote Similarity	NPC218323
0.575	Remote Similarity	NPC195787
0.575	Remote Similarity	NPC246140
0.5746	Remote Similarity	NPC33507
0.5745	Remote Similarity	NPC302235
0.5744	Remote Similarity	NPC161804
0.5741	Remote Similarity	NPC200555
0.5741	Remote Similarity	NPC196026
0.574	Remote Similarity	NPC308197
0.5737	Remote Similarity	NPC469830
0.5737	Remote Similarity	NPC232872
0.5731	Remote Similarity	NPC146370
0.573	Remote Similarity	NPC285635
0.5729	Remote Similarity	NPC470483
0.5723	Remote Similarity	NPC99078
0.5722	Remote Similarity	NPC206201
0.5722	Remote Similarity	NPC299582
0.5714	Remote Similarity	NPC212850
0.5714	Remote Similarity	NPC476518
0.5714	Remote Similarity	NPC198798
0.5714	Remote Similarity	NPC83289
0.5714	Remote Similarity	NPC323948
0.5714	Remote Similarity	NPC71124
0.5714	Remote Similarity	NPC189724
0.5707	Remote Similarity	NPC214368
0.5706	Remote Similarity	NPC116573
0.5705	Remote Similarity	NPC60589
0.5705	Remote Similarity	NPC469708
0.57	Remote Similarity	NPC473422
0.5698	Remote Similarity	NPC220523
0.5691	Remote Similarity	NPC59567
0.569	Remote Similarity	NPC40209
0.5689	Remote Similarity	NPC220923
0.5689	Remote Similarity	NPC252107
0.5689	Remote Similarity	NPC470707
0.5688	Remote Similarity	NPC314702
0.5685	Remote Similarity	NPC5374
0.5683	Remote Similarity	NPC85482
0.5683	Remote Similarity	NPC471604
0.5682	Remote Similarity	NPC270811
0.5682	Remote Similarity	NPC471073
0.568	Remote Similarity	NPC204546
0.5677	Remote Similarity	NPC474059
0.5673	Remote Similarity	NPC77777

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 NPC168750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	872
0.2-0.3	1189
0.3-0.4	2407
0.4-0.5	3229
0.5-0.6	1144
0.6-0.7	105
0.7-0.8	9
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
0.7756	Intermediate Similarity	NPD4201	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8330	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD822	Approved
0.7338	Intermediate Similarity	NPD2241	Approved
0.7255	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1678	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD204	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4020	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD254	Approved
0.7006	Intermediate Similarity	NPD2162	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4205	Phase 3
0.6975	Remote Similarity	NPD789	Phase 2
0.6923	Remote Similarity	NPD5847	Phase 1
0.6919	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1393	Approved
0.6863	Remote Similarity	NPD756	Suspended
0.686	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4428	Discontinued
0.6766	Remote Similarity	NPD1012	Discontinued
0.6765	Remote Similarity	NPD7126	Discontinued
0.6744	Remote Similarity	NPD5858	Discontinued
0.6743	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5938	Phase 3
0.6689	Remote Similarity	NPD848	Approved
0.6689	Remote Similarity	NPD849	Approved
0.6689	Remote Similarity	NPD850	Approved
0.6667	Remote Similarity	NPD2114	Discontinued
0.6647	Remote Similarity	NPD1769	Discontinued
0.6646	Remote Similarity	NPD1422	Approved
0.6607	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4255	Phase 1
0.6554	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1725	Approved
0.6522	Remote Similarity	NPD965	Approved
0.6519	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7752	Approved
0.65	Remote Similarity	NPD7753	Approved
0.6477	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4597	Approved
0.646	Remote Similarity	NPD4598	Approved
0.646	Remote Similarity	NPD5719	Approved
0.6441	Remote Similarity	NPD1212	Approved
0.6384	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6379	Discontinued
0.6375	Remote Similarity	NPD3260	Discontinued
0.6364	Remote Similarity	NPD9723	Approved
0.6354	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6644	Discontinued
0.6339	Remote Similarity	NPD4515	Suspended
0.6337	Remote Similarity	NPD1191	Discontinued
0.6335	Remote Similarity	NPD2498	Approved
0.6319	Remote Similarity	NPD9376	Approved
0.6316	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3580	Discontinued
0.631	Remote Similarity	NPD4003	Phase 3
0.6301	Remote Similarity	NPD8031	Discontinued
0.6296	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD9245	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6457	Approved
0.6272	Remote Similarity	NPD6357	Discontinued
0.6271	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5114	Approved
0.627	Remote Similarity	NPD5112	Approved
0.627	Remote Similarity	NPD5113	Approved
0.6267	Remote Similarity	NPD2594	Approved
0.6267	Remote Similarity	NPD2595	Approved
0.6257	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1861	Discovery
0.625	Remote Similarity	NPD3627	Approved
0.6243	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5994	Discontinued
0.6222	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD9342	Approved
0.6216	Remote Similarity	NPD7326	Phase 3
0.6207	Remote Similarity	NPD2673	Approved
0.6207	Remote Similarity	NPD2671	Approved
0.6199	Remote Similarity	NPD980	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5582	Discontinued
0.6185	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD3556	Approved
0.6185	Remote Similarity	NPD6063	Approved
0.6185	Remote Similarity	NPD3558	Approved
0.6185	Remote Similarity	NPD3560	Approved
0.6185	Remote Similarity	NPD3557	Approved
0.618	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6338	Approved
0.6175	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7877	Suspended
0.6175	Remote Similarity	NPD6337	Approved
0.6164	Remote Similarity	NPD308	Approved
0.6158	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6519	Phase 2
0.6139	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD313	Approved
0.6127	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6298	Discontinued
0.6117	Remote Similarity	NPD4372	Phase 1
0.6114	Remote Similarity	NPD6321	Discontinued
0.6111	Remote Similarity	NPD5373	Approved
0.6111	Remote Similarity	NPD5374	Approved
0.6111	Remote Similarity	NPD6636	Phase 3
0.6105	Remote Similarity	NPD6550	Discontinued
0.6105	Remote Similarity	NPD3778	Approved
0.6105	Remote Similarity	NPD3964	Approved
0.6104	Remote Similarity	NPD522	Approved
0.6102	Remote Similarity	NPD2681	Approved
0.6102	Remote Similarity	NPD2680	Approved
0.6102	Remote Similarity	NPD2247	Approved
0.6102	Remote Similarity	NPD3511	Discontinued
0.6102	Remote Similarity	NPD2249	Approved
0.6099	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3656	Approved
0.6094	Remote Similarity	NPD1880	Phase 3
0.6087	Remote Similarity	NPD9694	Discovery
0.6075	Remote Similarity	NPD4587	Phase 3
0.6074	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5186	Approved
0.6067	Remote Similarity	NPD5183	Approved
0.6065	Remote Similarity	NPD1158	Phase 2
0.6051	Remote Similarity	NPD2990	Approved
0.6051	Remote Similarity	NPD2987	Approved
0.6044	Remote Similarity	NPD3885	Approved
0.6042	Remote Similarity	NPD772	Phase 3
0.604	Remote Similarity	NPD286	Approved
0.6037	Remote Similarity	NPD3391	Approved
0.6032	Remote Similarity	NPD3479	Discontinued
0.6031	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3369	Phase 2
0.6021	Remote Similarity	NPD5512	Phase 3
0.6021	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6136	Phase 2
0.601	Remote Similarity	NPD6757	Phase 3
0.6	Remote Similarity	NPD9507	Approved
0.599	Remote Similarity	NPD6988	Phase 1
0.5989	Remote Similarity	NPD3793	Phase 3
0.5988	Remote Similarity	NPD5811	Approved
0.5981	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD4586	Phase 3
0.5963	Remote Similarity	NPD5745	Approved
0.596	Remote Similarity	NPD7043	Discontinued
0.5957	Remote Similarity	NPD2542	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4943	Phase 2
0.5955	Remote Similarity	NPD4944	Phase 2
0.5954	Remote Similarity	NPD3296	Phase 1
0.5949	Remote Similarity	NPD6238	Discontinued
0.5949	Remote Similarity	NPD1160	Phase 2
0.5946	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3536	Discontinued
0.5934	Remote Similarity	NPD4354	Approved
0.5932	Remote Similarity	NPD3453	Discontinued
0.593	Remote Similarity	NPD3563	Approved
0.593	Remote Similarity	NPD3562	Approved
0.593	Remote Similarity	NPD3564	Approved
0.593	Remote Similarity	NPD7467	Discontinued
0.5928	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3034	Discontinued
0.5921	Remote Similarity	NPD1103	Approved
0.5921	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD1102	Approved
0.592	Remote Similarity	NPD2366	Approved
0.5918	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD556	Approved
0.5917	Remote Similarity	NPD160	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD1639	Discontinued
0.5914	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD3912	Discontinued
0.5912	Remote Similarity	NPD9365	Approved
0.5909	Remote Similarity	NPD7318	Phase 3
0.5902	Remote Similarity	NPD7692	Discontinued
0.5901	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD565	Phase 2
0.5886	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD7256	Discontinued
0.5885	Remote Similarity	NPD6590	Discontinued
0.5879	Remote Similarity	NPD7263	Phase 2
0.5879	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1742	Approved
0.5876	Remote Similarity	NPD1743	Approved
0.5876	Remote Similarity	NPD6877	Discontinued
0.5876	Remote Similarity	NPD19	Approved
0.5874	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD3398	Discontinued
0.5871	Remote Similarity	NPD3447	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