NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.07
Volume:	220.974
LogP:	1.43
LogD:	1.109
LogS:	-2.54
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	3.527
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.647
MDCK Permeability:	9.240092367690522e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	84.46699523925781%
Volume Distribution (VD):	0.521
Pgp-substrate:	18.377607345581055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.367
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.37
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	16.184
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.544
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.657
Skin Sensitization:	0.505
Carcinogencity:	0.039
Eye Corrosion:	0.008
Eye Irritation:	0.21
Respiratory Toxicity:	0.292

Download Data

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

Natural Product: NPC472892

Natural Product ID:	NPC472892
*Common Name:**	QRTRJOXGGOWVOC-JTQLQIEISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QRTRJOXGGOWVOC-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C12H12O4/c1-6-2-10(15)12(16)11(6)7-3-8(13)5-9(14)4-7/h3-5,10,13-15H,2H2,1H3/t10-/m0/s1
SMILES:	Oc1cc(O)cc(c1)C1=C(C)C[C@@H](C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593567
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	>	100000.0	nM	PMID[476691]

☑ 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 NPC472892 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	261
0.1-0.2	1199
0.2-0.3	3468
0.3-0.4	9560
0.4-0.5	10227
0.5-0.6	5435
0.6-0.7	9821
0.7-0.8	2648
0.8-0.85	75
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8718	High Similarity	NPC162113
0.8718	High Similarity	NPC62546
0.8455	Intermediate Similarity	NPC248363
0.8385	Intermediate Similarity	NPC478190
0.8306	Intermediate Similarity	NPC146642
0.8295	Intermediate Similarity	NPC120488
0.8295	Intermediate Similarity	NPC102829
0.8231	Intermediate Similarity	NPC147757
0.8226	Intermediate Similarity	NPC294037
0.8211	Intermediate Similarity	NPC40649
0.8211	Intermediate Similarity	NPC209486
0.8209	Intermediate Similarity	NPC170742
0.8195	Intermediate Similarity	NPC70859
0.8195	Intermediate Similarity	NPC61153
0.8195	Intermediate Similarity	NPC130899
0.8195	Intermediate Similarity	NPC283590
0.816	Intermediate Similarity	NPC149246
0.8148	Intermediate Similarity	NPC175552
0.8143	Intermediate Similarity	NPC14098
0.814	Intermediate Similarity	NPC156539
0.8125	Intermediate Similarity	NPC10926
0.8125	Intermediate Similarity	NPC477454
0.8095	Intermediate Similarity	NPC215392
0.8092	Intermediate Similarity	NPC123
0.8092	Intermediate Similarity	NPC163169
0.8083	Intermediate Similarity	NPC212718
0.808	Intermediate Similarity	NPC294964
0.808	Intermediate Similarity	NPC159525
0.8077	Intermediate Similarity	NPC79332
0.8077	Intermediate Similarity	NPC24869
0.8062	Intermediate Similarity	NPC8745
0.8062	Intermediate Similarity	NPC473691
0.8051	Intermediate Similarity	NPC61033
0.8051	Intermediate Similarity	NPC305603
0.8047	Intermediate Similarity	NPC13238
0.8045	Intermediate Similarity	NPC139074
0.8045	Intermediate Similarity	NPC213485
0.8045	Intermediate Similarity	NPC40524
0.8033	Intermediate Similarity	NPC118288
0.8033	Intermediate Similarity	NPC276111
0.8031	Intermediate Similarity	NPC91105
0.803	Intermediate Similarity	NPC475042
0.8015	Intermediate Similarity	NPC109123
0.8015	Intermediate Similarity	NPC475974
0.8	Intermediate Similarity	NPC242178
0.8	Intermediate Similarity	NPC158222
0.8	Intermediate Similarity	NPC107672
0.8	Intermediate Similarity	NPC161617
0.7985	Intermediate Similarity	NPC474519
0.7984	Intermediate Similarity	NPC262671
0.7984	Intermediate Similarity	NPC475733
0.7984	Intermediate Similarity	NPC201728
0.7984	Intermediate Similarity	NPC121259
0.7971	Intermediate Similarity	NPC244923
0.797	Intermediate Similarity	NPC17843
0.7969	Intermediate Similarity	NPC472029
0.7969	Intermediate Similarity	NPC65761
0.7966	Intermediate Similarity	NPC317592
0.7956	Intermediate Similarity	NPC474655
0.7955	Intermediate Similarity	NPC62219
0.7953	Intermediate Similarity	NPC242895
0.7953	Intermediate Similarity	NPC226275
0.7951	Intermediate Similarity	NPC98543
0.7951	Intermediate Similarity	NPC11824
0.7941	Intermediate Similarity	NPC149372
0.7941	Intermediate Similarity	NPC178467
0.7941	Intermediate Similarity	NPC65837
0.7941	Intermediate Similarity	NPC474771
0.7941	Intermediate Similarity	NPC474849
0.7939	Intermediate Similarity	NPC179898
0.7939	Intermediate Similarity	NPC476024
0.7939	Intermediate Similarity	NPC41263
0.7929	Intermediate Similarity	NPC471906
0.7899	Intermediate Similarity	NPC34715
0.7895	Intermediate Similarity	NPC198249
0.7891	Intermediate Similarity	NPC309765
0.7891	Intermediate Similarity	NPC133909
0.7891	Intermediate Similarity	NPC32032
0.7883	Intermediate Similarity	NPC212693
0.7883	Intermediate Similarity	NPC94248
0.7883	Intermediate Similarity	NPC191835
0.7879	Intermediate Similarity	NPC92624
0.7868	Intermediate Similarity	NPC84699
0.7857	Intermediate Similarity	NPC476020
0.7857	Intermediate Similarity	NPC473767
0.7857	Intermediate Similarity	NPC354984
0.7852	Intermediate Similarity	NPC474394
0.7842	Intermediate Similarity	NPC204045
0.7842	Intermediate Similarity	NPC305845
0.784	Intermediate Similarity	NPC230349
0.7836	Intermediate Similarity	NPC476389
0.7826	Intermediate Similarity	NPC268052
0.7826	Intermediate Similarity	NPC139634
0.7826	Intermediate Similarity	NPC105456
0.7826	Intermediate Similarity	NPC268691
0.7826	Intermediate Similarity	NPC52358
0.782	Intermediate Similarity	NPC233056
0.782	Intermediate Similarity	NPC17840
0.782	Intermediate Similarity	NPC247477
0.782	Intermediate Similarity	NPC259942
0.7812	Intermediate Similarity	NPC45438
0.7812	Intermediate Similarity	NPC19174
0.7812	Intermediate Similarity	NPC73532
0.7812	Intermediate Similarity	NPC143427
0.7812	Intermediate Similarity	NPC156139
0.7812	Intermediate Similarity	NPC224273
0.7812	Intermediate Similarity	NPC303737
0.7812	Intermediate Similarity	NPC267552
0.7812	Intermediate Similarity	NPC115159
0.781	Intermediate Similarity	NPC70380
0.781	Intermediate Similarity	NPC71256
0.7794	Intermediate Similarity	NPC278375
0.7787	Intermediate Similarity	NPC114682
0.7786	Intermediate Similarity	NPC267846
0.7786	Intermediate Similarity	NPC474961
0.7786	Intermediate Similarity	NPC474944
0.7786	Intermediate Similarity	NPC135524
0.7778	Intermediate Similarity	NPC24407
0.7778	Intermediate Similarity	NPC41567
0.7778	Intermediate Similarity	NPC153783
0.7778	Intermediate Similarity	NPC48036
0.7778	Intermediate Similarity	NPC294186
0.7778	Intermediate Similarity	NPC267205
0.7778	Intermediate Similarity	NPC192032
0.7778	Intermediate Similarity	NPC63126
0.7778	Intermediate Similarity	NPC11280
0.7778	Intermediate Similarity	NPC137415
0.7778	Intermediate Similarity	NPC166313
0.7778	Intermediate Similarity	NPC147310
0.777	Intermediate Similarity	NPC37206
0.7769	Intermediate Similarity	NPC95172
0.7769	Intermediate Similarity	NPC474803
0.7761	Intermediate Similarity	NPC219892
0.7761	Intermediate Similarity	NPC189823
0.776	Intermediate Similarity	NPC123559
0.7754	Intermediate Similarity	NPC478200
0.7754	Intermediate Similarity	NPC33144
0.7754	Intermediate Similarity	NPC472403
0.7754	Intermediate Similarity	NPC177307
0.7754	Intermediate Similarity	NPC9121
0.7752	Intermediate Similarity	NPC475192
0.775	Intermediate Similarity	NPC226699
0.7744	Intermediate Similarity	NPC69235
0.7744	Intermediate Similarity	NPC212379
0.7744	Intermediate Similarity	NPC476119
0.7744	Intermediate Similarity	NPC474998
0.7742	Intermediate Similarity	NPC474114
0.7742	Intermediate Similarity	NPC474050
0.7742	Intermediate Similarity	NPC473931
0.7737	Intermediate Similarity	NPC38158
0.7737	Intermediate Similarity	NPC235115
0.7734	Intermediate Similarity	NPC297186
0.773	Intermediate Similarity	NPC148545
0.7727	Intermediate Similarity	NPC100067
0.7727	Intermediate Similarity	NPC103356
0.7727	Intermediate Similarity	NPC30501
0.7727	Intermediate Similarity	NPC162612
0.7727	Intermediate Similarity	NPC209959
0.7727	Intermediate Similarity	NPC105157
0.7727	Intermediate Similarity	NPC169250
0.7727	Intermediate Similarity	NPC98254
0.7727	Intermediate Similarity	NPC23126
0.7727	Intermediate Similarity	NPC128428
0.7727	Intermediate Similarity	NPC72158
0.7727	Intermediate Similarity	NPC116513
0.7727	Intermediate Similarity	NPC305518
0.7727	Intermediate Similarity	NPC266689
0.7727	Intermediate Similarity	NPC190043
0.7724	Intermediate Similarity	NPC473521
0.7724	Intermediate Similarity	NPC231717
0.7721	Intermediate Similarity	NPC166480
0.7721	Intermediate Similarity	NPC282780
0.7721	Intermediate Similarity	NPC248150
0.7717	Intermediate Similarity	NPC195262
0.7717	Intermediate Similarity	NPC188814
0.7714	Intermediate Similarity	NPC313123
0.7714	Intermediate Similarity	NPC478217
0.7714	Intermediate Similarity	NPC110810
0.7712	Intermediate Similarity	NPC106396
0.7712	Intermediate Similarity	NPC313030
0.7712	Intermediate Similarity	NPC85479
0.7712	Intermediate Similarity	NPC146798
0.7712	Intermediate Similarity	NPC94351
0.7712	Intermediate Similarity	NPC302219
0.7712	Intermediate Similarity	NPC24404
0.7712	Intermediate Similarity	NPC168303
0.7712	Intermediate Similarity	NPC242342
0.7712	Intermediate Similarity	NPC249828
0.7712	Intermediate Similarity	NPC53051
0.7712	Intermediate Similarity	NPC71002
0.7712	Intermediate Similarity	NPC222522
0.771	Intermediate Similarity	NPC472592
0.771	Intermediate Similarity	NPC167055
0.771	Intermediate Similarity	NPC240744
0.7704	Intermediate Similarity	NPC135801
0.7704	Intermediate Similarity	NPC477407
0.7698	Intermediate Similarity	NPC32360
0.7698	Intermediate Similarity	NPC4796
0.7698	Intermediate Similarity	NPC162939
0.7698	Intermediate Similarity	NPC190457

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 NPC472892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	866
0.2-0.3	1603
0.3-0.4	2850
0.4-0.5	2058
0.5-0.6	1129
0.6-0.7	366
0.7-0.8	36
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
0.7704	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD230	Phase 1
0.7615	Intermediate Similarity	NPD9269	Phase 2
0.7609	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9268	Approved
0.7482	Intermediate Similarity	NPD1510	Phase 2
0.7445	Intermediate Similarity	NPD1240	Approved
0.7376	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD1237	Approved
0.7339	Intermediate Similarity	NPD4750	Phase 3
0.7338	Intermediate Similarity	NPD1607	Approved
0.7333	Intermediate Similarity	NPD940	Approved
0.7333	Intermediate Similarity	NPD846	Approved
0.7324	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1549	Phase 2
0.7317	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1201	Approved
0.726	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1242	Phase 1
0.7192	Intermediate Similarity	NPD7390	Discontinued
0.7185	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD1934	Approved
0.7124	Intermediate Similarity	NPD3882	Suspended
0.7105	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD9495	Approved
0.7077	Intermediate Similarity	NPD9493	Approved
0.7077	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD6190	Approved
0.7045	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1755	Approved
0.7027	Intermediate Similarity	NPD2532	Approved
0.7027	Intermediate Similarity	NPD2533	Approved
0.7027	Intermediate Similarity	NPD2534	Approved
0.7025	Intermediate Similarity	NPD6166	Phase 2
0.7025	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4380	Phase 2
0.6992	Remote Similarity	NPD3019	Approved
0.6992	Remote Similarity	NPD2932	Approved
0.6984	Remote Similarity	NPD74	Approved
0.6984	Remote Similarity	NPD9266	Approved
0.6968	Remote Similarity	NPD7075	Discontinued
0.6963	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD1511	Approved
0.6944	Remote Similarity	NPD2796	Approved
0.6929	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD844	Approved
0.6905	Remote Similarity	NPD9264	Approved
0.6905	Remote Similarity	NPD9267	Approved
0.6905	Remote Similarity	NPD9263	Approved
0.6883	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.686	Remote Similarity	NPD288	Approved
0.6857	Remote Similarity	NPD3027	Phase 3
0.6846	Remote Similarity	NPD6799	Approved
0.6839	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9494	Approved
0.6829	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1551	Phase 2
0.6818	Remote Similarity	NPD6801	Discontinued
0.6803	Remote Similarity	NPD2800	Approved
0.68	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2629	Approved
0.6774	Remote Similarity	NPD7819	Suspended
0.6774	Remote Similarity	NPD2801	Approved
0.6763	Remote Similarity	NPD602	Approved
0.6763	Remote Similarity	NPD599	Approved
0.6763	Remote Similarity	NPD859	Approved
0.6763	Remote Similarity	NPD858	Approved
0.6761	Remote Similarity	NPD6663	Approved
0.6759	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4628	Phase 3
0.6757	Remote Similarity	NPD3750	Approved
0.6752	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD17	Approved
0.6736	Remote Similarity	NPD6651	Approved
0.6731	Remote Similarity	NPD3817	Phase 2
0.6731	Remote Similarity	NPD5402	Approved
0.673	Remote Similarity	NPD6959	Discontinued
0.6728	Remote Similarity	NPD3818	Discontinued
0.6718	Remote Similarity	NPD1241	Discontinued
0.6716	Remote Similarity	NPD3091	Approved
0.6714	Remote Similarity	NPD5736	Approved
0.6712	Remote Similarity	NPD2935	Discontinued
0.6711	Remote Similarity	NPD5403	Approved
0.6711	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6797	Phase 2
0.6707	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1164	Approved
0.6691	Remote Similarity	NPD3094	Phase 2
0.669	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD5401	Approved
0.6689	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6599	Discontinued
0.6687	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9281	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7251	Discontinued
0.6646	Remote Similarity	NPD7074	Phase 3
0.6645	Remote Similarity	NPD7411	Suspended
0.6644	Remote Similarity	NPD7033	Discontinued
0.6643	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3092	Approved
0.6642	Remote Similarity	NPD422	Phase 1
0.6639	Remote Similarity	NPD2860	Approved
0.6639	Remote Similarity	NPD2859	Approved
0.6627	Remote Similarity	NPD7808	Phase 3
0.6623	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD255	Approved
0.6617	Remote Similarity	NPD256	Approved
0.6614	Remote Similarity	NPD5048	Discontinued
0.6613	Remote Similarity	NPD3020	Approved
0.6604	Remote Similarity	NPD919	Approved
0.6603	Remote Similarity	NPD37	Approved
0.6599	Remote Similarity	NPD9570	Approved
0.6599	Remote Similarity	NPD5405	Approved
0.6599	Remote Similarity	NPD5408	Approved
0.6599	Remote Similarity	NPD5404	Approved
0.6599	Remote Similarity	NPD5406	Approved
0.6597	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1613	Approved
0.6594	Remote Similarity	NPD9717	Approved
0.6593	Remote Similarity	NPD1759	Phase 1
0.6587	Remote Similarity	NPD6647	Phase 2
0.6587	Remote Similarity	NPD9261	Approved
0.6585	Remote Similarity	NPD7054	Approved
0.6579	Remote Similarity	NPD9093	Approved
0.6577	Remote Similarity	NPD1243	Approved
0.6577	Remote Similarity	NPD2654	Approved
0.6577	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3268	Approved
0.6573	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3023	Approved
0.6569	Remote Similarity	NPD3026	Approved
0.6557	Remote Similarity	NPD2934	Approved
0.6557	Remote Similarity	NPD2933	Approved
0.6556	Remote Similarity	NPD3300	Phase 2
0.6554	Remote Similarity	NPD6005	Phase 3
0.6554	Remote Similarity	NPD6004	Phase 3
0.6554	Remote Similarity	NPD6002	Phase 3
0.6554	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4749	Approved
0.6545	Remote Similarity	NPD7472	Approved
0.6544	Remote Similarity	NPD3024	Approved
0.6544	Remote Similarity	NPD3025	Approved
0.6541	Remote Similarity	NPD9614	Approved
0.6541	Remote Similarity	NPD9618	Approved
0.6538	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3021	Approved
0.6538	Remote Similarity	NPD3022	Approved
0.6527	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD258	Approved
0.6525	Remote Similarity	NPD257	Approved
0.6522	Remote Similarity	NPD1247	Approved
0.6522	Remote Similarity	NPD1610	Phase 2
0.6522	Remote Similarity	NPD9089	Approved
0.6519	Remote Similarity	NPD1758	Phase 1
0.6509	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6653	Approved
0.6507	Remote Similarity	NPD2568	Approved
0.65	Remote Similarity	NPD1283	Approved
0.6496	Remote Similarity	NPD1778	Approved
0.6496	Remote Similarity	NPD3095	Discontinued
0.6496	Remote Similarity	NPD111	Approved
0.6494	Remote Similarity	NPD920	Approved
0.6485	Remote Similarity	NPD5844	Phase 1
0.6483	Remote Similarity	NPD826	Approved
0.6483	Remote Similarity	NPD825	Approved
0.6481	Remote Similarity	NPD6232	Discontinued
0.6478	Remote Similarity	NPD4967	Phase 2
0.6478	Remote Similarity	NPD4966	Approved
0.6478	Remote Similarity	NPD4965	Approved
0.6475	Remote Similarity	NPD3972	Approved
0.6475	Remote Similarity	NPD845	Approved
0.6471	Remote Similarity	NPD1548	Phase 1
0.6467	Remote Similarity	NPD6559	Discontinued
0.6463	Remote Similarity	NPD7473	Discontinued
0.646	Remote Similarity	NPD5494	Approved
0.6458	Remote Similarity	NPD411	Approved
0.6454	Remote Similarity	NPD1203	Approved
0.6454	Remote Similarity	NPD2797	Approved
0.6447	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2344	Approved
0.6438	Remote Similarity	NPD3749	Approved
0.6438	Remote Similarity	NPD6355	Discontinued
0.6438	Remote Similarity	NPD447	Suspended
0.6434	Remote Similarity	NPD4908	Phase 1
0.6434	Remote Similarity	NPD1444	Approved
0.6434	Remote Similarity	NPD1445	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