NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.09
Volume:	252.618
LogP:	-0.541
LogD:	-0.454
LogS:	-0.611
# Rotatable Bonds:	3
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	3.371
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.882
MDCK Permeability:	4.142939724260941e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.574
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	57.91551971435547%
Volume Distribution (VD):	0.447
Pgp-substrate:	45.89542770385742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.46
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.265
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	2.696
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.585
Carcinogencity:	0.216
Eye Corrosion:	0.029
Eye Irritation:	0.643
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC9248

Natural Product ID:	NPC9248
*Common Name:**	Pyrocatechol-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-hydroxyphenoxy)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	NMZWIAATAZXMRV-RMPHRYRLSA-N
Standard InCHI:	InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-4-2-1-3-6(7)14/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccccc2O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443206
PubChem CID:	9900144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	40.0	%	PMID[490582]

☑ 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 NPC9248 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	385
0.1-0.2	2422
0.2-0.3	8506
0.3-0.4	11373
0.4-0.5	5161
0.5-0.6	8813
0.6-0.7	4737
0.7-0.8	1186
0.8-0.85	87
0.85-0.9	18
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC228907
0.9369	High Similarity	NPC142319
0.9316	High Similarity	NPC221090
0.9231	High Similarity	NPC192810
0.9145	High Similarity	NPC152722
0.9083	High Similarity	NPC37074
0.9	High Similarity	NPC298845
0.9	High Similarity	NPC189589
0.9	High Similarity	NPC469622
0.8974	High Similarity	NPC276195
0.8833	High Similarity	NPC25817
0.879	High Similarity	NPC166168
0.879	High Similarity	NPC287780
0.877	High Similarity	NPC469621
0.875	High Similarity	NPC217854
0.8739	High Similarity	NPC57751
0.871	High Similarity	NPC60756
0.871	High Similarity	NPC208769
0.8655	High Similarity	NPC269242
0.8651	High Similarity	NPC60982
0.8629	High Similarity	NPC307110
0.8629	High Similarity	NPC248355
0.8629	High Similarity	NPC166040
0.8583	High Similarity	NPC226712
0.8583	High Similarity	NPC87696
0.8571	High Similarity	NPC60589
0.8571	High Similarity	NPC469708
0.8548	High Similarity	NPC247146
0.8548	High Similarity	NPC302378
0.8537	High Similarity	NPC171533
0.85	High Similarity	NPC198734
0.85	High Similarity	NPC469412
0.8492	Intermediate Similarity	NPC65942
0.8492	Intermediate Similarity	NPC248307
0.848	Intermediate Similarity	NPC26653
0.848	Intermediate Similarity	NPC270849
0.845	Intermediate Similarity	NPC186418
0.844	Intermediate Similarity	NPC314803
0.8425	Intermediate Similarity	NPC252833
0.8413	Intermediate Similarity	NPC472024
0.8413	Intermediate Similarity	NPC80600
0.8387	Intermediate Similarity	NPC233559
0.8385	Intermediate Similarity	NPC470413
0.8385	Intermediate Similarity	NPC138738
0.8385	Intermediate Similarity	NPC65530
0.8385	Intermediate Similarity	NPC59324
0.8359	Intermediate Similarity	NPC49074
0.8359	Intermediate Similarity	NPC25821
0.8359	Intermediate Similarity	NPC132895
0.8359	Intermediate Similarity	NPC6836
0.8346	Intermediate Similarity	NPC9912
0.8321	Intermediate Similarity	NPC100389
0.8321	Intermediate Similarity	NPC98777
0.8321	Intermediate Similarity	NPC212770
0.832	Intermediate Similarity	NPC140750
0.8308	Intermediate Similarity	NPC242028
0.8308	Intermediate Similarity	NPC203230
0.8306	Intermediate Similarity	NPC12308
0.8306	Intermediate Similarity	NPC470510
0.8295	Intermediate Similarity	NPC470881
0.8295	Intermediate Similarity	NPC35731
0.8281	Intermediate Similarity	NPC162093
0.8281	Intermediate Similarity	NPC299144
0.8281	Intermediate Similarity	NPC470270
0.8258	Intermediate Similarity	NPC202700
0.8258	Intermediate Similarity	NPC106944
0.8254	Intermediate Similarity	NPC198487
0.8254	Intermediate Similarity	NPC40377
0.8235	Intermediate Similarity	NPC175771
0.8226	Intermediate Similarity	NPC287429
0.822	Intermediate Similarity	NPC313193
0.8195	Intermediate Similarity	NPC469661
0.8189	Intermediate Similarity	NPC218003
0.8189	Intermediate Similarity	NPC97326
0.8168	Intermediate Similarity	NPC104167
0.8168	Intermediate Similarity	NPC199459
0.8168	Intermediate Similarity	NPC37468
0.8168	Intermediate Similarity	NPC164857
0.8168	Intermediate Similarity	NPC52277
0.8168	Intermediate Similarity	NPC177035
0.8168	Intermediate Similarity	NPC157554
0.8154	Intermediate Similarity	NPC187194
0.8154	Intermediate Similarity	NPC107478
0.8154	Intermediate Similarity	NPC476411
0.8154	Intermediate Similarity	NPC13745
0.8154	Intermediate Similarity	NPC251981
0.8154	Intermediate Similarity	NPC48863
0.8134	Intermediate Similarity	NPC475084
0.8134	Intermediate Similarity	NPC469559
0.8134	Intermediate Similarity	NPC189115
0.8134	Intermediate Similarity	NPC157816
0.8125	Intermediate Similarity	NPC470079
0.811	Intermediate Similarity	NPC146540
0.811	Intermediate Similarity	NPC72529
0.8106	Intermediate Similarity	NPC195196
0.8106	Intermediate Similarity	NPC304152
0.8092	Intermediate Similarity	NPC55040
0.8092	Intermediate Similarity	NPC470236
0.8077	Intermediate Similarity	NPC69513
0.8077	Intermediate Similarity	NPC215833
0.8074	Intermediate Similarity	NPC252169
0.8074	Intermediate Similarity	NPC478239
0.8074	Intermediate Similarity	NPC46092
0.8074	Intermediate Similarity	NPC470950
0.8074	Intermediate Similarity	NPC185307
0.807	Intermediate Similarity	NPC307875
0.8065	Intermediate Similarity	NPC476142
0.8062	Intermediate Similarity	NPC121376
0.806	Intermediate Similarity	NPC186406
0.8047	Intermediate Similarity	NPC86030
0.8047	Intermediate Similarity	NPC5851
0.8045	Intermediate Similarity	NPC226005
0.8034	Intermediate Similarity	NPC247871
0.8031	Intermediate Similarity	NPC183181
0.8031	Intermediate Similarity	NPC118787
0.8031	Intermediate Similarity	NPC163332
0.8031	Intermediate Similarity	NPC111247
0.8031	Intermediate Similarity	NPC292056
0.8031	Intermediate Similarity	NPC198798
0.8031	Intermediate Similarity	NPC41706
0.8031	Intermediate Similarity	NPC319625
0.8031	Intermediate Similarity	NPC147821
0.8015	Intermediate Similarity	NPC25292
0.8015	Intermediate Similarity	NPC283995
0.8015	Intermediate Similarity	NPC473045
0.8015	Intermediate Similarity	NPC129417
0.8015	Intermediate Similarity	NPC470235
0.8015	Intermediate Similarity	NPC232228
0.8	Intermediate Similarity	NPC476356
0.8	Intermediate Similarity	NPC85799
0.8	Intermediate Similarity	NPC165686
0.8	Intermediate Similarity	NPC26080
0.8	Intermediate Similarity	NPC303422
0.7984	Intermediate Similarity	NPC470804
0.7984	Intermediate Similarity	NPC262606
0.7984	Intermediate Similarity	NPC266045
0.797	Intermediate Similarity	NPC477797
0.797	Intermediate Similarity	NPC477798
0.7956	Intermediate Similarity	NPC279298
0.7956	Intermediate Similarity	NPC475096
0.7956	Intermediate Similarity	NPC476868
0.7956	Intermediate Similarity	NPC38041
0.7956	Intermediate Similarity	NPC469586
0.7956	Intermediate Similarity	NPC18979
0.7956	Intermediate Similarity	NPC476866
0.7956	Intermediate Similarity	NPC476869
0.7956	Intermediate Similarity	NPC476864
0.7956	Intermediate Similarity	NPC22150
0.7955	Intermediate Similarity	NPC101624
0.7955	Intermediate Similarity	NPC184938
0.7953	Intermediate Similarity	NPC58607
0.7953	Intermediate Similarity	NPC191037
0.7953	Intermediate Similarity	NPC178284
0.7941	Intermediate Similarity	NPC473044
0.7939	Intermediate Similarity	NPC115022
0.7939	Intermediate Similarity	NPC294166
0.7931	Intermediate Similarity	NPC124712
0.7926	Intermediate Similarity	NPC472711
0.7917	Intermediate Similarity	NPC157338
0.7909	Intermediate Similarity	NPC114325
0.7907	Intermediate Similarity	NPC295970
0.7899	Intermediate Similarity	NPC112861
0.7899	Intermediate Similarity	NPC476865
0.7899	Intermediate Similarity	NPC99515
0.7899	Intermediate Similarity	NPC125755
0.7899	Intermediate Similarity	NPC199928
0.7899	Intermediate Similarity	NPC190714
0.7895	Intermediate Similarity	NPC25695
0.7895	Intermediate Similarity	NPC172818
0.7886	Intermediate Similarity	NPC214289
0.7883	Intermediate Similarity	NPC469313
0.7883	Intermediate Similarity	NPC168579
0.7883	Intermediate Similarity	NPC138227
0.7883	Intermediate Similarity	NPC476867
0.7883	Intermediate Similarity	NPC76176
0.7883	Intermediate Similarity	NPC292443
0.7879	Intermediate Similarity	NPC130496
0.7879	Intermediate Similarity	NPC188555
0.7874	Intermediate Similarity	NPC194519
0.7869	Intermediate Similarity	NPC76915
0.7869	Intermediate Similarity	NPC151617
0.7868	Intermediate Similarity	NPC477800
0.7868	Intermediate Similarity	NPC477799
0.7868	Intermediate Similarity	NPC48309
0.7868	Intermediate Similarity	NPC60249
0.7868	Intermediate Similarity	NPC477794
0.7868	Intermediate Similarity	NPC140502
0.7868	Intermediate Similarity	NPC253878
0.7852	Intermediate Similarity	NPC210478
0.7845	Intermediate Similarity	NPC232654
0.7845	Intermediate Similarity	NPC41594
0.7842	Intermediate Similarity	NPC275284
0.7842	Intermediate Similarity	NPC15956
0.7842	Intermediate Similarity	NPC227902
0.7842	Intermediate Similarity	NPC114505
0.7842	Intermediate Similarity	NPC193473
0.7842	Intermediate Similarity	NPC41844
0.7842	Intermediate Similarity	NPC213074
0.7842	Intermediate Similarity	NPC224674
0.7842	Intermediate Similarity	NPC39657

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 NPC9248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	1018
0.2-0.3	2778
0.3-0.4	2630
0.4-0.5	1346
0.5-0.6	850
0.6-0.7	198
0.7-0.8	14
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD1091	Approved
0.8455	Intermediate Similarity	NPD291	Approved
0.8261	Intermediate Similarity	NPD556	Approved
0.7909	Intermediate Similarity	NPD9296	Approved
0.7798	Intermediate Similarity	NPD9365	Approved
0.773	Intermediate Similarity	NPD1653	Approved
0.7594	Intermediate Similarity	NPD1613	Approved
0.7594	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.746	Intermediate Similarity	NPD1357	Approved
0.7333	Intermediate Similarity	NPD9552	Approved
0.7333	Intermediate Similarity	NPD290	Approved
0.7302	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD191	Approved
0.7266	Intermediate Similarity	NPD7266	Discontinued
0.7218	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3454	Phase 3
0.7163	Intermediate Similarity	NPD6674	Discontinued
0.7154	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9295	Approved
0.7107	Intermediate Similarity	NPD968	Approved
0.7097	Intermediate Similarity	NPD228	Approved
0.7083	Intermediate Similarity	NPD9501	Approved
0.7054	Intermediate Similarity	NPD1797	Approved
0.7054	Intermediate Similarity	NPD1798	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6977	Remote Similarity	NPD7533	Approved
0.6977	Remote Similarity	NPD7534	Approved
0.6929	Remote Similarity	NPD9299	Approved
0.6912	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7843	Approved
0.6903	Remote Similarity	NPD9094	Approved
0.6899	Remote Similarity	NPD1102	Approved
0.6899	Remote Similarity	NPD1103	Approved
0.6899	Remote Similarity	NPD7054	Approved
0.6897	Remote Similarity	NPD5058	Phase 3
0.6855	Remote Similarity	NPD7472	Approved
0.6855	Remote Similarity	NPD7074	Phase 3
0.6846	Remote Similarity	NPD1548	Phase 1
0.6835	Remote Similarity	NPD3818	Discontinued
0.6818	Remote Similarity	NPD915	Approved
0.6791	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1610	Phase 2
0.6753	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7157	Approved
0.6728	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2250	Discontinued
0.6715	Remote Similarity	NPD2861	Phase 2
0.6714	Remote Similarity	NPD1558	Phase 1
0.6708	Remote Similarity	NPD6797	Phase 2
0.669	Remote Similarity	NPD4538	Approved
0.669	Remote Similarity	NPD4536	Approved
0.669	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1652	Phase 2
0.6667	Remote Similarity	NPD1375	Discontinued
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD2977	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD2978	Approved
0.6643	Remote Similarity	NPD5960	Phase 3
0.6643	Remote Similarity	NPD5588	Approved
0.6642	Remote Similarity	NPD5647	Approved
0.6626	Remote Similarity	NPD7808	Phase 3
0.6625	Remote Similarity	NPD7228	Approved
0.6622	Remote Similarity	NPD1774	Approved
0.662	Remote Similarity	NPD2223	Approved
0.662	Remote Similarity	NPD2224	Approved
0.6615	Remote Similarity	NPD6671	Approved
0.6603	Remote Similarity	NPD6234	Discontinued
0.6601	Remote Similarity	NPD1934	Approved
0.6571	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7685	Pre-registration
0.6544	Remote Similarity	NPD2983	Phase 2
0.6544	Remote Similarity	NPD2982	Phase 2
0.6544	Remote Similarity	NPD3685	Discontinued
0.6525	Remote Similarity	NPD6233	Phase 2
0.6519	Remote Similarity	NPD422	Phase 1
0.651	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1358	Approved
0.6503	Remote Similarity	NPD6653	Approved
0.65	Remote Similarity	NPD3180	Approved
0.65	Remote Similarity	NPD3179	Approved
0.6496	Remote Similarity	NPD8651	Approved
0.6494	Remote Similarity	NPD37	Approved
0.6493	Remote Similarity	NPD5846	Approved
0.6493	Remote Similarity	NPD5126	Approved
0.6493	Remote Similarity	NPD6516	Phase 2
0.6493	Remote Similarity	NPD5125	Phase 3
0.6484	Remote Similarity	NPD2673	Approved
0.6484	Remote Similarity	NPD2671	Approved
0.6479	Remote Similarity	NPD3620	Phase 2
0.6479	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4967	Phase 2
0.6474	Remote Similarity	NPD4966	Approved
0.6474	Remote Similarity	NPD4965	Approved
0.6471	Remote Similarity	NPD2981	Phase 2
0.6471	Remote Similarity	NPD2231	Phase 2
0.6471	Remote Similarity	NPD2235	Phase 2
0.6463	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5283	Phase 1
0.6458	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7097	Phase 1
0.6454	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD9549	Phase 2
0.6449	Remote Similarity	NPD2082	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6362	Approved
0.6447	Remote Similarity	NPD3687	Approved
0.6447	Remote Similarity	NPD3686	Approved
0.6434	Remote Similarity	NPD969	Suspended
0.6434	Remote Similarity	NPD4340	Discontinued
0.6434	Remote Similarity	NPD1933	Approved
0.6423	Remote Similarity	NPD4749	Approved
0.6419	Remote Similarity	NPD4628	Phase 3
0.6415	Remote Similarity	NPD7199	Phase 2
0.6414	Remote Similarity	NPD7033	Discontinued
0.6408	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6166	Phase 2
0.6385	Remote Similarity	NPD821	Approved
0.638	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6190	Approved
0.6376	Remote Similarity	NPD2677	Approved
0.6372	Remote Similarity	NPD9089	Approved
0.637	Remote Similarity	NPD1778	Approved
0.6364	Remote Similarity	NPD4060	Phase 1
0.6358	Remote Similarity	NPD4123	Phase 3
0.6357	Remote Similarity	NPD9494	Approved
0.6357	Remote Similarity	NPD3018	Phase 2
0.6351	Remote Similarity	NPD4236	Phase 3
0.6351	Remote Similarity	NPD4237	Approved
0.6351	Remote Similarity	NPD3060	Approved
0.6346	Remote Similarity	NPD5773	Approved
0.6346	Remote Similarity	NPD5772	Approved
0.6346	Remote Similarity	NPD2801	Approved
0.6338	Remote Similarity	NPD6798	Discontinued
0.6338	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1048	Approved
0.6327	Remote Similarity	NPD5763	Approved
0.6327	Remote Similarity	NPD5762	Approved
0.6324	Remote Similarity	NPD3496	Discontinued
0.6319	Remote Similarity	NPD447	Suspended
0.6319	Remote Similarity	NPD5124	Phase 1
0.6319	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD9088	Approved
0.6294	Remote Similarity	NPD4062	Phase 3
0.6291	Remote Similarity	NPD1511	Approved
0.6286	Remote Similarity	NPD558	Phase 2
0.6284	Remote Similarity	NPD2424	Discontinued
0.6283	Remote Similarity	NPD9093	Approved
0.6282	Remote Similarity	NPD3384	Approved
0.6282	Remote Similarity	NPD3382	Approved
0.6282	Remote Similarity	NPD3383	Approved
0.6277	Remote Similarity	NPD1535	Discovery
0.6277	Remote Similarity	NPD776	Approved
0.6275	Remote Similarity	NPD2122	Discontinued
0.6273	Remote Similarity	NPD3787	Discontinued
0.6269	Remote Similarity	NPD5536	Phase 2
0.6268	Remote Similarity	NPD4625	Phase 3
0.6266	Remote Similarity	NPD3882	Suspended
0.6265	Remote Similarity	NPD6559	Discontinued
0.626	Remote Similarity	NPD769	Approved
0.6259	Remote Similarity	NPD3225	Approved
0.6258	Remote Similarity	NPD4678	Approved
0.6258	Remote Similarity	NPD4675	Approved
0.625	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3536	Discontinued
0.6242	Remote Similarity	NPD4162	Approved
0.6242	Remote Similarity	NPD5177	Phase 3
0.6239	Remote Similarity	NPD9087	Approved
0.6235	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD1481	Phase 2
0.6224	Remote Similarity	NPD3144	Approved
0.6224	Remote Similarity	NPD3145	Approved
0.6216	Remote Similarity	NPD6005	Phase 3
0.6216	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6002	Phase 3
0.6216	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6004	Phase 3
0.6216	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1817	Approved
0.6214	Remote Similarity	NPD1818	Approved
0.6214	Remote Similarity	NPD1820	Approved
0.6214	Remote Similarity	NPD1794	Approved
0.6214	Remote Similarity	NPD1819	Approved
0.6209	Remote Similarity	NPD1512	Approved
0.6207	Remote Similarity	NPD6355	Discontinued
0.6207	Remote Similarity	NPD230	Phase 1
0.62	Remote Similarity	NPD4535	Phase 3

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