NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	284.885
LogP:	3.403
LogD:	3.241
LogS:	-3.76
# Rotatable Bonds:	5
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.821
Synthetic Accessibility Score:	1.847
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	1.423253161192406e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.427
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	95.54402923583984%
Volume Distribution (VD):	0.533
Pgp-substrate:	2.1279032230377197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.896
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	13.381
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.544
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.387
Skin Sensitization:	0.879
Carcinogencity:	0.539
Eye Corrosion:	0.012
Eye Irritation:	0.955
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC286336

Natural Product ID:	NPC286336
*Common Name:**	1-(2-Hydroxy-4-Methoxyphenyl)-3-(4-Hydroxyphenyl)Propan-1-One
IUPAC Name:	1-(2-hydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	MEZSKKITJGNMJJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-20-13-7-8-14(16(19)10-13)15(18)9-4-11-2-5-12(17)6-3-11/h2-3,5-8,10,17,19H,4,9H2,1H3
SMILES:	COc1ccc(c(c1)O)C(=O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490352
PubChem CID:	2762958
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO8485	Magnolia odora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12031	Schinopsis lorentzii	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8485	Magnolia odora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8391	Cortinarius sinapicolor	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10862	Mammillaria runyonii	Species	Cactaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[531712]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[531712]

☑ 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 NPC286336 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	335
0.1-0.2	1610
0.2-0.3	4362
0.3-0.4	10801
0.4-0.5	7069
0.5-0.6	3760
0.6-0.7	5945
0.7-0.8	5401
0.8-0.85	2000
0.85-0.9	942
0.9-0.95	377
0.95-1	95

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC312318
0.9922	High Similarity	NPC204960
0.9922	High Similarity	NPC263670
0.9922	High Similarity	NPC188646
0.9922	High Similarity	NPC18877
0.9922	High Similarity	NPC144051
0.9922	High Similarity	NPC82225
0.9922	High Similarity	NPC20560
0.9922	High Similarity	NPC28753
0.9922	High Similarity	NPC242294
0.9922	High Similarity	NPC175098
0.9922	High Similarity	NPC159623
0.9922	High Similarity	NPC56031
0.9922	High Similarity	NPC337373
0.9922	High Similarity	NPC192304
0.9922	High Similarity	NPC139813
0.9922	High Similarity	NPC472365
0.9922	High Similarity	NPC294593
0.9846	High Similarity	NPC477243
0.9846	High Similarity	NPC274109
0.9846	High Similarity	NPC66349
0.9846	High Similarity	NPC1486
0.9846	High Similarity	NPC186838
0.9846	High Similarity	NPC25287
0.9846	High Similarity	NPC168105
0.9846	High Similarity	NPC477244
0.9846	High Similarity	NPC477242
0.9846	High Similarity	NPC150399
0.9846	High Similarity	NPC41461
0.9846	High Similarity	NPC98115
0.9846	High Similarity	NPC249606
0.9846	High Similarity	NPC12165
0.9844	High Similarity	NPC87231
0.9844	High Similarity	NPC257756
0.9844	High Similarity	NPC212631
0.9844	High Similarity	NPC205468
0.9844	High Similarity	NPC129132
0.9771	High Similarity	NPC317119
0.9771	High Similarity	NPC472419
0.9771	High Similarity	NPC153979
0.9769	High Similarity	NPC156092
0.9769	High Similarity	NPC13575
0.9769	High Similarity	NPC131039
0.9766	High Similarity	NPC64359
0.9766	High Similarity	NPC313618
0.9766	High Similarity	NPC262359
0.9766	High Similarity	NPC186097
0.9766	High Similarity	NPC475009
0.9766	High Similarity	NPC128348
0.9766	High Similarity	NPC475008
0.9766	High Similarity	NPC189106
0.9766	High Similarity	NPC309717
0.9766	High Similarity	NPC66384
0.9766	High Similarity	NPC308037
0.9766	High Similarity	NPC112192
0.9766	High Similarity	NPC164236
0.9697	High Similarity	NPC124269
0.9697	High Similarity	NPC21350
0.9697	High Similarity	NPC472368
0.9695	High Similarity	NPC473391
0.9695	High Similarity	NPC472364
0.9695	High Similarity	NPC213603
0.9695	High Similarity	NPC476333
0.9695	High Similarity	NPC472367
0.9692	High Similarity	NPC103842
0.9624	High Similarity	NPC477956
0.9624	High Similarity	NPC472366
0.9624	High Similarity	NPC470211
0.9621	High Similarity	NPC303644
0.9621	High Similarity	NPC7013
0.9621	High Similarity	NPC116632
0.9621	High Similarity	NPC188879
0.9621	High Similarity	NPC209560
0.9621	High Similarity	NPC181124
0.9621	High Similarity	NPC294409
0.9621	High Similarity	NPC162680
0.9615	High Similarity	NPC27643
0.9609	High Similarity	NPC247779
0.9552	High Similarity	NPC215311
0.9552	High Similarity	NPC172250
0.9552	High Similarity	NPC204985
0.9552	High Similarity	NPC259166
0.9552	High Similarity	NPC219917
0.9552	High Similarity	NPC11056
0.9552	High Similarity	NPC213659
0.9552	High Similarity	NPC48624
0.9552	High Similarity	NPC144118
0.9552	High Similarity	NPC80962
0.9552	High Similarity	NPC326109
0.9549	High Similarity	NPC279668
0.9549	High Similarity	NPC309154
0.9549	High Similarity	NPC55162
0.9549	High Similarity	NPC243528
0.9549	High Similarity	NPC12175
0.9549	High Similarity	NPC278323
0.9549	High Similarity	NPC90665
0.9549	High Similarity	NPC471620
0.9549	High Similarity	NPC251681
0.9545	High Similarity	NPC240593
0.9531	High Similarity	NPC211120
0.9481	High Similarity	NPC470089
0.9481	High Similarity	NPC268204
0.9481	High Similarity	NPC52789
0.9481	High Similarity	NPC469404
0.9481	High Similarity	NPC321980
0.9481	High Similarity	NPC26051
0.9481	High Similarity	NPC110969
0.9481	High Similarity	NPC470087
0.9481	High Similarity	NPC49108
0.9481	High Similarity	NPC55832
0.9478	High Similarity	NPC283429
0.9478	High Similarity	NPC295384
0.9478	High Similarity	NPC109232
0.9474	High Similarity	NPC250266
0.9474	High Similarity	NPC266597
0.947	High Similarity	NPC39426
0.947	High Similarity	NPC234560
0.9453	High Similarity	NPC80694
0.9453	High Similarity	NPC186098
0.9412	High Similarity	NPC226636
0.9412	High Similarity	NPC11561
0.9407	High Similarity	NPC261227
0.9407	High Similarity	NPC241100
0.9407	High Similarity	NPC270883
0.9407	High Similarity	NPC188243
0.9407	High Similarity	NPC101366
0.9407	High Similarity	NPC69769
0.9407	High Similarity	NPC76445
0.9407	High Similarity	NPC6407
0.9407	High Similarity	NPC253822
0.9407	High Similarity	NPC284550
0.9407	High Similarity	NPC172986
0.9407	High Similarity	NPC159275
0.9407	High Similarity	NPC129853
0.9407	High Similarity	NPC265178
0.9407	High Similarity	NPC110228
0.9403	High Similarity	NPC188947
0.9403	High Similarity	NPC280284
0.9403	High Similarity	NPC99333
0.9398	High Similarity	NPC24394
0.9398	High Similarity	NPC13408
0.9398	High Similarity	NPC235428
0.9398	High Similarity	NPC231772
0.9398	High Similarity	NPC127447
0.9398	High Similarity	NPC29353
0.9398	High Similarity	NPC124784
0.9398	High Similarity	NPC47815
0.9398	High Similarity	NPC234133
0.9398	High Similarity	NPC87545
0.9398	High Similarity	NPC473887
0.9398	High Similarity	NPC194281
0.9394	High Similarity	NPC164136
0.9389	High Similarity	NPC215875
0.9389	High Similarity	NPC15834
0.938	High Similarity	NPC69235
0.938	High Similarity	NPC212379
0.9375	High Similarity	NPC128428
0.9375	High Similarity	NPC305518
0.9343	High Similarity	NPC301751
0.9343	High Similarity	NPC51887
0.9343	High Similarity	NPC18585
0.9343	High Similarity	NPC91560
0.9343	High Similarity	NPC68104
0.9343	High Similarity	NPC75049
0.9343	High Similarity	NPC221432
0.9343	High Similarity	NPC143896
0.9343	High Similarity	NPC245482
0.9343	High Similarity	NPC164980
0.9343	High Similarity	NPC175504
0.9343	High Similarity	NPC169591
0.9343	High Similarity	NPC39329
0.9343	High Similarity	NPC149026
0.9343	High Similarity	NPC257097
0.9343	High Similarity	NPC150408
0.9343	High Similarity	NPC106985
0.9343	High Similarity	NPC475705
0.9343	High Similarity	NPC476178
0.9343	High Similarity	NPC166138
0.9343	High Similarity	NPC310130
0.9343	High Similarity	NPC117836
0.9338	High Similarity	NPC3188
0.9338	High Similarity	NPC26238
0.9338	High Similarity	NPC103362
0.9338	High Similarity	NPC232021
0.9338	High Similarity	NPC156590
0.9338	High Similarity	NPC147688
0.9338	High Similarity	NPC205006
0.9338	High Similarity	NPC118840
0.9338	High Similarity	NPC126534
0.9338	High Similarity	NPC40118
0.9338	High Similarity	NPC64908
0.9338	High Similarity	NPC282300
0.9333	High Similarity	NPC301217
0.9333	High Similarity	NPC216978
0.9333	High Similarity	NPC274784
0.9333	High Similarity	NPC310135
0.9333	High Similarity	NPC53181
0.9333	High Similarity	NPC55018
0.9333	High Similarity	NPC96565
0.9333	High Similarity	NPC140890

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 NPC286336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	977
0.2-0.3	1464
0.3-0.4	2592
0.4-0.5	1944
0.5-0.6	1227
0.6-0.7	425
0.7-0.8	141
0.8-0.85	44
0.85-0.9	11
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9766	High Similarity	NPD1240	Approved
0.9615	High Similarity	NPD1607	Approved
0.947	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1549	Phase 2
0.9185	High Similarity	NPD1552	Clinical (unspecified phase)
0.9185	High Similarity	NPD1550	Clinical (unspecified phase)
0.9137	High Similarity	NPD4378	Clinical (unspecified phase)
0.9	High Similarity	NPD7410	Clinical (unspecified phase)
0.8971	High Similarity	NPD2796	Approved
0.8819	High Similarity	NPD4380	Phase 2
0.8794	High Similarity	NPD6799	Approved
0.8759	High Similarity	NPD7411	Suspended
0.8639	High Similarity	NPD2393	Clinical (unspecified phase)
0.8613	High Similarity	NPD6651	Approved
0.8591	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD1934	Approved
0.8562	High Similarity	NPD6599	Discontinued
0.8561	High Similarity	NPD2935	Discontinued
0.8531	High Similarity	NPD1511	Approved
0.8523	High Similarity	NPD3882	Suspended
0.8514	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD7096	Clinical (unspecified phase)
0.8514	High Similarity	NPD2801	Approved
0.8467	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD3750	Approved
0.8451	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD6801	Discontinued
0.8429	Intermediate Similarity	NPD1551	Phase 2
0.8414	Intermediate Similarity	NPD1512	Approved
0.838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD943	Approved
0.8278	Intermediate Similarity	NPD7768	Phase 2
0.8258	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD2800	Approved
0.8239	Intermediate Similarity	NPD2344	Approved
0.8224	Intermediate Similarity	NPD3749	Approved
0.8222	Intermediate Similarity	NPD1203	Approved
0.8162	Intermediate Similarity	NPD2798	Approved
0.8141	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6166	Phase 2
0.8141	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD3972	Approved
0.8129	Intermediate Similarity	NPD6232	Discontinued
0.8125	Intermediate Similarity	NPD2654	Approved
0.8125	Intermediate Similarity	NPD1243	Approved
0.8108	Intermediate Similarity	NPD5403	Approved
0.8099	Intermediate Similarity	NPD3748	Approved
0.8099	Intermediate Similarity	NPD2799	Discontinued
0.8099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2534	Approved
0.8095	Intermediate Similarity	NPD2533	Approved
0.8095	Intermediate Similarity	NPD2532	Approved
0.8092	Intermediate Similarity	NPD3817	Phase 2
0.8089	Intermediate Similarity	NPD7473	Discontinued
0.8065	Intermediate Similarity	NPD6959	Discontinued
0.8043	Intermediate Similarity	NPD6832	Phase 2
0.8038	Intermediate Similarity	NPD3818	Discontinued
0.8015	Intermediate Similarity	NPD9493	Approved
0.8014	Intermediate Similarity	NPD2309	Approved
0.8	Intermediate Similarity	NPD9717	Approved
0.8	Intermediate Similarity	NPD5953	Discontinued
0.7987	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD7286	Phase 2
0.7973	Intermediate Similarity	NPD5401	Approved
0.7959	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4628	Phase 3
0.7937	Intermediate Similarity	NPD7074	Phase 3
0.7926	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD9545	Approved
0.7885	Intermediate Similarity	NPD5494	Approved
0.7875	Intermediate Similarity	NPD7054	Approved
0.7867	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7472	Approved
0.7801	Intermediate Similarity	NPD3268	Approved
0.7801	Intermediate Similarity	NPD2313	Discontinued
0.7794	Intermediate Similarity	NPD422	Phase 1
0.7793	Intermediate Similarity	NPD6100	Approved
0.7793	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4908	Phase 1
0.7785	Intermediate Similarity	NPD7390	Discontinued
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7761	Intermediate Similarity	NPD1548	Phase 1
0.7742	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD3926	Phase 2
0.773	Intermediate Similarity	NPD6559	Discontinued
0.773	Intermediate Similarity	NPD7251	Discontinued
0.7724	Intermediate Similarity	NPD7033	Discontinued
0.7698	Intermediate Similarity	NPD2797	Approved
0.7683	Intermediate Similarity	NPD7808	Phase 3
0.7676	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1610	Phase 2
0.7647	Intermediate Similarity	NPD3226	Approved
0.7639	Intermediate Similarity	NPD230	Phase 1
0.7626	Intermediate Similarity	NPD1876	Approved
0.7603	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4308	Phase 3
0.7595	Intermediate Similarity	NPD919	Approved
0.7584	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1164	Approved
0.7571	Intermediate Similarity	NPD1470	Approved
0.7552	Intermediate Similarity	NPD3764	Approved
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7536	Intermediate Similarity	NPD1201	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7519	Intermediate Similarity	NPD1241	Discontinued
0.7517	Intermediate Similarity	NPD1933	Approved
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7482	Intermediate Similarity	NPD1608	Approved
0.7467	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5710	Approved
0.7453	Intermediate Similarity	NPD5711	Approved
0.7452	Intermediate Similarity	NPD1465	Phase 2
0.7447	Intermediate Similarity	NPD3266	Approved
0.7447	Intermediate Similarity	NPD3267	Approved
0.7445	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5406	Approved
0.7432	Intermediate Similarity	NPD5405	Approved
0.7432	Intermediate Similarity	NPD5408	Approved
0.7432	Intermediate Similarity	NPD5404	Approved
0.7431	Intermediate Similarity	NPD1296	Phase 2
0.7431	Intermediate Similarity	NPD411	Approved
0.7429	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6104	Discontinued
0.7405	Intermediate Similarity	NPD74	Approved
0.7405	Intermediate Similarity	NPD9266	Approved
0.7405	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD2296	Approved
0.7397	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD1019	Discontinued
0.7356	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7343	Intermediate Similarity	NPD9494	Approved
0.7341	Intermediate Similarity	NPD4360	Phase 2
0.7341	Intermediate Similarity	NPD4363	Phase 3
0.7338	Intermediate Similarity	NPD3847	Discontinued
0.7329	Intermediate Similarity	NPD4307	Phase 2
0.7328	Intermediate Similarity	NPD9263	Approved
0.7328	Intermediate Similarity	NPD9267	Approved
0.7328	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9264	Approved
0.7325	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD2354	Approved
0.7299	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4361	Phase 2
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5124	Phase 1
0.7279	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD4662	Approved
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD17	Approved
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3142	Approved
0.7211	Intermediate Similarity	NPD1613	Approved
0.7211	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3140	Approved
0.7209	Intermediate Similarity	NPD4287	Approved
0.7194	Intermediate Similarity	NPD1651	Approved
0.719	Intermediate Similarity	NPD3887	Approved
0.7183	Intermediate Similarity	NPD4749	Approved
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.717	Intermediate Similarity	NPD6280	Approved
0.717	Intermediate Similarity	NPD6279	Approved
0.7163	Intermediate Similarity	NPD1535	Discovery
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1283	Approved
0.7122	Intermediate Similarity	NPD1894	Discontinued
0.7115	Intermediate Similarity	NPD5049	Phase 3
0.7113	Intermediate Similarity	NPD9269	Phase 2
0.7107	Intermediate Similarity	NPD5889	Approved
0.7107	Intermediate Similarity	NPD5890	Approved
0.7103	Intermediate Similarity	NPD3018	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