NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	270.225
LogP:	2.761
LogD:	3.201
LogS:	-2.407
# Rotatable Bonds:	4
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.79
Synthetic Accessibility Score:	2.262
Fsp3:	0.2
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:	-4.907
MDCK Permeability:	1.4923675735190045e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	94.5034408569336%
Volume Distribution (VD):	0.86
Pgp-substrate:	3.8179125785827637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	13.996
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.955
Carcinogencity:	0.067
Eye Corrosion:	0.056
Eye Irritation:	0.954
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC121115

Natural Product ID:	NPC121115
*Common Name:**	3,3',5-Trihydroxy-2'-Methoxy-Bibenzyl
IUPAC Name:	5-[2-(3-hydroxy-2-methoxyphenyl)ethyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	FNNQAZPVTHKZOI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-19-15-11(3-2-4-14(15)18)6-5-10-7-12(16)9-13(17)8-10/h2-4,7-9,16-18H,5-6H2,1H3
SMILES:	COc1c(cccc1O)CCc1cc(cc(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474811
PubChem CID:	44156958
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	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
IC50	4
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	1.8	ug.mL-1	PMID[568330]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[568330]
NPT1	Others	Radical scavenging activity		IC50	=	46.7	ug.mL-1	PMID[568330]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[568330]
NPT2	Others	Unspecified		Ratio IC50	=	55.6	n.a.	PMID[568330]

☑ 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 NPC121115 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	449
0.1-0.2	1819
0.2-0.3	5884
0.3-0.4	13428
0.4-0.5	3684
0.5-0.6	4445
0.6-0.7	7799
0.7-0.8	3977
0.8-0.85	659
0.85-0.9	373
0.9-0.95	154
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC293054
0.9667	High Similarity	NPC324112
0.9667	High Similarity	NPC124452
0.9667	High Similarity	NPC82679
0.9667	High Similarity	NPC159968
0.9667	High Similarity	NPC169474
0.9667	High Similarity	NPC236791
0.9667	High Similarity	NPC246620
0.9667	High Similarity	NPC282000
0.9667	High Similarity	NPC74817
0.9667	High Similarity	NPC236760
0.9661	High Similarity	NPC228922
0.9661	High Similarity	NPC95168
0.9661	High Similarity	NPC197757
0.9587	High Similarity	NPC266691
0.9587	High Similarity	NPC154866
0.9583	High Similarity	NPC78974
0.9583	High Similarity	NPC223136
0.9583	High Similarity	NPC214406
0.9583	High Similarity	NPC103823
0.9583	High Similarity	NPC18924
0.9583	High Similarity	NPC28730
0.9583	High Similarity	NPC44748
0.9576	High Similarity	NPC41562
0.9508	High Similarity	NPC212015
0.9504	High Similarity	NPC252131
0.9504	High Similarity	NPC266555
0.95	High Similarity	NPC234400
0.95	High Similarity	NPC17943
0.95	High Similarity	NPC60885
0.95	High Similarity	NPC82483
0.95	High Similarity	NPC57490
0.95	High Similarity	NPC203133
0.95	High Similarity	NPC298757
0.95	High Similarity	NPC475169
0.95	High Similarity	NPC472093
0.95	High Similarity	NPC193544
0.95	High Similarity	NPC233410
0.95	High Similarity	NPC221077
0.95	High Similarity	NPC251855
0.95	High Similarity	NPC105925
0.95	High Similarity	NPC117214
0.95	High Similarity	NPC208950
0.95	High Similarity	NPC116907
0.95	High Similarity	NPC299584
0.95	High Similarity	NPC265483
0.9492	High Similarity	NPC75713
0.9431	High Similarity	NPC126836
0.9431	High Similarity	NPC299221
0.9431	High Similarity	NPC234488
0.9431	High Similarity	NPC51840
0.9431	High Similarity	NPC311680
0.9426	High Similarity	NPC28765
0.9421	High Similarity	NPC223953
0.9355	High Similarity	NPC232275
0.935	High Similarity	NPC10225
0.935	High Similarity	NPC58164
0.9344	High Similarity	NPC127587
0.9333	High Similarity	NPC233526
0.9333	High Similarity	NPC136319
0.9333	High Similarity	NPC282496
0.9322	High Similarity	NPC10932
0.9322	High Similarity	NPC247364
0.9322	High Similarity	NPC61516
0.9322	High Similarity	NPC232084
0.928	High Similarity	NPC6451
0.9268	High Similarity	NPC470213
0.9268	High Similarity	NPC186843
0.9268	High Similarity	NPC98631
0.9268	High Similarity	NPC206615
0.9262	High Similarity	NPC112596
0.9262	High Similarity	NPC76451
0.9256	High Similarity	NPC206487
0.9256	High Similarity	NPC5796
0.925	High Similarity	NPC71579
0.925	High Similarity	NPC473411
0.925	High Similarity	NPC135414
0.925	High Similarity	NPC262253
0.9224	High Similarity	NPC808
0.9206	High Similarity	NPC32778
0.9206	High Similarity	NPC475840
0.92	High Similarity	NPC12275
0.92	High Similarity	NPC45715
0.92	High Similarity	NPC474356
0.9194	High Similarity	NPC170844
0.9194	High Similarity	NPC476968
0.9187	High Similarity	NPC210355
0.9187	High Similarity	NPC216836
0.9174	High Similarity	NPC84086
0.916	High Similarity	NPC474565
0.9145	High Similarity	NPC150624
0.9134	High Similarity	NPC317380
0.9127	High Similarity	NPC86655
0.9127	High Similarity	NPC202762
0.9127	High Similarity	NPC127624
0.912	High Similarity	NPC224157
0.912	High Similarity	NPC192687
0.9098	High Similarity	NPC183446
0.9091	High Similarity	NPC246967
0.9083	High Similarity	NPC166759
0.9076	High Similarity	NPC20674
0.9076	High Similarity	NPC226629
0.9068	High Similarity	NPC69261
0.9068	High Similarity	NPC293619
0.9068	High Similarity	NPC33270
0.9062	High Similarity	NPC200557
0.9062	High Similarity	NPC470356
0.9062	High Similarity	NPC94750
0.9062	High Similarity	NPC474206
0.9062	High Similarity	NPC281521
0.9062	High Similarity	NPC294884
0.9062	High Similarity	NPC201357
0.9062	High Similarity	NPC112246
0.9062	High Similarity	NPC283009
0.9062	High Similarity	NPC121812
0.9062	High Similarity	NPC108198
0.9062	High Similarity	NPC134968
0.9062	High Similarity	NPC261873
0.9062	High Similarity	NPC158142
0.9062	High Similarity	NPC69029
0.9062	High Similarity	NPC255147
0.9062	High Similarity	NPC256262
0.9062	High Similarity	NPC313081
0.9062	High Similarity	NPC112939
0.9062	High Similarity	NPC10314
0.9055	High Similarity	NPC471391
0.9055	High Similarity	NPC471390
0.9055	High Similarity	NPC168059
0.9055	High Similarity	NPC229442
0.9048	High Similarity	NPC15543
0.9048	High Similarity	NPC474017
0.904	High Similarity	NPC469963
0.904	High Similarity	NPC45824
0.904	High Similarity	NPC469951
0.904	High Similarity	NPC158477
0.904	High Similarity	NPC190144
0.9032	High Similarity	NPC242032
0.9032	High Similarity	NPC50368
0.9032	High Similarity	NPC470699
0.9008	High Similarity	NPC49341
0.8992	High Similarity	NPC472334
0.8992	High Similarity	NPC227503
0.8992	High Similarity	NPC202846
0.8992	High Similarity	NPC16435
0.8992	High Similarity	NPC162659
0.8992	High Similarity	NPC474639
0.8992	High Similarity	NPC476639
0.8992	High Similarity	NPC230734
0.8992	High Similarity	NPC143139
0.8992	High Similarity	NPC306441
0.8992	High Similarity	NPC472336
0.8992	High Similarity	NPC190514
0.8992	High Similarity	NPC114155
0.8992	High Similarity	NPC270456
0.8992	High Similarity	NPC265433
0.8992	High Similarity	NPC300846
0.8992	High Similarity	NPC248727
0.8992	High Similarity	NPC470626
0.8984	High Similarity	NPC188378
0.8984	High Similarity	NPC555
0.8984	High Similarity	NPC103967
0.8984	High Similarity	NPC56764
0.8984	High Similarity	NPC160697
0.8984	High Similarity	NPC469659
0.8984	High Similarity	NPC209199
0.8984	High Similarity	NPC125649
0.8984	High Similarity	NPC7515
0.8984	High Similarity	NPC276026
0.8984	High Similarity	NPC289258
0.8984	High Similarity	NPC206737
0.8976	High Similarity	NPC201587
0.8976	High Similarity	NPC253105
0.8974	High Similarity	NPC276737
0.8974	High Similarity	NPC22610
0.8968	High Similarity	NPC214860
0.8968	High Similarity	NPC91291
0.8968	High Similarity	NPC220935
0.8968	High Similarity	NPC472338
0.8968	High Similarity	NPC184814
0.896	High Similarity	NPC46274
0.896	High Similarity	NPC63179
0.896	High Similarity	NPC226331
0.8952	High Similarity	NPC181361
0.8952	High Similarity	NPC245060
0.8943	High Similarity	NPC122792
0.8943	High Similarity	NPC228972
0.8934	High Similarity	NPC474864
0.8923	High Similarity	NPC242715
0.8923	High Similarity	NPC276490
0.8923	High Similarity	NPC25111
0.8923	High Similarity	NPC107551
0.8923	High Similarity	NPC73535
0.8923	High Similarity	NPC272157
0.8923	High Similarity	NPC90615
0.8923	High Similarity	NPC474282
0.8923	High Similarity	NPC211549
0.8923	High Similarity	NPC326797
0.8923	High Similarity	NPC201145
0.8923	High Similarity	NPC103976
0.8923	High Similarity	NPC102904

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 NPC121115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	977
0.2-0.3	1772
0.3-0.4	2752
0.4-0.5	1606
0.5-0.6	949
0.6-0.7	574
0.7-0.8	110
0.8-0.85	7
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD3027	Phase 3
0.896	High Similarity	NPD1529	Clinical (unspecified phase)
0.888	High Similarity	NPD1530	Clinical (unspecified phase)
0.8828	High Similarity	NPD1613	Approved
0.8828	High Similarity	NPD1612	Clinical (unspecified phase)
0.8559	High Similarity	NPD228	Approved
0.8438	Intermediate Similarity	NPD3018	Phase 2
0.8268	Intermediate Similarity	NPD2982	Phase 2
0.8268	Intermediate Similarity	NPD2983	Phase 2
0.8264	Intermediate Similarity	NPD5283	Phase 1
0.8189	Intermediate Similarity	NPD2981	Phase 2
0.8125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1610	Phase 2
0.8092	Intermediate Similarity	NPD4908	Phase 1
0.808	Intermediate Similarity	NPD1548	Phase 1
0.803	Intermediate Similarity	NPD4625	Phase 3
0.7984	Intermediate Similarity	NPD4749	Approved
0.797	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD3022	Approved
0.7934	Intermediate Similarity	NPD3021	Approved
0.7877	Intermediate Similarity	NPD1934	Approved
0.7823	Intermediate Similarity	NPD2801	Approved
0.7803	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD940	Approved
0.7797	Intermediate Similarity	NPD846	Approved
0.7787	Intermediate Similarity	NPD4750	Phase 3
0.777	Intermediate Similarity	NPD3540	Phase 1
0.7721	Intermediate Similarity	NPD1558	Phase 1
0.7718	Intermediate Similarity	NPD3882	Suspended
0.7712	Intermediate Similarity	NPD1242	Phase 1
0.771	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3539	Phase 1
0.7698	Intermediate Similarity	NPD6671	Approved
0.7692	Intermediate Similarity	NPD1511	Approved
0.7623	Intermediate Similarity	NPD290	Approved
0.7603	Intermediate Similarity	NPD1653	Approved
0.7591	Intermediate Similarity	NPD4060	Phase 1
0.7591	Intermediate Similarity	NPD3620	Phase 2
0.7591	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1512	Approved
0.7586	Intermediate Similarity	NPD9296	Approved
0.7578	Intermediate Similarity	NPD5536	Phase 2
0.7557	Intermediate Similarity	NPD1091	Approved
0.7557	Intermediate Similarity	NPD422	Phase 1
0.7535	Intermediate Similarity	NPD5177	Phase 3
0.7519	Intermediate Similarity	NPD2922	Phase 1
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2861	Phase 2
0.7464	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD943	Approved
0.7462	Intermediate Similarity	NPD1357	Approved
0.7448	Intermediate Similarity	NPD4357	Discontinued
0.7445	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2684	Approved
0.7413	Intermediate Similarity	NPD3060	Approved
0.74	Intermediate Similarity	NPD37	Approved
0.7398	Intermediate Similarity	NPD968	Approved
0.7391	Intermediate Similarity	NPD2674	Phase 3
0.7379	Intermediate Similarity	NPD7124	Phase 2
0.7376	Intermediate Similarity	NPD1510	Phase 2
0.7373	Intermediate Similarity	NPD844	Approved
0.7357	Intermediate Similarity	NPD1607	Approved
0.7355	Intermediate Similarity	NPD6232	Discontinued
0.7324	Intermediate Similarity	NPD6099	Approved
0.7324	Intermediate Similarity	NPD6100	Approved
0.7323	Intermediate Similarity	NPD7843	Approved
0.732	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4005	Discontinued
0.7303	Intermediate Similarity	NPD3817	Phase 2
0.7296	Intermediate Similarity	NPD7074	Phase 3
0.7293	Intermediate Similarity	NPD3705	Approved
0.729	Intermediate Similarity	NPD7199	Phase 2
0.7287	Intermediate Similarity	NPD7157	Approved
0.7287	Intermediate Similarity	NPD709	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7267	Intermediate Similarity	NPD4675	Approved
0.7267	Intermediate Similarity	NPD4678	Approved
0.7255	Intermediate Similarity	NPD4966	Approved
0.7255	Intermediate Similarity	NPD4965	Approved
0.7255	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD3892	Phase 2
0.7239	Intermediate Similarity	NPD2233	Approved
0.7239	Intermediate Similarity	NPD2232	Approved
0.7239	Intermediate Similarity	NPD2230	Approved
0.7237	Intermediate Similarity	NPD1465	Phase 2
0.7233	Intermediate Similarity	NPD7054	Approved
0.7227	Intermediate Similarity	NPD2860	Approved
0.7227	Intermediate Similarity	NPD2859	Approved
0.7226	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD7473	Discontinued
0.7214	Intermediate Similarity	NPD2238	Phase 2
0.7213	Intermediate Similarity	NPD291	Approved
0.7211	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4055	Discovery
0.7203	Intermediate Similarity	NPD2935	Discontinued
0.7197	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5110	Phase 2
0.7194	Intermediate Similarity	NPD3145	Approved
0.7194	Intermediate Similarity	NPD5111	Phase 2
0.7194	Intermediate Similarity	NPD3144	Approved
0.7194	Intermediate Similarity	NPD5109	Approved
0.7192	Intermediate Similarity	NPD2219	Phase 1
0.719	Intermediate Similarity	NPD3020	Approved
0.7188	Intermediate Similarity	NPD7472	Approved
0.7183	Intermediate Similarity	NPD6111	Discontinued
0.7181	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7228	Approved
0.7167	Intermediate Similarity	NPD288	Approved
0.7163	Intermediate Similarity	NPD230	Phase 1
0.7163	Intermediate Similarity	NPD447	Suspended
0.7162	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7447	Phase 1
0.7153	Intermediate Similarity	NPD5762	Approved
0.7153	Intermediate Similarity	NPD5763	Approved
0.7153	Intermediate Similarity	NPD7266	Discontinued
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2934	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD2933	Approved
0.7132	Intermediate Similarity	NPD8651	Approved
0.7131	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7095	Approved
0.7114	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1549	Phase 2
0.7095	Intermediate Similarity	NPD7212	Phase 2
0.7095	Intermediate Similarity	NPD7213	Phase 3
0.709	Intermediate Similarity	NPD3496	Discontinued
0.7087	Intermediate Similarity	NPD5451	Approved
0.7083	Intermediate Similarity	NPD1551	Phase 2
0.708	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD8053	Approved
0.7073	Intermediate Similarity	NPD8054	Approved
0.7071	Intermediate Similarity	NPD6798	Discontinued
0.7069	Intermediate Similarity	NPD9094	Approved
0.7063	Intermediate Similarity	NPD4538	Approved
0.7063	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4536	Approved
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.7055	Intermediate Similarity	NPD4236	Phase 3
0.7055	Intermediate Similarity	NPD4237	Approved
0.705	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7015	Intermediate Similarity	NPD5846	Approved
0.7015	Intermediate Similarity	NPD1778	Approved
0.7015	Intermediate Similarity	NPD6516	Phase 2
0.7014	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2978	Approved
0.7013	Intermediate Similarity	NPD2977	Approved
0.7007	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD6696	Suspended
0.6994	Remote Similarity	NPD7251	Discontinued
0.6993	Remote Similarity	NPD4097	Suspended
0.6993	Remote Similarity	NPD5090	Approved
0.6993	Remote Similarity	NPD5089	Approved
0.6987	Remote Similarity	NPD7075	Discontinued
0.698	Remote Similarity	NPD6799	Approved
0.698	Remote Similarity	NPD1774	Approved
0.6974	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6032	Approved
0.6963	Remote Similarity	NPD3847	Discontinued
0.6959	Remote Similarity	NPD2677	Approved
0.6951	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7808	Phase 3
0.695	Remote Similarity	NPD5718	Phase 2
0.695	Remote Similarity	NPD3268	Approved
0.6944	Remote Similarity	NPD6895	Approved
0.6944	Remote Similarity	NPD6896	Approved
0.694	Remote Similarity	NPD1651	Approved
0.6939	Remote Similarity	NPD4162	Approved
0.6934	Remote Similarity	NPD6582	Phase 2
0.6934	Remote Similarity	NPD6583	Phase 3
0.6934	Remote Similarity	NPD1669	Approved
0.6933	Remote Similarity	NPD4123	Phase 3
0.6933	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1424	Approved
0.6929	Remote Similarity	NPD596	Approved
0.6929	Remote Similarity	NPD600	Approved
0.6923	Remote Similarity	NPD7635	Approved
0.6923	Remote Similarity	NPD5123	Clinical (unspecified phase)

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