NPASS Compound

Structure

CID233526 OpenBabel06191716032D 21 22 0 0 0 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	2.905
LogD:	3.272
LogS:	-3.736
# Rotatable Bonds:	6
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.886
Synthetic Accessibility Score:	1.783
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.756
MDCK Permeability:	1.676239844528027e-05
Pgp-inhibitor:	0.084
Pgp-substrate:	0.804
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	93.1288833618164%
Volume Distribution (VD):	0.897
Pgp-substrate:	2.879336357116699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.694

ADMET: Excretion

Clearance (CL):	11.721
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.352
Skin Sensitization:	0.942
Carcinogencity:	0.113
Eye Corrosion:	0.064
Eye Irritation:	0.556
Respiratory Toxicity:	0.131

Download Data

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

Natural Product: NPC233526

Natural Product ID:	NPC233526
*Common Name:**	4-[2-(3,4,5-Trimethoxyphenyl)Ethyl]Phenol
IUPAC Name:	4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol
Synonyms:
Standard InCHIKey:	WYMYMRJMKNLHSF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-19-15-10-13(11-16(20-2)17(15)21-3)5-4-12-6-8-14(18)9-7-12/h6-11,18H,4-5H2,1-3H3
SMILES:	COc1cc(CCc2ccc(cc2)O)cc(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL313688
PubChem CID:	3084744
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
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19228038]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404149]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3598594]
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668557]
NPO203	Dendrobium amoenum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO203	Dendrobium amoenum	Species	Orchidaceae	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
ED50	6
IC50	2
Others	4

Activity Type	# Activity
Cell Line	8
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	25.0	uM	PMID[506753]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	25.0	uM	PMID[506753]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	25.0	uM	PMID[506753]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	>	25.0	uM	PMID[506753]
NPT3958	Cell Line	MLM		ED50	>	25.0	uM	PMID[506753]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	25.0	%	PMID[506754]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	50000.0	nM	PMID[506754]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.25	Ug/ml	PMID[506754]
NPT2	Others	Unspecified		Inhibition	=	43.0	%	PMID[506754]
NPT2	Others	Unspecified		Inhibition	=	77.0	%	PMID[506754]
NPT2	Others	Unspecified		Inhibition	=	89.0	%	PMID[506754]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[506754]

☑ 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 NPC233526 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	369
0.1-0.2	1733
0.2-0.3	5278
0.3-0.4	13601
0.4-0.5	3858
0.5-0.6	4340
0.6-0.7	7372
0.7-0.8	4574
0.8-0.85	842
0.85-0.9	489
0.9-0.95	193
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282496
0.9831	High Similarity	NPC57490
0.9831	High Similarity	NPC251855
0.9831	High Similarity	NPC472093
0.9831	High Similarity	NPC193544
0.9831	High Similarity	NPC298757
0.9831	High Similarity	NPC475169
0.9831	High Similarity	NPC116907
0.9831	High Similarity	NPC105925
0.9831	High Similarity	NPC117214
0.9831	High Similarity	NPC208950
0.9831	High Similarity	NPC221077
0.9831	High Similarity	NPC17943
0.9831	High Similarity	NPC203133
0.9831	High Similarity	NPC233410
0.9741	High Similarity	NPC166759
0.9667	High Similarity	NPC293054
0.9667	High Similarity	NPC324112
0.9667	High Similarity	NPC74817
0.9667	High Similarity	NPC82679
0.9667	High Similarity	NPC159968
0.9667	High Similarity	NPC236791
0.9667	High Similarity	NPC246620
0.9667	High Similarity	NPC169474
0.9667	High Similarity	NPC282000
0.9667	High Similarity	NPC127587
0.9667	High Similarity	NPC124452
0.9661	High Similarity	NPC136319
0.9661	High Similarity	NPC228922
0.9661	High Similarity	NPC197757
0.9655	High Similarity	NPC474565
0.9587	High Similarity	NPC206615
0.9587	High Similarity	NPC98631
0.9587	High Similarity	NPC470213
0.9587	High Similarity	NPC186843
0.9583	High Similarity	NPC78974
0.9583	High Similarity	NPC223136
0.9583	High Similarity	NPC214406
0.9583	High Similarity	NPC223953
0.9583	High Similarity	NPC103823
0.9583	High Similarity	NPC18924
0.9583	High Similarity	NPC76451
0.9583	High Similarity	NPC28730
0.9583	High Similarity	NPC44748
0.9576	High Similarity	NPC41562
0.9576	High Similarity	NPC473411
0.9576	High Similarity	NPC262253
0.9576	High Similarity	NPC71579
0.9569	High Similarity	NPC475961
0.9569	High Similarity	NPC254625
0.9508	High Similarity	NPC476968
0.9508	High Similarity	NPC170844
0.9504	High Similarity	NPC210355
0.95	High Similarity	NPC60885
0.95	High Similarity	NPC82483
0.95	High Similarity	NPC234400
0.95	High Similarity	NPC299584
0.95	High Similarity	NPC265483
0.9492	High Similarity	NPC75713
0.9431	High Similarity	NPC63574
0.9431	High Similarity	NPC299221
0.9431	High Similarity	NPC126836
0.9431	High Similarity	NPC234488
0.9431	High Similarity	NPC51840
0.9431	High Similarity	NPC224157
0.9431	High Similarity	NPC192687
0.9431	High Similarity	NPC311680
0.9426	High Similarity	NPC28765
0.9426	High Similarity	NPC154866
0.9417	High Similarity	NPC5796
0.9417	High Similarity	NPC206487
0.9397	High Similarity	NPC474933
0.9355	High Similarity	NPC474017
0.935	High Similarity	NPC10225
0.935	High Similarity	NPC190144
0.935	High Similarity	NPC212015
0.935	High Similarity	NPC58164
0.935	High Similarity	NPC469963
0.935	High Similarity	NPC469951
0.9344	High Similarity	NPC470699
0.9344	High Similarity	NPC266555
0.9344	High Similarity	NPC252131
0.9344	High Similarity	NPC236760
0.9344	High Similarity	NPC242032
0.9333	High Similarity	NPC95168
0.9333	High Similarity	NPC121115
0.9333	High Similarity	NPC84086
0.9328	High Similarity	NPC477886
0.9322	High Similarity	NPC232084
0.9322	High Similarity	NPC10932
0.9322	High Similarity	NPC247364
0.9322	High Similarity	NPC61516
0.931	High Similarity	NPC123948
0.931	High Similarity	NPC141090
0.928	High Similarity	NPC6451
0.928	High Similarity	NPC201587
0.928	High Similarity	NPC253105
0.9274	High Similarity	NPC472338
0.9268	High Similarity	NPC266691
0.9262	High Similarity	NPC181361
0.9256	High Similarity	NPC228972
0.9256	High Similarity	NPC122792
0.9244	High Similarity	NPC472596
0.9237	High Similarity	NPC20674
0.9237	High Similarity	NPC15805
0.9237	High Similarity	NPC226629
0.9231	High Similarity	NPC219070
0.9231	High Similarity	NPC15860
0.9231	High Similarity	NPC127894
0.9231	High Similarity	NPC470759
0.9224	High Similarity	NPC53906
0.9206	High Similarity	NPC32778
0.9206	High Similarity	NPC158331
0.9206	High Similarity	NPC475840
0.92	High Similarity	NPC12275
0.92	High Similarity	NPC45715
0.92	High Similarity	NPC232275
0.92	High Similarity	NPC474356
0.92	High Similarity	NPC472597
0.92	High Similarity	NPC470096
0.92	High Similarity	NPC470095
0.9194	High Similarity	NPC470258
0.9194	High Similarity	NPC285339
0.9194	High Similarity	NPC222004
0.9194	High Similarity	NPC273295
0.9194	High Similarity	NPC3439
0.9194	High Similarity	NPC210623
0.9194	High Similarity	NPC218856
0.9194	High Similarity	NPC190629
0.9194	High Similarity	NPC202582
0.9194	High Similarity	NPC226788
0.9187	High Similarity	NPC474119
0.9174	High Similarity	NPC471693
0.9167	High Similarity	NPC49341
0.9167	High Similarity	NPC476633
0.9153	High Similarity	NPC470626
0.9153	High Similarity	NPC63083
0.9145	High Similarity	NPC114064
0.9138	High Similarity	NPC22610
0.9138	High Similarity	NPC180508
0.9138	High Similarity	NPC276737
0.9138	High Similarity	NPC228287
0.9134	High Similarity	NPC317380
0.9134	High Similarity	NPC287745
0.9127	High Similarity	NPC175067
0.9127	High Similarity	NPC14224
0.9127	High Similarity	NPC86655
0.9127	High Similarity	NPC16208
0.9127	High Similarity	NPC204215
0.9127	High Similarity	NPC161958
0.9127	High Similarity	NPC160991
0.9127	High Similarity	NPC202762
0.9127	High Similarity	NPC470752
0.9127	High Similarity	NPC35932
0.9127	High Similarity	NPC127624
0.9127	High Similarity	NPC7903
0.9127	High Similarity	NPC184447
0.912	High Similarity	NPC184814
0.9091	High Similarity	NPC261661
0.9068	High Similarity	NPC69261
0.9068	High Similarity	NPC293619
0.9068	High Similarity	NPC195466
0.9068	High Similarity	NPC33270
0.9068	High Similarity	NPC259638
0.9062	High Similarity	NPC99572
0.9062	High Similarity	NPC470356
0.9062	High Similarity	NPC94750
0.9062	High Similarity	NPC126409
0.9062	High Similarity	NPC195022
0.9062	High Similarity	NPC474206
0.9062	High Similarity	NPC200557
0.9062	High Similarity	NPC112246
0.9062	High Similarity	NPC108198
0.9062	High Similarity	NPC158142
0.9062	High Similarity	NPC111655
0.9062	High Similarity	NPC294884
0.9062	High Similarity	NPC69029
0.9062	High Similarity	NPC256262
0.9062	High Similarity	NPC313081
0.9062	High Similarity	NPC121812
0.9062	High Similarity	NPC112939
0.9062	High Similarity	NPC10314
0.9062	High Similarity	NPC61946
0.9055	High Similarity	NPC471391
0.9055	High Similarity	NPC471390
0.9055	High Similarity	NPC168059
0.9055	High Similarity	NPC229442
0.9052	High Similarity	NPC204120
0.9048	High Similarity	NPC469625
0.9048	High Similarity	NPC15543
0.9048	High Similarity	NPC309787
0.9048	High Similarity	NPC30043
0.9048	High Similarity	NPC469613
0.904	High Similarity	NPC470633
0.904	High Similarity	NPC228769
0.9032	High Similarity	NPC165045
0.9032	High Similarity	NPC5428
0.9032	High Similarity	NPC118533
0.9024	High Similarity	NPC148627
0.9016	High Similarity	NPC220598

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 NPC233526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	992
0.2-0.3	1678
0.3-0.4	2741
0.4-0.5	1672
0.5-0.6	931
0.6-0.7	643
0.7-0.8	141
0.8-0.85	10
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9508	High Similarity	NPD3027	Phase 3
0.8862	High Similarity	NPD2983	Phase 2
0.8862	High Similarity	NPD2982	Phase 2
0.881	High Similarity	NPD1529	Clinical (unspecified phase)
0.878	High Similarity	NPD2981	Phase 2
0.873	High Similarity	NPD1530	Clinical (unspecified phase)
0.873	High Similarity	NPD3018	Phase 2
0.8729	High Similarity	NPD5283	Phase 1
0.8682	High Similarity	NPD1613	Approved
0.8682	High Similarity	NPD1612	Clinical (unspecified phase)
0.8559	High Similarity	NPD228	Approved
0.8372	Intermediate Similarity	NPD4908	Phase 1
0.8268	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD1610	Phase 2
0.8244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD1548	Phase 1
0.8083	Intermediate Similarity	NPD3022	Approved
0.8083	Intermediate Similarity	NPD3021	Approved
0.803	Intermediate Similarity	NPD4625	Phase 3
0.8029	Intermediate Similarity	NPD3540	Phase 1
0.8017	Intermediate Similarity	NPD1242	Phase 1
0.8	Intermediate Similarity	NPD5536	Phase 2
0.7984	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD3539	Phase 1
0.7943	Intermediate Similarity	NPD4357	Discontinued
0.7929	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1934	Approved
0.7872	Intermediate Similarity	NPD7124	Phase 2
0.7852	Intermediate Similarity	NPD1558	Phase 1
0.7846	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3705	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
0.7793	Intermediate Similarity	NPD4005	Discontinued
0.7786	Intermediate Similarity	NPD3060	Approved
0.7755	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD2861	Phase 2
0.774	Intermediate Similarity	NPD4675	Approved
0.774	Intermediate Similarity	NPD4678	Approved
0.7734	Intermediate Similarity	NPD1357	Approved
0.7721	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD3620	Phase 2
0.7718	Intermediate Similarity	NPD3882	Suspended
0.7705	Intermediate Similarity	NPD2684	Approved
0.7704	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD422	Phase 1
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD6111	Discontinued
0.7676	Intermediate Similarity	NPD2219	Phase 1
0.7672	Intermediate Similarity	NPD2860	Approved
0.7672	Intermediate Similarity	NPD2859	Approved
0.7655	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4750	Phase 3
0.7627	Intermediate Similarity	NPD3020	Approved
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD7843	Approved
0.76	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD4967	Phase 2
0.76	Intermediate Similarity	NPD4965	Approved
0.7591	Intermediate Similarity	NPD1240	Approved
0.7591	Intermediate Similarity	NPD4060	Phase 1
0.7586	Intermediate Similarity	NPD2934	Approved
0.7586	Intermediate Similarity	NPD2933	Approved
0.7582	Intermediate Similarity	NPD6232	Discontinued
0.7574	Intermediate Similarity	NPD5111	Phase 2
0.7574	Intermediate Similarity	NPD5110	Phase 2
0.7574	Intermediate Similarity	NPD5109	Approved
0.7569	Intermediate Similarity	NPD1511	Approved
0.7559	Intermediate Similarity	NPD6671	Approved
0.7559	Intermediate Similarity	NPD7157	Approved
0.755	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6584	Phase 3
0.7535	Intermediate Similarity	NPD4236	Phase 3
0.7535	Intermediate Similarity	NPD4237	Approved
0.7518	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD1510	Phase 2
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)
0.7483	Intermediate Similarity	NPD1653	Approved
0.7482	Intermediate Similarity	NPD1607	Approved
0.7466	Intermediate Similarity	NPD1512	Approved
0.7436	Intermediate Similarity	NPD7473	Discontinued
0.7434	Intermediate Similarity	NPD4055	Discovery
0.7432	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3817	Phase 2
0.7413	Intermediate Similarity	NPD5177	Phase 3
0.7403	Intermediate Similarity	NPD7199	Phase 2
0.7398	Intermediate Similarity	NPD968	Approved
0.7397	Intermediate Similarity	NPD4123	Phase 3
0.7397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7447	Phase 1
0.7394	Intermediate Similarity	NPD7266	Discontinued
0.7388	Intermediate Similarity	NPD2922	Phase 1
0.7372	Intermediate Similarity	NPD7095	Approved
0.7348	Intermediate Similarity	NPD3847	Discontinued
0.7347	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2238	Phase 2
0.7329	Intermediate Similarity	NPD7213	Phase 3
0.7329	Intermediate Similarity	NPD7212	Phase 2
0.7324	Intermediate Similarity	NPD6099	Approved
0.7324	Intermediate Similarity	NPD2935	Discontinued
0.7324	Intermediate Similarity	NPD6100	Approved
0.7323	Intermediate Similarity	NPD5535	Approved
0.7319	Intermediate Similarity	NPD3144	Approved
0.7319	Intermediate Similarity	NPD3145	Approved
0.7319	Intermediate Similarity	NPD5718	Phase 2
0.7315	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6583	Phase 3
0.7313	Intermediate Similarity	NPD6582	Phase 2
0.7308	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4538	Approved
0.7305	Intermediate Similarity	NPD6895	Approved
0.7305	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4536	Approved
0.7305	Intermediate Similarity	NPD6896	Approved
0.7296	Intermediate Similarity	NPD7074	Phase 3
0.7293	Intermediate Similarity	NPD1091	Approved
0.7292	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD9296	Approved
0.7286	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD2668	Approved
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD1375	Discontinued
0.7273	Intermediate Similarity	NPD2667	Approved
0.7273	Intermediate Similarity	NPD6516	Phase 2
0.7273	Intermediate Similarity	NPD5846	Approved
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.7259	Intermediate Similarity	NPD8651	Approved
0.7241	Intermediate Similarity	NPD6331	Phase 2
0.7241	Intermediate Similarity	NPD4110	Phase 3
0.7241	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3892	Phase 2
0.7241	Intermediate Similarity	NPD3750	Approved
0.7239	Intermediate Similarity	NPD2232	Approved
0.7239	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD2233	Approved
0.7239	Intermediate Similarity	NPD2230	Approved
0.7233	Intermediate Similarity	NPD5844	Phase 1
0.7233	Intermediate Similarity	NPD7054	Approved
0.7226	Intermediate Similarity	NPD9494	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD5089	Approved
0.7219	Intermediate Similarity	NPD5090	Approved
0.7214	Intermediate Similarity	NPD943	Approved
0.7211	Intermediate Similarity	NPD5297	Approved
0.72	Intermediate Similarity	NPD290	Approved
0.7197	Intermediate Similarity	NPD1651	Approved
0.7192	Intermediate Similarity	NPD5241	Discontinued
0.7188	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD1669	Approved
0.7172	Intermediate Similarity	NPD6674	Discontinued
0.7172	Intermediate Similarity	NPD4162	Approved
0.7163	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5124	Phase 1
0.7163	Intermediate Similarity	NPD3657	Discovery
0.7153	Intermediate Similarity	NPD4624	Approved
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6788	Approved
0.7143	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7132	Intermediate Similarity	NPD1283	Approved
0.7124	Intermediate Similarity	NPD2977	Approved
0.7124	Intermediate Similarity	NPD1465	Phase 2
0.7124	Intermediate Similarity	NPD2978	Approved
0.7124	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4628	Phase 3
0.7123	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5494	Approved
0.7113	Intermediate Similarity	NPD4097	Suspended
0.7103	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD844	Approved
0.7083	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD2161	Phase 2
0.7075	Intermediate Similarity	NPD6190	Approved
0.7073	Intermediate Similarity	NPD8053	Approved
0.7073	Intermediate Similarity	NPD8054	Approved
0.7073	Intermediate Similarity	NPD291	Approved
0.7071	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD1358	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