NPASS Compound

Structure

NPC470626 OpenBabel07101719512D 21 22 0 0 0 0 0 0 0 0999 V2000 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -2.5981 1.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 3.0000 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 -3.4641 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 -4.3301 3.5000 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 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 2 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 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:	2.935
LogD:	3.372
LogS:	-3.866
# 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:	1.747
Fsp3:	0.294
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:	-4.819
MDCK Permeability:	1.901367613754701e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.92
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.2

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	96.28074645996094%
Volume Distribution (VD):	0.871
Pgp-substrate:	1.7205241918563843%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.724
CYP2D6-substrate:	0.942
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	12.521
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.365
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.503
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.927
Carcinogencity:	0.193
Eye Corrosion:	0.039
Eye Irritation:	0.452
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC470626

Natural Product ID:	NPC470626
*Common Name:**	5-[2-(3,4-Dimethoxyphenyl)Ethyl]-2-Methoxyphenol
IUPAC Name:	5-[2-(3,4-dimethoxyphenyl)ethyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	UPOANTHMCQBWOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-19-15-8-6-12(10-14(15)18)4-5-13-7-9-16(20-2)17(11-13)21-3/h6-11,18H,4-5H2,1-3H3
SMILES:	COC1=C(C=C(C=C1)CCC2=CC(=C(C=C2)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2093988
PubChem CID:	152354
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]

☑ 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	7
Others	5

Activity Type	# Activity
Cell Line	7
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	3000.0	nM	PMID[486686]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	25.0	%	PMID[486686]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4790.0	nM	PMID[486687]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4050.0	nM	PMID[486687]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	81.0	nM	PMID[486687]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	>	25000.0	nM	PMID[486687]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5260.0	nM	PMID[486687]
NPT2	Others	Unspecified		Inhibition	=	7.0	%	PMID[486686]
NPT2	Others	Unspecified		Inhibition	=	19.0	%	PMID[486686]
NPT2	Others	Unspecified		Inhibition	=	71.0	%	PMID[486686]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[486686]
NPT617	Organism	Danio rerio	Danio rerio	MED	=	40.0	uM	PMID[486687]

☑ 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 NPC470626 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	312
0.1-0.2	1750
0.2-0.3	5165
0.3-0.4	13672
0.4-0.5	4014
0.5-0.6	5448
0.6-0.7	8014
0.7-0.8	3205
0.8-0.85	632
0.85-0.9	342
0.9-0.95	117
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC293619
0.9821	High Similarity	NPC95614
0.9821	High Similarity	NPC165133
0.9821	High Similarity	NPC56214
0.9821	High Similarity	NPC117780
0.9821	High Similarity	NPC227217
0.9821	High Similarity	NPC242885
0.9821	High Similarity	NPC232316
0.9735	High Similarity	NPC207613
0.9732	High Similarity	NPC310338
0.9732	High Similarity	NPC281298
0.9649	High Similarity	NPC343720
0.9649	High Similarity	NPC184651
0.9649	High Similarity	NPC324571
0.9649	High Similarity	NPC470212
0.9649	High Similarity	NPC113865
0.9649	High Similarity	NPC160380
0.9649	High Similarity	NPC54872
0.9649	High Similarity	NPC38996
0.9649	High Similarity	NPC312675
0.9649	High Similarity	NPC473853
0.9649	High Similarity	NPC262156
0.9565	High Similarity	NPC85488
0.9483	High Similarity	NPC471693
0.9483	High Similarity	NPC317769
0.9483	High Similarity	NPC280704
0.9483	High Similarity	NPC31344
0.9386	High Similarity	NPC311595
0.9386	High Similarity	NPC24474
0.9381	High Similarity	NPC164386
0.9381	High Similarity	NPC86947
0.9364	High Similarity	NPC173746
0.9364	High Similarity	NPC8547
0.9364	High Similarity	NPC156840
0.9364	High Similarity	NPC257124
0.9322	High Similarity	NPC251855
0.9322	High Similarity	NPC9067
0.9322	High Similarity	NPC266705
0.9322	High Similarity	NPC53305
0.9322	High Similarity	NPC472093
0.9322	High Similarity	NPC117214
0.9322	High Similarity	NPC208950
0.9322	High Similarity	NPC29008
0.9322	High Similarity	NPC475169
0.9322	High Similarity	NPC57490
0.9322	High Similarity	NPC193544
0.9322	High Similarity	NPC233410
0.9322	High Similarity	NPC203133
0.9322	High Similarity	NPC221077
0.9322	High Similarity	NPC228771
0.9322	High Similarity	NPC257589
0.9322	High Similarity	NPC116907
0.9322	High Similarity	NPC17943
0.9322	High Similarity	NPC298757
0.9322	High Similarity	NPC148627
0.9316	High Similarity	NPC197757
0.9316	High Similarity	NPC228922
0.931	High Similarity	NPC127389
0.931	High Similarity	NPC290451
0.9298	High Similarity	NPC474040
0.9298	High Similarity	NPC474214
0.9244	High Similarity	NPC127937
0.9244	High Similarity	NPC92207
0.9244	High Similarity	NPC304630
0.9244	High Similarity	NPC274356
0.9244	High Similarity	NPC17837
0.9231	High Similarity	NPC41562
0.9224	High Similarity	NPC14007
0.9224	High Similarity	NPC60962
0.9224	High Similarity	NPC189844
0.9224	High Similarity	NPC224814
0.9224	High Similarity	NPC109083
0.9224	High Similarity	NPC269843
0.9217	High Similarity	NPC474320
0.9196	High Similarity	NPC165106
0.9182	High Similarity	NPC246358
0.9182	High Similarity	NPC233731
0.9182	High Similarity	NPC7097
0.9182	High Similarity	NPC36108
0.9167	High Similarity	NPC293054
0.9167	High Similarity	NPC118533
0.9167	High Similarity	NPC82679
0.9167	High Similarity	NPC21563
0.9167	High Similarity	NPC324112
0.9167	High Similarity	NPC106511
0.9167	High Similarity	NPC246620
0.9167	High Similarity	NPC282000
0.9167	High Similarity	NPC124452
0.9167	High Similarity	NPC169474
0.9167	High Similarity	NPC74817
0.9167	High Similarity	NPC159968
0.9167	High Similarity	NPC5428
0.9167	High Similarity	NPC127587
0.9167	High Similarity	NPC165045
0.9167	High Similarity	NPC236791
0.916	High Similarity	NPC194519
0.9153	High Similarity	NPC282496
0.9153	High Similarity	NPC136319
0.9153	High Similarity	NPC233526
0.9091	High Similarity	NPC474178
0.9091	High Similarity	NPC45774
0.9091	High Similarity	NPC11258
0.9091	High Similarity	NPC128208
0.9091	High Similarity	NPC470213
0.9091	High Similarity	NPC252307
0.9091	High Similarity	NPC307050
0.9091	High Similarity	NPC186843
0.9091	High Similarity	NPC98631
0.9091	High Similarity	NPC245826
0.9091	High Similarity	NPC282703
0.9091	High Similarity	NPC184733
0.9091	High Similarity	NPC21867
0.9091	High Similarity	NPC75440
0.9091	High Similarity	NPC277458
0.9091	High Similarity	NPC226661
0.9091	High Similarity	NPC206615
0.9091	High Similarity	NPC129570
0.9083	High Similarity	NPC120225
0.9083	High Similarity	NPC214406
0.9083	High Similarity	NPC303680
0.9083	High Similarity	NPC44748
0.9083	High Similarity	NPC18924
0.9083	High Similarity	NPC28730
0.9083	High Similarity	NPC76451
0.9083	High Similarity	NPC191037
0.9083	High Similarity	NPC178284
0.9083	High Similarity	NPC58607
0.9083	High Similarity	NPC78974
0.9083	High Similarity	NPC223136
0.9083	High Similarity	NPC84076
0.9083	High Similarity	NPC90128
0.9083	High Similarity	NPC213552
0.9083	High Similarity	NPC103823
0.9076	High Similarity	NPC114901
0.9076	High Similarity	NPC293701
0.9076	High Similarity	NPC48990
0.9068	High Similarity	NPC30462
0.9068	High Similarity	NPC473411
0.9068	High Similarity	NPC262253
0.9068	High Similarity	NPC71579
0.9035	High Similarity	NPC475815
0.9035	High Similarity	NPC47194
0.9035	High Similarity	NPC473264
0.9018	High Similarity	NPC139617
0.9018	High Similarity	NPC78918
0.9018	High Similarity	NPC195873
0.9016	High Similarity	NPC212015
0.9016	High Similarity	NPC170844
0.9016	High Similarity	NPC476968
0.9016	High Similarity	NPC304622
0.9016	High Similarity	NPC475875
0.9008	High Similarity	NPC123228
0.9008	High Similarity	NPC147821
0.9008	High Similarity	NPC41706
0.9008	High Similarity	NPC163332
0.9008	High Similarity	NPC151167
0.9008	High Similarity	NPC292056
0.9008	High Similarity	NPC319625
0.9008	High Similarity	NPC276466
0.9008	High Similarity	NPC111247
0.9008	High Similarity	NPC252131
0.9008	High Similarity	NPC123722
0.9008	High Similarity	NPC210355
0.9008	High Similarity	NPC183181
0.9008	High Similarity	NPC118787
0.9008	High Similarity	NPC5018
0.9	High Similarity	NPC234400
0.9	High Similarity	NPC289459
0.9	High Similarity	NPC82483
0.9	High Similarity	NPC299584
0.9	High Similarity	NPC60885
0.9	High Similarity	NPC265483
0.9	High Similarity	NPC105925
0.8992	High Similarity	NPC229084
0.8992	High Similarity	NPC18984
0.8992	High Similarity	NPC163083
0.8992	High Similarity	NPC160900
0.8992	High Similarity	NPC121115
0.8992	High Similarity	NPC249788
0.8992	High Similarity	NPC106659
0.8983	High Similarity	NPC476343
0.8983	High Similarity	NPC201777
0.8974	High Similarity	NPC10932
0.8974	High Similarity	NPC61516
0.8974	High Similarity	NPC474565
0.8974	High Similarity	NPC247364
0.8974	High Similarity	NPC232084
0.8966	High Similarity	NPC255675
0.8957	High Similarity	NPC9341
0.8957	High Similarity	NPC221049
0.8957	High Similarity	NPC81067
0.8943	High Similarity	NPC153739
0.8943	High Similarity	NPC275724
0.8943	High Similarity	NPC65935
0.8943	High Similarity	NPC311680
0.8943	High Similarity	NPC123196
0.8943	High Similarity	NPC241522
0.8943	High Similarity	NPC51840
0.8943	High Similarity	NPC92164
0.8943	High Similarity	NPC275950

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 NPC470626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	1042
0.2-0.3	1484
0.3-0.4	2678
0.4-0.5	1813
0.5-0.6	964
0.6-0.7	701
0.7-0.8	149
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9364	High Similarity	NPD228	Approved
0.9196	High Similarity	NPD5283	Phase 1
0.9016	High Similarity	NPD3027	Phase 3
0.8992	High Similarity	NPD4379	Clinical (unspecified phase)
0.8839	High Similarity	NPD3021	Approved
0.8839	High Similarity	NPD3022	Approved
0.8403	Intermediate Similarity	NPD5536	Phase 2
0.8359	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8359	Intermediate Similarity	NPD3620	Phase 2
0.8333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2684	Approved
0.8254	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1613	Approved
0.814	Intermediate Similarity	NPD2674	Phase 3
0.8136	Intermediate Similarity	NPD7843	Approved
0.8115	Intermediate Similarity	NPD1357	Approved
0.8091	Intermediate Similarity	NPD2860	Approved
0.8091	Intermediate Similarity	NPD2859	Approved
0.8083	Intermediate Similarity	NPD7157	Approved
0.808	Intermediate Similarity	NPD2982	Phase 2
0.808	Intermediate Similarity	NPD2983	Phase 2
0.8077	Intermediate Similarity	NPD1558	Phase 1
0.8077	Intermediate Similarity	NPD4060	Phase 1
0.8036	Intermediate Similarity	NPD3020	Approved
0.8	Intermediate Similarity	NPD2981	Phase 2
0.8	Intermediate Similarity	NPD2933	Approved
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD9296	Approved
0.7969	Intermediate Similarity	NPD3018	Phase 2
0.7934	Intermediate Similarity	NPD6671	Approved
0.7923	Intermediate Similarity	NPD3144	Approved
0.7923	Intermediate Similarity	NPD5111	Phase 2
0.7923	Intermediate Similarity	NPD5110	Phase 2
0.7923	Intermediate Similarity	NPD3145	Approved
0.7923	Intermediate Similarity	NPD5109	Approved
0.7891	Intermediate Similarity	NPD6584	Phase 3
0.7881	Intermediate Similarity	NPD5451	Approved
0.7868	Intermediate Similarity	NPD3060	Approved
0.7846	Intermediate Similarity	NPD7095	Approved
0.7829	Intermediate Similarity	NPD9494	Approved
0.7778	Intermediate Similarity	NPD3705	Approved
0.7778	Intermediate Similarity	NPD968	Approved
0.7769	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5846	Approved
0.776	Intermediate Similarity	NPD6516	Phase 2
0.7734	Intermediate Similarity	NPD2922	Phase 1
0.7698	Intermediate Similarity	NPD3847	Discontinued
0.7692	Intermediate Similarity	NPD2861	Phase 2
0.7686	Intermediate Similarity	NPD5535	Approved
0.7656	Intermediate Similarity	NPD6582	Phase 2
0.7656	Intermediate Similarity	NPD6583	Phase 3
0.7652	Intermediate Similarity	NPD5718	Phase 2
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4908	Phase 1
0.763	Intermediate Similarity	NPD6896	Approved
0.763	Intermediate Similarity	NPD6895	Approved
0.7619	Intermediate Similarity	NPD2668	Approved
0.7619	Intermediate Similarity	NPD2667	Approved
0.7619	Intermediate Similarity	NPD4626	Approved
0.7609	Intermediate Similarity	NPD4162	Approved
0.7578	Intermediate Similarity	NPD2232	Approved
0.7578	Intermediate Similarity	NPD2230	Approved
0.7578	Intermediate Similarity	NPD2233	Approved
0.7563	Intermediate Similarity	NPD290	Approved
0.7554	Intermediate Similarity	NPD6331	Phase 2
0.7554	Intermediate Similarity	NPD4110	Phase 3
0.7554	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1651	Approved
0.7522	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6798	Discontinued
0.7519	Intermediate Similarity	NPD1669	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5241	Discontinued
0.7482	Intermediate Similarity	NPD5177	Phase 3
0.7482	Intermediate Similarity	NPD4237	Approved
0.7482	Intermediate Similarity	NPD4236	Phase 3
0.7481	Intermediate Similarity	NPD6355	Discontinued
0.7481	Intermediate Similarity	NPD4624	Approved
0.7481	Intermediate Similarity	NPD3657	Discovery
0.7466	Intermediate Similarity	NPD1934	Approved
0.7464	Intermediate Similarity	NPD7266	Discontinued
0.7463	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1283	Approved
0.746	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD844	Approved
0.7445	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD291	Approved
0.7417	Intermediate Similarity	NPD1358	Approved
0.7415	Intermediate Similarity	NPD2977	Approved
0.7415	Intermediate Similarity	NPD2978	Approved
0.7415	Intermediate Similarity	NPD2801	Approved
0.741	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3053	Approved
0.7405	Intermediate Similarity	NPD3055	Approved
0.7398	Intermediate Similarity	NPD9377	Approved
0.7398	Intermediate Similarity	NPD821	Approved
0.7398	Intermediate Similarity	NPD9379	Approved
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD2161	Phase 2
0.7372	Intermediate Similarity	NPD4538	Approved
0.7372	Intermediate Similarity	NPD4536	Approved
0.7372	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD709	Approved
0.7353	Intermediate Similarity	NPD5735	Approved
0.735	Intermediate Similarity	NPD1242	Phase 1
0.7343	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD3540	Phase 1
0.7338	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6233	Phase 2
0.7333	Intermediate Similarity	NPD4062	Phase 3
0.7328	Intermediate Similarity	NPD5310	Approved
0.7328	Intermediate Similarity	NPD5311	Approved
0.7328	Intermediate Similarity	NPD8651	Approved
0.7315	Intermediate Similarity	NPD3882	Suspended
0.7313	Intermediate Similarity	NPD4625	Phase 3
0.7308	Intermediate Similarity	NPD2235	Phase 2
0.7308	Intermediate Similarity	NPD2231	Phase 2
0.7305	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3596	Phase 2
0.7297	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3496	Discontinued
0.7286	Intermediate Similarity	NPD2808	Discontinued
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7266	Intermediate Similarity	NPD5691	Approved
0.7266	Intermediate Similarity	NPD3539	Phase 1
0.7254	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4749	Approved
0.7252	Intermediate Similarity	NPD5327	Phase 3
0.7241	Intermediate Similarity	NPD288	Approved
0.7236	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6674	Discontinued
0.7234	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1535	Discovery
0.7231	Intermediate Similarity	NPD1281	Approved
0.7231	Intermediate Similarity	NPD3092	Approved
0.7222	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6234	Discontinued
0.7214	Intermediate Similarity	NPD1375	Discontinued
0.7203	Intermediate Similarity	NPD3028	Approved
0.7203	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7124	Phase 2
0.7194	Intermediate Similarity	NPD5588	Approved
0.7194	Intermediate Similarity	NPD5960	Phase 3
0.719	Intermediate Similarity	NPD3134	Approved
0.7188	Intermediate Similarity	NPD1894	Discontinued
0.7188	Intermediate Similarity	NPD3091	Approved
0.7188	Intermediate Similarity	NPD6581	Approved
0.7188	Intermediate Similarity	NPD6580	Approved
0.7188	Intermediate Similarity	NPD1182	Approved
0.7185	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD8166	Discontinued
0.7183	Intermediate Similarity	NPD4628	Phase 3
0.7182	Intermediate Similarity	NPD111	Approved
0.7176	Intermediate Similarity	NPD1481	Phase 2
0.7176	Intermediate Similarity	NPD1608	Approved
0.7174	Intermediate Similarity	NPD4097	Suspended
0.7163	Intermediate Similarity	NPD7153	Discontinued
0.7153	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD3062	Approved
0.7153	Intermediate Similarity	NPD4140	Approved
0.7153	Intermediate Similarity	NPD3061	Approved
0.7153	Intermediate Similarity	NPD3059	Approved
0.7153	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD940	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7132	Intermediate Similarity	NPD5585	Approved
0.7132	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3685	Discontinued
0.712	Intermediate Similarity	NPD7635	Approved
0.7114	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD37	Approved
0.7103	Intermediate Similarity	NPD4584	Approved
0.7101	Intermediate Similarity	NPD4340	Discontinued
0.7099	Intermediate Similarity	NPD1091	Approved
0.7097	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6166	Phase 2
0.7097	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7028	Phase 2
0.7095	Intermediate Similarity	NPD4678	Approved
0.7095	Intermediate Similarity	NPD4675	Approved
0.7092	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD5762	Approved
0.709	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2557	Approved
0.7087	Intermediate Similarity	NPD6387	Discontinued
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9295	Approved
0.7078	Intermediate Similarity	NPD4010	Discontinued
0.7077	Intermediate Similarity	NPD9384	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