NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.1
Volume:	232.167
LogP:	1.944
LogD:	1.973
LogS:	-2.707
# Rotatable Bonds:	4
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	2.418
Fsp3:	0.333
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:	-4.621
MDCK Permeability:	1.4015830856806133e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.626
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	88.28043365478516%
Volume Distribution (VD):	0.874
Pgp-substrate:	11.300896644592285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.231
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	6.437
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.432
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.702
Carcinogencity:	0.143
Eye Corrosion:	0.076
Eye Irritation:	0.925
Respiratory Toxicity:	0.3

Download Data

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

Natural Product: NPC183446

Natural Product ID:	NPC183446
*Common Name:**	2,3,6-Trimethoxy-5-(1-Propenyl)Phenol
IUPAC Name:	2,3,6-trimethoxy-5-[(E)-prop-1-enyl]phenol
Synonyms:
Standard InCHIKey:	LNULYVLKYVWZFB-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C12H16O4/c1-5-6-8-7-9(14-2)12(16-4)10(13)11(8)15-3/h5-7,13H,1-4H3/b6-5+
SMILES:	C/C=C/c1cc(c(c(c1OC)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501754
PubChem CID:	10955197
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO6580	Smirnowia iranica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502308]
NPO6580	Smirnowia iranica	Species	Fabaceae	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	7

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	125000.0	nM	PMID[533000]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	198000.0	nM	PMID[533000]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	232000.0	nM	PMID[533000]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	387000.0	nM	PMID[533000]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	589000.0	nM	PMID[533000]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	200000.0	nM	PMID[533000]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	800000.0	nM	PMID[533000]

☑ 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 NPC183446 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	397
0.1-0.2	2009
0.2-0.3	7188
0.3-0.4	12543
0.4-0.5	3577
0.5-0.6	4515
0.6-0.7	7509
0.7-0.8	3887
0.8-0.85	607
0.85-0.9	330
0.9-0.95	127
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC10225
0.959	High Similarity	NPC58164
0.9576	High Similarity	NPC285289
0.9512	High Similarity	NPC299221
0.9512	High Similarity	NPC234488
0.9512	High Similarity	NPC51840
0.9512	High Similarity	NPC311680
0.9504	High Similarity	NPC112596
0.9496	High Similarity	NPC270326
0.9431	High Similarity	NPC45824
0.9421	High Similarity	NPC82483
0.9421	High Similarity	NPC265483
0.9421	High Similarity	NPC299584
0.936	High Similarity	NPC6451
0.9355	High Similarity	NPC214860
0.935	High Similarity	NPC266691
0.9344	High Similarity	NPC18924
0.9344	High Similarity	NPC214406
0.9344	High Similarity	NPC78974
0.9344	High Similarity	NPC223136
0.9344	High Similarity	NPC28730
0.9344	High Similarity	NPC103823
0.9344	High Similarity	NPC44748
0.9333	High Similarity	NPC474864
0.9333	High Similarity	NPC135414
0.9333	High Similarity	NPC246967
0.9322	High Similarity	NPC308217
0.9322	High Similarity	NPC20674
0.9316	High Similarity	NPC259638
0.9316	High Similarity	NPC52464
0.9316	High Similarity	NPC304208
0.928	High Similarity	NPC232275
0.928	High Similarity	NPC474356
0.928	High Similarity	NPC45715
0.928	High Similarity	NPC12275
0.9268	High Similarity	NPC159968
0.9268	High Similarity	NPC236791
0.9268	High Similarity	NPC293054
0.9268	High Similarity	NPC324112
0.9268	High Similarity	NPC246620
0.9268	High Similarity	NPC74817
0.9268	High Similarity	NPC169474
0.9268	High Similarity	NPC124452
0.9268	High Similarity	NPC82679
0.9268	High Similarity	NPC282000
0.9268	High Similarity	NPC216836
0.9262	High Similarity	NPC60885
0.9262	High Similarity	NPC234400
0.9256	High Similarity	NPC95168
0.9256	High Similarity	NPC165375
0.9256	High Similarity	NPC220598
0.925	High Similarity	NPC49341
0.9244	High Similarity	NPC229401
0.9231	High Similarity	NPC193067
0.92	High Similarity	NPC192687
0.92	High Similarity	NPC224157
0.92	High Similarity	NPC220935
0.9194	High Similarity	NPC154866
0.9187	High Similarity	NPC245060
0.9174	High Similarity	NPC262253
0.9174	High Similarity	NPC473411
0.9174	High Similarity	NPC71579
0.9141	High Similarity	NPC472337
0.912	High Similarity	NPC190144
0.912	High Similarity	NPC158477
0.9113	High Similarity	NPC266555
0.9106	High Similarity	NPC117214
0.9106	High Similarity	NPC221077
0.9106	High Similarity	NPC193544
0.9106	High Similarity	NPC298757
0.9106	High Similarity	NPC17943
0.9106	High Similarity	NPC208950
0.9106	High Similarity	NPC203133
0.9106	High Similarity	NPC475169
0.9106	High Similarity	NPC233410
0.9106	High Similarity	NPC116907
0.9106	High Similarity	NPC105925
0.9106	High Similarity	NPC472093
0.9106	High Similarity	NPC251855
0.9106	High Similarity	NPC57490
0.9098	High Similarity	NPC121115
0.9098	High Similarity	NPC228922
0.9098	High Similarity	NPC197757
0.9091	High Similarity	NPC75713
0.9083	High Similarity	NPC232084
0.9083	High Similarity	NPC247364
0.9083	High Similarity	NPC10932
0.9083	High Similarity	NPC61516
0.907	High Similarity	NPC472334
0.907	High Similarity	NPC472336
0.9048	High Similarity	NPC126836
0.904	High Similarity	NPC28765
0.904	High Similarity	NPC19694
0.9032	High Similarity	NPC223953
0.9016	High Similarity	NPC41562
0.9008	High Similarity	NPC166759
0.9	High Similarity	NPC176051
0.9	High Similarity	NPC474282
0.9	High Similarity	NPC73535
0.9	High Similarity	NPC90615
0.9	High Similarity	NPC272157
0.9	High Similarity	NPC226629
0.9	High Similarity	NPC276490
0.9	High Similarity	NPC6262
0.9	High Similarity	NPC107551
0.9	High Similarity	NPC326797
0.9	High Similarity	NPC201145
0.9	High Similarity	NPC25111
0.9	High Similarity	NPC102904
0.9	High Similarity	NPC103976
0.8984	High Similarity	NPC229442
0.8984	High Similarity	NPC168059
0.8984	High Similarity	NPC94236
0.8984	High Similarity	NPC37196
0.8976	High Similarity	NPC82503
0.8968	High Similarity	NPC476968
0.8968	High Similarity	NPC212015
0.8968	High Similarity	NPC170844
0.896	High Similarity	NPC252131
0.896	High Similarity	NPC236760
0.896	High Similarity	NPC210355
0.896	High Similarity	NPC127587
0.8943	High Similarity	NPC282496
0.8943	High Similarity	NPC136319
0.8943	High Similarity	NPC238810
0.8943	High Similarity	NPC233526
0.8934	High Similarity	NPC470804
0.8931	High Similarity	NPC127218
0.8931	High Similarity	NPC25966
0.8931	High Similarity	NPC245207
0.8931	High Similarity	NPC212942
0.8931	High Similarity	NPC79622
0.8931	High Similarity	NPC29868
0.8931	High Similarity	NPC319647
0.8926	High Similarity	NPC474565
0.8926	High Similarity	NPC35071
0.8926	High Similarity	NPC177475
0.8926	High Similarity	NPC148615
0.8923	High Similarity	NPC476639
0.8923	High Similarity	NPC114155
0.8923	High Similarity	NPC300846
0.8917	High Similarity	NPC474612
0.8917	High Similarity	NPC63083
0.8915	High Similarity	NPC310854
0.8915	High Similarity	NPC106215
0.8906	High Similarity	NPC127624
0.8906	High Similarity	NPC86655
0.8906	High Similarity	NPC161203
0.8906	High Similarity	NPC202762
0.8889	High Similarity	NPC470213
0.8889	High Similarity	NPC98631
0.8889	High Similarity	NPC206615
0.8889	High Similarity	NPC186843
0.888	High Similarity	NPC476006
0.888	High Similarity	NPC76451
0.8871	High Similarity	NPC5796
0.8871	High Similarity	NPC206487
0.8864	High Similarity	NPC160283
0.8864	High Similarity	NPC295719
0.8864	High Similarity	NPC284464
0.8864	High Similarity	NPC165026
0.8864	High Similarity	NPC73505
0.8864	High Similarity	NPC254759
0.8864	High Similarity	NPC34431
0.8862	High Similarity	NPC194626
0.8855	High Similarity	NPC148835
0.8855	High Similarity	NPC52086
0.8855	High Similarity	NPC139548
0.8855	High Similarity	NPC20511
0.8855	High Similarity	NPC95162
0.8855	High Similarity	NPC76336
0.8846	High Similarity	NPC255147
0.8846	High Similarity	NPC112246
0.8846	High Similarity	NPC474206
0.8846	High Similarity	NPC94750
0.8846	High Similarity	NPC281521
0.8846	High Similarity	NPC283009
0.8846	High Similarity	NPC261873
0.8846	High Similarity	NPC201357
0.8846	High Similarity	NPC195022
0.8846	High Similarity	NPC470356
0.8846	High Similarity	NPC121812
0.8846	High Similarity	NPC134968
0.8846	High Similarity	NPC111655
0.8846	High Similarity	NPC256262
0.8846	High Similarity	NPC112939
0.8843	High Similarity	NPC320987
0.8843	High Similarity	NPC135961
0.8843	High Similarity	NPC181969
0.8837	High Similarity	NPC474810
0.8837	High Similarity	NPC36661
0.8837	High Similarity	NPC475840
0.8837	High Similarity	NPC32778
0.8837	High Similarity	NPC471390
0.8837	High Similarity	NPC471391
0.8828	High Similarity	NPC470095
0.8828	High Similarity	NPC470096
0.8828	High Similarity	NPC472597
0.8828	High Similarity	NPC474017
0.8814	High Similarity	NPC204120

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 NPC183446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	989
0.2-0.3	2328
0.3-0.4	2631
0.4-0.5	1422
0.5-0.6	850
0.6-0.7	473
0.7-0.8	85
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD3027	Phase 3
0.874	High Similarity	NPD1529	Clinical (unspecified phase)
0.8661	High Similarity	NPD1530	Clinical (unspecified phase)
0.8644	High Similarity	NPD228	Approved
0.8615	High Similarity	NPD1612	Clinical (unspecified phase)
0.8615	High Similarity	NPD1613	Approved
0.8372	Intermediate Similarity	NPD3018	Phase 2
0.8203	Intermediate Similarity	NPD2982	Phase 2
0.8203	Intermediate Similarity	NPD2983	Phase 2
0.8169	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD2981	Phase 2
0.8014	Intermediate Similarity	NPD2801	Approved
0.7923	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1548	Phase 1
0.7769	Intermediate Similarity	NPD1610	Phase 2
0.7761	Intermediate Similarity	NPD4908	Phase 1
0.776	Intermediate Similarity	NPD5283	Phase 1
0.7731	Intermediate Similarity	NPD940	Approved
0.7731	Intermediate Similarity	NPD846	Approved
0.7714	Intermediate Similarity	NPD3540	Phase 1
0.7703	Intermediate Similarity	NPD1934	Approved
0.7674	Intermediate Similarity	NPD1357	Approved
0.7652	Intermediate Similarity	NPD4749	Approved
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3539	Phase 1
0.7639	Intermediate Similarity	NPD1511	Approved
0.7638	Intermediate Similarity	NPD6671	Approved
0.7634	Intermediate Similarity	NPD422	Phase 1
0.7634	Intermediate Similarity	NPD1091	Approved
0.7634	Intermediate Similarity	NPD3705	Approved
0.7622	Intermediate Similarity	NPD2219	Phase 1
0.7609	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD290	Approved
0.7556	Intermediate Similarity	NPD2861	Phase 2
0.755	Intermediate Similarity	NPD3882	Suspended
0.7536	Intermediate Similarity	NPD1558	Phase 1
0.7534	Intermediate Similarity	NPD1512	Approved
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9296	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.7481	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2674	Phase 3
0.7445	Intermediate Similarity	NPD4625	Phase 3
0.744	Intermediate Similarity	NPD3021	Approved
0.744	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD9494	Approved
0.7397	Intermediate Similarity	NPD4357	Discontinued
0.7391	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3144	Approved
0.7391	Intermediate Similarity	NPD3145	Approved
0.7385	Intermediate Similarity	NPD5536	Phase 2
0.736	Intermediate Similarity	NPD2684	Approved
0.7339	Intermediate Similarity	NPD968	Approved
0.7338	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD4675	Approved
0.7333	Intermediate Similarity	NPD4678	Approved
0.7325	Intermediate Similarity	NPD6166	Phase 2
0.7325	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4750	Phase 3
0.7297	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3496	Discontinued
0.7286	Intermediate Similarity	NPD3620	Phase 2
0.7286	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7843	Approved
0.726	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.7254	Intermediate Similarity	NPD6111	Discontinued
0.7244	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1652	Phase 2
0.7237	Intermediate Similarity	NPD37	Approved
0.7234	Intermediate Similarity	NPD447	Suspended
0.7231	Intermediate Similarity	NPD7157	Approved
0.7213	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6696	Suspended
0.7197	Intermediate Similarity	NPD6232	Discontinued
0.7188	Intermediate Similarity	NPD7054	Approved
0.7172	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1240	Approved
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD291	Approved
0.7153	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7125	Intermediate Similarity	NPD3818	Discontinued
0.7123	Intermediate Similarity	NPD3060	Approved
0.7122	Intermediate Similarity	NPD596	Approved
0.7122	Intermediate Similarity	NPD600	Approved
0.7117	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1424	Approved
0.7103	Intermediate Similarity	NPD1375	Discontinued
0.7103	Intermediate Similarity	NPD7266	Discontinued
0.7097	Intermediate Similarity	NPD4966	Approved
0.7097	Intermediate Similarity	NPD4965	Approved
0.7097	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD7124	Phase 2
0.7094	Intermediate Similarity	NPD9295	Approved
0.7092	Intermediate Similarity	NPD840	Approved
0.7092	Intermediate Similarity	NPD839	Approved
0.709	Intermediate Similarity	NPD4626	Approved
0.709	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD1510	Phase 2
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.708	Intermediate Similarity	NPD2922	Phase 1
0.708	Intermediate Similarity	NPD8651	Approved
0.7078	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD7473	Discontinued
0.7063	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD5090	Approved
0.7059	Intermediate Similarity	NPD5089	Approved
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7042	Intermediate Similarity	NPD943	Approved
0.7039	Intermediate Similarity	NPD4005	Discontinued
0.7027	Intermediate Similarity	NPD6190	Approved
0.7025	Intermediate Similarity	NPD844	Approved
0.7025	Intermediate Similarity	NPD7199	Phase 2
0.7019	Intermediate Similarity	NPD7228	Approved
0.7009	Intermediate Similarity	NPD9094	Approved
0.7008	Intermediate Similarity	NPD1358	Approved
0.7007	Intermediate Similarity	NPD4237	Approved
0.7007	Intermediate Similarity	NPD4236	Phase 3
0.7007	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6674	Discontinued
0.7007	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4123	Phase 3
0.6994	Remote Similarity	NPD6797	Phase 2
0.6993	Remote Similarity	NPD4380	Phase 2
0.6986	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9381	Approved
0.6963	Remote Similarity	NPD9384	Approved
0.6962	Remote Similarity	NPD5494	Approved
0.6951	Remote Similarity	NPD7251	Discontinued
0.6944	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4055	Discovery
0.6937	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1774	Approved
0.6933	Remote Similarity	NPD5297	Approved
0.6923	Remote Similarity	NPD2238	Phase 2
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6913	Remote Similarity	NPD2677	Approved
0.6909	Remote Similarity	NPD7549	Discontinued
0.6909	Remote Similarity	NPD7808	Phase 3
0.6908	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7447	Phase 1
0.6884	Remote Similarity	NPD9622	Approved
0.6875	Remote Similarity	NPD5124	Phase 1
0.6875	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9379	Approved
0.687	Remote Similarity	NPD821	Approved
0.687	Remote Similarity	NPD9377	Approved
0.6863	Remote Similarity	NPD3686	Approved
0.6863	Remote Similarity	NPD3687	Approved
0.6859	Remote Similarity	NPD2977	Approved
0.6859	Remote Similarity	NPD2978	Approved
0.6853	Remote Similarity	NPD6233	Phase 2
0.6846	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD288	Approved
0.6826	Remote Similarity	NPD8053	Approved
0.6826	Remote Similarity	NPD8054	Approved
0.6824	Remote Similarity	NPD1549	Phase 2
0.6821	Remote Similarity	NPD7213	Phase 3
0.6821	Remote Similarity	NPD7212	Phase 2
0.6821	Remote Similarity	NPD6799	Approved
0.6818	Remote Similarity	NPD1398	Phase 1
0.6818	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5402	Approved
0.6813	Remote Similarity	NPD1247	Approved
0.6812	Remote Similarity	NPD2230	Approved
0.6812	Remote Similarity	NPD2232	Approved
0.6812	Remote Similarity	NPD2233	Approved
0.6803	Remote Similarity	NPD2933	Approved
0.6803	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1551	Phase 2
0.6803	Remote Similarity	NPD2934	Approved
0.6788	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5110	Phase 2
0.6783	Remote Similarity	NPD5111	Phase 2
0.6783	Remote Similarity	NPD5109	Approved
0.6781	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4536	Approved
0.6781	Remote Similarity	NPD4538	Approved
0.6776	Remote Similarity	NPD2532	Approved
0.6776	Remote Similarity	NPD2534	Approved
0.6776	Remote Similarity	NPD2533	Approved
0.6776	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5691	Approved
0.6765	Remote Similarity	NPD9268	Approved
0.6761	Remote Similarity	NPD5752	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