NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.08
Volume:	238.321
LogP:	2.117
LogD:	3.142
LogS:	-2.638
# Rotatable Bonds:	5
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	2.016
Fsp3:	0.25
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:	-4.605
MDCK Permeability:	1.7739248505677097e-05
Pgp-inhibitor:	0.128
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.242
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916
Plasma Protein Binding (PPB):	89.74697875976562%
Volume Distribution (VD):	0.441
Pgp-substrate:	9.252381324768066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.363
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	10.006
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.318
Maximum Recommended Daily Dose:	0.177
Skin Sensitization:	0.938
Carcinogencity:	0.114
Eye Corrosion:	0.034
Eye Irritation:	0.147
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC58279

Natural Product ID:	NPC58279
*Common Name:**	Methyl Sinapate
IUPAC Name:	methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Synonyms:	Methyl Sinapate
Standard InCHIKey:	JHLPYWLKSLVYOI-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)17-3)7-10(16-2)12(9)14/h4-7,14H,1-3H3/b5-4+
SMILES:	COC(=O)/C=C/c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL146713
PubChem CID:	5321318
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50097a033]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27905	Eritrichium sericeum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28556	Streptomyces pentaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28070	Chrysosplenium americanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28263	Anemone tomentosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20714	Lobophytum schoedei	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23326	Bohadschia vitiensis	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28422	Sabia japonica	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28646	Streptomyces argenteolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28195	Phlogacanthus tubiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27829	Aplophyllum pedicellatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	93.0	uM	PMID[468539]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	44.0	%	PMID[468540]

☑ 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 NPC58279 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	307
0.1-0.2	1767
0.2-0.3	5713
0.3-0.4	12128
0.4-0.5	4936
0.5-0.6	4660
0.6-0.7	8070
0.7-0.8	4377
0.8-0.85	552
0.85-0.9	160
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300326
0.9752	High Similarity	NPC109275
0.9672	High Similarity	NPC48315
0.9664	High Similarity	NPC238810
0.9661	High Similarity	NPC310373
0.9504	High Similarity	NPC271985
0.9344	High Similarity	NPC27352
0.9328	High Similarity	NPC222175
0.9322	High Similarity	NPC70744
0.9322	High Similarity	NPC272471
0.9322	High Similarity	NPC137537
0.9322	High Similarity	NPC107588
0.9322	High Similarity	NPC164706
0.9291	High Similarity	NPC92830
0.9291	High Similarity	NPC111635
0.9237	High Similarity	NPC259638
0.9167	High Similarity	NPC229401
0.9167	High Similarity	NPC202474
0.9153	High Similarity	NPC193067
0.9134	High Similarity	NPC245120
0.9098	High Similarity	NPC288238
0.9091	High Similarity	NPC204466
0.9083	High Similarity	NPC20674
0.9077	High Similarity	NPC20511
0.9077	High Similarity	NPC95162
0.9077	High Similarity	NPC52086
0.9077	High Similarity	NPC139548
0.9077	High Similarity	NPC76336
0.9077	High Similarity	NPC148835
0.9055	High Similarity	NPC73738
0.9016	High Similarity	NPC70752
0.9008	High Similarity	NPC2058
0.9008	High Similarity	NPC13067
0.9008	High Similarity	NPC232084
0.9008	High Similarity	NPC10932
0.9008	High Similarity	NPC247364
0.9008	High Similarity	NPC61516
0.9	High Similarity	NPC82271
0.9	High Similarity	NPC126682
0.8983	High Similarity	NPC294941
0.8943	High Similarity	NPC473411
0.8943	High Similarity	NPC71579
0.8943	High Similarity	NPC262253
0.8931	High Similarity	NPC25305
0.8931	High Similarity	NPC112068
0.8931	High Similarity	NPC95679
0.8931	High Similarity	NPC125417
0.8931	High Similarity	NPC110899
0.8926	High Similarity	NPC226629
0.8862	High Similarity	NPC49341
0.8837	High Similarity	NPC5423
0.881	High Similarity	NPC127604
0.88	High Similarity	NPC146886
0.88	High Similarity	NPC246704
0.88	High Similarity	NPC183446
0.88	High Similarity	NPC20443
0.88	High Similarity	NPC60517
0.878	High Similarity	NPC166759
0.8769	High Similarity	NPC36490
0.8769	High Similarity	NPC26673
0.876	High Similarity	NPC39793
0.874	High Similarity	NPC194841
0.873	High Similarity	NPC299584
0.873	High Similarity	NPC233410
0.873	High Similarity	NPC203133
0.873	High Similarity	NPC472093
0.873	High Similarity	NPC82483
0.873	High Similarity	NPC193544
0.873	High Similarity	NPC117214
0.873	High Similarity	NPC208950
0.873	High Similarity	NPC116907
0.873	High Similarity	NPC221077
0.873	High Similarity	NPC57490
0.873	High Similarity	NPC173608
0.873	High Similarity	NPC251855
0.873	High Similarity	NPC17943
0.873	High Similarity	NPC265483
0.873	High Similarity	NPC298757
0.873	High Similarity	NPC289459
0.873	High Similarity	NPC475169
0.8729	High Similarity	NPC226250
0.872	High Similarity	NPC220598
0.872	High Similarity	NPC197757
0.872	High Similarity	NPC228922
0.872	High Similarity	NPC165375
0.871	High Similarity	NPC145780
0.8702	High Similarity	NPC135127
0.8702	High Similarity	NPC155098
0.8699	High Similarity	NPC474565
0.8692	High Similarity	NPC137949
0.8689	High Similarity	NPC124916
0.8676	High Similarity	NPC297342
0.8661	High Similarity	NPC28730
0.8661	High Similarity	NPC120225
0.8661	High Similarity	NPC214406
0.8661	High Similarity	NPC78974
0.8661	High Similarity	NPC223136
0.8661	High Similarity	NPC18924
0.8661	High Similarity	NPC213552
0.8661	High Similarity	NPC103823
0.8661	High Similarity	NPC44748
0.8651	High Similarity	NPC5796
0.8651	High Similarity	NPC206487
0.8647	High Similarity	NPC474886
0.864	High Similarity	NPC41562
0.8636	High Similarity	NPC274613
0.8636	High Similarity	NPC208760
0.8629	High Similarity	NPC60962
0.8629	High Similarity	NPC269843
0.8629	High Similarity	NPC109083
0.8629	High Similarity	NPC224814
0.8629	High Similarity	NPC189844
0.8629	High Similarity	NPC14007
0.8626	High Similarity	NPC159418
0.8626	High Similarity	NPC277021
0.8626	High Similarity	NPC283823
0.8618	High Similarity	NPC37858
0.8605	High Similarity	NPC228769
0.8605	High Similarity	NPC470633
0.8603	High Similarity	NPC110067
0.8603	High Similarity	NPC91492
0.8603	High Similarity	NPC7439
0.8603	High Similarity	NPC236419
0.8603	High Similarity	NPC34245
0.8603	High Similarity	NPC256555
0.8594	High Similarity	NPC74817
0.8594	High Similarity	NPC282000
0.8594	High Similarity	NPC324112
0.8594	High Similarity	NPC266555
0.8594	High Similarity	NPC293054
0.8594	High Similarity	NPC281020
0.8594	High Similarity	NPC236791
0.8594	High Similarity	NPC124452
0.8594	High Similarity	NPC246620
0.8594	High Similarity	NPC82679
0.8594	High Similarity	NPC127587
0.8594	High Similarity	NPC159968
0.8594	High Similarity	NPC169474
0.8594	High Similarity	NPC210355
0.8583	High Similarity	NPC234400
0.8583	High Similarity	NPC60885
0.8583	High Similarity	NPC95381
0.8582	High Similarity	NPC43500
0.8582	High Similarity	NPC164148
0.8571	High Similarity	NPC136319
0.8571	High Similarity	NPC157554
0.8571	High Similarity	NPC282496
0.8571	High Similarity	NPC84086
0.8571	High Similarity	NPC203924
0.8571	High Similarity	NPC233526
0.8571	High Similarity	NPC108545
0.8571	High Similarity	NPC95168
0.8561	High Similarity	NPC237330
0.856	High Similarity	NPC194416
0.856	High Similarity	NPC285289
0.856	High Similarity	NPC177291
0.8559	High Similarity	NPC246358
0.8559	High Similarity	NPC36108
0.8559	High Similarity	NPC7097
0.8559	High Similarity	NPC165386
0.8559	High Similarity	NPC233731
0.855	High Similarity	NPC111888
0.8548	High Similarity	NPC148615
0.8548	High Similarity	NPC177475
0.8548	High Similarity	NPC35071
0.854	High Similarity	NPC471763
0.8538	High Similarity	NPC19242
0.8538	High Similarity	NPC240722
0.8538	High Similarity	NPC244799
0.8537	High Similarity	NPC63083
0.8537	High Similarity	NPC255675
0.8527	High Similarity	NPC154866
0.8527	High Similarity	NPC110313
0.8527	High Similarity	NPC206615
0.8527	High Similarity	NPC470213
0.8527	High Similarity	NPC98631
0.8527	High Similarity	NPC478215
0.8527	High Similarity	NPC186843
0.8525	High Similarity	NPC221049
0.8519	High Similarity	NPC144284
0.8519	High Similarity	NPC267291
0.8516	High Similarity	NPC76451
0.8512	High Similarity	NPC261453
0.8512	High Similarity	NPC33749
0.8512	High Similarity	NPC217472
0.8512	High Similarity	NPC328593
0.8507	High Similarity	NPC126206
0.8492	Intermediate Similarity	NPC286573
0.8489	Intermediate Similarity	NPC476347
0.8489	Intermediate Similarity	NPC178129
0.8489	Intermediate Similarity	NPC231149
0.8485	Intermediate Similarity	NPC474810
0.848	Intermediate Similarity	NPC199023
0.848	Intermediate Similarity	NPC158949
0.8473	Intermediate Similarity	NPC264145
0.8468	Intermediate Similarity	NPC57501
0.8468	Intermediate Similarity	NPC320987
0.8468	Intermediate Similarity	NPC181969
0.8467	Intermediate Similarity	NPC6568
0.8467	Intermediate Similarity	NPC230157

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 NPC58279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	953
0.2-0.3	2015
0.3-0.4	2824
0.4-0.5	1553
0.5-0.6	985
0.6-0.7	461
0.7-0.8	85
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8425	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD228	Approved
0.8346	Intermediate Similarity	NPD230	Phase 1
0.8239	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD422	Phase 1
0.8106	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD9494	Approved
0.803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2982	Phase 2
0.8	Intermediate Similarity	NPD1613	Approved
0.7934	Intermediate Similarity	NPD1358	Approved
0.7923	Intermediate Similarity	NPD2981	Phase 2
0.7874	Intermediate Similarity	NPD5536	Phase 2
0.7832	Intermediate Similarity	NPD4357	Discontinued
0.7786	Intermediate Similarity	NPD9269	Phase 2
0.7761	Intermediate Similarity	NPD3018	Phase 2
0.7681	Intermediate Similarity	NPD447	Suspended
0.766	Intermediate Similarity	NPD7266	Discontinued
0.7651	Intermediate Similarity	NPD1934	Approved
0.7616	Intermediate Similarity	NPD3882	Suspended
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1357	Approved
0.7606	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2801	Approved
0.7586	Intermediate Similarity	NPD1511	Approved
0.7561	Intermediate Similarity	NPD3134	Approved
0.7551	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD1465	Phase 2
0.7481	Intermediate Similarity	NPD9268	Approved
0.7466	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD9296	Approved
0.7448	Intermediate Similarity	NPD2219	Phase 1
0.7448	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD1242	Phase 1
0.7434	Intermediate Similarity	NPD3817	Phase 2
0.7431	Intermediate Similarity	NPD1652	Phase 2
0.7424	Intermediate Similarity	NPD4626	Approved
0.7422	Intermediate Similarity	NPD5283	Phase 1
0.7405	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD9545	Approved
0.7403	Intermediate Similarity	NPD6234	Discontinued
0.7372	Intermediate Similarity	NPD6232	Discontinued
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1558	Phase 1
0.7357	Intermediate Similarity	NPD1240	Approved
0.7347	Intermediate Similarity	NPD5297	Approved
0.7343	Intermediate Similarity	NPD1551	Phase 2
0.7338	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3705	Approved
0.7313	Intermediate Similarity	NPD1610	Phase 2
0.7303	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD3750	Approved
0.726	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1607	Approved
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7234	Intermediate Similarity	NPD4060	Phase 1
0.7234	Intermediate Similarity	NPD943	Approved
0.7233	Intermediate Similarity	NPD7473	Discontinued
0.723	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7214	Intermediate Similarity	NPD3144	Approved
0.7214	Intermediate Similarity	NPD3145	Approved
0.7194	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4908	Phase 1
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7183	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5124	Phase 1
0.7172	Intermediate Similarity	NPD3540	Phase 1
0.717	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6166	Phase 2
0.717	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1778	Approved
0.7163	Intermediate Similarity	NPD2674	Phase 3
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9717	Approved
0.7124	Intermediate Similarity	NPD5090	Approved
0.7124	Intermediate Similarity	NPD5089	Approved
0.7121	Intermediate Similarity	NPD9493	Approved
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7109	Intermediate Similarity	NPD3022	Approved
0.7109	Intermediate Similarity	NPD3021	Approved
0.7103	Intermediate Similarity	NPD3539	Phase 1
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7097	Intermediate Similarity	NPD940	Approved
0.7097	Intermediate Similarity	NPD846	Approved
0.7097	Intermediate Similarity	NPD291	Approved
0.7097	Intermediate Similarity	NPD5353	Approved
0.7092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5691	Approved
0.7089	Intermediate Similarity	NPD7199	Phase 2
0.7087	Intermediate Similarity	NPD290	Approved
0.7081	Intermediate Similarity	NPD7228	Approved
0.708	Intermediate Similarity	NPD4749	Approved
0.7073	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD919	Approved
0.7063	Intermediate Similarity	NPD4340	Discontinued
0.7059	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3686	Approved
0.7039	Intermediate Similarity	NPD3687	Approved
0.7034	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2684	Approved
0.7029	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD7095	Approved
0.7007	Intermediate Similarity	NPD1549	Phase 2
0.7007	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1203	Approved
0.6972	Remote Similarity	NPD411	Approved
0.6972	Remote Similarity	NPD1296	Phase 2
0.697	Remote Similarity	NPD7549	Discontinued
0.6966	Remote Similarity	NPD6111	Discontinued
0.6954	Remote Similarity	NPD2533	Approved
0.6954	Remote Similarity	NPD2532	Approved
0.6954	Remote Similarity	NPD2534	Approved
0.6951	Remote Similarity	NPD6797	Phase 2
0.6949	Remote Similarity	NPD9094	Approved
0.6948	Remote Similarity	NPD4675	Approved
0.6948	Remote Similarity	NPD4678	Approved
0.6948	Remote Similarity	NPD4380	Phase 2
0.6948	Remote Similarity	NPD6599	Discontinued
0.6947	Remote Similarity	NPD7843	Approved
0.6944	Remote Similarity	NPD1933	Approved
0.6939	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9697	Approved
0.6929	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7819	Suspended
0.6918	Remote Similarity	NPD3748	Approved
0.6917	Remote Similarity	NPD7157	Approved
0.6913	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4110	Phase 3
0.6913	Remote Similarity	NPD8166	Discontinued
0.6909	Remote Similarity	NPD7251	Discontinued
0.6909	Remote Similarity	NPD7685	Pre-registration
0.6906	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD4625	Phase 3
0.6897	Remote Similarity	NPD6653	Approved
0.6894	Remote Similarity	NPD5242	Approved
0.6883	Remote Similarity	NPD824	Approved
0.6879	Remote Similarity	NPD5402	Approved
0.6867	Remote Similarity	NPD7808	Phase 3
0.6867	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5403	Approved
0.6861	Remote Similarity	NPD3847	Discontinued
0.6859	Remote Similarity	NPD6801	Discontinued
0.6857	Remote Similarity	NPD987	Approved
0.6853	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3060	Approved
0.6845	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5401	Approved
0.6835	Remote Similarity	NPD7768	Phase 2
0.6824	Remote Similarity	NPD1375	Discontinued
0.6822	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7124	Phase 2
0.6818	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD4585	Approved
0.6812	Remote Similarity	NPD1535	Discovery
0.6809	Remote Similarity	NPD257	Approved
0.6809	Remote Similarity	NPD258	Approved
0.6806	Remote Similarity	NPD6233	Phase 2
0.6806	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD259	Phase 1
0.6797	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7411	Suspended
0.6795	Remote Similarity	NPD6386	Approved
0.6795	Remote Similarity	NPD6385	Approved
0.6792	Remote Similarity	NPD6971	Discontinued
0.6792	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD17	Approved
0.6786	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2653	Approved
0.6781	Remote Similarity	NPD2492	Phase 1
0.6774	Remote Similarity	NPD3111	Phase 1
0.6774	Remote Similarity	NPD4005	Discontinued
0.6774	Remote Similarity	NPD3455	Phase 2
0.6767	Remote Similarity	NPD1241	Discontinued
0.6763	Remote Similarity	NPD1481	Phase 2
0.6759	Remote Similarity	NPD826	Approved
0.6759	Remote Similarity	NPD825	Approved
0.6744	Remote Similarity	NPD968	Approved
0.6738	Remote Similarity	NPD2797	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