NPASS Compound

Structure

NPC34436 OpenBabel07101719152D 33 37 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5078 -4.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5024 -2.0741 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 0.8660 -0.5000 0.0000 C 0 0 1 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3281 -2.7763 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 -4.3301 -1.5000 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 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6704 -3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0246 -2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6356 -2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0979 -3.4145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8538 -3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6514 -4.0776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.0860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 29 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 1 1 1 0 0 0 5 12 1 0 0 0 0 5 30 1 0 0 0 0 6 11 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 20 1 0 0 0 0 8 16 2 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 31 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 12 14 1 0 0 0 0 12 23 1 6 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 1 0 0 0 15 21 1 0 0 0 0 15 26 1 1 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 27 2 0 0 0 0 19 32 1 0 0 0 0 20 28 2 0 0 0 0 20 33 1 0 0 0 0 21 30 1 0 0 0 0 21 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.08
Volume:	413.381
LogP:	0.517
LogD:	0.237
LogS:	-5.098
# Rotatable Bonds:	3
TPSA:	189.26
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	4.32
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.291
MDCK Permeability:	3.2966661819955334e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	72.94428253173828%
Volume Distribution (VD):	0.965
Pgp-substrate:	30.092599868774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.329
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.488
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.372
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.696
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC34436

Natural Product ID:	NPC34436
*Common Name:**	IAYGIELPGJHKME-UKZWKHHHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IAYGIELPGJHKME-UKZWKHHHSA-N
Standard InCHI:	InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-10-11-6(19(27)32-17(10)13(9)24)3-8(22)16(29-2)18(11)33-20(7)28/h3-5,12,14-15,21-26H,1-2H3/t5-,12-,14+,15+,21-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc2c3c4c(cc(c(c4oc2=O)OC)O)c(=O)oc3c1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460463
PubChem CID:	44560360
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO33358	phyllanthus acutissima	Species	n.a.	Eukaryota	aerial parts	n.a.	n.a.	PMID[18271551]

☑ 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
EC50	1
ED50	6
IC50	3
MIC	1
Others	1

Activity Type	# Activity
Cell Line	5
CELL-LINE	3
Individual Protein	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	-9.2	%	PMID[546576]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[546576]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[546576]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[546576]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[546576]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[546576]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	125.0	ug.mL-1	PMID[546576]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	125.0	ug.mL-1	PMID[546576]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[546576]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	180000.0	nM	PMID[546577]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	260000.0	nM	PMID[546577]
NPT20950	CELL-LINE	Erythrocyte	n.a.	MIC	=	340000.0	nM	PMID[546577]

☑ 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 NPC34436 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	454
0.1-0.2	2025
0.2-0.3	4449
0.3-0.4	9791
0.4-0.5	8306
0.5-0.6	4551
0.6-0.7	5594
0.7-0.8	5237
0.8-0.85	1441
0.85-0.9	668
0.9-0.95	172
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263119
1.0	High Similarity	NPC46640
1.0	High Similarity	NPC219600
1.0	High Similarity	NPC166674
0.9877	High Similarity	NPC473550
0.9876	High Similarity	NPC181778
0.9693	High Similarity	NPC38438
0.9636	High Similarity	NPC297574
0.9408	High Similarity	NPC123259
0.9408	High Similarity	NPC129533
0.9405	High Similarity	NPC80956
0.9349	High Similarity	NPC208797
0.9349	High Similarity	NPC53680
0.9317	High Similarity	NPC40702
0.9317	High Similarity	NPC267627
0.9317	High Similarity	NPC37502
0.9286	High Similarity	NPC472723
0.9259	High Similarity	NPC24627
0.9255	High Similarity	NPC247713
0.9244	High Similarity	NPC237202
0.9191	High Similarity	NPC173872
0.9191	High Similarity	NPC477083
0.9191	High Similarity	NPC477081
0.9191	High Similarity	NPC119094
0.9191	High Similarity	NPC269046
0.9172	High Similarity	NPC473713
0.9172	High Similarity	NPC67629
0.9172	High Similarity	NPC79736
0.9167	High Similarity	NPC163165
0.9157	High Similarity	NPC298847
0.9141	High Similarity	NPC239966
0.9141	High Similarity	NPC203020
0.9136	High Similarity	NPC1913
0.9118	High Similarity	NPC267549
0.9102	High Similarity	NPC183036
0.9102	High Similarity	NPC229687
0.9091	High Similarity	NPC121290
0.908	High Similarity	NPC142291
0.908	High Similarity	NPC160780
0.908	High Similarity	NPC7839
0.908	High Similarity	NPC289811
0.9075	High Similarity	NPC261623
0.9075	High Similarity	NPC111490
0.9068	High Similarity	NPC116850
0.9068	High Similarity	NPC144801
0.9068	High Similarity	NPC178134
0.9068	High Similarity	NPC238672
0.9068	High Similarity	NPC197188
0.9068	High Similarity	NPC43872
0.9068	High Similarity	NPC291510
0.9053	High Similarity	NPC239549
0.9053	High Similarity	NPC51774
0.9053	High Similarity	NPC236191
0.9048	High Similarity	NPC51326
0.9048	High Similarity	NPC105095
0.9048	High Similarity	NPC474434
0.9048	High Similarity	NPC44328
0.9048	High Similarity	NPC231194
0.9048	High Similarity	NPC177731
0.9048	High Similarity	NPC79056
0.9042	High Similarity	NPC116745
0.9042	High Similarity	NPC249977
0.9042	High Similarity	NPC45400
0.9042	High Similarity	NPC473818
0.903	High Similarity	NPC285108
0.903	High Similarity	NPC33298
0.903	High Similarity	NPC14030
0.903	High Similarity	NPC148273
0.903	High Similarity	NPC291957
0.9029	High Similarity	NPC93065
0.9029	High Similarity	NPC472721
0.9029	High Similarity	NPC31208
0.9029	High Similarity	NPC187632
0.9029	High Similarity	NPC469652
0.9029	High Similarity	NPC160543
0.9029	High Similarity	NPC472724
0.9029	High Similarity	NPC472720
0.9024	High Similarity	NPC166277
0.9024	High Similarity	NPC119125
0.9018	High Similarity	NPC472860
0.9018	High Similarity	NPC474010
0.9018	High Similarity	NPC135222
0.9017	High Similarity	NPC231254
0.9012	High Similarity	NPC170203
0.9012	High Similarity	NPC8940
0.9012	High Similarity	NPC125352
0.9006	High Similarity	NPC476620
0.9006	High Similarity	NPC472387
0.9006	High Similarity	NPC476623
0.9006	High Similarity	NPC476618
0.9006	High Similarity	NPC476619
0.9006	High Similarity	NPC476622
0.9006	High Similarity	NPC476621
0.9	High Similarity	NPC142996
0.8994	High Similarity	NPC472386
0.8994	High Similarity	NPC156977
0.8994	High Similarity	NPC267254
0.8994	High Similarity	NPC47140
0.8994	High Similarity	NPC301683
0.8994	High Similarity	NPC67134
0.8988	High Similarity	NPC61791
0.8988	High Similarity	NPC658
0.8988	High Similarity	NPC197708
0.8988	High Similarity	NPC43587
0.8988	High Similarity	NPC293629
0.8988	High Similarity	NPC210042
0.8988	High Similarity	NPC95855
0.8983	High Similarity	NPC477082
0.8982	High Similarity	NPC236934
0.8982	High Similarity	NPC5778
0.8977	High Similarity	NPC264302
0.8976	High Similarity	NPC67959
0.8976	High Similarity	NPC470898
0.8971	High Similarity	NPC223534
0.8971	High Similarity	NPC158214
0.8971	High Similarity	NPC290289
0.8971	High Similarity	NPC240200
0.897	High Similarity	NPC472859
0.897	High Similarity	NPC25389
0.897	High Similarity	NPC311803
0.8966	High Similarity	NPC469650
0.8963	High Similarity	NPC87317
0.8953	High Similarity	NPC212290
0.8944	High Similarity	NPC228662
0.8941	High Similarity	NPC175230
0.8941	High Similarity	NPC472993
0.8941	High Similarity	NPC172033
0.8941	High Similarity	NPC88560
0.8935	High Similarity	NPC52598
0.8935	High Similarity	NPC183357
0.8935	High Similarity	NPC224462
0.8935	High Similarity	NPC22195
0.8935	High Similarity	NPC21190
0.8935	High Similarity	NPC34287
0.8935	High Similarity	NPC149011
0.8935	High Similarity	NPC471416
0.8935	High Similarity	NPC470272
0.8935	High Similarity	NPC204937
0.8935	High Similarity	NPC44558
0.8929	High Similarity	NPC311389
0.8929	High Similarity	NPC229729
0.8929	High Similarity	NPC93099
0.8929	High Similarity	NPC477502
0.8929	High Similarity	NPC470271
0.8922	High Similarity	NPC99216
0.8922	High Similarity	NPC165720
0.8922	High Similarity	NPC7752
0.892	High Similarity	NPC201814
0.8916	High Similarity	NPC41009
0.8914	High Similarity	NPC65489
0.8914	High Similarity	NPC105591
0.8914	High Similarity	NPC469649
0.8914	High Similarity	NPC260521
0.8909	High Similarity	NPC24164
0.8909	High Similarity	NPC53889
0.8909	High Similarity	NPC289346
0.8895	High Similarity	NPC120952
0.8889	High Similarity	NPC169645
0.8889	High Similarity	NPC63105
0.8889	High Similarity	NPC102028
0.8889	High Similarity	NPC310661
0.8889	High Similarity	NPC105827
0.8889	High Similarity	NPC84482
0.8882	High Similarity	NPC307518
0.8882	High Similarity	NPC5786
0.8882	High Similarity	NPC254540
0.8882	High Similarity	NPC102851
0.8882	High Similarity	NPC256760
0.8882	High Similarity	NPC172807
0.8882	High Similarity	NPC48773
0.8882	High Similarity	NPC205076
0.8882	High Similarity	NPC211594
0.8876	High Similarity	NPC471457
0.8876	High Similarity	NPC195257
0.8876	High Similarity	NPC472381
0.8876	High Similarity	NPC105283
0.8876	High Similarity	NPC112755
0.8876	High Similarity	NPC170675
0.8876	High Similarity	NPC209296
0.8876	High Similarity	NPC472383
0.887	High Similarity	NPC471091
0.887	High Similarity	NPC97924
0.887	High Similarity	NPC40078
0.8869	High Similarity	NPC210073
0.8869	High Similarity	NPC175793
0.8869	High Similarity	NPC115674
0.8862	High Similarity	NPC284960
0.8862	High Similarity	NPC222936
0.8862	High Similarity	NPC88043
0.8862	High Similarity	NPC29830
0.8848	High Similarity	NPC74319
0.8848	High Similarity	NPC287872
0.8844	High Similarity	NPC84494
0.8844	High Similarity	NPC245059
0.8841	High Similarity	NPC88803
0.8841	High Similarity	NPC300845
0.8841	High Similarity	NPC250436
0.8841	High Similarity	NPC471405
0.8841	High Similarity	NPC104983
0.8841	High Similarity	NPC291948

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 NPC34436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1048
0.2-0.3	2209
0.3-0.4	2644
0.4-0.5	1727
0.5-0.6	743
0.6-0.7	227
0.7-0.8	114
0.8-0.85	19
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9068	High Similarity	NPD1465	Phase 2
0.9048	High Similarity	NPD7074	Phase 3
0.8876	High Similarity	NPD7054	Approved
0.8841	High Similarity	NPD4868	Clinical (unspecified phase)
0.8824	High Similarity	NPD7472	Approved
0.8706	High Similarity	NPD3818	Discontinued
0.8671	High Similarity	NPD4338	Clinical (unspecified phase)
0.8663	High Similarity	NPD6797	Phase 2
0.8655	High Similarity	NPD5844	Phase 1
0.8613	High Similarity	NPD7251	Discontinued
0.8596	High Similarity	NPD7228	Approved
0.8563	High Similarity	NPD7808	Phase 3
0.8555	High Similarity	NPD7993	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6166	Phase 2
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1934	Approved
0.8294	Intermediate Similarity	NPD6234	Discontinued
0.8229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD37	Approved
0.8198	Intermediate Similarity	NPD7199	Phase 2
0.8193	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD4967	Phase 2
0.8166	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6232	Discontinued
0.8092	Intermediate Similarity	NPD6959	Discontinued
0.809	Intermediate Similarity	NPD6559	Discontinued
0.809	Intermediate Similarity	NPD7240	Approved
0.809	Intermediate Similarity	NPD7685	Pre-registration
0.8077	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD3817	Phase 2
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3882	Suspended
0.7953	Intermediate Similarity	NPD7819	Suspended
0.7931	Intermediate Similarity	NPD5494	Approved
0.7927	Intermediate Similarity	NPD8151	Discontinued
0.7919	Intermediate Similarity	NPD7075	Discontinued
0.7917	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7865	Intermediate Similarity	NPD3751	Discontinued
0.7849	Intermediate Similarity	NPD8455	Phase 2
0.7846	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7783	Phase 2
0.7805	Intermediate Similarity	NPD7266	Discontinued
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD3750	Approved
0.7746	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3787	Discontinued
0.7738	Intermediate Similarity	NPD1511	Approved
0.7737	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD230	Phase 1
0.7714	Intermediate Similarity	NPD3749	Approved
0.7701	Intermediate Similarity	NPD5402	Approved
0.7665	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1512	Approved
0.7633	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7411	Suspended
0.7577	Intermediate Similarity	NPD7435	Discontinued
0.7577	Intermediate Similarity	NPD7680	Approved
0.7546	Intermediate Similarity	NPD1613	Approved
0.7546	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6799	Approved
0.7515	Intermediate Similarity	NPD6190	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6599	Discontinued
0.747	Intermediate Similarity	NPD3748	Approved
0.7458	Intermediate Similarity	NPD7768	Phase 2
0.7414	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7698	Approved
0.7398	Intermediate Similarity	NPD7696	Phase 3
0.7398	Intermediate Similarity	NPD7697	Approved
0.7396	Intermediate Similarity	NPD6674	Discontinued
0.7384	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD919	Approved
0.7362	Intermediate Similarity	NPD3027	Phase 3
0.736	Intermediate Similarity	NPD8319	Approved
0.736	Intermediate Similarity	NPD8320	Phase 1
0.735	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7874	Approved
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7585	Approved
0.7337	Intermediate Similarity	NPD7701	Phase 2
0.7321	Intermediate Similarity	NPD2796	Approved
0.7317	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD3226	Approved
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7301	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8127	Discontinued
0.7289	Intermediate Similarity	NPD1933	Approved
0.7289	Intermediate Similarity	NPD447	Suspended
0.7287	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7583	Approved
0.7283	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7262	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6823	Phase 2
0.7254	Intermediate Similarity	NPD6535	Approved
0.7254	Intermediate Similarity	NPD6534	Approved
0.7251	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7700	Phase 2
0.7231	Intermediate Similarity	NPD7699	Phase 2
0.7213	Intermediate Similarity	NPD5242	Approved
0.7211	Intermediate Similarity	NPD8150	Discontinued
0.7207	Intermediate Similarity	NPD5353	Approved
0.72	Intermediate Similarity	NPD920	Approved
0.7158	Intermediate Similarity	NPD7229	Phase 3
0.7157	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7126	Intermediate Similarity	NPD1240	Approved
0.7126	Intermediate Similarity	NPD943	Approved
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7118	Intermediate Similarity	NPD2935	Discontinued
0.7118	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD6099	Approved
0.7118	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD7584	Approved
0.7104	Intermediate Similarity	NPD1247	Approved
0.709	Intermediate Similarity	NPD7549	Discontinued
0.7083	Intermediate Similarity	NPD6843	Phase 3
0.7083	Intermediate Similarity	NPD6841	Approved
0.7083	Intermediate Similarity	NPD6842	Approved
0.7076	Intermediate Similarity	NPD2346	Discontinued
0.7065	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD5711	Approved
0.7041	Intermediate Similarity	NPD1607	Approved
0.7037	Intermediate Similarity	NPD9269	Phase 2
0.703	Intermediate Similarity	NPD9494	Approved
0.7029	Intermediate Similarity	NPD7390	Discontinued
0.7026	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6212	Phase 3
0.7026	Intermediate Similarity	NPD6213	Phase 3
0.7017	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD5006	Approved
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1652	Phase 2
0.6994	Remote Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD2800	Approved
0.6989	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4908	Phase 1
0.6984	Remote Similarity	NPD5953	Discontinued
0.6982	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5124	Phase 1
0.6968	Remote Similarity	NPD7286	Phase 2
0.6959	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7930	Approved
0.6954	Remote Similarity	NPD7003	Approved
0.6947	Remote Similarity	NPD7039	Approved
0.6947	Remote Similarity	NPD7038	Approved
0.6944	Remote Similarity	NPD6385	Approved
0.6944	Remote Similarity	NPD6386	Approved
0.6944	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4060	Phase 1
0.6919	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7177	Discontinued
0.6909	Remote Similarity	NPD2797	Approved
0.6905	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3764	Approved
0.6905	Remote Similarity	NPD6798	Discontinued
0.6905	Remote Similarity	NPD3268	Approved
0.6901	Remote Similarity	NPD7097	Phase 1
0.6886	Remote Similarity	NPD6832	Phase 2
0.6884	Remote Similarity	NPD4420	Approved
0.6882	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4287	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