NPASS Compound

Structure

CID289771 OpenBabel06191716092D 33 36 0 0 1 0 0 0 0 0999 V2000 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -6.0622 -0.5000 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 -4.3301 1.5000 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 2 2 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 22 1 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 9 25 1 0 0 0 0 10 13 2 0 0 0 0 10 32 1 0 0 0 0 11 5 1 6 0 0 0 11 14 1 0 0 0 0 11 33 1 0 0 0 0 12 15 2 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 26 1 1 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 19 1 0 0 0 0 17 29 1 6 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 19 31 1 1 0 0 0 20 32 1 0 0 0 0 21 12 1 6 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.1
Volume:	421.937
LogP:	0.079
LogD:	-0.192
LogS:	-2.992
# Rotatable Bonds:	3
TPSA:	221.51
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	4.159
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.318
MDCK Permeability:	4.315979822422378e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.883
Human Intestinal Absorption (HIA):	0.887
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	92.90829467773438%
Volume Distribution (VD):	0.796
Pgp-substrate:	13.56098461151123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	3.358
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.864
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.812
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC289771

Natural Product ID:	NPC289771
*Common Name:**	Quercetin-6-C-Beta-D-Glucopyranoside
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms:
Standard InCHIKey:	IDPMRJRWHIXCDU-DSTJRUDUSA-N
Standard InCHI:	InChI=1S/C21H20O12/c22-5-11-14(26)17(29)19(31)21(33-11)12-9(25)4-10-13(15(12)27)16(28)18(30)20(32-10)6-1-2-7(23)8(24)3-6/h1-4,11,14,17,19,21-27,29-31H,5H2/t11-,14-,17+,19-,21+/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561741
PubChem CID:	21676320
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides

*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
NPO7764	Ulmus wallichiana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19596573]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7764	Ulmus wallichiana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10904	Panax arboreus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24507	Kalmia angustifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15288	Zelkova serrata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23797	Skimmia reevesiana	Species	Rutaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	15.6	%	PMID[533095]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	8.56	%	PMID[533095]

☑ 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 NPC289771 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	474
0.1-0.2	1816
0.2-0.3	4293
0.3-0.4	10146
0.4-0.5	7892
0.5-0.6	3949
0.6-0.7	5058
0.7-0.8	4873
0.8-0.85	2051
0.85-0.9	1452
0.9-0.95	682
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC117418
0.9868	High Similarity	NPC53545
0.9742	High Similarity	NPC472625
0.974	High Similarity	NPC26326
0.974	High Similarity	NPC471499
0.9739	High Similarity	NPC22192
0.9682	High Similarity	NPC260266
0.9675	High Similarity	NPC470326
0.9675	High Similarity	NPC282009
0.9675	High Similarity	NPC287328
0.9618	High Similarity	NPC471213
0.9613	High Similarity	NPC474038
0.9613	High Similarity	NPC142252
0.9605	High Similarity	NPC268193
0.9548	High Similarity	NPC119209
0.9548	High Similarity	NPC475784
0.9548	High Similarity	NPC118256
0.9548	High Similarity	NPC192686
0.9545	High Similarity	NPC474055
0.9545	High Similarity	NPC472598
0.9542	High Similarity	NPC111341
0.9542	High Similarity	NPC321779
0.9542	High Similarity	NPC304745
0.9539	High Similarity	NPC19721
0.9539	High Similarity	NPC240476
0.9539	High Similarity	NPC9743
0.9539	High Similarity	NPC61506
0.9539	High Similarity	NPC260491
0.9539	High Similarity	NPC36835
0.9539	High Similarity	NPC246162
0.9487	High Similarity	NPC472632
0.9487	High Similarity	NPC472634
0.9481	High Similarity	NPC291878
0.9481	High Similarity	NPC195796
0.9481	High Similarity	NPC471500
0.9481	High Similarity	NPC250922
0.9481	High Similarity	NPC35038
0.9481	High Similarity	NPC278778
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9477	High Similarity	NPC27532
0.9477	High Similarity	NPC192083
0.9477	High Similarity	NPC325028
0.9477	High Similarity	NPC246328
0.9477	High Similarity	NPC213896
0.9477	High Similarity	NPC256346
0.9474	High Similarity	NPC209846
0.9474	High Similarity	NPC328740
0.9474	High Similarity	NPC289774
0.9474	High Similarity	NPC477897
0.9437	High Similarity	NPC102277
0.9437	High Similarity	NPC279209
0.943	High Similarity	NPC277205
0.943	High Similarity	NPC36
0.943	High Similarity	NPC36916
0.943	High Similarity	NPC470457
0.943	High Similarity	NPC62261
0.943	High Similarity	NPC72787
0.943	High Similarity	NPC7154
0.943	High Similarity	NPC7688
0.943	High Similarity	NPC125039
0.943	High Similarity	NPC58223
0.9427	High Similarity	NPC476247
0.9427	High Similarity	NPC211107
0.9427	High Similarity	NPC474033
0.9427	High Similarity	NPC472635
0.9427	High Similarity	NPC474034
0.9423	High Similarity	NPC174953
0.9423	High Similarity	NPC470183
0.9423	High Similarity	NPC472631
0.9423	High Similarity	NPC472630
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC291508
0.9419	High Similarity	NPC473272
0.9419	High Similarity	NPC471209
0.9419	High Similarity	NPC284820
0.9419	High Similarity	NPC27337
0.9416	High Similarity	NPC259710
0.9416	High Similarity	NPC48579
0.9416	High Similarity	NPC304207
0.9416	High Similarity	NPC217706
0.9416	High Similarity	NPC45849
0.9416	High Similarity	NPC200761
0.9416	High Similarity	NPC470327
0.9416	High Similarity	NPC133392
0.9416	High Similarity	NPC477503
0.9416	High Similarity	NPC207809
0.9412	High Similarity	NPC244583
0.9412	High Similarity	NPC56232
0.9412	High Similarity	NPC106976
0.9412	High Similarity	NPC157784
0.9412	High Similarity	NPC150123
0.9412	High Similarity	NPC37684
0.9412	High Similarity	NPC161881
0.9412	High Similarity	NPC10807
0.9412	High Similarity	NPC63187
0.9383	High Similarity	NPC294629
0.9379	High Similarity	NPC257667
0.9379	High Similarity	NPC186847
0.9379	High Similarity	NPC472454
0.9375	High Similarity	NPC107627
0.9375	High Similarity	NPC475212
0.9371	High Similarity	NPC308404
0.9371	High Similarity	NPC253662
0.9371	High Similarity	NPC276222
0.9371	High Similarity	NPC145038
0.9371	High Similarity	NPC88789
0.9371	High Similarity	NPC179950
0.9371	High Similarity	NPC13481
0.9371	High Similarity	NPC197285
0.9371	High Similarity	NPC118284
0.9371	High Similarity	NPC274618
0.9371	High Similarity	NPC56077
0.9371	High Similarity	NPC281131
0.9371	High Similarity	NPC21100
0.9371	High Similarity	NPC207575
0.9367	High Similarity	NPC470459
0.9367	High Similarity	NPC186686
0.9363	High Similarity	NPC288131
0.9363	High Similarity	NPC305987
0.9363	High Similarity	NPC471211
0.9363	High Similarity	NPC158188
0.9363	High Similarity	NPC198829
0.9363	High Similarity	NPC66618
0.9363	High Similarity	NPC113163
0.9363	High Similarity	NPC228383
0.9363	High Similarity	NPC471212
0.9363	High Similarity	NPC84324
0.9363	High Similarity	NPC112418
0.9363	High Similarity	NPC471210
0.9363	High Similarity	NPC165970
0.9359	High Similarity	NPC172202
0.9359	High Similarity	NPC284127
0.9359	High Similarity	NPC476410
0.9359	High Similarity	NPC473990
0.9355	High Similarity	NPC209614
0.9355	High Similarity	NPC470328
0.9355	High Similarity	NPC201837
0.9355	High Similarity	NPC472626
0.9351	High Similarity	NPC141212
0.9351	High Similarity	NPC326592
0.9351	High Similarity	NPC109594
0.9351	High Similarity	NPC244250
0.9351	High Similarity	NPC20907
0.9351	High Similarity	NPC248793
0.9351	High Similarity	NPC298692
0.9351	High Similarity	NPC112701
0.9351	High Similarity	NPC74924
0.9351	High Similarity	NPC18727
0.9351	High Similarity	NPC180301
0.9346	High Similarity	NPC278476
0.9346	High Similarity	NPC304295
0.9346	High Similarity	NPC262039
0.9346	High Similarity	NPC254412
0.9346	High Similarity	NPC319910
0.9346	High Similarity	NPC205046
0.9346	High Similarity	NPC262038
0.9346	High Similarity	NPC59162
0.9317	High Similarity	NPC78734
0.9317	High Similarity	NPC218488
0.9317	High Similarity	NPC150767
0.9313	High Similarity	NPC295082
0.9313	High Similarity	NPC127546
0.9313	High Similarity	NPC158761
0.9313	High Similarity	NPC52550
0.9313	High Similarity	NPC317489
0.9313	High Similarity	NPC470456
0.9313	High Similarity	NPC92565
0.9313	High Similarity	NPC84362
0.9313	High Similarity	NPC160156
0.9313	High Similarity	NPC173637
0.9313	High Similarity	NPC223424
0.9308	High Similarity	NPC475888
0.9308	High Similarity	NPC19388
0.9308	High Similarity	NPC55786
0.9308	High Similarity	NPC240431
0.9304	High Similarity	NPC471745
0.9304	High Similarity	NPC474150
0.9304	High Similarity	NPC219927
0.9304	High Similarity	NPC474162
0.9304	High Similarity	NPC77660
0.9304	High Similarity	NPC220912
0.9304	High Similarity	NPC189142
0.9299	High Similarity	NPC328102
0.9299	High Similarity	NPC472624
0.9299	High Similarity	NPC101731
0.9299	High Similarity	NPC471744
0.9299	High Similarity	NPC263449
0.9299	High Similarity	NPC36217
0.9299	High Similarity	NPC321399
0.9295	High Similarity	NPC183851
0.9295	High Similarity	NPC223787
0.9295	High Similarity	NPC52889
0.9295	High Similarity	NPC67876
0.9295	High Similarity	NPC63454
0.9295	High Similarity	NPC237418
0.929	High Similarity	NPC226025

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 NPC289771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	932
0.2-0.3	1880
0.3-0.4	2652
0.4-0.5	1794
0.5-0.6	940
0.6-0.7	357
0.7-0.8	118
0.8-0.85	20
0.85-0.9	23
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD2393	Clinical (unspecified phase)
0.943	High Similarity	NPD6167	Clinical (unspecified phase)
0.943	High Similarity	NPD6168	Clinical (unspecified phase)
0.943	High Similarity	NPD6166	Phase 2
0.9286	High Similarity	NPD1934	Approved
0.9281	High Similarity	NPD4380	Phase 2
0.9145	High Similarity	NPD1512	Approved
0.9141	High Similarity	NPD6797	Phase 2
0.9085	High Similarity	NPD7251	Discontinued
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.9018	High Similarity	NPD7054	Approved
0.9013	High Similarity	NPD1511	Approved
0.8981	High Similarity	NPD2801	Approved
0.8963	High Similarity	NPD7472	Approved
0.8963	High Similarity	NPD7074	Phase 3
0.8957	High Similarity	NPD3818	Discontinued
0.8954	High Similarity	NPD4378	Clinical (unspecified phase)
0.8931	High Similarity	NPD7075	Discontinued
0.8931	High Similarity	NPD4381	Clinical (unspecified phase)
0.8924	High Similarity	NPD3817	Phase 2
0.8916	High Similarity	NPD7808	Phase 3
0.8902	High Similarity	NPD7804	Clinical (unspecified phase)
0.8868	High Similarity	NPD3882	Suspended
0.8868	High Similarity	NPD4868	Clinical (unspecified phase)
0.8797	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8683	High Similarity	NPD7993	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8589	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD5402	Approved
0.8562	High Similarity	NPD1549	Phase 2
0.8481	Intermediate Similarity	NPD5403	Approved
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8354	Intermediate Similarity	NPD5401	Approved
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8312	Intermediate Similarity	NPD2796	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8291	Intermediate Similarity	NPD6799	Approved
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8098	Intermediate Similarity	NPD6599	Discontinued
0.8095	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD919	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1607	Approved
0.7875	Intermediate Similarity	NPD3750	Approved
0.7861	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7836	Intermediate Similarity	NPD3787	Discontinued
0.7826	Intermediate Similarity	NPD6190	Approved
0.7814	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3027	Phase 3
0.7758	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2800	Approved
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7683	Intermediate Similarity	NPD2534	Approved
0.7683	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD2533	Approved
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7609	Intermediate Similarity	NPD4360	Phase 2
0.7609	Intermediate Similarity	NPD4363	Phase 3
0.7595	Intermediate Similarity	NPD230	Phase 1
0.7594	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7562	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7557	Intermediate Similarity	NPD7228	Approved
0.7547	Intermediate Similarity	NPD6651	Approved
0.7539	Intermediate Similarity	NPD7584	Approved
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD3226	Approved
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD1243	Approved
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7416	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7375	Intermediate Similarity	NPD5124	Phase 1
0.7375	Intermediate Similarity	NPD447	Suspended
0.7375	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7256	Intermediate Similarity	NPD2344	Approved
0.7247	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD5711	Approved
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD9494	Approved
0.7212	Intermediate Similarity	NPD2424	Discontinued
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7209	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7208	Intermediate Similarity	NPD7801	Approved
0.7205	Intermediate Similarity	NPD4060	Phase 1
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7179	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD6355	Discontinued
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD7585	Approved
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7104	Intermediate Similarity	NPD7240	Approved
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7092	Intermediate Similarity	NPD7583	Approved
0.7083	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.7066	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2403	Approved
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3823	Discontinued
0.7044	Intermediate Similarity	NPD4665	Approved
0.7044	Intermediate Similarity	NPD4111	Phase 1
0.7044	Intermediate Similarity	NPD2798	Approved
0.7039	Intermediate Similarity	NPD7229	Phase 3
0.7025	Intermediate Similarity	NPD3225	Approved
0.701	Intermediate Similarity	NPD2493	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