NPASS Compound

Structure

CID34531 OpenBabel06191715362D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3794 1.2260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 2.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 -0.7626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 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 -0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 9 1 0 0 0 0 2 6 1 0 0 0 0 2 10 2 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 21 1 0 0 0 0 6 18 1 0 0 0 0 7 22 1 0 0 0 0 8 13 2 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 30 1 0 0 0 0 12 5 1 1 0 0 0 12 15 1 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 6 0 0 0 16 19 1 0 0 0 0 16 28 2 0 0 0 0 17 20 1 0 0 0 0 17 29 1 1 0 0 0 18 19 2 0 0 0 0 18 30 1 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.08
Volume:	404.641
LogP:	0.602
LogD:	-0.051
LogS:	-4.186
# Rotatable Bonds:	4
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	3.98
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.244
MDCK Permeability:	8.377064659725875e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.623
Human Intestinal Absorption (HIA):	0.721
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	88.35578918457031%
Volume Distribution (VD):	0.863
Pgp-substrate:	16.457311630249023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.242
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	4.927
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.947
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.855
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC34531

Natural Product ID:	NPC34531
*Common Name:**	Myricetin-3-O-Alpha-L-Arabinofuranoside
IUPAC Name:	3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	OXJKSVCEIOYZQL-IEGSVRCHSA-N
Standard InCHI:	InChI=1S/C20H18O12/c21-5-12-15(27)17(29)20(31-12)32-19-16(28)13-8(23)3-7(22)4-11(13)30-18(19)6-1-9(24)14(26)10(25)2-6/h1-4,12,15,17,20-27,29H,5H2/t12-,15-,17+,20-/m0/s1
SMILES:	c1c(cc(c(c1O)O)O)c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497046
PubChem CID:	14524431
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/S1572-557X(05)02007-6]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	27800.0	nM	PMID[523467]

☑ 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 NPC34531 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	453
0.1-0.2	1864
0.2-0.3	4198
0.3-0.4	9590
0.4-0.5	8829
0.5-0.6	4157
0.6-0.7	5243
0.7-0.8	5344
0.8-0.85	1681
0.85-0.9	1092
0.9-0.95	233
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC255615
0.9936	High Similarity	NPC67037
0.981	High Similarity	NPC476771
0.9809	High Similarity	NPC254306
0.9747	High Similarity	NPC48640
0.9747	High Similarity	NPC149244
0.9745	High Similarity	NPC55786
0.9745	High Similarity	NPC19388
0.9745	High Similarity	NPC240431
0.9688	High Similarity	NPC245452
0.9688	High Similarity	NPC476772
0.9684	High Similarity	NPC253662
0.9684	High Similarity	NPC88789
0.9684	High Similarity	NPC135599
0.9684	High Similarity	NPC274618
0.9684	High Similarity	NPC277174
0.9684	High Similarity	NPC113968
0.9684	High Similarity	NPC118284
0.9684	High Similarity	NPC179950
0.9684	High Similarity	NPC73855
0.9684	High Similarity	NPC328940
0.9684	High Similarity	NPC281131
0.9684	High Similarity	NPC145038
0.9684	High Similarity	NPC56077
0.9684	High Similarity	NPC276222
0.9684	High Similarity	NPC308404
0.9625	High Similarity	NPC72249
0.9623	High Similarity	NPC127546
0.9623	High Similarity	NPC223424
0.9623	High Similarity	NPC325555
0.9623	High Similarity	NPC52550
0.9623	High Similarity	NPC84362
0.9623	High Similarity	NPC173637
0.9623	High Similarity	NPC317489
0.9623	High Similarity	NPC265530
0.9623	High Similarity	NPC226304
0.962	High Similarity	NPC277205
0.9563	High Similarity	NPC219904
0.9563	High Similarity	NPC225434
0.9563	High Similarity	NPC138927
0.9563	High Similarity	NPC203050
0.9563	High Similarity	NPC223747
0.9563	High Similarity	NPC120099
0.956	High Similarity	NPC197285
0.956	High Similarity	NPC21100
0.9509	High Similarity	NPC296018
0.9509	High Similarity	NPC154741
0.9503	High Similarity	NPC116864
0.9503	High Similarity	NPC255157
0.9503	High Similarity	NPC95866
0.9503	High Similarity	NPC235260
0.9503	High Similarity	NPC20505
0.9503	High Similarity	NPC155763
0.9503	High Similarity	NPC206123
0.9503	High Similarity	NPC254855
0.9503	High Similarity	NPC67326
0.9503	High Similarity	NPC29958
0.9503	High Similarity	NPC244776
0.9503	High Similarity	NPC259896
0.9503	High Similarity	NPC156869
0.9503	High Similarity	NPC136042
0.95	High Similarity	NPC92565
0.95	High Similarity	NPC160156
0.95	High Similarity	NPC275454
0.9494	High Similarity	NPC77660
0.9494	High Similarity	NPC473043
0.9494	High Similarity	NPC189142
0.9487	High Similarity	NPC288084
0.9451	High Similarity	NPC476773
0.9444	High Similarity	NPC60735
0.9444	High Similarity	NPC190003
0.9444	High Similarity	NPC153755
0.9444	High Similarity	NPC175107
0.9444	High Similarity	NPC203259
0.9444	High Similarity	NPC33054
0.9444	High Similarity	NPC471748
0.9444	High Similarity	NPC176740
0.9444	High Similarity	NPC471725
0.9444	High Similarity	NPC26230
0.9444	High Similarity	NPC155877
0.9444	High Similarity	NPC134532
0.9441	High Similarity	NPC52382
0.9441	High Similarity	NPC270578
0.9441	High Similarity	NPC227508
0.9434	High Similarity	NPC284960
0.9434	High Similarity	NPC168822
0.9434	High Similarity	NPC19709
0.9434	High Similarity	NPC191306
0.9434	High Similarity	NPC270335
0.9434	High Similarity	NPC222936
0.9387	High Similarity	NPC101026
0.9387	High Similarity	NPC169977
0.9387	High Similarity	NPC42773
0.9387	High Similarity	NPC4390
0.9387	High Similarity	NPC24043
0.9387	High Similarity	NPC45522
0.9387	High Similarity	NPC21666
0.9383	High Similarity	NPC67105
0.9383	High Similarity	NPC245014
0.9383	High Similarity	NPC84265
0.9383	High Similarity	NPC282987
0.9383	High Similarity	NPC285197
0.9379	High Similarity	NPC76482
0.9375	High Similarity	NPC22832
0.9375	High Similarity	NPC311830
0.9371	High Similarity	NPC300537
0.9371	High Similarity	NPC127782
0.9337	High Similarity	NPC473071
0.9337	High Similarity	NPC473073
0.9329	High Similarity	NPC19108
0.9329	High Similarity	NPC237435
0.9329	High Similarity	NPC135277
0.9329	High Similarity	NPC210094
0.9329	High Similarity	NPC49344
0.9329	High Similarity	NPC101191
0.9329	High Similarity	NPC294629
0.9329	High Similarity	NPC253685
0.9329	High Similarity	NPC473327
0.9329	High Similarity	NPC476472
0.9329	High Similarity	NPC223426
0.9329	High Similarity	NPC81042
0.9329	High Similarity	NPC34267
0.9329	High Similarity	NPC16194
0.9329	High Similarity	NPC115760
0.9329	High Similarity	NPC220173
0.9329	High Similarity	NPC214621
0.9329	High Similarity	NPC294815
0.9329	High Similarity	NPC43211
0.9325	High Similarity	NPC476405
0.9325	High Similarity	NPC235575
0.9325	High Similarity	NPC117260
0.9317	High Similarity	NPC8856
0.9317	High Similarity	NPC115674
0.9317	High Similarity	NPC210073
0.9313	High Similarity	NPC309025
0.9313	High Similarity	NPC29830
0.9313	High Similarity	NPC243930
0.9313	High Similarity	NPC88043
0.9313	High Similarity	NPC88023
0.9299	High Similarity	NPC261866
0.9281	High Similarity	NPC473072
0.9273	High Similarity	NPC8573
0.9273	High Similarity	NPC89127
0.9273	High Similarity	NPC472385
0.9273	High Similarity	NPC198324
0.9273	High Similarity	NPC470949
0.9273	High Similarity	NPC65563
0.9273	High Similarity	NPC292019
0.9273	High Similarity	NPC144097
0.9273	High Similarity	NPC122467
0.9273	High Similarity	NPC219043
0.9273	High Similarity	NPC61904
0.9273	High Similarity	NPC471669
0.9273	High Similarity	NPC14187
0.9273	High Similarity	NPC202908
0.9264	High Similarity	NPC212748
0.9259	High Similarity	NPC229729
0.9259	High Similarity	NPC42892
0.9259	High Similarity	NPC58716
0.9259	High Similarity	NPC146792
0.9259	High Similarity	NPC45618
0.9255	High Similarity	NPC165720
0.925	High Similarity	NPC150164
0.9245	High Similarity	NPC269906
0.9245	High Similarity	NPC110349
0.9241	High Similarity	NPC133671
0.9241	High Similarity	NPC54802
0.9241	High Similarity	NPC197304
0.9241	High Similarity	NPC135391
0.9241	High Similarity	NPC78263
0.9241	High Similarity	NPC77672
0.9217	High Similarity	NPC217520
0.9217	High Similarity	NPC37668
0.9217	High Similarity	NPC251417
0.9217	High Similarity	NPC173837
0.9217	High Similarity	NPC258044
0.9217	High Similarity	NPC139571
0.9217	High Similarity	NPC113836
0.9217	High Similarity	NPC35167
0.9217	High Similarity	NPC217387
0.9217	High Similarity	NPC293626
0.9217	High Similarity	NPC267680
0.9217	High Similarity	NPC168584
0.9217	High Similarity	NPC196127
0.9217	High Similarity	NPC89052
0.9217	High Similarity	NPC253521
0.9212	High Similarity	NPC472607
0.9212	High Similarity	NPC264735
0.9212	High Similarity	NPC477848
0.9207	High Similarity	NPC261254
0.9202	High Similarity	NPC58053
0.9202	High Similarity	NPC195257
0.9202	High Similarity	NPC186807
0.9202	High Similarity	NPC226294
0.9202	High Similarity	NPC86008
0.9202	High Similarity	NPC469931
0.9202	High Similarity	NPC201292
0.9202	High Similarity	NPC93337
0.9202	High Similarity	NPC475942
0.9202	High Similarity	NPC209296

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 NPC34531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	911
0.2-0.3	2089
0.3-0.4	2699
0.4-0.5	1772
0.5-0.6	859
0.6-0.7	279
0.7-0.8	108
0.8-0.85	13
0.85-0.9	21
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD3818	Discontinued
0.9444	High Similarity	NPD6797	Phase 2
0.9387	High Similarity	NPD7251	Discontinued
0.9329	High Similarity	NPD4338	Clinical (unspecified phase)
0.9212	High Similarity	NPD7808	Phase 3
0.9202	High Similarity	NPD7054	Approved
0.9146	High Similarity	NPD7472	Approved
0.903	High Similarity	NPD7074	Phase 3
0.9	High Similarity	NPD4381	Clinical (unspecified phase)
0.8938	High Similarity	NPD3882	Suspended
0.8875	High Similarity	NPD3817	Phase 2
0.8855	High Similarity	NPD7804	Clinical (unspecified phase)
0.8846	High Similarity	NPD1512	Approved
0.8788	High Similarity	NPD6168	Clinical (unspecified phase)
0.8788	High Similarity	NPD6167	Clinical (unspecified phase)
0.8788	High Similarity	NPD6166	Phase 2
0.875	High Similarity	NPD1934	Approved
0.8718	High Similarity	NPD1511	Approved
0.8696	High Similarity	NPD2801	Approved
0.8696	High Similarity	NPD2393	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6559	Discontinued
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7075	Discontinued
0.8415	Intermediate Similarity	NPD5402	Approved
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD5403	Approved
0.8314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6799	Approved
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5401	Approved
0.8101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1549	Phase 2
0.8049	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7953	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD919	Approved
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7925	Intermediate Similarity	NPD2796	Approved
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD37	Approved
0.7849	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD7228	Approved
0.7824	Intermediate Similarity	NPD4966	Approved
0.7824	Intermediate Similarity	NPD4967	Phase 2
0.7824	Intermediate Similarity	NPD4965	Approved
0.7811	Intermediate Similarity	NPD1465	Phase 2
0.7811	Intermediate Similarity	NPD7819	Suspended
0.7803	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7765	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3926	Phase 2
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7685	Pre-registration
0.7746	Intermediate Similarity	NPD6959	Discontinued
0.7722	Intermediate Similarity	NPD1613	Approved
0.7722	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7411	Suspended
0.7684	Intermediate Similarity	NPD5844	Phase 1
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD943	Approved
0.761	Intermediate Similarity	NPD1240	Approved
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7562	Intermediate Similarity	NPD230	Phase 1
0.7545	Intermediate Similarity	NPD2534	Approved
0.7545	Intermediate Similarity	NPD2532	Approved
0.7545	Intermediate Similarity	NPD2533	Approved
0.7516	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3750	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7471	Intermediate Similarity	NPD3749	Approved
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2800	Approved
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7439	Intermediate Similarity	NPD7266	Discontinued
0.7423	Intermediate Similarity	NPD7584	Approved
0.7423	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7416	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7240	Approved
0.7353	Intermediate Similarity	NPD920	Approved
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7349	Intermediate Similarity	NPD1243	Approved
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD1933	Approved
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7768	Phase 2
0.7299	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7697	Approved
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD447	Suspended
0.7231	Intermediate Similarity	NPD7871	Phase 2
0.7231	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7874	Approved
0.7212	Intermediate Similarity	NPD3748	Approved
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7208	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD1091	Approved
0.7127	Intermediate Similarity	NPD2403	Approved
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2344	Approved
0.712	Intermediate Similarity	NPD5953	Discontinued
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.71	Intermediate Similarity	NPD7801	Approved
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7098	Intermediate Similarity	NPD7700	Phase 2
0.7098	Intermediate Similarity	NPD7699	Phase 2
0.7091	Intermediate Similarity	NPD6651	Approved
0.7069	Intermediate Similarity	NPD3226	Approved
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7056	Intermediate Similarity	NPD8319	Approved
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD2163	Approved
0.7041	Intermediate Similarity	NPD6823	Phase 2
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7035	Intermediate Similarity	NPD7585	Approved
0.7026	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2798	Approved
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.7011	Intermediate Similarity	NPD7286	Phase 2
0.6987	Remote Similarity	NPD1548	Phase 1
0.6985	Remote Similarity	NPD7583	Approved
0.6984	Remote Similarity	NPD8150	Discontinued
0.6981	Remote Similarity	NPD9269	Phase 2
0.6977	Remote Similarity	NPD7390	Discontinued
0.6975	Remote Similarity	NPD9494	Approved
0.6971	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2309	Approved
0.6943	Remote Similarity	NPD4360	Phase 2
0.6943	Remote Similarity	NPD4363	Phase 3
0.6941	Remote Similarity	NPD6674	Discontinued
0.6941	Remote Similarity	NPD2654	Approved
0.6941	Remote Similarity	NPD1652	Phase 2
0.6937	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7680	Approved
0.6918	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7930	Approved
0.6907	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4361	Phase 2
0.6905	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2799	Discontinued
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5353	Approved
0.6869	Remote Similarity	NPD5006	Approved
0.6869	Remote Similarity	NPD5005	Approved
0.6867	Remote Similarity	NPD4060	Phase 1
0.6854	Remote Similarity	NPD6844	Discontinued
0.6848	Remote Similarity	NPD3268	Approved
0.6839	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7229	Phase 3
0.6829	Remote Similarity	NPD4908	Phase 1
0.6826	Remote Similarity	NPD4340	Discontinued
0.6824	Remote Similarity	NPD2346	Discontinued
0.6813	Remote Similarity	NPD1610	Phase 2

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