NPASS Compound

Structure

NPC475366 OpenBabel07101719252D 45 49 0 0 1 0 0 0 0 0999 V2000 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 1.7321 3.0000 0.0000 O 0 0 0 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -0.8660 -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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 40 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 41 1 0 0 0 0 12 1 1 1 0 0 0 12 23 1 0 0 0 0 12 42 1 0 0 0 0 13 17 1 0 0 0 0 14 43 1 0 0 0 0 15 22 1 0 0 0 0 15 31 2 0 0 0 0 16 18 2 0 0 0 0 16 38 1 0 0 0 0 17 44 1 0 0 0 0 18 39 1 0 0 0 0 19 22 2 0 0 0 0 19 40 1 0 0 0 0 20 22 1 0 0 0 0 20 44 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 45 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 26 1 0 0 0 0 24 33 1 6 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 26 28 1 0 0 0 0 26 35 1 1 0 0 0 27 29 1 0 0 0 0 27 36 1 6 0 0 0 28 30 1 0 0 0 0 28 37 1 6 0 0 0 29 41 1 6 0 0 0 29 42 1 0 0 0 0 30 43 1 1 0 0 0 30 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.21
Volume:	595.415
LogP:	1.354
LogD:	1.17
LogS:	-4.103
# Rotatable Bonds:	9
TPSA:	216.2
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	4.614
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.219
MDCK Permeability:	5.2010400395374745e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.805
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	66.63922119140625%
Volume Distribution (VD):	0.648
Pgp-substrate:	18.161439895629883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.188
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	2.036
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.608
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.485
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.166
Carcinogencity:	0.158
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC475366

Natural Product ID:	NPC475366
*Common Name:**	5,7,4'-Trimethoxyflavone-7-O-Glucorhamnoside
IUPAC Name:	2-(3,4-dimethoxyphenyl)-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	BZSRRACZBYSKRB-UPMDXQIVSA-N
Standard InCHI:	InChI=1S/C30H36O15/c1-12-23(32)25(34)27(36)29(42-12)41-11-21-24(33)26(35)28(37)30(45-21)43-14-8-19(40-4)22-15(31)10-17(44-20(22)9-14)13-5-6-16(38-2)18(7-13)39-3/h5-10,12,21,23-30,32-37H,11H2,1-4H3/t12-,21-,23-,24-,25+,26+,27-,28-,29+,30-/m1/s1
SMILES:	COc1cc(O[C@@H]2O[C@H](CO[C@H]3O[C@H](C)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)cc2c1c(=O)cc(o2)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504375
PubChem CID:	44575347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Inhibition	=	67.0	%	PMID[456380]

☑ 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 NPC475366 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	438
0.1-0.2	1776
0.2-0.3	3918
0.3-0.4	9537
0.4-0.5	8740
0.5-0.6	4683
0.6-0.7	5606
0.7-0.8	5401
0.8-0.85	1616
0.85-0.9	543
0.9-0.95	364
0.95-1	75

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475497
1.0	High Similarity	NPC284277
0.9872	High Similarity	NPC15358
0.981	High Similarity	NPC195257
0.981	High Similarity	NPC209296
0.9806	High Similarity	NPC182045
0.9742	High Similarity	NPC110349
0.9688	High Similarity	NPC475155
0.9686	High Similarity	NPC86008
0.9686	High Similarity	NPC61791
0.9686	High Similarity	NPC293629
0.9684	High Similarity	NPC210073
0.9684	High Similarity	NPC115674
0.9682	High Similarity	NPC309025
0.9682	High Similarity	NPC88023
0.9682	High Similarity	NPC243930
0.9627	High Similarity	NPC208668
0.9627	High Similarity	NPC204693
0.9625	High Similarity	NPC44328
0.9625	High Similarity	NPC177731
0.9625	High Similarity	NPC293004
0.9625	High Similarity	NPC79056
0.9625	High Similarity	NPC231194
0.9625	High Similarity	NPC105095
0.9625	High Similarity	NPC51326
0.962	High Similarity	NPC311830
0.962	High Similarity	NPC22832
0.9568	High Similarity	NPC473327
0.9568	High Similarity	NPC198199
0.9568	High Similarity	NPC476472
0.9568	High Similarity	NPC19108
0.9568	High Similarity	NPC220173
0.9568	High Similarity	NPC294815
0.9568	High Similarity	NPC16194
0.9565	High Similarity	NPC256760
0.9565	High Similarity	NPC180918
0.9563	High Similarity	NPC43587
0.956	High Similarity	NPC5778
0.956	High Similarity	NPC236934
0.956	High Similarity	NPC8856
0.9557	High Similarity	NPC284960
0.9557	High Similarity	NPC19709
0.9557	High Similarity	NPC191306
0.9557	High Similarity	NPC222936
0.9557	High Similarity	NPC270335
0.9548	High Similarity	NPC473657
0.9548	High Similarity	NPC295613
0.9509	High Similarity	NPC48984
0.9503	High Similarity	NPC67105
0.9503	High Similarity	NPC285197
0.9503	High Similarity	NPC150767
0.9503	High Similarity	NPC52353
0.9503	High Similarity	NPC95866
0.9503	High Similarity	NPC78734
0.9503	High Similarity	NPC194483
0.95	High Similarity	NPC229729
0.95	High Similarity	NPC135345
0.9494	High Similarity	NPC77660
0.9494	High Similarity	NPC473043
0.9494	High Similarity	NPC189142
0.9451	High Similarity	NPC173837
0.9451	High Similarity	NPC475261
0.9451	High Similarity	NPC251417
0.9451	High Similarity	NPC89052
0.9451	High Similarity	NPC120952
0.9448	High Similarity	NPC102028
0.9444	High Similarity	NPC60735
0.9444	High Similarity	NPC203259
0.9444	High Similarity	NPC267254
0.9444	High Similarity	NPC33054
0.9444	High Similarity	NPC261254
0.9444	High Similarity	NPC471748
0.9444	High Similarity	NPC176740
0.9444	High Similarity	NPC471725
0.9444	High Similarity	NPC3583
0.9444	High Similarity	NPC26230
0.9444	High Similarity	NPC155877
0.9444	High Similarity	NPC259152
0.9444	High Similarity	NPC134532
0.9441	High Similarity	NPC472383
0.9441	High Similarity	NPC226294
0.9441	High Similarity	NPC229687
0.9441	High Similarity	NPC203050
0.9441	High Similarity	NPC219904
0.9441	High Similarity	NPC472381
0.9441	High Similarity	NPC58053
0.9441	High Similarity	NPC186807
0.9441	High Similarity	NPC475942
0.9441	High Similarity	NPC105025
0.9441	High Similarity	NPC469931
0.9441	High Similarity	NPC223747
0.9441	High Similarity	NPC105283
0.9441	High Similarity	NPC227508
0.9441	High Similarity	NPC45638
0.9441	High Similarity	NPC120099
0.9441	High Similarity	NPC225434
0.9441	High Similarity	NPC201292
0.9441	High Similarity	NPC93337
0.9437	High Similarity	NPC197285
0.9437	High Similarity	NPC21100
0.9434	High Similarity	NPC29830
0.9434	High Similarity	NPC168822
0.9427	High Similarity	NPC138811
0.9427	High Similarity	NPC22062
0.9427	High Similarity	NPC473634
0.9394	High Similarity	NPC473571
0.9394	High Similarity	NPC192539
0.9394	High Similarity	NPC126784
0.9394	High Similarity	NPC470444
0.9394	High Similarity	NPC470443
0.9394	High Similarity	NPC473895
0.9394	High Similarity	NPC473682
0.9394	High Similarity	NPC110941
0.9394	High Similarity	NPC241423
0.939	High Similarity	NPC14187
0.939	High Similarity	NPC169733
0.939	High Similarity	NPC122467
0.939	High Similarity	NPC202908
0.939	High Similarity	NPC219043
0.939	High Similarity	NPC292019
0.939	High Similarity	NPC255799
0.939	High Similarity	NPC471669
0.939	High Similarity	NPC89127
0.9387	High Similarity	NPC51774
0.9387	High Similarity	NPC25724
0.9387	High Similarity	NPC239549
0.9387	High Similarity	NPC472993
0.9387	High Similarity	NPC236191
0.9383	High Similarity	NPC255157
0.9383	High Similarity	NPC254855
0.9383	High Similarity	NPC22195
0.9383	High Similarity	NPC183357
0.9383	High Similarity	NPC136042
0.9383	High Similarity	NPC206123
0.9383	High Similarity	NPC67326
0.9383	High Similarity	NPC259896
0.9383	High Similarity	NPC105511
0.9383	High Similarity	NPC218488
0.9383	High Similarity	NPC156869
0.9383	High Similarity	NPC21190
0.9383	High Similarity	NPC29958
0.9383	High Similarity	NPC44558
0.9379	High Similarity	NPC45618
0.9379	High Similarity	NPC265530
0.9379	High Similarity	NPC58716
0.9379	High Similarity	NPC173637
0.9379	High Similarity	NPC477502
0.9379	High Similarity	NPC127546
0.9379	High Similarity	NPC317489
0.9379	High Similarity	NPC52550
0.9379	High Similarity	NPC45400
0.9379	High Similarity	NPC146792
0.9379	High Similarity	NPC223424
0.9379	High Similarity	NPC275454
0.9379	High Similarity	NPC226304
0.9379	High Similarity	NPC84362
0.9379	High Similarity	NPC325555
0.9379	High Similarity	NPC93099
0.9375	High Similarity	NPC277205
0.9371	High Similarity	NPC300537
0.9371	High Similarity	NPC127782
0.9367	High Similarity	NPC473623
0.9363	High Similarity	NPC129827
0.9363	High Similarity	NPC44931
0.9363	High Similarity	NPC65003
0.9363	High Similarity	NPC473512
0.9329	High Similarity	NPC294629
0.9329	High Similarity	NPC142996
0.9325	High Similarity	NPC301683
0.9325	High Similarity	NPC205076
0.9325	High Similarity	NPC156977
0.9325	High Similarity	NPC476405
0.9325	High Similarity	NPC472386
0.9325	High Similarity	NPC307518
0.9325	High Similarity	NPC211594
0.9325	High Similarity	NPC117260
0.9325	High Similarity	NPC48773
0.9325	High Similarity	NPC235575
0.9325	High Similarity	NPC254540
0.9325	High Similarity	NPC172807
0.9325	High Similarity	NPC153755
0.9321	High Similarity	NPC95855
0.9321	High Similarity	NPC270578
0.9321	High Similarity	NPC210042
0.9321	High Similarity	NPC112755
0.9321	High Similarity	NPC170675
0.9321	High Similarity	NPC471457
0.9321	High Similarity	NPC52382
0.9317	High Similarity	NPC88789
0.9317	High Similarity	NPC145038
0.9317	High Similarity	NPC253662
0.9317	High Similarity	NPC113968
0.9317	High Similarity	NPC118284
0.9317	High Similarity	NPC179950
0.9317	High Similarity	NPC277174
0.9317	High Similarity	NPC70441
0.9317	High Similarity	NPC73855
0.9317	High Similarity	NPC328940
0.9317	High Similarity	NPC281131
0.9317	High Similarity	NPC135599

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 NPC475366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	931
0.2-0.3	1870
0.3-0.4	2754
0.4-0.5	1876
0.5-0.6	892
0.6-0.7	293
0.7-0.8	114
0.8-0.85	22
0.85-0.9	4
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.981	High Similarity	NPD7054	Approved
0.9748	High Similarity	NPD7472	Approved
0.9625	High Similarity	NPD7074	Phase 3
0.9568	High Similarity	NPD7808	Phase 3
0.9506	High Similarity	NPD7251	Discontinued
0.9444	High Similarity	NPD6797	Phase 2
0.9141	High Similarity	NPD3818	Discontinued
0.9119	High Similarity	NPD4381	Clinical (unspecified phase)
0.9096	High Similarity	NPD4338	Clinical (unspecified phase)
0.9085	High Similarity	NPD7804	Clinical (unspecified phase)
0.9018	High Similarity	NPD6167	Clinical (unspecified phase)
0.9018	High Similarity	NPD6166	Phase 2
0.9018	High Similarity	NPD6168	Clinical (unspecified phase)
0.8875	High Similarity	NPD3817	Phase 2
0.8868	High Similarity	NPD1934	Approved
0.8696	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD2801	Approved
0.8509	High Similarity	NPD4380	Phase 2
0.8481	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD1512	Approved
0.8372	Intermediate Similarity	NPD6559	Discontinued
0.8364	Intermediate Similarity	NPD3882	Suspended
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8208	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5402	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8153	Intermediate Similarity	NPD2796	Approved
0.8137	Intermediate Similarity	NPD6799	Approved
0.8101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5403	Approved
0.8092	Intermediate Similarity	NPD5844	Phase 1
0.8086	Intermediate Similarity	NPD5401	Approved
0.8086	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7199	Phase 2
0.8059	Intermediate Similarity	NPD6959	Discontinued
0.805	Intermediate Similarity	NPD1549	Phase 2
0.8049	Intermediate Similarity	NPD1653	Approved
0.8035	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD3787	Discontinued
0.7977	Intermediate Similarity	NPD7473	Discontinued
0.7966	Intermediate Similarity	NPD8313	Approved
0.7966	Intermediate Similarity	NPD8312	Approved
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7685	Pre-registration
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7917	Intermediate Similarity	NPD8455	Phase 2
0.7917	Intermediate Similarity	NPD1465	Phase 2
0.7907	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.7861	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7240	Approved
0.7844	Intermediate Similarity	NPD6599	Discontinued
0.7785	Intermediate Similarity	NPD1933	Approved
0.7764	Intermediate Similarity	NPD7266	Discontinued
0.7751	Intermediate Similarity	NPD37	Approved
0.7747	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD919	Approved
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4965	Approved
0.7714	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD8151	Discontinued
0.7707	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7584	Approved
0.7657	Intermediate Similarity	NPD3926	Phase 2
0.7644	Intermediate Similarity	NPD1247	Approved
0.763	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD1240	Approved
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6776	Approved
0.7566	Intermediate Similarity	NPD6778	Approved
0.7566	Intermediate Similarity	NPD6782	Approved
0.7566	Intermediate Similarity	NPD6777	Approved
0.7566	Intermediate Similarity	NPD6781	Approved
0.7566	Intermediate Similarity	NPD6780	Approved
0.7566	Intermediate Similarity	NPD6779	Approved
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7697	Approved
0.7539	Intermediate Similarity	NPD7698	Approved
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7516	Intermediate Similarity	NPD1607	Approved
0.7515	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7455	Intermediate Similarity	NPD6674	Discontinued
0.7453	Intermediate Similarity	NPD447	Suspended
0.7423	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7396	Intermediate Similarity	NPD6823	Phase 2
0.7391	Intermediate Similarity	NPD943	Approved
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7371	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.7358	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6832	Phase 2
0.7353	Intermediate Similarity	NPD920	Approved
0.7349	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD230	Phase 1
0.7341	Intermediate Similarity	NPD6844	Discontinued
0.7333	Intermediate Similarity	NPD7583	Approved
0.7316	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7302	Intermediate Similarity	NPD6535	Approved
0.7302	Intermediate Similarity	NPD6534	Approved
0.7296	Intermediate Similarity	NPD7585	Approved
0.7296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7801	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7262	Intermediate Similarity	NPD6190	Approved
0.7257	Intermediate Similarity	NPD5353	Approved
0.7246	Intermediate Similarity	NPD1243	Approved
0.7246	Intermediate Similarity	NPD1652	Phase 2
0.7244	Intermediate Similarity	NPD1091	Approved
0.724	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2534	Approved
0.7235	Intermediate Similarity	NPD2532	Approved
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2533	Approved
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2798	Approved
0.7231	Intermediate Similarity	NPD8319	Approved
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7222	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7179	Intermediate Similarity	NPD7680	Approved
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7168	Intermediate Similarity	NPD3226	Approved
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD2800	Approved
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6841	Approved
0.7128	Intermediate Similarity	NPD6843	Phase 3
0.7128	Intermediate Similarity	NPD6842	Approved
0.7126	Intermediate Similarity	NPD2346	Discontinued
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD5953	Discontinued
0.7108	Intermediate Similarity	NPD2799	Discontinued
0.7104	Intermediate Similarity	NPD7286	Phase 2
0.7091	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD6385	Approved
0.7076	Intermediate Similarity	NPD7390	Discontinued
0.7072	Intermediate Similarity	NPD5242	Approved
0.7068	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6213	Phase 3
0.7068	Intermediate Similarity	NPD6212	Phase 3
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7048	Intermediate Similarity	NPD7097	Phase 1
0.7041	Intermediate Similarity	NPD5006	Approved
0.7041	Intermediate Similarity	NPD5005	Approved
0.7037	Intermediate Similarity	NPD4908	Phase 1
0.703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6355	Discontinued
0.703	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9494	Approved
0.6975	Remote Similarity	NPD3018	Phase 2
0.6971	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7549	Discontinued
0.6951	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD2344	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