NPASS Compound

Structure

NPC475155 OpenBabel07101719252D 45 49 0 0 1 0 0 0 0 0999 V2000 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 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 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 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 -4.3301 -3.5000 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 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 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 -3.4641 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 4.3301 2.5000 0.0000 C 0 0 1 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 2 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 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -3.4641 0.0000 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 2.5981 1.5000 0.0000 C 0 0 2 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 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 5.1962 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 3.4641 -0.0000 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 -8.6603 -5.0000 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 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 2.5981 2.5000 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 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 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 41 1 0 0 0 0 11 42 1 0 0 0 0 12 1 1 1 0 0 0 12 20 1 0 0 0 0 12 43 1 0 0 0 0 13 15 1 0 0 0 0 14 38 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 41 1 0 0 0 0 17 27 2 0 0 0 0 17 44 1 0 0 0 0 18 11 1 6 0 0 0 18 22 1 0 0 0 0 18 45 1 0 0 0 0 19 21 1 0 0 0 0 19 28 2 0 0 0 0 20 23 1 0 0 0 0 20 31 1 6 0 0 0 21 32 2 0 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 0 0 0 0 23 34 1 1 0 0 0 24 26 1 0 0 0 0 24 35 1 6 0 0 0 25 29 1 0 0 0 0 25 36 1 1 0 0 0 26 30 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 42 1 6 0 0 0 29 43 1 0 0 0 0 30 44 1 6 0 0 0 30 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.21
Volume:	595.415
LogP:	1.119
LogD:	0.749
LogS:	-3.813
# 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:	4.679
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:	-6.395
MDCK Permeability:	6.071214738767594e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.232
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	68.98479461669922%
Volume Distribution (VD):	0.478
Pgp-substrate:	15.586769104003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.238
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	1.818
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.655
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.503
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.579
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC475155

Natural Product ID:	NPC475155
*Common Name:**	4',5,6-Trimethoxyisoflavone-7-O-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	5,6-dimethoxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	ACYJGXHSBCMABJ-RMRQORCVSA-N
Standard InCHI:	InChI=1S/C30H36O15/c1-12-20(31)23(34)25(36)29(43-12)42-11-18-22(33)24(35)26(37)30(45-18)44-17-9-16-19(28(40-4)27(17)39-3)21(32)15(10-41-16)13-5-7-14(38-2)8-6-13/h5-10,12,18,20,22-26,29-31,33-37H,11H2,1-4H3/t12-,18+,20-,22+,23+,24-,25+,26+,29+,30+/m0/s1
SMILES:	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(C(=C4C(=C3)OC=C(C4=O)C5=CC=C(C=C5)OC)OC)OC)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499535
PubChem CID:	25178391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid 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
NPO2687	Baphia bancoensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19007285]
NPO2687	Baphia bancoensis	Species	Fabaceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	48400.0	nM	PMID[506597]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	48400.0	nM	PMID[506597]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	196300.0	nM	PMID[506597]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	196300.0	nM	PMID[506597]

☑ 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 NPC475155 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	452
0.1-0.2	1858
0.2-0.3	4008
0.3-0.4	9765
0.4-0.5	8680
0.5-0.6	4575
0.6-0.7	5871
0.7-0.8	5250
0.8-0.85	1347
0.85-0.9	630
0.9-0.95	237
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9814	High Similarity	NPC293004
0.9812	High Similarity	NPC135345
0.9756	High Similarity	NPC475261
0.9752	High Similarity	NPC61791
0.9697	High Similarity	NPC473895
0.9693	High Similarity	NPC204693
0.9691	High Similarity	NPC194483
0.9691	High Similarity	NPC52353
0.9691	High Similarity	NPC105511
0.9691	High Similarity	NPC44558
0.9688	High Similarity	NPC284277
0.9688	High Similarity	NPC475366
0.9688	High Similarity	NPC475497
0.9634	High Similarity	NPC102028
0.9632	High Similarity	NPC205076
0.9632	High Similarity	NPC307518
0.9632	High Similarity	NPC48773
0.9632	High Similarity	NPC267254
0.963	High Similarity	NPC472383
0.963	High Similarity	NPC472381
0.9573	High Similarity	NPC51774
0.9573	High Similarity	NPC236191
0.9573	High Similarity	NPC239549
0.9571	High Similarity	NPC183357
0.9571	High Similarity	NPC224462
0.9571	High Similarity	NPC51326
0.9571	High Similarity	NPC22195
0.9571	High Similarity	NPC34287
0.9571	High Similarity	NPC474434
0.9571	High Similarity	NPC471416
0.9571	High Similarity	NPC231194
0.9571	High Similarity	NPC21190
0.9568	High Similarity	NPC93099
0.9565	High Similarity	NPC15358
0.9518	High Similarity	NPC472387
0.9515	High Similarity	NPC142996
0.9512	High Similarity	NPC301683
0.9512	High Similarity	NPC156977
0.9512	High Similarity	NPC3583
0.9512	High Similarity	NPC259152
0.9512	High Similarity	NPC472386
0.9509	High Similarity	NPC45638
0.9509	High Similarity	NPC95855
0.9509	High Similarity	NPC201292
0.9509	High Similarity	NPC210042
0.9509	High Similarity	NPC58053
0.9509	High Similarity	NPC195257
0.9509	High Similarity	NPC170675
0.9509	High Similarity	NPC293629
0.9509	High Similarity	NPC105025
0.9509	High Similarity	NPC209296
0.9509	High Similarity	NPC475942
0.9509	High Similarity	NPC229687
0.9509	High Similarity	NPC186807
0.9509	High Similarity	NPC183036
0.9509	High Similarity	NPC93337
0.9509	High Similarity	NPC471457
0.9509	High Similarity	NPC112755
0.9509	High Similarity	NPC226294
0.9509	High Similarity	NPC469931
0.95	High Similarity	NPC182045
0.9464	High Similarity	NPC473883
0.9461	High Similarity	NPC470444
0.9461	High Similarity	NPC473682
0.9461	High Similarity	NPC126784
0.9461	High Similarity	NPC470443
0.9461	High Similarity	NPC110941
0.9461	High Similarity	NPC241423
0.9461	High Similarity	NPC473571
0.9458	High Similarity	NPC169733
0.9455	High Similarity	NPC208668
0.9451	High Similarity	NPC79056
0.9451	High Similarity	NPC105095
0.9451	High Similarity	NPC44328
0.9451	High Similarity	NPC177731
0.9448	High Similarity	NPC229729
0.9448	High Similarity	NPC58716
0.9448	High Similarity	NPC45618
0.9448	High Similarity	NPC45400
0.9448	High Similarity	NPC146792
0.9437	High Similarity	NPC110349
0.9408	High Similarity	NPC148710
0.9401	High Similarity	NPC476619
0.9401	High Similarity	NPC476622
0.9401	High Similarity	NPC476621
0.9401	High Similarity	NPC476623
0.9401	High Similarity	NPC476620
0.9401	High Similarity	NPC476618
0.9394	High Similarity	NPC172807
0.9394	High Similarity	NPC256760
0.9394	High Similarity	NPC254540
0.9394	High Similarity	NPC211594
0.9394	High Similarity	NPC476405
0.9394	High Similarity	NPC117260
0.939	High Similarity	NPC86008
0.939	High Similarity	NPC43587
0.9387	High Similarity	NPC115674
0.9387	High Similarity	NPC99957
0.9387	High Similarity	NPC181616
0.9387	High Similarity	NPC210073
0.9387	High Similarity	NPC236934
0.9387	High Similarity	NPC5778
0.9387	High Similarity	NPC70441
0.9383	High Similarity	NPC127415
0.9383	High Similarity	NPC309025
0.9383	High Similarity	NPC88023
0.9383	High Similarity	NPC243930
0.9349	High Similarity	NPC473072
0.9349	High Similarity	NPC470445
0.9349	High Similarity	NPC470449
0.9349	High Similarity	NPC470447
0.9349	High Similarity	NPC470446
0.9341	High Similarity	NPC472382
0.9341	High Similarity	NPC8573
0.9341	High Similarity	NPC472991
0.9341	High Similarity	NPC470949
0.9341	High Similarity	NPC257714
0.9341	High Similarity	NPC472992
0.9341	High Similarity	NPC65563
0.9341	High Similarity	NPC472380
0.9341	High Similarity	NPC472384
0.9337	High Similarity	NPC45522
0.9337	High Similarity	NPC24043
0.9337	High Similarity	NPC101026
0.9337	High Similarity	NPC21666
0.9337	High Similarity	NPC169977
0.9337	High Similarity	NPC42773
0.9333	High Similarity	NPC78734
0.9333	High Similarity	NPC245014
0.9333	High Similarity	NPC282987
0.9333	High Similarity	NPC150767
0.9333	High Similarity	NPC84265
0.9325	High Similarity	NPC311830
0.9325	High Similarity	NPC165720
0.9325	High Similarity	NPC22832
0.9321	High Similarity	NPC148273
0.9294	High Similarity	NPC470455
0.9294	High Similarity	NPC470451
0.929	High Similarity	NPC473073
0.929	High Similarity	NPC473071
0.9286	High Similarity	NPC168584
0.9281	High Similarity	NPC294815
0.9281	High Similarity	NPC264735
0.9281	High Similarity	NPC19108
0.9281	High Similarity	NPC477848
0.9281	High Similarity	NPC476472
0.9281	High Similarity	NPC198199
0.9281	High Similarity	NPC16194
0.9281	High Similarity	NPC472607
0.9281	High Similarity	NPC220173
0.9281	High Similarity	NPC473327
0.9277	High Similarity	NPC261254
0.9277	High Similarity	NPC235575
0.9277	High Similarity	NPC180918
0.9273	High Similarity	NPC105283
0.9268	High Similarity	NPC8856
0.9264	High Similarity	NPC94777
0.9264	High Similarity	NPC270335
0.9264	High Similarity	NPC88043
0.9264	High Similarity	NPC222936
0.9264	High Similarity	NPC29830
0.9264	High Similarity	NPC284960
0.9264	High Similarity	NPC168822
0.9264	High Similarity	NPC191306
0.9264	High Similarity	NPC19709
0.9259	High Similarity	NPC303913
0.925	High Similarity	NPC473657
0.925	High Similarity	NPC295613
0.925	High Similarity	NPC45165
0.9235	High Similarity	NPC36138
0.9226	High Similarity	NPC255799
0.9226	High Similarity	NPC48984
0.9226	High Similarity	NPC233994
0.9226	High Similarity	NPC268533
0.9226	High Similarity	NPC211532
0.9226	High Similarity	NPC472385
0.9226	High Similarity	NPC198324
0.9222	High Similarity	NPC25724
0.9222	High Similarity	NPC163165
0.9222	High Similarity	NPC472993
0.9217	High Similarity	NPC285197
0.9217	High Similarity	NPC67105
0.9217	High Similarity	NPC210808
0.9217	High Similarity	NPC95866
0.9217	High Similarity	NPC212748
0.9217	High Similarity	NPC206123
0.9217	High Similarity	NPC199079
0.9217	High Similarity	NPC218488
0.9212	High Similarity	NPC243877
0.9212	High Similarity	NPC14662
0.9212	High Similarity	NPC477502
0.9212	High Similarity	NPC116745
0.9202	High Similarity	NPC127782
0.9202	High Similarity	NPC300537
0.9202	High Similarity	NPC473043
0.9202	High Similarity	NPC77660
0.9202	High Similarity	NPC189142
0.9181	High Similarity	NPC470416
0.9172	High Similarity	NPC89052
0.9172	High Similarity	NPC120952

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 NPC475155 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	947
0.2-0.3	1933
0.3-0.4	2789
0.4-0.5	1817
0.5-0.6	855
0.6-0.7	274
0.7-0.8	106
0.8-0.85	11
0.85-0.9	5
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9509	High Similarity	NPD7054	Approved
0.9451	High Similarity	NPD7074	Phase 3
0.9451	High Similarity	NPD7472	Approved
0.9281	High Similarity	NPD7808	Phase 3
0.9222	High Similarity	NPD7251	Discontinued
0.9212	High Similarity	NPD3818	Discontinued
0.9167	High Similarity	NPD4338	Clinical (unspecified phase)
0.9162	High Similarity	NPD6797	Phase 2
0.9074	High Similarity	NPD4381	Clinical (unspecified phase)
0.8929	High Similarity	NPD7804	Clinical (unspecified phase)
0.8862	High Similarity	NPD6167	Clinical (unspecified phase)
0.8862	High Similarity	NPD6168	Clinical (unspecified phase)
0.8862	High Similarity	NPD6166	Phase 2
0.8773	High Similarity	NPD2801	Approved
0.8735	High Similarity	NPD5494	Approved
0.8712	High Similarity	NPD1934	Approved
0.8606	High Similarity	NPD3817	Phase 2
0.8545	High Similarity	NPD2393	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD4380	Phase 2
0.8443	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5402	Approved
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7075	Discontinued
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD6801	Discontinued
0.8133	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD1512	Approved
0.8072	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD8312	Approved
0.8045	Intermediate Similarity	NPD8313	Approved
0.8025	Intermediate Similarity	NPD1549	Phase 2
0.8022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7228	Approved
0.8011	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD6799	Approved
0.7989	Intermediate Similarity	NPD3787	Discontinued
0.7988	Intermediate Similarity	NPD7411	Suspended
0.7964	Intermediate Similarity	NPD5403	Approved
0.7963	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7473	Discontinued
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5401	Approved
0.7952	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7685	Pre-registration
0.7931	Intermediate Similarity	NPD1247	Approved
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7931	Intermediate Similarity	NPD6959	Discontinued
0.7886	Intermediate Similarity	NPD6232	Discontinued
0.7844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7833	Intermediate Similarity	NPD7240	Approved
0.7831	Intermediate Similarity	NPD6781	Approved
0.7831	Intermediate Similarity	NPD6778	Approved
0.7831	Intermediate Similarity	NPD6782	Approved
0.7831	Intermediate Similarity	NPD6777	Approved
0.7831	Intermediate Similarity	NPD6776	Approved
0.7831	Intermediate Similarity	NPD6780	Approved
0.7831	Intermediate Similarity	NPD6779	Approved
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7801	Intermediate Similarity	NPD7698	Approved
0.7801	Intermediate Similarity	NPD7697	Approved
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7801	Intermediate Similarity	NPD7696	Phase 3
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD8151	Discontinued
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD37	Approved
0.7732	Intermediate Similarity	NPD7701	Phase 2
0.7714	Intermediate Similarity	NPD919	Approved
0.7704	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD7783	Phase 2
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4965	Approved
0.7701	Intermediate Similarity	NPD4966	Approved
0.7697	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7584	Approved
0.7668	Intermediate Similarity	NPD7871	Phase 2
0.7668	Intermediate Similarity	NPD7870	Phase 2
0.7656	Intermediate Similarity	NPD6823	Phase 2
0.7654	Intermediate Similarity	NPD1933	Approved
0.7636	Intermediate Similarity	NPD7266	Discontinued
0.7632	Intermediate Similarity	NPD7699	Phase 2
0.7632	Intermediate Similarity	NPD7700	Phase 2
0.7614	Intermediate Similarity	NPD6234	Discontinued
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1240	Approved
0.7574	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6535	Approved
0.7566	Intermediate Similarity	NPD6534	Approved
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7529	Intermediate Similarity	NPD6844	Discontinued
0.7525	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD1613	Approved
0.7485	Intermediate Similarity	NPD943	Approved
0.7485	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3749	Approved
0.7442	Intermediate Similarity	NPD920	Approved
0.7439	Intermediate Similarity	NPD447	Suspended
0.741	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD6190	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.734	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD6674	Discontinued
0.7337	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD230	Phase 1
0.733	Intermediate Similarity	NPD6212	Phase 3
0.733	Intermediate Similarity	NPD6213	Phase 3
0.733	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7583	Approved
0.731	Intermediate Similarity	NPD8320	Phase 1
0.731	Intermediate Similarity	NPD8319	Approved
0.7306	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3027	Phase 3
0.7286	Intermediate Similarity	NPD7585	Approved
0.7262	Intermediate Similarity	NPD1551	Phase 2
0.7257	Intermediate Similarity	NPD3226	Approved
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7247	Intermediate Similarity	NPD5353	Approved
0.7239	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7235	Intermediate Similarity	NPD1243	Approved
0.7231	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2533	Approved
0.7225	Intermediate Similarity	NPD2534	Approved
0.7225	Intermediate Similarity	NPD2532	Approved
0.7222	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5953	Discontinued
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.7198	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7286	Phase 2
0.7178	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7680	Approved
0.7158	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD2800	Approved
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6841	Approved
0.712	Intermediate Similarity	NPD6843	Phase 3
0.712	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6842	Approved
0.7101	Intermediate Similarity	NPD7033	Discontinued
0.7079	Intermediate Similarity	NPD6386	Approved
0.7079	Intermediate Similarity	NPD6385	Approved
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7041	Intermediate Similarity	NPD7097	Phase 1
0.7037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD1652	Phase 2
0.7035	Intermediate Similarity	NPD5006	Approved
0.7028	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8059	Phase 3
0.7026	Intermediate Similarity	NPD4360	Phase 2
0.7026	Intermediate Similarity	NPD4363	Phase 3
0.7024	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1091	Approved
0.7018	Intermediate Similarity	NPD2344	Approved
0.7015	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6651	Approved
0.6971	Remote Similarity	NPD7390	Discontinued
0.697	Remote Similarity	NPD9494	Approved
0.6967	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD4908	Phase 1
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5124	Phase 1
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD4420	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