NPASS Compound

Structure

NPC199079 OpenBabel07101718182D 45 49 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -5.1962 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 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 1.7321 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -0.0000 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 6.0622 -0.5000 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 4.3301 2.5000 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 0.8660 2.5000 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 -0.8660 1.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 13 1 0 0 0 0 7 19 2 0 0 0 0 8 16 1 0 0 0 0 8 18 1 0 0 0 0 9 30 1 0 0 0 0 10 1 1 6 0 0 0 10 22 1 0 0 0 0 10 40 1 0 0 0 0 11 31 2 0 0 0 0 11 41 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 17 2 0 0 0 0 15 21 2 0 0 0 0 15 34 1 0 0 0 0 16 21 1 0 0 0 0 16 35 2 0 0 0 0 17 43 1 0 0 0 0 18 14 1 6 0 0 0 18 42 1 0 0 0 0 19 21 1 0 0 0 0 19 42 1 0 0 0 0 20 9 1 1 0 0 0 20 23 1 0 0 0 0 20 44 1 0 0 0 0 22 26 1 0 0 0 0 22 36 1 1 0 0 0 23 24 1 0 0 0 0 23 37 1 6 0 0 0 24 25 1 0 0 0 0 24 38 1 1 0 0 0 25 28 1 0 0 0 0 25 39 1 6 0 0 0 26 27 1 0 0 0 0 26 45 1 6 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 44 1 0 0 0 0 28 45 1 1 0 0 0 29 40 1 0 0 0 0 29 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.18
Volume:	586.91
LogP:	0.332
LogD:	0.21
LogS:	-4.773
# Rotatable Bonds:	8
TPSA:	251.36
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	4.957
Fsp3:	0.517
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.735
MDCK Permeability:	5.328382758307271e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	66.98966217041016%
Volume Distribution (VD):	0.316
Pgp-substrate:	33.74937057495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.382
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.194
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	1.443
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.202
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.431
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.426
Carcinogencity:	0.21
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC199079

Natural Product ID:	NPC199079
*Common Name:**	(2S)-5,7,5'-Trihydroxyflavanone 2'-O-Beta-D-Glucopyranosyl-(1->3)-Alpha-L-2-O-Acetylrhamnopyanoside
IUPAC Name:	[(2S,3R,4R,5S,6S)-2-[2-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-hydroxyphenoxy]-5-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	QLBVBCPJNCEFDN-QLAWMWOCSA-N
Standard InCHI:	InChI=1S/C29H34O16/c1-10-22(36)26(45-28-25(39)24(38)23(37)20(9-30)44-28)27(41-11(2)31)29(40-10)43-17-4-3-12(32)5-14(17)18-8-16(35)21-15(34)6-13(33)7-19(21)42-18/h3-7,10,18,20,22-30,32-34,36-39H,8-9H2,1-2H3/t10-,18-,20+,22-,23+,24-,25+,26+,27+,28-,29-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1[C@@H]1CC(=O)c2c(cc(cc2O1)O)O)O)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506566
PubChem CID:	11995072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO26960	Cyclosorus acuminatus	Species	Thelypteridaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[17125239]
NPO26960	Cyclosorus acuminatus	Species	Thelypteridaceae	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	=	128.0	ug.mL-1	PMID[549985]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[549985]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32.0	ug.mL-1	PMID[549985]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	32.0	ug.mL-1	PMID[549985]

☑ 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 NPC199079 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	379
0.1-0.2	1556
0.2-0.3	3421
0.3-0.4	7763
0.4-0.5	9586
0.5-0.6	5578
0.6-0.7	5348
0.7-0.8	6474
0.8-0.85	1614
0.85-0.9	860
0.9-0.95	110
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC210808
0.9938	High Similarity	NPC288152
0.9938	High Similarity	NPC9002
0.9938	High Similarity	NPC137871
0.9938	High Similarity	NPC257011
0.9811	High Similarity	NPC70441
0.9573	High Similarity	NPC102028
0.95	High Similarity	NPC298171
0.9497	High Similarity	NPC271270
0.9497	High Similarity	NPC246469
0.9497	High Similarity	NPC142860
0.9497	High Similarity	NPC97285
0.9455	High Similarity	NPC142996
0.9451	High Similarity	NPC267254
0.9451	High Similarity	NPC301683
0.9451	High Similarity	NPC156977
0.9451	High Similarity	NPC472386
0.9448	High Similarity	NPC43587
0.9448	High Similarity	NPC293629
0.9448	High Similarity	NPC105283
0.9444	High Similarity	NPC262222
0.9444	High Similarity	NPC298666
0.9444	High Similarity	NPC68592
0.9437	High Similarity	NPC101636
0.9394	High Similarity	NPC51774
0.9394	High Similarity	NPC239549
0.9394	High Similarity	NPC236191
0.939	High Similarity	NPC79056
0.939	High Similarity	NPC105095
0.939	High Similarity	NPC293004
0.939	High Similarity	NPC177731
0.939	High Similarity	NPC194483
0.939	High Similarity	NPC52353
0.939	High Similarity	NPC44328
0.9383	High Similarity	NPC99216
0.9379	High Similarity	NPC190450
0.9379	High Similarity	NPC475382
0.9341	High Similarity	NPC120952
0.9341	High Similarity	NPC472387
0.9329	High Similarity	NPC472383
0.9329	High Similarity	NPC472381
0.9325	High Similarity	NPC64425
0.9321	High Similarity	NPC257566
0.9321	High Similarity	NPC473644
0.9321	High Similarity	NPC311850
0.9321	High Similarity	NPC124155
0.9317	High Similarity	NPC303913
0.9313	High Similarity	NPC22062
0.9313	High Similarity	NPC473634
0.9313	High Similarity	NPC138811
0.9308	High Similarity	NPC206378
0.9308	High Similarity	NPC127406
0.929	High Similarity	NPC470447
0.929	High Similarity	NPC470446
0.929	High Similarity	NPC470449
0.929	High Similarity	NPC470445
0.9281	High Similarity	NPC471669
0.9281	High Similarity	NPC472380
0.9281	High Similarity	NPC472384
0.9281	High Similarity	NPC89127
0.9281	High Similarity	NPC472382
0.9277	High Similarity	NPC204693
0.9273	High Similarity	NPC22195
0.9273	High Similarity	NPC44558
0.9273	High Similarity	NPC21190
0.9273	High Similarity	NPC183357
0.9268	High Similarity	NPC93099
0.9268	High Similarity	NPC249977
0.9264	High Similarity	NPC287889
0.9264	High Similarity	NPC135358
0.9259	High Similarity	NPC44947
0.9259	High Similarity	NPC472876
0.9255	High Similarity	NPC473623
0.925	High Similarity	NPC129827
0.925	High Similarity	NPC473512
0.925	High Similarity	NPC43638
0.925	High Similarity	NPC65003
0.925	High Similarity	NPC60966
0.925	High Similarity	NPC44931
0.9245	High Similarity	NPC26195
0.9245	High Similarity	NPC97052
0.9245	High Similarity	NPC169248
0.9245	High Similarity	NPC72649
0.9245	High Similarity	NPC39351
0.9235	High Similarity	NPC470451
0.9235	High Similarity	NPC470455
0.9231	High Similarity	NPC470453
0.9231	High Similarity	NPC164047
0.9231	High Similarity	NPC470448
0.9231	High Similarity	NPC470452
0.9226	High Similarity	NPC476623
0.9226	High Similarity	NPC476618
0.9226	High Similarity	NPC476619
0.9226	High Similarity	NPC476622
0.9226	High Similarity	NPC475261
0.9226	High Similarity	NPC476620
0.9226	High Similarity	NPC476621
0.9226	High Similarity	NPC173837
0.9222	High Similarity	NPC198199
0.9217	High Similarity	NPC475155
0.9217	High Similarity	NPC67134
0.9217	High Similarity	NPC3583
0.9217	High Similarity	NPC47140
0.9217	High Similarity	NPC254540
0.9217	High Similarity	NPC259152
0.9217	High Similarity	NPC172807
0.9217	High Similarity	NPC211594
0.9217	High Similarity	NPC180918
0.9212	High Similarity	NPC210042
0.9212	High Similarity	NPC86008
0.9212	High Similarity	NPC209296
0.9212	High Similarity	NPC112755
0.9212	High Similarity	NPC95855
0.9212	High Similarity	NPC195257
0.9212	High Similarity	NPC170675
0.9212	High Similarity	NPC61791
0.9212	High Similarity	NPC471457
0.9207	High Similarity	NPC32641
0.9207	High Similarity	NPC5778
0.9207	High Similarity	NPC476470
0.9207	High Similarity	NPC221342
0.9207	High Similarity	NPC142142
0.9207	High Similarity	NPC477613
0.9207	High Similarity	NPC186816
0.9207	High Similarity	NPC12013
0.9207	High Similarity	NPC210073
0.9207	High Similarity	NPC115674
0.9207	High Similarity	NPC11432
0.9207	High Similarity	NPC189564
0.9207	High Similarity	NPC256188
0.9207	High Similarity	NPC203145
0.9207	High Similarity	NPC236934
0.9207	High Similarity	NPC8856
0.9202	High Similarity	NPC29830
0.9198	High Similarity	NPC47923
0.9193	High Similarity	NPC43761
0.9193	High Similarity	NPC308265
0.9193	High Similarity	NPC73511
0.9187	High Similarity	NPC261866
0.9187	High Similarity	NPC170475
0.9187	High Similarity	NPC473657
0.9187	High Similarity	NPC295613
0.9182	High Similarity	NPC106625
0.9182	High Similarity	NPC299435
0.9182	High Similarity	NPC260604
0.9172	High Similarity	NPC245059
0.9172	High Similarity	NPC473571
0.9172	High Similarity	NPC473682
0.9172	High Similarity	NPC470443
0.9172	High Similarity	NPC110941
0.9172	High Similarity	NPC84494
0.9172	High Similarity	NPC470444
0.9172	High Similarity	NPC126784
0.9172	High Similarity	NPC473895
0.9172	High Similarity	NPC241423
0.9167	High Similarity	NPC255799
0.9167	High Similarity	NPC65563
0.9167	High Similarity	NPC292019
0.9167	High Similarity	NPC470949
0.9167	High Similarity	NPC268533
0.9167	High Similarity	NPC202908
0.9167	High Similarity	NPC48984
0.9167	High Similarity	NPC473862
0.9167	High Similarity	NPC14187
0.9167	High Similarity	NPC122467
0.9167	High Similarity	NPC169733
0.9162	High Similarity	NPC25724
0.9162	High Similarity	NPC208668
0.9157	High Similarity	NPC175429
0.9157	High Similarity	NPC34287
0.9157	High Similarity	NPC474434
0.9157	High Similarity	NPC471416
0.9157	High Similarity	NPC67105
0.9157	High Similarity	NPC78734
0.9157	High Similarity	NPC209550
0.9157	High Similarity	NPC51326
0.9157	High Similarity	NPC277532
0.9157	High Similarity	NPC231194
0.9157	High Similarity	NPC105511
0.9157	High Similarity	NPC76047
0.9157	High Similarity	NPC138990
0.9157	High Similarity	NPC150767
0.9157	High Similarity	NPC218488
0.9146	High Similarity	NPC76831
0.9146	High Similarity	NPC475366
0.9146	High Similarity	NPC15358
0.9146	High Similarity	NPC7752
0.9146	High Similarity	NPC292929
0.9146	High Similarity	NPC284277
0.9146	High Similarity	NPC475497
0.9146	High Similarity	NPC289667
0.9141	High Similarity	NPC244875
0.9141	High Similarity	NPC300537
0.9141	High Similarity	NPC259834
0.9141	High Similarity	NPC240306
0.9141	High Similarity	NPC127782
0.9136	High Similarity	NPC271479
0.9136	High Similarity	NPC136761
0.9136	High Similarity	NPC328093
0.9136	High Similarity	NPC472320

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 NPC199079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	896
0.2-0.3	1838
0.3-0.4	2588
0.4-0.5	1956
0.5-0.6	1013
0.6-0.7	340
0.7-0.8	147
0.8-0.85	22
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.939	High Similarity	NPD7074	Phase 3
0.9273	High Similarity	NPD7472	Approved
0.9212	High Similarity	NPD7054	Approved
0.9162	High Similarity	NPD7251	Discontinued
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.9107	High Similarity	NPD7808	Phase 3
0.9102	High Similarity	NPD6797	Phase 2
0.9096	High Similarity	NPD7804	Clinical (unspecified phase)
0.8994	High Similarity	NPD4338	Clinical (unspecified phase)
0.8698	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD6168	Clinical (unspecified phase)
0.869	High Similarity	NPD6167	Clinical (unspecified phase)
0.869	High Similarity	NPD6166	Phase 2
0.8667	High Similarity	NPD7075	Discontinued
0.8605	High Similarity	NPD6559	Discontinued
0.8537	High Similarity	NPD1934	Approved
0.8528	High Similarity	NPD4380	Phase 2
0.8485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5402	Approved
0.84	Intermediate Similarity	NPD8313	Approved
0.84	Intermediate Similarity	NPD8312	Approved
0.8383	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD2801	Approved
0.8373	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8253	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.816	Intermediate Similarity	NPD6799	Approved
0.8155	Intermediate Similarity	NPD8455	Phase 2
0.8129	Intermediate Similarity	NPD5494	Approved
0.8121	Intermediate Similarity	NPD5403	Approved
0.8115	Intermediate Similarity	NPD7783	Phase 2
0.8115	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1511	Approved
0.8046	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD7435	Discontinued
0.801	Intermediate Similarity	NPD8151	Discontinued
0.8	Intermediate Similarity	NPD5401	Approved
0.7976	Intermediate Similarity	NPD6599	Discontinued
0.7964	Intermediate Similarity	NPD1653	Approved
0.7955	Intermediate Similarity	NPD7228	Approved
0.7953	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD2796	Approved
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7892	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7872	Intermediate Similarity	NPD6778	Approved
0.7872	Intermediate Similarity	NPD6779	Approved
0.7872	Intermediate Similarity	NPD6776	Approved
0.7872	Intermediate Similarity	NPD6781	Approved
0.7872	Intermediate Similarity	NPD6782	Approved
0.7872	Intermediate Similarity	NPD6780	Approved
0.7872	Intermediate Similarity	NPD6777	Approved
0.7869	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7849	Intermediate Similarity	NPD7768	Phase 2
0.7842	Intermediate Similarity	NPD7697	Approved
0.7842	Intermediate Similarity	NPD7696	Phase 3
0.7842	Intermediate Similarity	NPD7698	Approved
0.784	Intermediate Similarity	NPD2935	Discontinued
0.7836	Intermediate Similarity	NPD1465	Phase 2
0.7829	Intermediate Similarity	NPD6232	Discontinued
0.7829	Intermediate Similarity	NPD3787	Discontinued
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7874	Approved
0.7772	Intermediate Similarity	NPD7701	Phase 2
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7758	Intermediate Similarity	NPD3750	Approved
0.7758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD1240	Approved
0.7744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7584	Approved
0.7708	Intermediate Similarity	NPD7870	Phase 2
0.7708	Intermediate Similarity	NPD7871	Phase 2
0.7701	Intermediate Similarity	NPD3749	Approved
0.7696	Intermediate Similarity	NPD6823	Phase 2
0.7683	Intermediate Similarity	NPD7266	Discontinued
0.768	Intermediate Similarity	NPD7240	Approved
0.768	Intermediate Similarity	NPD7685	Pre-registration
0.7672	Intermediate Similarity	NPD7700	Phase 2
0.7672	Intermediate Similarity	NPD7699	Phase 2
0.7654	Intermediate Similarity	NPD1607	Approved
0.7622	Intermediate Similarity	NPD1551	Phase 2
0.7617	Intermediate Similarity	NPD8319	Approved
0.7617	Intermediate Similarity	NPD8320	Phase 1
0.7609	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6534	Approved
0.7606	Intermediate Similarity	NPD6535	Approved
0.7602	Intermediate Similarity	NPD7458	Discontinued
0.759	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD2532	Approved
0.7572	Intermediate Similarity	NPD37	Approved
0.7563	Intermediate Similarity	NPD7801	Approved
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD4965	Approved
0.7526	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7585	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3748	Approved
0.7449	Intermediate Similarity	NPD7583	Approved
0.7432	Intermediate Similarity	NPD5953	Discontinued
0.7423	Intermediate Similarity	NPD1613	Approved
0.7423	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7402	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD6832	Phase 2
0.7384	Intermediate Similarity	NPD920	Approved
0.7378	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6212	Phase 3
0.7368	Intermediate Similarity	NPD6213	Phase 3
0.736	Intermediate Similarity	NPD919	Approved
0.7349	Intermediate Similarity	NPD7033	Discontinued
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7278	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7229	Intermediate Similarity	NPD6651	Approved
0.7216	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD943	Approved
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.7205	Intermediate Similarity	NPD1203	Approved
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD6798	Discontinued
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7192	Intermediate Similarity	NPD7930	Approved
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.7178	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1652	Phase 2
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD447	Suspended
0.7169	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5124	Phase 1
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7121	Intermediate Similarity	NPD7680	Approved
0.7117	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3268	Approved
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8059	Phase 3
0.7062	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2344	Approved
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7229	Phase 3
0.7019	Intermediate Similarity	NPD9717	Approved
0.7019	Intermediate Similarity	NPD1608	Approved
0.7012	Intermediate Similarity	NPD2861	Phase 2
0.6994	Remote Similarity	NPD2797	Approved
0.6977	Remote Similarity	NPD6674	Discontinued
0.6957	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD422	Phase 1
0.6941	Remote Similarity	NPD4308	Phase 3
0.6941	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3225	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