NPASS Compound

Structure

CID45400 OpenBabel06191715382D 32 35 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -1.5000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 8.6603 1.0000 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 8.6603 0.0000 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 6.0622 -0.5000 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 -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 0.0000 -2.0000 0.0000 C 0 0 1 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 -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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 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 9.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.7321 -2.0000 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 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 1 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 14 1 0 0 0 0 7 22 1 0 0 0 0 9 11 1 0 0 0 0 9 20 2 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 24 2 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 13 31 1 0 0 0 0 14 8 1 6 0 0 0 14 30 1 0 0 0 0 15 7 1 1 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 21 1 0 0 0 0 19 29 1 6 0 0 0 20 30 1 0 0 0 0 21 31 1 1 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.12
Volume:	415.784
LogP:	-0.144
LogD:	-0.19
LogS:	-3.959
# Rotatable Bonds:	4
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	4.177
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.274
MDCK Permeability:	1.3695655979972798e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.534
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	87.0485610961914%
Volume Distribution (VD):	0.541
Pgp-substrate:	21.23603630065918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.264
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	6.94
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.633
Rat Oral Acute Toxicity:	0.499
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.935
Carcinogencity:	0.588
Eye Corrosion:	0.003
Eye Irritation:	0.3
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC45400

Natural Product ID:	NPC45400
*Common Name:**	Flavanomarein
IUPAC Name:	(2S)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:	Flavanomarein
Standard InCHIKey:	DGGOLFCPSUVVHX-RTHJTPBESA-N
Standard InCHI:	InChI=1S/C21H22O11/c22-7-15-16(26)18(28)19(29)21(32-15)31-13-4-2-9-11(24)6-14(30-20(9)17(13)27)8-1-3-10(23)12(25)5-8/h1-5,14-16,18-19,21-23,25-29H,6-7H2/t14-,15+,16+,18-,19+,21+/m0/s1
SMILES:	c1cc(c(cc1[C@@H]1CC(=O)c2ccc(c(c2O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1405715
PubChem CID:	101781
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
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[25282892]
NPO21625	Bidens tripartita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21625	Bidens tripartita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29396	Bidens bipinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21625	Bidens tripartita	Species	Asteraceae	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	4
Potency	3

Activity Type	# Activity
CELL-LINE	1
Individual Protein	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	2667.9	nM	PMID[524812]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	8.08	%	PMID[524813]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[524812]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	3.1	%	PMID[524813]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[524812]
NPT22036	CELL-LINE	HL	Homo sapiens	Activity	=	82.6	%	PMID[524814]
NPT5310	Organism	Chlamydophila pneumoniae	Chlamydophila pneumoniae	Inhibition	=	22.1	%	PMID[524814]

☑ 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 NPC45400 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	427
0.1-0.2	1733
0.2-0.3	3984
0.3-0.4	9426
0.4-0.5	8648
0.5-0.6	3980
0.6-0.7	4902
0.7-0.8	5721
0.8-0.85	2363
0.85-0.9	1060
0.9-0.95	408
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC229687
0.9874	High Similarity	NPC471416
0.9874	High Similarity	NPC34287
0.9873	High Similarity	NPC165720
0.9811	High Similarity	NPC471457
0.9811	High Similarity	NPC112755
0.9811	High Similarity	NPC170675
0.981	High Similarity	NPC5778
0.981	High Similarity	NPC236934
0.9809	High Similarity	NPC88043
0.9809	High Similarity	NPC29830
0.975	High Similarity	NPC231194
0.975	High Similarity	NPC44558
0.975	High Similarity	NPC51326
0.975	High Similarity	NPC474434
0.975	High Similarity	NPC183357
0.975	High Similarity	NPC22195
0.975	High Similarity	NPC21190
0.9748	High Similarity	NPC229729
0.9689	High Similarity	NPC48773
0.9689	High Similarity	NPC307518
0.9689	High Similarity	NPC205076
0.9688	High Similarity	NPC210042
0.9688	High Similarity	NPC183036
0.9688	High Similarity	NPC472383
0.9688	High Similarity	NPC95855
0.9688	High Similarity	NPC472381
0.9684	High Similarity	NPC270335
0.9684	High Similarity	NPC191306
0.9684	High Similarity	NPC168822
0.963	High Similarity	NPC239549
0.963	High Similarity	NPC51774
0.963	High Similarity	NPC236191
0.9627	High Similarity	NPC44328
0.9627	High Similarity	NPC224462
0.9627	High Similarity	NPC149011
0.9627	High Similarity	NPC105511
0.9627	High Similarity	NPC212748
0.9627	High Similarity	NPC177731
0.9627	High Similarity	NPC79056
0.9627	High Similarity	NPC204937
0.9627	High Similarity	NPC105095
0.9625	High Similarity	NPC92565
0.9625	High Similarity	NPC146792
0.9625	High Similarity	NPC477502
0.9625	High Similarity	NPC58716
0.9625	High Similarity	NPC116745
0.9625	High Similarity	NPC93099
0.9625	High Similarity	NPC160156
0.9625	High Similarity	NPC45618
0.9623	High Similarity	NPC311830
0.9623	High Similarity	NPC22832
0.962	High Similarity	NPC300537
0.962	High Similarity	NPC189142
0.962	High Similarity	NPC77660
0.962	High Similarity	NPC127782
0.9573	High Similarity	NPC476623
0.9573	High Similarity	NPC476620
0.9573	High Similarity	NPC476622
0.9573	High Similarity	NPC476618
0.9573	High Similarity	NPC476619
0.9573	High Similarity	NPC476621
0.9568	High Similarity	NPC235575
0.9568	High Similarity	NPC259152
0.9568	High Similarity	NPC301683
0.9568	High Similarity	NPC47140
0.9568	High Similarity	NPC256760
0.9568	High Similarity	NPC261254
0.9568	High Similarity	NPC67134
0.9568	High Similarity	NPC3583
0.9568	High Similarity	NPC472386
0.9568	High Similarity	NPC267254
0.9565	High Similarity	NPC86008
0.9565	High Similarity	NPC293629
0.9565	High Similarity	NPC186807
0.9565	High Similarity	NPC105025
0.9565	High Similarity	NPC201292
0.9565	High Similarity	NPC209296
0.9565	High Similarity	NPC58053
0.9565	High Similarity	NPC61791
0.9565	High Similarity	NPC52382
0.9565	High Similarity	NPC43587
0.9565	High Similarity	NPC475942
0.9565	High Similarity	NPC270578
0.9565	High Similarity	NPC105283
0.9565	High Similarity	NPC195257
0.9565	High Similarity	NPC93337
0.9565	High Similarity	NPC226294
0.9565	High Similarity	NPC469931
0.9565	High Similarity	NPC45638
0.9563	High Similarity	NPC8856
0.9563	High Similarity	NPC115674
0.9563	High Similarity	NPC21100
0.9563	High Similarity	NPC197285
0.9563	High Similarity	NPC210073
0.956	High Similarity	NPC243930
0.956	High Similarity	NPC284960
0.956	High Similarity	NPC309025
0.956	High Similarity	NPC19709
0.956	High Similarity	NPC222936
0.956	High Similarity	NPC88023
0.956	High Similarity	NPC127415
0.9512	High Similarity	NPC268533
0.9509	High Similarity	NPC88560
0.9509	High Similarity	NPC208668
0.9509	High Similarity	NPC204693
0.9509	High Similarity	NPC172033
0.9509	High Similarity	NPC175230
0.9506	High Similarity	NPC285197
0.9506	High Similarity	NPC206123
0.9506	High Similarity	NPC245014
0.9506	High Similarity	NPC84265
0.9506	High Similarity	NPC150767
0.9506	High Similarity	NPC78734
0.9506	High Similarity	NPC218488
0.9506	High Similarity	NPC282987
0.9506	High Similarity	NPC72249
0.9503	High Similarity	NPC135345
0.95	High Similarity	NPC277205
0.9497	High Similarity	NPC473043
0.9497	High Similarity	NPC148273
0.9455	High Similarity	NPC472387
0.9451	High Similarity	NPC472607
0.9451	High Similarity	NPC102028
0.9451	High Similarity	NPC142996
0.9451	High Similarity	NPC108202
0.9448	High Similarity	NPC254540
0.9448	High Similarity	NPC60735
0.9448	High Similarity	NPC476405
0.9448	High Similarity	NPC172807
0.9448	High Similarity	NPC156977
0.9448	High Similarity	NPC475155
0.9448	High Similarity	NPC117260
0.9448	High Similarity	NPC211594
0.9448	High Similarity	NPC26230
0.9448	High Similarity	NPC180918
0.9444	High Similarity	NPC203050
0.9444	High Similarity	NPC219904
0.9444	High Similarity	NPC223747
0.9444	High Similarity	NPC120099
0.9444	High Similarity	NPC225434
0.9441	High Similarity	NPC56077
0.9441	High Similarity	NPC181616
0.9441	High Similarity	NPC145038
0.9441	High Similarity	NPC281131
0.9441	High Similarity	NPC274618
0.9441	High Similarity	NPC276222
0.9441	High Similarity	NPC253662
0.9441	High Similarity	NPC308404
0.9441	High Similarity	NPC88789
0.9441	High Similarity	NPC99957
0.9441	High Similarity	NPC179950
0.9441	High Similarity	NPC118284
0.9434	High Similarity	NPC182045
0.9427	High Similarity	NPC170475
0.9394	High Similarity	NPC169733
0.9394	High Similarity	NPC472992
0.9394	High Similarity	NPC472380
0.9394	High Similarity	NPC472382
0.9394	High Similarity	NPC472991
0.9394	High Similarity	NPC472384
0.9394	High Similarity	NPC8573
0.939	High Similarity	NPC4390
0.939	High Similarity	NPC169977
0.939	High Similarity	NPC24043
0.939	High Similarity	NPC42773
0.939	High Similarity	NPC45522
0.939	High Similarity	NPC21666
0.939	High Similarity	NPC472993
0.939	High Similarity	NPC101026
0.9387	High Similarity	NPC255157
0.9387	High Similarity	NPC254855
0.9387	High Similarity	NPC67105
0.9387	High Similarity	NPC136042
0.9387	High Similarity	NPC20505
0.9387	High Similarity	NPC67326
0.9387	High Similarity	NPC155763
0.9387	High Similarity	NPC95866
0.9387	High Similarity	NPC259896
0.9387	High Similarity	NPC156869
0.9387	High Similarity	NPC235260
0.9387	High Similarity	NPC29958
0.9387	High Similarity	NPC293004
0.9383	High Similarity	NPC84362
0.9383	High Similarity	NPC275454
0.9383	High Similarity	NPC226304
0.9383	High Similarity	NPC149244
0.9383	High Similarity	NPC325555
0.9383	High Similarity	NPC223424
0.9383	High Similarity	NPC173637
0.9383	High Similarity	NPC127546
0.9383	High Similarity	NPC48640
0.9383	High Similarity	NPC265530
0.9383	High Similarity	NPC317489
0.9383	High Similarity	NPC52550
0.9379	High Similarity	NPC284277
0.9379	High Similarity	NPC55786
0.9379	High Similarity	NPC475497
0.9379	High Similarity	NPC240431
0.9379	High Similarity	NPC19388

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 NPC45400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	908
0.2-0.3	1894
0.3-0.4	2680
0.4-0.5	1810
0.5-0.6	923
0.6-0.7	369
0.7-0.8	131
0.8-0.85	25
0.85-0.9	13
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9627	High Similarity	NPD7074	Phase 3
0.9625	High Similarity	NPD3818	Discontinued
0.9565	High Similarity	NPD7054	Approved
0.9506	High Similarity	NPD7472	Approved
0.9367	High Similarity	NPD4381	Clinical (unspecified phase)
0.9333	High Similarity	NPD4338	Clinical (unspecified phase)
0.9329	High Similarity	NPD6797	Phase 2
0.9273	High Similarity	NPD7251	Discontinued
0.9217	High Similarity	NPD7808	Phase 3
0.9141	High Similarity	NPD6168	Clinical (unspecified phase)
0.9141	High Similarity	NPD6166	Phase 2
0.9141	High Similarity	NPD6167	Clinical (unspecified phase)
0.9114	High Similarity	NPD1934	Approved
0.8944	High Similarity	NPD4868	Clinical (unspecified phase)
0.8938	High Similarity	NPD2393	Clinical (unspecified phase)
0.8862	High Similarity	NPD7804	Clinical (unspecified phase)
0.882	High Similarity	NPD2801	Approved
0.875	High Similarity	NPD4380	Phase 2
0.8712	High Similarity	NPD3882	Suspended
0.8647	High Similarity	NPD7993	Clinical (unspecified phase)
0.8608	High Similarity	NPD1511	Approved
0.8596	High Similarity	NPD6559	Discontinued
0.8554	High Similarity	NPD5494	Approved
0.8537	High Similarity	NPD3817	Phase 2
0.85	High Similarity	NPD1512	Approved
0.8476	Intermediate Similarity	NPD1465	Phase 2
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5402	Approved
0.8282	Intermediate Similarity	NPD1653	Approved
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD8312	Approved
0.8182	Intermediate Similarity	NPD8313	Approved
0.815	Intermediate Similarity	NPD7228	Approved
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD6232	Discontinued
0.811	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5403	Approved
0.8101	Intermediate Similarity	NPD1510	Phase 2
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7473	Discontinued
0.807	Intermediate Similarity	NPD6959	Discontinued
0.8068	Intermediate Similarity	NPD7685	Pre-registration
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2796	Approved
0.8046	Intermediate Similarity	NPD3751	Discontinued
0.8037	Intermediate Similarity	NPD6799	Approved
0.7988	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5401	Approved
0.7965	Intermediate Similarity	NPD7199	Phase 2
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD3787	Discontinued
0.7889	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7266	Discontinued
0.787	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7848	Intermediate Similarity	NPD1240	Approved
0.7836	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD8151	Discontinued
0.7791	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7766	Intermediate Similarity	NPD6781	Approved
0.7766	Intermediate Similarity	NPD6777	Approved
0.7766	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD6776	Approved
0.7766	Intermediate Similarity	NPD6782	Approved
0.7766	Intermediate Similarity	NPD6779	Approved
0.7766	Intermediate Similarity	NPD6778	Approved
0.775	Intermediate Similarity	NPD1607	Approved
0.7744	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7584	Approved
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6190	Approved
0.7688	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD1933	Approved
0.7667	Intermediate Similarity	NPD7240	Approved
0.7658	Intermediate Similarity	NPD3027	Phase 3
0.7657	Intermediate Similarity	NPD1247	Approved
0.7644	Intermediate Similarity	NPD7698	Approved
0.7644	Intermediate Similarity	NPD7697	Approved
0.7644	Intermediate Similarity	NPD7696	Phase 3
0.7644	Intermediate Similarity	NPD919	Approved
0.7644	Intermediate Similarity	NPD7435	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4628	Phase 3
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7607	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD447	Suspended
0.7577	Intermediate Similarity	NPD7701	Phase 2
0.7551	Intermediate Similarity	NPD7783	Phase 2
0.7551	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7699	Phase 2
0.747	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD2532	Approved
0.7439	Intermediate Similarity	NPD3748	Approved
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5953	Discontinued
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3226	Approved
0.7374	Intermediate Similarity	NPD7801	Approved
0.7368	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD2800	Approved
0.7353	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD8319	Approved
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9494	Approved
0.731	Intermediate Similarity	NPD7585	Approved
0.7308	Intermediate Similarity	NPD7286	Phase 2
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD7458	Discontinued
0.7282	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7263	Intermediate Similarity	NPD6213	Phase 3
0.7263	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6212	Phase 3
0.7262	Intermediate Similarity	NPD6674	Discontinued
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1091	Approved
0.7259	Intermediate Similarity	NPD7583	Approved
0.7246	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD2344	Approved
0.7235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2799	Discontinued
0.7188	Intermediate Similarity	NPD1203	Approved
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7184	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5242	Approved
0.7175	Intermediate Similarity	NPD5353	Approved
0.717	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD6832	Phase 2
0.7159	Intermediate Similarity	NPD6844	Discontinued
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2798	Approved
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6651	Approved
0.7107	Intermediate Similarity	NPD9269	Phase 2
0.7093	Intermediate Similarity	NPD7390	Discontinued
0.7076	Intermediate Similarity	NPD2309	Approved
0.7073	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7056	Intermediate Similarity	NPD5006	Approved
0.7056	Intermediate Similarity	NPD5005	Approved
0.7053	Intermediate Similarity	NPD6843	Phase 3
0.7053	Intermediate Similarity	NPD6841	Approved
0.7053	Intermediate Similarity	NPD6842	Approved
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7033	Intermediate Similarity	NPD5711	Approved
0.7033	Intermediate Similarity	NPD5710	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.6984	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD7784	Clinical (unspecified phase)

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