NPASS Compound

Structure

NPC300537 OpenBabel07101718202D 33 35 0 0 1 0 0 0 0 0999 V2000 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 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 -3.4641 3.0000 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 -0.8660 4.5000 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 0.8660 -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 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -1.7321 4.0000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 2 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 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 -7.7942 2.5000 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 2.5981 -0.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 23 1 0 0 0 0 11 31 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 25 2 0 0 0 0 14 26 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 17 9 1 1 0 0 0 17 19 1 0 0 0 0 17 33 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 32 1 1 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.15
Volume:	441.636
LogP:	0.667
LogD:	0.553
LogS:	-3.231
# Rotatable Bonds:	8
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	3.85
Fsp3:	0.409
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.416
MDCK Permeability:	6.62936145090498e-06
Pgp-inhibitor:	0.018
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	90.58963012695312%
Volume Distribution (VD):	0.702
Pgp-substrate:	7.116474151611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.387
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.511
CYP2D6-inhibitor:	0.406
CYP2D6-substrate:	0.297
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	10.873
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.927
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.195
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC300537

Natural Product ID:	NPC300537
*Common Name:**	2',3,4,6'-Tetrahydroxy-4'-Methoxydihydrochalcone 2'-O-Beta-D-Glucopyranoside
IUPAC Name:	3-(3,4-dihydroxyphenyl)-1-[2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propan-1-one
Synonyms:	3-hydroxyasebotin
Standard InCHIKey:	IWJPQQXPWSVXAG-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H26O11/c1-31-11-7-15(27)18(13(25)5-3-10-2-4-12(24)14(26)6-10)16(8-11)32-22-21(30)20(29)19(28)17(9-23)33-22/h2,4,6-8,17,19-24,26-30H,3,5,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc(c2C(=O)CCc2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480475
PubChem CID:	11340276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13961	Pieris japonica	Species	Ericaceae	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	6

Activity Type	# Activity
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	23.95	10'-3cpm	PMID[497361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.1	10'-3cpm	PMID[497361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.16	10'-3cpm	PMID[497361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	33.03	10'-3cpm	PMID[497361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	71.45	10'-3cpm	PMID[497361]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.72	10'-3cpm	PMID[497361]

☑ 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 NPC300537 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	389
0.1-0.2	1559
0.2-0.3	3589
0.3-0.4	8770
0.4-0.5	9462
0.5-0.6	3995
0.6-0.7	4690
0.7-0.8	5821
0.8-0.85	2771
0.85-0.9	1240
0.9-0.95	377
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC127782
0.9808	High Similarity	NPC236934
0.9808	High Similarity	NPC5778
0.9806	High Similarity	NPC29830
0.9806	High Similarity	NPC19709
0.9745	High Similarity	NPC229729
0.9744	High Similarity	NPC165720
0.9744	High Similarity	NPC311830
0.9744	High Similarity	NPC22832
0.9742	High Similarity	NPC189142
0.9742	High Similarity	NPC473043
0.9742	High Similarity	NPC77660
0.9684	High Similarity	NPC43587
0.9684	High Similarity	NPC52382
0.9684	High Similarity	NPC229687
0.9684	High Similarity	NPC270578
0.9682	High Similarity	NPC210073
0.9682	High Similarity	NPC115674
0.9679	High Similarity	NPC222936
0.9679	High Similarity	NPC243930
0.9679	High Similarity	NPC88023
0.9679	High Similarity	NPC191306
0.9679	High Similarity	NPC168822
0.9679	High Similarity	NPC88043
0.9679	High Similarity	NPC284960
0.9679	High Similarity	NPC309025
0.9679	High Similarity	NPC270335
0.9623	High Similarity	NPC183357
0.9623	High Similarity	NPC21190
0.9623	High Similarity	NPC44328
0.9623	High Similarity	NPC78734
0.9623	High Similarity	NPC150767
0.9623	High Similarity	NPC212748
0.9623	High Similarity	NPC177731
0.9623	High Similarity	NPC22195
0.9623	High Similarity	NPC79056
0.9623	High Similarity	NPC231194
0.9623	High Similarity	NPC105095
0.9623	High Similarity	NPC51326
0.962	High Similarity	NPC52550
0.962	High Similarity	NPC116745
0.962	High Similarity	NPC45400
0.962	High Similarity	NPC317489
0.962	High Similarity	NPC127546
0.962	High Similarity	NPC477502
0.962	High Similarity	NPC223424
0.962	High Similarity	NPC84362
0.962	High Similarity	NPC173637
0.962	High Similarity	NPC160156
0.962	High Similarity	NPC92565
0.9618	High Similarity	NPC277205
0.9563	High Similarity	NPC261254
0.9563	High Similarity	NPC256760
0.9563	High Similarity	NPC235575
0.9563	High Similarity	NPC205076
0.9563	High Similarity	NPC301683
0.9563	High Similarity	NPC307518
0.9563	High Similarity	NPC48773
0.956	High Similarity	NPC170675
0.956	High Similarity	NPC93337
0.956	High Similarity	NPC223747
0.956	High Similarity	NPC210042
0.956	High Similarity	NPC105025
0.956	High Similarity	NPC472381
0.956	High Similarity	NPC293629
0.956	High Similarity	NPC105283
0.956	High Similarity	NPC120099
0.956	High Similarity	NPC209296
0.956	High Similarity	NPC469931
0.956	High Similarity	NPC225434
0.956	High Similarity	NPC58053
0.956	High Similarity	NPC475942
0.956	High Similarity	NPC45638
0.956	High Similarity	NPC201292
0.956	High Similarity	NPC195257
0.956	High Similarity	NPC472383
0.956	High Similarity	NPC471457
0.956	High Similarity	NPC219904
0.956	High Similarity	NPC95855
0.956	High Similarity	NPC203050
0.956	High Similarity	NPC186807
0.956	High Similarity	NPC112755
0.956	High Similarity	NPC226294
0.9557	High Similarity	NPC197285
0.9557	High Similarity	NPC88789
0.9557	High Similarity	NPC21100
0.9557	High Similarity	NPC113968
0.9557	High Similarity	NPC277174
0.9557	High Similarity	NPC276222
0.9557	High Similarity	NPC73855
0.9557	High Similarity	NPC274618
0.9557	High Similarity	NPC145038
0.9557	High Similarity	NPC118284
0.9557	High Similarity	NPC135599
0.9557	High Similarity	NPC281131
0.9557	High Similarity	NPC8856
0.9557	High Similarity	NPC179950
0.9557	High Similarity	NPC56077
0.9557	High Similarity	NPC253662
0.9557	High Similarity	NPC308404
0.9557	High Similarity	NPC328940
0.9551	High Similarity	NPC182045
0.9542	High Similarity	NPC106625
0.9503	High Similarity	NPC236191
0.9503	High Similarity	NPC208668
0.9503	High Similarity	NPC239549
0.9503	High Similarity	NPC51774
0.95	High Similarity	NPC218488
0.95	High Similarity	NPC474434
0.95	High Similarity	NPC224462
0.95	High Similarity	NPC206123
0.95	High Similarity	NPC95866
0.95	High Similarity	NPC44558
0.95	High Similarity	NPC116864
0.95	High Similarity	NPC471416
0.95	High Similarity	NPC34287
0.95	High Similarity	NPC244776
0.95	High Similarity	NPC67105
0.95	High Similarity	NPC105511
0.9497	High Similarity	NPC93099
0.9497	High Similarity	NPC58716
0.9497	High Similarity	NPC146792
0.9497	High Similarity	NPC325555
0.9497	High Similarity	NPC48640
0.9497	High Similarity	NPC226304
0.9497	High Similarity	NPC149244
0.9497	High Similarity	NPC265530
0.9497	High Similarity	NPC45618
0.9494	High Similarity	NPC240431
0.9494	High Similarity	NPC19388
0.9494	High Similarity	NPC55786
0.9487	High Similarity	NPC110349
0.9481	High Similarity	NPC99233
0.9477	High Similarity	NPC121001
0.9477	High Similarity	NPC259182
0.9444	High Similarity	NPC294629
0.9441	High Similarity	NPC254540
0.9441	High Similarity	NPC47140
0.9441	High Similarity	NPC153755
0.9441	High Similarity	NPC476405
0.9441	High Similarity	NPC172807
0.9441	High Similarity	NPC472386
0.9441	High Similarity	NPC203259
0.9441	High Similarity	NPC33054
0.9441	High Similarity	NPC471748
0.9441	High Similarity	NPC176740
0.9441	High Similarity	NPC190003
0.9441	High Similarity	NPC117260
0.9441	High Similarity	NPC67134
0.9441	High Similarity	NPC471725
0.9441	High Similarity	NPC245452
0.9441	High Similarity	NPC175107
0.9441	High Similarity	NPC211594
0.9441	High Similarity	NPC267254
0.9441	High Similarity	NPC155877
0.9441	High Similarity	NPC134532
0.9437	High Similarity	NPC86008
0.9437	High Similarity	NPC227508
0.9437	High Similarity	NPC183036
0.9434	High Similarity	NPC67037
0.9434	High Similarity	NPC255615
0.9434	High Similarity	NPC254306
0.943	High Similarity	NPC94777
0.9423	High Similarity	NPC73511
0.9419	High Similarity	NPC206378
0.9419	High Similarity	NPC261866
0.9419	High Similarity	NPC127406
0.9416	High Similarity	NPC18727
0.9383	High Similarity	NPC88560
0.9383	High Similarity	NPC25724
0.9383	High Similarity	NPC21666
0.9383	High Similarity	NPC101026
0.9383	High Similarity	NPC169977
0.9383	High Similarity	NPC472993
0.9383	High Similarity	NPC42773
0.9383	High Similarity	NPC175230
0.9383	High Similarity	NPC4390
0.9383	High Similarity	NPC204693
0.9383	High Similarity	NPC24043
0.9383	High Similarity	NPC45522
0.9383	High Similarity	NPC172033
0.9379	High Similarity	NPC156869
0.9379	High Similarity	NPC72249
0.9379	High Similarity	NPC20505
0.9379	High Similarity	NPC155763
0.9379	High Similarity	NPC259896
0.9379	High Similarity	NPC149011
0.9379	High Similarity	NPC235260
0.9379	High Similarity	NPC29958
0.9379	High Similarity	NPC254855
0.9379	High Similarity	NPC255157
0.9379	High Similarity	NPC245014
0.9379	High Similarity	NPC285197
0.9379	High Similarity	NPC136042
0.9379	High Similarity	NPC84265
0.9379	High Similarity	NPC282987
0.9379	High Similarity	NPC204937
0.9379	High Similarity	NPC67326
0.9375	High Similarity	NPC135345
0.9375	High Similarity	NPC275454

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 NPC300537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	895
0.2-0.3	1770
0.3-0.4	2630
0.4-0.5	1868
0.5-0.6	1008
0.6-0.7	434
0.7-0.8	153
0.8-0.85	29
0.85-0.9	11
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9623	High Similarity	NPD7074	Phase 3
0.956	High Similarity	NPD7054	Approved
0.95	High Similarity	NPD7472	Approved
0.9497	High Similarity	NPD3818	Discontinued
0.9441	High Similarity	NPD6797	Phase 2
0.9383	High Similarity	NPD7251	Discontinued
0.9359	High Similarity	NPD4381	Clinical (unspecified phase)
0.9351	High Similarity	NPD1934	Approved
0.929	High Similarity	NPD2393	Clinical (unspecified phase)
0.9207	High Similarity	NPD4338	Clinical (unspecified phase)
0.9207	High Similarity	NPD7808	Phase 3
0.913	High Similarity	NPD6168	Clinical (unspecified phase)
0.913	High Similarity	NPD6166	Phase 2
0.913	High Similarity	NPD6167	Clinical (unspecified phase)
0.8963	High Similarity	NPD7804	Clinical (unspecified phase)
0.8924	High Similarity	NPD2801	Approved
0.8831	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD4868	Clinical (unspecified phase)
0.8802	High Similarity	NPD6559	Discontinued
0.875	High Similarity	NPD3817	Phase 2
0.8734	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.8696	High Similarity	NPD3882	Suspended
0.8642	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1549	Phase 2
0.8457	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8313	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1653	Approved
0.8258	Intermediate Similarity	NPD2796	Approved
0.8239	Intermediate Similarity	NPD6799	Approved
0.8221	Intermediate Similarity	NPD7411	Suspended
0.8214	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD5402	Approved
0.8176	Intermediate Similarity	NPD7473	Discontinued
0.817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1613	Approved
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD7199	Phase 2
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.8086	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1240	Approved
0.8049	Intermediate Similarity	NPD6599	Discontinued
0.8045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6234	Discontinued
0.8023	Intermediate Similarity	NPD7228	Approved
0.7963	Intermediate Similarity	NPD5401	Approved
0.7955	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD8313	Approved
0.7953	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD37	Approved
0.7949	Intermediate Similarity	NPD1607	Approved
0.7943	Intermediate Similarity	NPD7685	Pre-registration
0.7935	Intermediate Similarity	NPD943	Approved
0.7919	Intermediate Similarity	NPD3751	Discontinued
0.7917	Intermediate Similarity	NPD4967	Phase 2
0.7917	Intermediate Similarity	NPD4966	Approved
0.7917	Intermediate Similarity	NPD4965	Approved
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3787	Discontinued
0.7862	Intermediate Similarity	NPD7266	Discontinued
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7826	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7584	Approved
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD1933	Approved
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3926	Phase 2
0.7742	Intermediate Similarity	NPD6780	Approved
0.7742	Intermediate Similarity	NPD6782	Approved
0.7742	Intermediate Similarity	NPD6779	Approved
0.7742	Intermediate Similarity	NPD6778	Approved
0.7742	Intermediate Similarity	NPD6781	Approved
0.7742	Intermediate Similarity	NPD6777	Approved
0.7742	Intermediate Similarity	NPD6776	Approved
0.7719	Intermediate Similarity	NPD919	Approved
0.7716	Intermediate Similarity	NPD3750	Approved
0.7706	Intermediate Similarity	NPD7768	Phase 2
0.7696	Intermediate Similarity	NPD8151	Discontinued
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7688	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD1551	Phase 2
0.7669	Intermediate Similarity	NPD6190	Approved
0.7661	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2533	Approved
0.7636	Intermediate Similarity	NPD2534	Approved
0.7636	Intermediate Similarity	NPD2532	Approved
0.763	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD7435	Discontinued
0.7547	Intermediate Similarity	NPD447	Suspended
0.7546	Intermediate Similarity	NPD2800	Approved
0.7542	Intermediate Similarity	NPD7240	Approved
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7783	Phase 2
0.7526	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7461	Intermediate Similarity	NPD7701	Phase 2
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7451	Intermediate Similarity	NPD1091	Approved
0.744	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7033	Discontinued
0.7407	Intermediate Similarity	NPD3748	Approved
0.7403	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6651	Approved
0.7385	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7874	Approved
0.7374	Intermediate Similarity	NPD7286	Phase 2
0.7371	Intermediate Similarity	NPD7585	Approved
0.7354	Intermediate Similarity	NPD7700	Phase 2
0.7354	Intermediate Similarity	NPD7699	Phase 2
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7347	Intermediate Similarity	NPD7801	Approved
0.7342	Intermediate Similarity	NPD6832	Phase 2
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD1243	Approved
0.7325	Intermediate Similarity	NPD2798	Approved
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7583	Approved
0.7317	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD2344	Approved
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2799	Discontinued
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7278	Intermediate Similarity	NPD9494	Approved
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD1203	Approved
0.725	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7234	Intermediate Similarity	NPD6213	Phase 3
0.7234	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6212	Phase 3
0.7229	Intermediate Similarity	NPD1652	Phase 2
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8319	Approved
0.7216	Intermediate Similarity	NPD8320	Phase 1
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5711	Approved
0.7168	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7930	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7117	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5005	Approved
0.7113	Intermediate Similarity	NPD5006	Approved
0.7112	Intermediate Similarity	NPD6842	Approved
0.7112	Intermediate Similarity	NPD6843	Phase 3
0.7112	Intermediate Similarity	NPD6841	Approved
0.7099	Intermediate Similarity	NPD6233	Phase 2
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.707	Intermediate Similarity	NPD1608	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