NPASS Compound

Structure

CID65563 OpenBabel06191715402D 43 47 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 3.4641 -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 4.3301 0.5000 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 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 1.7321 -3.0000 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 0.8660 -2.5000 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 -0.0000 -4.0000 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 -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 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 6.0622 0.5000 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 -5.1962 -3.0000 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 -1.7321 2.0000 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 -0.0000 -1.0000 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 -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 2.5981 -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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 39 1 0 0 0 0 8 1 1 1 0 0 0 8 15 1 0 0 0 0 8 40 1 0 0 0 0 9 24 1 0 0 0 0 10 28 1 0 0 0 0 11 16 1 0 0 0 0 11 29 1 0 0 0 0 12 14 2 0 0 0 0 12 41 1 0 0 0 0 13 7 1 6 0 0 0 13 17 1 0 0 0 0 13 42 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 30 1 6 0 0 0 16 18 2 0 0 0 0 16 31 1 0 0 0 0 17 21 1 0 0 0 0 17 32 1 1 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 34 2 0 0 0 0 20 22 1 0 0 0 0 20 35 1 1 0 0 0 21 23 1 0 0 0 0 21 36 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 1 0 0 0 23 27 1 0 0 0 0 23 38 1 1 0 0 0 24 25 2 0 0 0 0 24 41 1 0 0 0 0 25 43 1 0 0 0 0 26 39 1 6 0 0 0 26 40 1 0 0 0 0 27 42 1 0 0 0 0 27 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.15
Volume:	552.318
LogP:	-0.17
LogD:	-0.361
LogS:	-2.818
# Rotatable Bonds:	6
TPSA:	269.43
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.772
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.495
MDCK Permeability:	1.6174853953998536e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.864
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	89.66343688964844%
Volume Distribution (VD):	0.695
Pgp-substrate:	15.695527076721191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.212
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.833
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.931
Carcinogencity:	0.092
Eye Corrosion:	0.003
Eye Irritation:	0.392
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC65563

Natural Product ID:	NPC65563
*Common Name:**	5,6,7,4'-Tetrahydroxyflavonol 3-O-(6-Alpha-L-Rhamnopyransyl-Beta-D-Glucopyranoside)
IUPAC Name:	5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-[(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:	QYRJNVCANQPMCH-QGAVNTNWSA-N
Standard InCHI:	InChI=1S/C27H30O16/c1-8-15(30)20(35)22(37)26(40-8)39-7-13-17(32)21(36)23(38)27(42-13)43-25-19(34)14-12(6-11(29)16(31)18(14)33)41-24(25)9-2-4-10(28)5-3-9/h2-6,8,13,15,17,20-23,26-33,35-38H,7H2,1H3/t8-,13+,15-,17+,20+,21-,22+,23+,26+,27-/m0/s1
SMILES:	Oc1ccc(cc1)c1oc2cc(O)c(c(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449793
PubChem CID:	10371537
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	43.2	ug.mL-1	PMID[550480]

☑ 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 NPC65563 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	464
0.1-0.2	1893
0.2-0.3	4401
0.3-0.4	10005
0.4-0.5	8099
0.5-0.6	4588
0.6-0.7	5711
0.7-0.8	4894
0.8-0.85	1489
0.85-0.9	602
0.9-0.95	418
0.95-1	133

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470949
0.9879	High Similarity	NPC473682
0.9879	High Similarity	NPC241423
0.9879	High Similarity	NPC110941
0.9879	High Similarity	NPC470444
0.9879	High Similarity	NPC126784
0.9879	High Similarity	NPC473571
0.9879	High Similarity	NPC470443
0.9878	High Similarity	NPC8573
0.9878	High Similarity	NPC169733
0.9819	High Similarity	NPC473073
0.9819	High Similarity	NPC473071
0.9816	High Similarity	NPC471725
0.9816	High Similarity	NPC203259
0.9816	High Similarity	NPC134532
0.9816	High Similarity	NPC33054
0.9816	High Similarity	NPC155877
0.9816	High Similarity	NPC176740
0.9816	High Similarity	NPC471748
0.976	High Similarity	NPC470446
0.976	High Similarity	NPC470449
0.976	High Similarity	NPC470445
0.976	High Similarity	NPC470447
0.976	High Similarity	NPC473072
0.9756	High Similarity	NPC45522
0.9756	High Similarity	NPC169977
0.9756	High Similarity	NPC21666
0.9756	High Similarity	NPC42773
0.9756	High Similarity	NPC24043
0.9756	High Similarity	NPC101026
0.9755	High Similarity	NPC29958
0.9755	High Similarity	NPC67105
0.9755	High Similarity	NPC259896
0.9755	High Similarity	NPC136042
0.9755	High Similarity	NPC67326
0.9755	High Similarity	NPC156869
0.9755	High Similarity	NPC254855
0.9755	High Similarity	NPC255157
0.9755	High Similarity	NPC95866
0.9702	High Similarity	NPC470455
0.9702	High Similarity	NPC148710
0.9702	High Similarity	NPC470451
0.9697	High Similarity	NPC476472
0.9697	High Similarity	NPC294815
0.9697	High Similarity	NPC253685
0.9697	High Similarity	NPC16194
0.9697	High Similarity	NPC473327
0.9697	High Similarity	NPC19108
0.9697	High Similarity	NPC220173
0.9695	High Similarity	NPC3583
0.9695	High Similarity	NPC476405
0.9695	High Similarity	NPC117260
0.9695	High Similarity	NPC26230
0.9695	High Similarity	NPC60735
0.9695	High Similarity	NPC259152
0.9693	High Similarity	NPC227508
0.9639	High Similarity	NPC89127
0.9639	High Similarity	NPC14187
0.9639	High Similarity	NPC472385
0.9639	High Similarity	NPC471669
0.9639	High Similarity	NPC202908
0.9639	High Similarity	NPC292019
0.9639	High Similarity	NPC198324
0.9639	High Similarity	NPC122467
0.9636	High Similarity	NPC204693
0.9634	High Similarity	NPC285197
0.9634	High Similarity	NPC245014
0.9634	High Similarity	NPC282987
0.9634	High Similarity	NPC84265
0.9632	High Similarity	NPC275454
0.9632	High Similarity	NPC52550
0.9632	High Similarity	NPC84362
0.9632	High Similarity	NPC223424
0.9632	High Similarity	NPC317489
0.9632	High Similarity	NPC173637
0.9632	High Similarity	NPC127546
0.9581	High Similarity	NPC168584
0.9581	High Similarity	NPC173837
0.9581	High Similarity	NPC89052
0.9581	High Similarity	NPC251417
0.9578	High Similarity	NPC264735
0.9578	High Similarity	NPC115760
0.9578	High Similarity	NPC294629
0.9578	High Similarity	NPC135277
0.9578	High Similarity	NPC237435
0.9578	High Similarity	NPC43211
0.9578	High Similarity	NPC49344
0.9578	High Similarity	NPC210094
0.9578	High Similarity	NPC101191
0.9578	High Similarity	NPC477848
0.9576	High Similarity	NPC301683
0.9576	High Similarity	NPC190003
0.9576	High Similarity	NPC175107
0.9573	High Similarity	NPC186807
0.9573	High Similarity	NPC219904
0.9573	High Similarity	NPC120099
0.9573	High Similarity	NPC93337
0.9573	High Similarity	NPC226294
0.9573	High Similarity	NPC270578
0.9573	High Similarity	NPC469931
0.9573	High Similarity	NPC45638
0.9573	High Similarity	NPC225434
0.9573	High Similarity	NPC201292
0.9573	High Similarity	NPC105025
0.9573	High Similarity	NPC58053
0.9573	High Similarity	NPC203050
0.9573	High Similarity	NPC52382
0.9573	High Similarity	NPC475942
0.9573	High Similarity	NPC223747
0.9571	High Similarity	NPC308404
0.9571	High Similarity	NPC113968
0.9571	High Similarity	NPC277174
0.9571	High Similarity	NPC73855
0.9571	High Similarity	NPC274618
0.9571	High Similarity	NPC145038
0.9571	High Similarity	NPC88789
0.9571	High Similarity	NPC118284
0.9571	High Similarity	NPC281131
0.9571	High Similarity	NPC135599
0.9571	High Similarity	NPC8856
0.9571	High Similarity	NPC56077
0.9571	High Similarity	NPC115674
0.9571	High Similarity	NPC276222
0.9571	High Similarity	NPC179950
0.9571	High Similarity	NPC210073
0.9571	High Similarity	NPC253662
0.9571	High Similarity	NPC328940
0.9527	High Similarity	NPC36138
0.9524	High Similarity	NPC192539
0.9521	High Similarity	NPC233994
0.9521	High Similarity	NPC211532
0.9521	High Similarity	NPC472380
0.9521	High Similarity	NPC219043
0.9521	High Similarity	NPC472384
0.9521	High Similarity	NPC48984
0.9521	High Similarity	NPC472382
0.9521	High Similarity	NPC473862
0.9521	High Similarity	NPC268533
0.9518	High Similarity	NPC4390
0.9518	High Similarity	NPC236191
0.9518	High Similarity	NPC51774
0.9518	High Similarity	NPC239549
0.9515	High Similarity	NPC21190
0.9515	High Similarity	NPC244776
0.9515	High Similarity	NPC22195
0.9515	High Similarity	NPC116864
0.9515	High Similarity	NPC235260
0.9515	High Similarity	NPC20505
0.9515	High Similarity	NPC155763
0.9515	High Similarity	NPC206123
0.9515	High Similarity	NPC183357
0.9512	High Similarity	NPC265530
0.9512	High Similarity	NPC146792
0.9512	High Similarity	NPC45618
0.9512	High Similarity	NPC226304
0.9512	High Similarity	NPC160156
0.9512	High Similarity	NPC92565
0.9512	High Similarity	NPC325555
0.9512	High Similarity	NPC58716
0.9509	High Similarity	NPC277205
0.9509	High Similarity	NPC55786
0.9509	High Similarity	NPC19388
0.9509	High Similarity	NPC240431
0.9471	High Similarity	NPC470416
0.9464	High Similarity	NPC267680
0.9464	High Similarity	NPC293626
0.9464	High Similarity	NPC253521
0.9464	High Similarity	NPC217387
0.9464	High Similarity	NPC37668
0.9464	High Similarity	NPC196127
0.9464	High Similarity	NPC258044
0.9464	High Similarity	NPC113836
0.9464	High Similarity	NPC35167
0.9461	High Similarity	NPC142996
0.9461	High Similarity	NPC102028
0.9458	High Similarity	NPC211594
0.9458	High Similarity	NPC172807
0.9458	High Similarity	NPC307518
0.9458	High Similarity	NPC267254
0.9458	High Similarity	NPC245452
0.9458	High Similarity	NPC254540
0.9458	High Similarity	NPC153755
0.9458	High Similarity	NPC48773
0.9458	High Similarity	NPC156977
0.9458	High Similarity	NPC205076
0.9455	High Similarity	NPC471457
0.9455	High Similarity	NPC472381
0.9455	High Similarity	NPC86008
0.9455	High Similarity	NPC210042
0.9455	High Similarity	NPC195257
0.9455	High Similarity	NPC95855
0.9455	High Similarity	NPC170675
0.9455	High Similarity	NPC472383
0.9455	High Similarity	NPC209296
0.9455	High Similarity	NPC112755
0.9455	High Similarity	NPC138927
0.9451	High Similarity	NPC99957
0.9451	High Similarity	NPC197285
0.9451	High Similarity	NPC181616
0.9451	High Similarity	NPC21100

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 NPC65563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	967
0.2-0.3	2044
0.3-0.4	2745
0.4-0.5	1786
0.5-0.6	808
0.6-0.7	258
0.7-0.8	98
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9816	High Similarity	NPD6797	Phase 2
0.9756	High Similarity	NPD7251	Discontinued
0.9578	High Similarity	NPD4338	Clinical (unspecified phase)
0.9578	High Similarity	NPD7808	Phase 3
0.9515	High Similarity	NPD7472	Approved
0.9455	High Similarity	NPD7054	Approved
0.9281	High Similarity	NPD7074	Phase 3
0.9107	High Similarity	NPD7804	Clinical (unspecified phase)
0.9048	High Similarity	NPD3818	Discontinued
0.9042	High Similarity	NPD6168	Clinical (unspecified phase)
0.9042	High Similarity	NPD6167	Clinical (unspecified phase)
0.9042	High Similarity	NPD6166	Phase 2
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8841	High Similarity	NPD2801	Approved
0.8675	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD1934	Approved
0.8623	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8563	High Similarity	NPD7993	Clinical (unspecified phase)
0.8563	High Similarity	NPD5402	Approved
0.8528	High Similarity	NPD1512	Approved
0.8405	Intermediate Similarity	NPD1511	Approved
0.8402	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7075	Discontinued
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD5494	Approved
0.8225	Intermediate Similarity	NPD6801	Discontinued
0.8202	Intermediate Similarity	NPD6559	Discontinued
0.8182	Intermediate Similarity	NPD3751	Discontinued
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3787	Discontinued
0.8144	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1653	Approved
0.8072	Intermediate Similarity	NPD6799	Approved
0.8024	Intermediate Similarity	NPD5401	Approved
0.7933	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8312	Approved
0.7912	Intermediate Similarity	NPD8313	Approved
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD6777	Approved
0.7895	Intermediate Similarity	NPD6776	Approved
0.7895	Intermediate Similarity	NPD6779	Approved
0.7895	Intermediate Similarity	NPD6782	Approved
0.7895	Intermediate Similarity	NPD6781	Approved
0.7895	Intermediate Similarity	NPD6778	Approved
0.7895	Intermediate Similarity	NPD6780	Approved
0.7879	Intermediate Similarity	NPD1549	Phase 2
0.7877	Intermediate Similarity	NPD7228	Approved
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7861	Intermediate Similarity	NPD1465	Phase 2
0.7816	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7685	Pre-registration
0.7797	Intermediate Similarity	NPD1247	Approved
0.7796	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7772	Intermediate Similarity	NPD7698	Approved
0.7772	Intermediate Similarity	NPD7696	Phase 3
0.7772	Intermediate Similarity	NPD7697	Approved
0.7759	Intermediate Similarity	NPD7819	Suspended
0.7758	Intermediate Similarity	NPD2796	Approved
0.7753	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD7411	Suspended
0.7738	Intermediate Similarity	NPD6190	Approved
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7473	Discontinued
0.7709	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD7701	Phase 2
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7665	Intermediate Similarity	NPD8151	Discontinued
0.7641	Intermediate Similarity	NPD7870	Phase 2
0.7641	Intermediate Similarity	NPD7871	Phase 2
0.7632	Intermediate Similarity	NPD6534	Approved
0.7632	Intermediate Similarity	NPD6535	Approved
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7266	Discontinued
0.7604	Intermediate Similarity	NPD7699	Phase 2
0.7604	Intermediate Similarity	NPD7700	Phase 2
0.7598	Intermediate Similarity	NPD7199	Phase 2
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD919	Approved
0.7574	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.7557	Intermediate Similarity	NPD8455	Phase 2
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7475	Intermediate Similarity	NPD7584	Approved
0.7472	Intermediate Similarity	NPD4965	Approved
0.7472	Intermediate Similarity	NPD4967	Phase 2
0.7472	Intermediate Similarity	NPD4966	Approved
0.7456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD943	Approved
0.7455	Intermediate Similarity	NPD1240	Approved
0.7449	Intermediate Similarity	NPD6823	Phase 2
0.741	Intermediate Similarity	NPD230	Phase 1
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD8319	Approved
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.7341	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD3749	Approved
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8434	Phase 2
0.7316	Intermediate Similarity	NPD8150	Discontinued
0.7305	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7229	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7207	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.7186	Intermediate Similarity	NPD6233	Phase 2
0.7121	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD920	Approved
0.711	Intermediate Similarity	NPD2800	Approved
0.711	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7585	Approved
0.709	Intermediate Similarity	NPD5953	Discontinued
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3748	Approved
0.7065	Intermediate Similarity	NPD7680	Approved
0.7044	Intermediate Similarity	NPD7583	Approved
0.7039	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7024	Intermediate Similarity	NPD6798	Discontinued
0.7016	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.6994	Remote Similarity	NPD1091	Approved
0.6984	Remote Similarity	NPD7286	Phase 2
0.6977	Remote Similarity	NPD7033	Discontinued
0.6949	Remote Similarity	NPD7390	Discontinued
0.6946	Remote Similarity	NPD9494	Approved
0.6936	Remote Similarity	NPD6099	Approved
0.6936	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6914	Remote Similarity	NPD6674	Discontinued
0.6914	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD1243	Approved
0.6905	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD4908	Phase 1
0.6901	Remote Similarity	NPD6355	Discontinued
0.6897	Remote Similarity	NPD2344	Approved
0.6897	Remote Similarity	NPD2346	Discontinued
0.6893	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD2799	Discontinued
0.686	Remote Similarity	NPD6651	Approved
0.6852	Remote Similarity	NPD8059	Phase 3
0.6852	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5353	Approved
0.6839	Remote Similarity	NPD7549	Discontinued
0.6826	Remote Similarity	NPD1203	Approved
0.6825	Remote Similarity	NPD2403	Approved
0.6824	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5711	Approved
0.6809	Remote Similarity	NPD5710	Approved
0.6807	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5124	Phase 1
0.6802	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5242	Approved
0.6765	Remote Similarity	NPD5005	Approved
0.6765	Remote Similarity	NPD5006	Approved
0.6758	Remote Similarity	NPD5808	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