NPASS Compound

Structure

CID160156 OpenBabel06191715532D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -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 1.0000 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 -5.1962 -0.0000 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 -0.0000 3.0000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 -2.5981 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 1 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 2.5981 -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 -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 0.8660 2.5000 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 -0.0000 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 -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 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 31 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 20 1 0 0 0 0 16 28 2 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 1 0 0 0 19 7 1 1 0 0 0 19 20 1 0 0 0 0 19 31 1 0 0 0 0 20 33 1 6 0 0 0 21 32 1 0 0 0 0 21 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.11
Volume:	424.574
LogP:	-0.326
LogD:	0.001
LogS:	-3.142
# Rotatable Bonds:	4
TPSA:	206.6
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	4.344
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.667
MDCK Permeability:	5.681128186552087e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.875
20% Bioavailability (F20%):	0.32
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	90.29976654052734%
Volume Distribution (VD):	0.569
Pgp-substrate:	12.383943557739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.093
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.412
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	2.4
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.715
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.913
Carcinogencity:	0.255
Eye Corrosion:	0.003
Eye Irritation:	0.672
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC160156

Natural Product ID:	NPC160156
*Common Name:**	(2R,3R)-(+)-Glucodistylin
IUPAC Name:	(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:	(2R,3R)-(+)-Glucodistylin
Standard InCHIKey:	FVQOMEDMFUMIMO-UTZHSPHRSA-N
Standard InCHI:	InChI=1S/C21H22O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-27,29-30H,6H2/t13-,15-,17+,18-,19-,20+,21+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2[C@H](Oc3c(C2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332678
PubChem CID:	14187089
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
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540981]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18007	Agrimonia pilosa	Species	Rosaceae	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
ED50	1
Others	2

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	101.45	%	PMID[573867]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	35.55	%	PMID[573867]
NPT1	Others	Radical scavenging activity		ED50	=	33.55	uM	PMID[573867]

☑ 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 NPC160156 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	425
0.1-0.2	1744
0.2-0.3	4078
0.3-0.4	9593
0.4-0.5	8402
0.5-0.6	4177
0.6-0.7	5108
0.7-0.8	5782
0.8-0.85	2146
0.85-0.9	910
0.9-0.95	303
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92565
0.9937	High Similarity	NPC52382
0.9937	High Similarity	NPC270578
0.981	High Similarity	NPC145038
0.981	High Similarity	NPC281131
0.981	High Similarity	NPC308404
0.981	High Similarity	NPC88789
0.981	High Similarity	NPC253662
0.981	High Similarity	NPC118284
0.981	High Similarity	NPC56077
0.981	High Similarity	NPC274618
0.981	High Similarity	NPC276222
0.981	High Similarity	NPC179950
0.9809	High Similarity	NPC29830
0.975	High Similarity	NPC95866
0.975	High Similarity	NPC254855
0.975	High Similarity	NPC156869
0.975	High Similarity	NPC136042
0.975	High Similarity	NPC255157
0.975	High Similarity	NPC67326
0.975	High Similarity	NPC259896
0.975	High Similarity	NPC29958
0.9748	High Similarity	NPC317489
0.9748	High Similarity	NPC52550
0.9748	High Similarity	NPC223424
0.9748	High Similarity	NPC84362
0.9748	High Similarity	NPC173637
0.9748	High Similarity	NPC127546
0.9747	High Similarity	NPC277205
0.9747	High Similarity	NPC240431
0.9747	High Similarity	NPC19388
0.9747	High Similarity	NPC55786
0.9691	High Similarity	NPC294629
0.9689	High Similarity	NPC155877
0.9689	High Similarity	NPC471725
0.9689	High Similarity	NPC134532
0.9689	High Similarity	NPC60735
0.9689	High Similarity	NPC471748
0.9689	High Similarity	NPC33054
0.9689	High Similarity	NPC26230
0.9689	High Similarity	NPC176740
0.9689	High Similarity	NPC203259
0.9688	High Similarity	NPC225434
0.9688	High Similarity	NPC219904
0.9688	High Similarity	NPC120099
0.9688	High Similarity	NPC203050
0.9688	High Similarity	NPC223747
0.9686	High Similarity	NPC5778
0.9686	High Similarity	NPC21100
0.9686	High Similarity	NPC236934
0.9686	High Similarity	NPC113968
0.9686	High Similarity	NPC135599
0.9686	High Similarity	NPC277174
0.9686	High Similarity	NPC73855
0.9686	High Similarity	NPC328940
0.9686	High Similarity	NPC197285
0.9632	High Similarity	NPC268533
0.9627	High Similarity	NPC235260
0.9627	High Similarity	NPC20505
0.9627	High Similarity	NPC285197
0.9627	High Similarity	NPC155763
0.9627	High Similarity	NPC206123
0.9627	High Similarity	NPC244776
0.9627	High Similarity	NPC116864
0.9627	High Similarity	NPC67105
0.9625	High Similarity	NPC48640
0.9625	High Similarity	NPC265530
0.9625	High Similarity	NPC45400
0.9625	High Similarity	NPC275454
0.9625	High Similarity	NPC226304
0.9625	High Similarity	NPC149244
0.9625	High Similarity	NPC325555
0.962	High Similarity	NPC300537
0.962	High Similarity	NPC189142
0.962	High Similarity	NPC127782
0.962	High Similarity	NPC77660
0.9571	High Similarity	NPC220173
0.9571	High Similarity	NPC294815
0.9571	High Similarity	NPC16194
0.9571	High Similarity	NPC473327
0.9571	High Similarity	NPC19108
0.9571	High Similarity	NPC476472
0.9571	High Similarity	NPC253685
0.9568	High Similarity	NPC245452
0.9568	High Similarity	NPC175107
0.9568	High Similarity	NPC153755
0.9568	High Similarity	NPC190003
0.9565	High Similarity	NPC170675
0.9565	High Similarity	NPC229687
0.9565	High Similarity	NPC138927
0.9565	High Similarity	NPC105283
0.9565	High Similarity	NPC112755
0.9565	High Similarity	NPC43587
0.9565	High Similarity	NPC227508
0.9565	High Similarity	NPC471457
0.9563	High Similarity	NPC8856
0.9563	High Similarity	NPC115674
0.9563	High Similarity	NPC255615
0.9563	High Similarity	NPC67037
0.9563	High Similarity	NPC210073
0.956	High Similarity	NPC270335
0.956	High Similarity	NPC19709
0.956	High Similarity	NPC191306
0.956	High Similarity	NPC168822
0.9512	High Similarity	NPC292019
0.9512	High Similarity	NPC202908
0.9512	High Similarity	NPC472382
0.9512	High Similarity	NPC89127
0.9512	High Similarity	NPC122467
0.9512	High Similarity	NPC65563
0.9512	High Similarity	NPC472380
0.9512	High Similarity	NPC8573
0.9512	High Similarity	NPC219043
0.9512	High Similarity	NPC472384
0.9512	High Similarity	NPC471669
0.9512	High Similarity	NPC470949
0.9512	High Similarity	NPC14187
0.9509	High Similarity	NPC21666
0.9509	High Similarity	NPC45522
0.9509	High Similarity	NPC169977
0.9509	High Similarity	NPC42773
0.9509	High Similarity	NPC101026
0.9509	High Similarity	NPC4390
0.9509	High Similarity	NPC24043
0.9506	High Similarity	NPC105095
0.9506	High Similarity	NPC34287
0.9506	High Similarity	NPC471416
0.9506	High Similarity	NPC245014
0.9506	High Similarity	NPC177731
0.9506	High Similarity	NPC84265
0.9506	High Similarity	NPC72249
0.9506	High Similarity	NPC150767
0.9506	High Similarity	NPC231194
0.9506	High Similarity	NPC21190
0.9506	High Similarity	NPC79056
0.9506	High Similarity	NPC78734
0.9506	High Similarity	NPC282987
0.9506	High Similarity	NPC218488
0.9506	High Similarity	NPC51326
0.9506	High Similarity	NPC44328
0.9506	High Similarity	NPC183357
0.9506	High Similarity	NPC22195
0.9503	High Similarity	NPC477502
0.9503	High Similarity	NPC229729
0.95	High Similarity	NPC34531
0.95	High Similarity	NPC165720
0.95	High Similarity	NPC311830
0.95	High Similarity	NPC22832
0.9497	High Similarity	NPC473043
0.9494	High Similarity	NPC153342
0.9455	High Similarity	NPC173837
0.9455	High Similarity	NPC168584
0.9455	High Similarity	NPC251417
0.9455	High Similarity	NPC89052
0.9451	High Similarity	NPC49344
0.9451	High Similarity	NPC223426
0.9451	High Similarity	NPC81042
0.9451	High Similarity	NPC101191
0.9451	High Similarity	NPC214621
0.9451	High Similarity	NPC34267
0.9451	High Similarity	NPC210094
0.9451	High Similarity	NPC108202
0.9451	High Similarity	NPC237435
0.9451	High Similarity	NPC115760
0.9451	High Similarity	NPC43211
0.9451	High Similarity	NPC135277
0.9448	High Similarity	NPC476405
0.9448	High Similarity	NPC47140
0.9448	High Similarity	NPC117260
0.9448	High Similarity	NPC256760
0.9448	High Similarity	NPC67134
0.9448	High Similarity	NPC261254
0.9448	High Similarity	NPC301683
0.9444	High Similarity	NPC472383
0.9444	High Similarity	NPC210042
0.9444	High Similarity	NPC195257
0.9444	High Similarity	NPC293629
0.9444	High Similarity	NPC472381
0.9444	High Similarity	NPC86008
0.9444	High Similarity	NPC95855
0.9444	High Similarity	NPC209296
0.9441	High Similarity	NPC254306
0.9437	High Similarity	NPC88043
0.9437	High Similarity	NPC243930
0.9437	High Similarity	NPC284960
0.9437	High Similarity	NPC309025
0.9437	High Similarity	NPC222936
0.9437	High Similarity	NPC88023
0.9398	High Similarity	NPC473571
0.9398	High Similarity	NPC126784
0.9398	High Similarity	NPC192539
0.9398	High Similarity	NPC470444
0.9398	High Similarity	NPC470443
0.9398	High Similarity	NPC473682
0.9398	High Similarity	NPC110941
0.9398	High Similarity	NPC241423
0.9394	High Similarity	NPC61904
0.9394	High Similarity	NPC169733
0.9394	High Similarity	NPC472385
0.9394	High Similarity	NPC198324

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 NPC160156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	911
0.2-0.3	1901
0.3-0.4	2662
0.4-0.5	1843
0.5-0.6	910
0.6-0.7	378
0.7-0.8	121
0.8-0.85	22
0.85-0.9	8
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD6797	Phase 2
0.963	High Similarity	NPD7251	Discontinued
0.9506	High Similarity	NPD7074	Phase 3
0.9451	High Similarity	NPD4338	Clinical (unspecified phase)
0.9451	High Similarity	NPD7808	Phase 3
0.9444	High Similarity	NPD7054	Approved
0.9387	High Similarity	NPD7472	Approved
0.9264	High Similarity	NPD3818	Discontinued
0.9259	High Similarity	NPD6168	Clinical (unspecified phase)
0.9259	High Similarity	NPD6167	Clinical (unspecified phase)
0.9259	High Similarity	NPD6166	Phase 2
0.9245	High Similarity	NPD4381	Clinical (unspecified phase)
0.9207	High Similarity	NPD7804	Clinical (unspecified phase)
0.8994	High Similarity	NPD1934	Approved
0.8938	High Similarity	NPD2393	Clinical (unspecified phase)
0.8765	High Similarity	NPD3817	Phase 2
0.8734	High Similarity	NPD1512	Approved
0.8712	High Similarity	NPD4868	Clinical (unspecified phase)
0.8712	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD7075	Discontinued
0.8647	High Similarity	NPD7993	Clinical (unspecified phase)
0.8634	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD1511	Approved
0.8589	High Similarity	NPD2801	Approved
0.8488	Intermediate Similarity	NPD6559	Discontinued
0.8476	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1549	Phase 2
0.8261	Intermediate Similarity	NPD6799	Approved
0.8225	Intermediate Similarity	NPD5494	Approved
0.821	Intermediate Similarity	NPD5401	Approved
0.8167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD3751	Discontinued
0.8144	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD3787	Discontinued
0.8095	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6599	Discontinued
0.807	Intermediate Similarity	NPD6959	Discontinued
0.8061	Intermediate Similarity	NPD1653	Approved
0.8036	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7978	Intermediate Similarity	NPD8313	Approved
0.7978	Intermediate Similarity	NPD8312	Approved
0.7977	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD2796	Approved
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.7879	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7199	Phase 2
0.7805	Intermediate Similarity	NPD6190	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7266	Discontinued
0.7766	Intermediate Similarity	NPD6777	Approved
0.7766	Intermediate Similarity	NPD6781	Approved
0.7766	Intermediate Similarity	NPD6779	Approved
0.7766	Intermediate Similarity	NPD6782	Approved
0.7766	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD6776	Approved
0.7766	Intermediate Similarity	NPD6778	Approved
0.7765	Intermediate Similarity	NPD7685	Pre-registration
0.7746	Intermediate Similarity	NPD919	Approved
0.7746	Intermediate Similarity	NPD6234	Discontinued
0.7737	Intermediate Similarity	NPD7435	Discontinued
0.7736	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD943	Approved
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8455	Phase 2
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7663	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD37	Approved
0.7657	Intermediate Similarity	NPD1247	Approved
0.7644	Intermediate Similarity	NPD7698	Approved
0.7644	Intermediate Similarity	NPD7696	Phase 3
0.7644	Intermediate Similarity	NPD7697	Approved
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.7636	Intermediate Similarity	NPD3750	Approved
0.763	Intermediate Similarity	NPD4965	Approved
0.763	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD4966	Approved
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.7617	Intermediate Similarity	NPD7584	Approved
0.7605	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3749	Approved
0.7577	Intermediate Similarity	NPD7701	Phase 2
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.753	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD7874	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7699	Phase 2
0.7473	Intermediate Similarity	NPD7240	Approved
0.7469	Intermediate Similarity	NPD1933	Approved
0.7469	Intermediate Similarity	NPD230	Phase 1
0.7462	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7783	Phase 2
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD8320	Phase 1
0.7423	Intermediate Similarity	NPD8319	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7801	Approved
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD3748	Approved
0.732	Intermediate Similarity	NPD6823	Phase 2
0.7284	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD2800	Approved
0.7261	Intermediate Similarity	NPD1091	Approved
0.7256	Intermediate Similarity	NPD447	Suspended
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD7585	Approved
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7184	Intermediate Similarity	NPD7458	Discontinued
0.7184	Intermediate Similarity	NPD3226	Approved
0.7172	Intermediate Similarity	NPD7583	Approved
0.7168	Intermediate Similarity	NPD920	Approved
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7108	Intermediate Similarity	NPD6651	Approved
0.7107	Intermediate Similarity	NPD7680	Approved
0.7093	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6212	Phase 3
0.7083	Intermediate Similarity	NPD6213	Phase 3
0.7081	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7073	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7041	Intermediate Similarity	NPD2346	Discontinued
0.7041	Intermediate Similarity	NPD2344	Approved
0.7037	Intermediate Similarity	NPD2798	Approved
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD4060	Phase 1
0.6966	Remote Similarity	NPD6844	Discontinued
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2403	Approved
0.6954	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5124	Phase 1
0.6946	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD5710	Approved
0.6927	Remote Similarity	NPD7930	Approved
0.6923	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5242	Approved
0.6899	Remote Similarity	NPD1548	Phase 1
0.6894	Remote Similarity	NPD9269	Phase 2
0.689	Remote Similarity	NPD2861	Phase 2
0.6889	Remote Similarity	NPD5353	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