NPASS Compound

Structure

NPC293004 OpenBabel07101718242D 42 46 0 0 1 0 0 0 0 0999 V2000 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 5.1962 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 4.3301 -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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 -5.1962 1.0000 0.0000 C 0 0 2 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 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 2.5981 -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 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 -5.1962 0.0000 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 3.4641 1.0000 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 -4.3301 -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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 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 -6.0622 1.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 -2.5981 -0.5000 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 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 5 2 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 10 1 0 0 0 0 7 15 2 0 0 0 0 8 11 1 0 0 0 0 8 38 1 0 0 0 0 9 39 1 0 0 0 0 10 35 1 0 0 0 0 11 19 1 0 0 0 0 11 28 1 6 0 0 0 12 18 2 0 0 0 0 12 36 1 0 0 0 0 13 25 2 0 0 0 0 13 37 1 0 0 0 0 14 17 2 0 0 0 0 14 40 1 0 0 0 0 15 17 1 0 0 0 0 15 41 1 0 0 0 0 16 9 1 1 0 0 0 16 20 1 0 0 0 0 16 42 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 29 1 1 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 31 2 0 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 33 1 6 0 0 0 24 27 1 0 0 0 0 24 34 1 6 0 0 0 25 40 1 0 0 0 0 26 38 1 0 0 0 0 26 39 1 1 0 0 0 27 41 1 1 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.17
Volume:	546.164
LogP:	0.303
LogD:	0.035
LogS:	-4.399
# Rotatable Bonds:	8
TPSA:	216.2
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.165
Synthetic Accessibility Score:	4.622
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.218
MDCK Permeability:	4.332192838774063e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.736
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	63.59637451171875%
Volume Distribution (VD):	0.698
Pgp-substrate:	23.345523834228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.149
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.444
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.752
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.19
Carcinogencity:	0.257
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC293004

Natural Product ID:	NPC293004
*Common Name:**	1-O-[Beta-D-Xylopyranosyl-(1->6)-Beta-D-Glucopyranosyl]-3,5,8-Trimethoxyxanthone
IUPAC Name:	3,5,8-trimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
Synonyms:
Standard InCHIKey:	ZGNFNPROZXLZQC-IJEUNHHQSA-N
Standard InCHI:	InChI=1S/C27H32O15/c1-35-10-6-14-17(21(31)18-12(36-2)4-5-13(37-3)25(18)40-14)15(7-10)41-27-24(34)22(32)20(30)16(42-27)9-39-26-23(33)19(29)11(28)8-38-26/h4-7,11,16,19-20,22-24,26-30,32-34H,8-9H2,1-3H3/t11-,16-,19+,20-,22+,23-,24-,26+,27-/m1/s1
SMILES:	COc1cc2c(c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O1)O)O)O)c(=O)c1c(ccc(c1o2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409390
PubChem CID:	71747860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23805995]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
NPT2	Others	Unspecified		IC50	=	360000.0	nM	PMID[495915]

☑ 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 NPC293004 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	457
0.1-0.2	1867
0.2-0.3	4207
0.3-0.4	9890
0.4-0.5	8374
0.5-0.6	4734
0.6-0.7	5874
0.7-0.8	4988
0.8-0.85	1346
0.85-0.9	505
0.9-0.95	364
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC52353
0.9875	High Similarity	NPC194483
0.9815	High Similarity	NPC102028
0.9814	High Similarity	NPC267254
0.9814	High Similarity	NPC475155
0.9812	High Similarity	NPC61791
0.9753	High Similarity	NPC51774
0.9753	High Similarity	NPC239549
0.9753	High Similarity	NPC236191
0.9695	High Similarity	NPC475261
0.9693	High Similarity	NPC142996
0.9691	High Similarity	NPC301683
0.9691	High Similarity	NPC156977
0.9689	High Similarity	NPC472383
0.9689	High Similarity	NPC472381
0.9689	High Similarity	NPC293629
0.9636	High Similarity	NPC473895
0.9632	High Similarity	NPC204693
0.963	High Similarity	NPC183357
0.963	High Similarity	NPC44328
0.963	High Similarity	NPC22195
0.963	High Similarity	NPC21190
0.963	High Similarity	NPC105095
0.963	High Similarity	NPC44558
0.963	High Similarity	NPC79056
0.963	High Similarity	NPC177731
0.9627	High Similarity	NPC93099
0.9627	High Similarity	NPC135345
0.9625	High Similarity	NPC284277
0.9625	High Similarity	NPC475366
0.9625	High Similarity	NPC475497
0.9571	High Similarity	NPC472386
0.9568	High Similarity	NPC95855
0.9568	High Similarity	NPC170675
0.9568	High Similarity	NPC43587
0.9568	High Similarity	NPC210042
0.9568	High Similarity	NPC471457
0.9568	High Similarity	NPC112755
0.9565	High Similarity	NPC70441
0.9521	High Similarity	NPC473883
0.9509	High Similarity	NPC34287
0.9509	High Similarity	NPC471416
0.9509	High Similarity	NPC474434
0.9509	High Similarity	NPC105511
0.9503	High Similarity	NPC15358
0.9458	High Similarity	NPC472387
0.9451	High Similarity	NPC3583
0.9451	High Similarity	NPC307518
0.9451	High Similarity	NPC259152
0.9451	High Similarity	NPC48773
0.9451	High Similarity	NPC205076
0.9448	High Similarity	NPC226294
0.9448	High Similarity	NPC229687
0.9448	High Similarity	NPC58053
0.9448	High Similarity	NPC186807
0.9448	High Similarity	NPC475942
0.9448	High Similarity	NPC105025
0.9448	High Similarity	NPC105283
0.9448	High Similarity	NPC183036
0.9448	High Similarity	NPC469931
0.9448	High Similarity	NPC195257
0.9448	High Similarity	NPC45638
0.9448	High Similarity	NPC201292
0.9448	High Similarity	NPC209296
0.9448	High Similarity	NPC93337
0.9444	High Similarity	NPC236934
0.9444	High Similarity	NPC5778
0.9437	High Similarity	NPC182045
0.9401	High Similarity	NPC110941
0.9401	High Similarity	NPC473682
0.9401	High Similarity	NPC470443
0.9401	High Similarity	NPC470444
0.9401	High Similarity	NPC126784
0.9401	High Similarity	NPC241423
0.9401	High Similarity	NPC473571
0.9398	High Similarity	NPC472380
0.9398	High Similarity	NPC472382
0.9398	High Similarity	NPC472384
0.9398	High Similarity	NPC169733
0.9394	High Similarity	NPC208668
0.939	High Similarity	NPC231194
0.939	High Similarity	NPC51326
0.939	High Similarity	NPC210808
0.939	High Similarity	NPC199079
0.939	High Similarity	NPC224462
0.9387	High Similarity	NPC45400
0.9387	High Similarity	NPC146792
0.9387	High Similarity	NPC58716
0.9387	High Similarity	NPC45618
0.9375	High Similarity	NPC110349
0.9349	High Similarity	NPC148710
0.9341	High Similarity	NPC476619
0.9341	High Similarity	NPC476622
0.9341	High Similarity	NPC476618
0.9341	High Similarity	NPC476623
0.9341	High Similarity	NPC476620
0.9341	High Similarity	NPC476621
0.9337	High Similarity	NPC198199
0.9333	High Similarity	NPC137871
0.9333	High Similarity	NPC256760
0.9333	High Similarity	NPC117260
0.9333	High Similarity	NPC180918
0.9333	High Similarity	NPC172807
0.9333	High Similarity	NPC254540
0.9333	High Similarity	NPC257011
0.9333	High Similarity	NPC211594
0.9333	High Similarity	NPC288152
0.9333	High Similarity	NPC476405
0.9333	High Similarity	NPC9002
0.9333	High Similarity	NPC261254
0.9329	High Similarity	NPC86008
0.9325	High Similarity	NPC115674
0.9325	High Similarity	NPC99957
0.9325	High Similarity	NPC181616
0.9325	High Similarity	NPC210073
0.9321	High Similarity	NPC88023
0.9321	High Similarity	NPC127415
0.9321	High Similarity	NPC309025
0.9321	High Similarity	NPC29830
0.9321	High Similarity	NPC243930
0.929	High Similarity	NPC470447
0.929	High Similarity	NPC470445
0.929	High Similarity	NPC473072
0.929	High Similarity	NPC470446
0.929	High Similarity	NPC470449
0.9281	High Similarity	NPC48984
0.9281	High Similarity	NPC255799
0.9281	High Similarity	NPC268533
0.9281	High Similarity	NPC8573
0.9281	High Similarity	NPC65563
0.9281	High Similarity	NPC470949
0.9277	High Similarity	NPC42773
0.9277	High Similarity	NPC101026
0.9277	High Similarity	NPC21666
0.9277	High Similarity	NPC24043
0.9277	High Similarity	NPC169977
0.9277	High Similarity	NPC45522
0.9273	High Similarity	NPC150767
0.9273	High Similarity	NPC245014
0.9273	High Similarity	NPC84265
0.9273	High Similarity	NPC282987
0.9273	High Similarity	NPC78734
0.9268	High Similarity	NPC477502
0.9268	High Similarity	NPC229729
0.9264	High Similarity	NPC165720
0.9264	High Similarity	NPC22832
0.9264	High Similarity	NPC311830
0.9259	High Similarity	NPC127782
0.9259	High Similarity	NPC148273
0.9259	High Similarity	NPC300537
0.9255	High Similarity	NPC271270
0.9255	High Similarity	NPC97285
0.9255	High Similarity	NPC142860
0.9255	High Similarity	NPC246469
0.9235	High Similarity	NPC470451
0.9235	High Similarity	NPC470455
0.9231	High Similarity	NPC473071
0.9231	High Similarity	NPC473073
0.9226	High Similarity	NPC251417
0.9226	High Similarity	NPC120952
0.9226	High Similarity	NPC89052
0.9226	High Similarity	NPC168584
0.9222	High Similarity	NPC473327
0.9222	High Similarity	NPC19108
0.9222	High Similarity	NPC294815
0.9222	High Similarity	NPC477848
0.9222	High Similarity	NPC476472
0.9222	High Similarity	NPC16194
0.9222	High Similarity	NPC264735
0.9222	High Similarity	NPC472607
0.9222	High Similarity	NPC220173
0.9212	High Similarity	NPC52382
0.9212	High Similarity	NPC270578
0.9207	High Similarity	NPC113093
0.9207	High Similarity	NPC8856
0.9202	High Similarity	NPC191306
0.9202	High Similarity	NPC19709
0.9202	High Similarity	NPC270335
0.9202	High Similarity	NPC222936
0.9202	High Similarity	NPC284960
0.9202	High Similarity	NPC88043
0.9202	High Similarity	NPC94777
0.9187	High Similarity	NPC295613
0.9187	High Similarity	NPC473657
0.9186	High Similarity	NPC473618
0.9172	High Similarity	NPC192539
0.9167	High Similarity	NPC292019
0.9167	High Similarity	NPC198324
0.9167	High Similarity	NPC472385
0.9167	High Similarity	NPC202908
0.9167	High Similarity	NPC211532
0.9167	High Similarity	NPC219043
0.9167	High Similarity	NPC472991
0.9167	High Similarity	NPC14187
0.9167	High Similarity	NPC472992
0.9167	High Similarity	NPC257714
0.9167	High Similarity	NPC122467
0.9167	High Similarity	NPC233994
0.9162	High Similarity	NPC25724
0.9157	High Similarity	NPC95866

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 NPC293004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	955
0.2-0.3	1987
0.3-0.4	2741
0.4-0.5	1840
0.5-0.6	820
0.6-0.7	280
0.7-0.8	94
0.8-0.85	17
0.85-0.9	5
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.963	High Similarity	NPD7074	Phase 3
0.9448	High Similarity	NPD7054	Approved
0.939	High Similarity	NPD7472	Approved
0.9222	High Similarity	NPD7808	Phase 3
0.9162	High Similarity	NPD7251	Discontinued
0.9107	High Similarity	NPD4338	Clinical (unspecified phase)
0.9102	High Similarity	NPD6797	Phase 2
0.9036	High Similarity	NPD3818	Discontinued
0.8916	High Similarity	NPD6167	Clinical (unspecified phase)
0.8916	High Similarity	NPD6168	Clinical (unspecified phase)
0.8916	High Similarity	NPD6166	Phase 2
0.8896	High Similarity	NPD4381	Clinical (unspecified phase)
0.8869	High Similarity	NPD7804	Clinical (unspecified phase)
0.8765	High Similarity	NPD1934	Approved
0.8712	High Similarity	NPD2801	Approved
0.8675	High Similarity	NPD5494	Approved
0.8598	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD3817	Phase 2
0.8383	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD4380	Phase 2
0.8286	Intermediate Similarity	NPD6559	Discontinued
0.8274	Intermediate Similarity	NPD3882	Suspended
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7075	Discontinued
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8214	Intermediate Similarity	NPD5402	Approved
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD1511	Approved
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD1512	Approved
0.8057	Intermediate Similarity	NPD7228	Approved
0.8035	Intermediate Similarity	NPD3787	Discontinued
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD8312	Approved
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7977	Intermediate Similarity	NPD6959	Discontinued
0.7977	Intermediate Similarity	NPD7199	Phase 2
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD1653	Approved
0.7963	Intermediate Similarity	NPD1549	Phase 2
0.7955	Intermediate Similarity	NPD3751	Discontinued
0.795	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD1465	Phase 2
0.7939	Intermediate Similarity	NPD6799	Approved
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7240	Approved
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7835	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7783	Phase 2
0.7798	Intermediate Similarity	NPD5403	Approved
0.7784	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7778	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD1247	Approved
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.7749	Intermediate Similarity	NPD7696	Phase 3
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.7749	Intermediate Similarity	NPD7697	Approved
0.7749	Intermediate Similarity	NPD7698	Approved
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD4965	Approved
0.7732	Intermediate Similarity	NPD8151	Discontinued
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.768	Intermediate Similarity	NPD7701	Phase 2
0.7679	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1510	Phase 2
0.7657	Intermediate Similarity	NPD6234	Discontinued
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.7604	Intermediate Similarity	NPD6823	Phase 2
0.7593	Intermediate Similarity	NPD1933	Approved
0.7579	Intermediate Similarity	NPD7700	Phase 2
0.7579	Intermediate Similarity	NPD7699	Phase 2
0.7576	Intermediate Similarity	NPD7266	Discontinued
0.7557	Intermediate Similarity	NPD919	Approved
0.7538	Intermediate Similarity	NPD7584	Approved
0.7531	Intermediate Similarity	NPD1240	Approved
0.7531	Intermediate Similarity	NPD1613	Approved
0.7531	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6534	Approved
0.7475	Intermediate Similarity	NPD7801	Approved
0.7443	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4628	Phase 3
0.7439	Intermediate Similarity	NPD1607	Approved
0.7423	Intermediate Similarity	NPD943	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.7401	Intermediate Similarity	NPD3749	Approved
0.7381	Intermediate Similarity	NPD6674	Discontinued
0.7378	Intermediate Similarity	NPD447	Suspended
0.7371	Intermediate Similarity	NPD6844	Discontinued
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7346	Intermediate Similarity	NPD3027	Phase 3
0.7337	Intermediate Similarity	NPD3750	Approved
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD6190	Approved
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7284	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD920	Approved
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6212	Phase 3
0.7277	Intermediate Similarity	NPD6213	Phase 3
0.7277	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7268	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7680	Approved
0.7202	Intermediate Similarity	NPD1551	Phase 2
0.72	Intermediate Similarity	NPD3226	Approved
0.7191	Intermediate Similarity	NPD5353	Approved
0.7186	Intermediate Similarity	NPD7583	Approved
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD2800	Approved
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7585	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7104	Intermediate Similarity	NPD5242	Approved
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7076	Intermediate Similarity	NPD1243	Approved
0.7071	Intermediate Similarity	NPD5005	Approved
0.7071	Intermediate Similarity	NPD5006	Approved
0.7068	Intermediate Similarity	NPD6842	Approved
0.7068	Intermediate Similarity	NPD6843	Phase 3
0.7068	Intermediate Similarity	NPD6841	Approved
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD2798	Approved
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD6651	Approved
0.7022	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6385	Approved
0.7011	Intermediate Similarity	NPD7390	Discontinued
0.6988	Remote Similarity	NPD6798	Discontinued
0.6984	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7549	Discontinued
0.6981	Remote Similarity	NPD8059	Phase 3
0.6981	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1652	Phase 2
0.6974	Remote Similarity	NPD4363	Phase 3
0.6974	Remote Similarity	NPD4360	Phase 2
0.6973	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4908	Phase 1
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6355	Discontinued
0.6964	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD7229	Phase 3
0.6954	Remote Similarity	NPD4420	Approved
0.6941	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2424	Discontinued
0.6919	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9494	Approved
0.6886	Remote Similarity	NPD4907	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