NPASS Compound

Structure

NPC267254 OpenBabel07101718182D 41 45 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 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 1.7321 3.0000 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 6.0622 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 5.1962 1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 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 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 -2.5981 2.5000 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 -1.7321 3.0000 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 -0.8660 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 5.1962 0.0000 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 -1.7321 -2.0000 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 4.0000 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 -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 6.9282 3.0000 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 3.4641 3.0000 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 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 36 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 27 1 0 0 0 0 8 1 1 1 0 0 0 8 17 1 0 0 0 0 8 37 1 0 0 0 0 9 36 1 0 0 0 0 10 15 2 0 0 0 0 10 28 1 0 0 0 0 11 16 2 0 0 0 0 11 38 1 0 0 0 0 12 24 2 0 0 0 0 12 39 1 0 0 0 0 13 15 1 0 0 0 0 13 38 1 0 0 0 0 14 7 1 1 0 0 0 14 18 1 0 0 0 0 14 40 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 6 0 0 0 19 31 2 0 0 0 0 20 22 1 0 0 0 0 20 32 1 1 0 0 0 21 23 1 0 0 0 0 21 33 1 1 0 0 0 22 25 1 0 0 0 0 22 34 1 1 0 0 0 23 26 1 0 0 0 0 23 35 1 6 0 0 0 24 41 1 0 0 0 0 25 37 1 0 0 0 0 25 39 1 6 0 0 0 26 40 1 0 0 0 0 26 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.16
Volume:	528.868
LogP:	-0.068
LogD:	-0.244
LogS:	-4.251
# Rotatable Bonds:	6
TPSA:	238.2
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	4.714
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407
MDCK Permeability:	6.512366235256195e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.795
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	71.20027160644531%
Volume Distribution (VD):	0.691
Pgp-substrate:	19.91322135925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.538
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	1.289
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.726
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.424
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC267254

Natural Product ID:	NPC267254
*Common Name:**	7-O-(Alpha-L-Rhamnopyranosyl)-8-O-(Beta-D-Glucopyranosyl)-1-Hydroxy-3-Methoxyxanthone
IUPAC Name:	8-hydroxy-6-methoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyxanthen-9-one
Synonyms:
Standard InCHIKey:	HWWPEIMHGPFLAK-PZHXEPITSA-N
Standard InCHI:	InChI=1S/C26H30O15/c1-8-17(29)20(32)22(34)25(37-8)39-12-4-3-11-16(19(31)15-10(28)5-9(36-2)6-13(15)38-11)24(12)41-26-23(35)21(33)18(30)14(7-27)40-26/h3-6,8,14,17-18,20-23,25-30,32-35H,7H2,1-2H3/t8-,14+,17-,18+,20+,21-,22+,23+,25-,26-/m0/s1
SMILES:	COc1cc(O)c2c(c1)oc1c(c2=O)c(O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c(cc1)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409396
PubChem CID:	71745330
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	=	714000.0	nM	PMID[542965]

☑ 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 NPC267254 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	444
0.1-0.2	1833
0.2-0.3	4149
0.3-0.4	9777
0.4-0.5	8477
0.5-0.6	4452
0.6-0.7	5495
0.7-0.8	5258
0.8-0.85	1693
0.85-0.9	646
0.9-0.95	373
0.95-1	100

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC236191
0.9938	High Similarity	NPC239549
0.9938	High Similarity	NPC51774
0.9877	High Similarity	NPC102028
0.9876	High Similarity	NPC301683
0.9876	High Similarity	NPC156977
0.9875	High Similarity	NPC472383
0.9875	High Similarity	NPC472381
0.9814	High Similarity	NPC183357
0.9814	High Similarity	NPC21190
0.9814	High Similarity	NPC44558
0.9814	High Similarity	NPC22195
0.9814	High Similarity	NPC293004
0.9812	High Similarity	NPC93099
0.9755	High Similarity	NPC142996
0.9753	High Similarity	NPC472386
0.9752	High Similarity	NPC293629
0.9752	High Similarity	NPC95855
0.9752	High Similarity	NPC170675
0.9752	High Similarity	NPC112755
0.9752	High Similarity	NPC210042
0.9752	High Similarity	NPC471457
0.9693	High Similarity	NPC204693
0.9691	High Similarity	NPC471416
0.9691	High Similarity	NPC79056
0.9691	High Similarity	NPC194483
0.9691	High Similarity	NPC105095
0.9691	High Similarity	NPC44328
0.9691	High Similarity	NPC34287
0.9691	High Similarity	NPC52353
0.9691	High Similarity	NPC474434
0.9691	High Similarity	NPC105511
0.9691	High Similarity	NPC177731
0.9636	High Similarity	NPC472387
0.9632	High Similarity	NPC205076
0.9632	High Similarity	NPC3583
0.9632	High Similarity	NPC307518
0.9632	High Similarity	NPC48773
0.9632	High Similarity	NPC259152
0.9632	High Similarity	NPC475155
0.963	High Similarity	NPC201292
0.963	High Similarity	NPC229687
0.963	High Similarity	NPC43587
0.963	High Similarity	NPC186807
0.963	High Similarity	NPC226294
0.963	High Similarity	NPC93337
0.963	High Similarity	NPC105025
0.963	High Similarity	NPC45638
0.963	High Similarity	NPC61791
0.963	High Similarity	NPC183036
0.963	High Similarity	NPC475942
0.963	High Similarity	NPC469931
0.963	High Similarity	NPC58053
0.9627	High Similarity	NPC236934
0.9627	High Similarity	NPC70441
0.9627	High Similarity	NPC5778
0.9576	High Similarity	NPC169733
0.9576	High Similarity	NPC472382
0.9576	High Similarity	NPC472380
0.9576	High Similarity	NPC472384
0.9571	High Similarity	NPC224462
0.9571	High Similarity	NPC51326
0.9571	High Similarity	NPC231194
0.9568	High Similarity	NPC135345
0.9568	High Similarity	NPC58716
0.9568	High Similarity	NPC45618
0.9568	High Similarity	NPC45400
0.9568	High Similarity	NPC146792
0.9518	High Similarity	NPC476621
0.9518	High Similarity	NPC476623
0.9518	High Similarity	NPC475261
0.9518	High Similarity	NPC476620
0.9518	High Similarity	NPC476618
0.9518	High Similarity	NPC476619
0.9518	High Similarity	NPC476622
0.9512	High Similarity	NPC172807
0.9512	High Similarity	NPC211594
0.9512	High Similarity	NPC117260
0.9512	High Similarity	NPC256760
0.9512	High Similarity	NPC476405
0.9512	High Similarity	NPC254540
0.9509	High Similarity	NPC195257
0.9509	High Similarity	NPC209296
0.9509	High Similarity	NPC105283
0.9506	High Similarity	NPC115674
0.9506	High Similarity	NPC99957
0.9506	High Similarity	NPC181616
0.9506	High Similarity	NPC210073
0.9503	High Similarity	NPC243930
0.9503	High Similarity	NPC29830
0.9503	High Similarity	NPC88023
0.9503	High Similarity	NPC309025
0.9503	High Similarity	NPC127415
0.9461	High Similarity	NPC470444
0.9461	High Similarity	NPC473682
0.9461	High Similarity	NPC473895
0.9461	High Similarity	NPC126784
0.9461	High Similarity	NPC470443
0.9461	High Similarity	NPC110941
0.9461	High Similarity	NPC241423
0.9461	High Similarity	NPC473571
0.9458	High Similarity	NPC65563
0.9458	High Similarity	NPC268533
0.9458	High Similarity	NPC8573
0.9458	High Similarity	NPC470949
0.9455	High Similarity	NPC101026
0.9455	High Similarity	NPC42773
0.9455	High Similarity	NPC45522
0.9455	High Similarity	NPC21666
0.9455	High Similarity	NPC24043
0.9455	High Similarity	NPC208668
0.9455	High Similarity	NPC169977
0.9451	High Similarity	NPC199079
0.9451	High Similarity	NPC84265
0.9451	High Similarity	NPC150767
0.9451	High Similarity	NPC78734
0.9451	High Similarity	NPC245014
0.9451	High Similarity	NPC282987
0.9451	High Similarity	NPC210808
0.9448	High Similarity	NPC229729
0.9448	High Similarity	NPC477502
0.9444	High Similarity	NPC165720
0.9444	High Similarity	NPC284277
0.9444	High Similarity	NPC311830
0.9444	High Similarity	NPC22832
0.9444	High Similarity	NPC475497
0.9444	High Similarity	NPC475366
0.9441	High Similarity	NPC127782
0.9441	High Similarity	NPC300537
0.9408	High Similarity	NPC148710
0.9405	High Similarity	NPC473071
0.9405	High Similarity	NPC473073
0.9401	High Similarity	NPC168584
0.9398	High Similarity	NPC264735
0.9398	High Similarity	NPC472607
0.9398	High Similarity	NPC477848
0.9398	High Similarity	NPC198199
0.9394	High Similarity	NPC180918
0.9394	High Similarity	NPC9002
0.9394	High Similarity	NPC257011
0.9394	High Similarity	NPC288152
0.9394	High Similarity	NPC261254
0.9394	High Similarity	NPC137871
0.939	High Similarity	NPC270578
0.939	High Similarity	NPC86008
0.939	High Similarity	NPC52382
0.9387	High Similarity	NPC8856
0.9383	High Similarity	NPC94777
0.9383	High Similarity	NPC270335
0.9383	High Similarity	NPC191306
0.9383	High Similarity	NPC19709
0.9383	High Similarity	NPC222936
0.9383	High Similarity	NPC284960
0.9383	High Similarity	NPC88043
0.9379	High Similarity	NPC182045
0.9357	High Similarity	NPC473618
0.9349	High Similarity	NPC470449
0.9349	High Similarity	NPC473072
0.9349	High Similarity	NPC470445
0.9349	High Similarity	NPC470447
0.9349	High Similarity	NPC473883
0.9349	High Similarity	NPC470446
0.9341	High Similarity	NPC48984
0.9341	High Similarity	NPC472385
0.9341	High Similarity	NPC472991
0.9341	High Similarity	NPC198324
0.9341	High Similarity	NPC472992
0.9341	High Similarity	NPC233994
0.9341	High Similarity	NPC211532
0.9341	High Similarity	NPC255799
0.9333	High Similarity	NPC95866
0.9333	High Similarity	NPC218488
0.9333	High Similarity	NPC285197
0.9333	High Similarity	NPC212748
0.9333	High Similarity	NPC67105
0.9329	High Similarity	NPC92565
0.9329	High Similarity	NPC116745
0.9329	High Similarity	NPC160156
0.9329	High Similarity	NPC14662
0.9325	High Similarity	NPC15358
0.9321	High Similarity	NPC148273
0.9321	High Similarity	NPC77660
0.9321	High Similarity	NPC473043
0.9321	High Similarity	NPC189142
0.9317	High Similarity	NPC97285
0.9317	High Similarity	NPC142860
0.9317	High Similarity	NPC110349
0.9317	High Similarity	NPC246469
0.9317	High Similarity	NPC271270
0.9298	High Similarity	NPC179947
0.9294	High Similarity	NPC470455
0.9294	High Similarity	NPC470451
0.9286	High Similarity	NPC89052
0.9286	High Similarity	NPC251417
0.9286	High Similarity	NPC120952
0.9281	High Similarity	NPC294815
0.9281	High Similarity	NPC49344
0.9281	High Similarity	NPC108202
0.9281	High Similarity	NPC115760
0.9281	High Similarity	NPC135277

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 NPC267254 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	946
0.2-0.3	1948
0.3-0.4	2761
0.4-0.5	1806
0.5-0.6	862
0.6-0.7	279
0.7-0.8	112
0.8-0.85	23
0.85-0.9	4
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9691	High Similarity	NPD7074	Phase 3
0.9509	High Similarity	NPD7054	Approved
0.9451	High Similarity	NPD7472	Approved
0.9281	High Similarity	NPD7808	Phase 3
0.9281	High Similarity	NPD4338	Clinical (unspecified phase)
0.9277	High Similarity	NPD6797	Phase 2
0.9222	High Similarity	NPD7251	Discontinued
0.9212	High Similarity	NPD3818	Discontinued
0.9091	High Similarity	NPD6167	Clinical (unspecified phase)
0.9091	High Similarity	NPD6166	Phase 2
0.9091	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD4381	Clinical (unspecified phase)
0.8944	High Similarity	NPD1934	Approved
0.8929	High Similarity	NPD7804	Clinical (unspecified phase)
0.8889	High Similarity	NPD2801	Approved
0.8773	High Similarity	NPD2393	Clinical (unspecified phase)
0.8623	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD3817	Phase 2
0.8476	Intermediate Similarity	NPD4380	Phase 2
0.8448	Intermediate Similarity	NPD6559	Discontinued
0.8443	Intermediate Similarity	NPD3882	Suspended
0.8391	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1511	Approved
0.8284	Intermediate Similarity	NPD7075	Discontinued
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8274	Intermediate Similarity	NPD5402	Approved
0.8232	Intermediate Similarity	NPD1512	Approved
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6959	Discontinued
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8133	Intermediate Similarity	NPD1653	Approved
0.8114	Intermediate Similarity	NPD7228	Approved
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7473	Discontinued
0.8047	Intermediate Similarity	NPD6801	Discontinued
0.8045	Intermediate Similarity	NPD8312	Approved
0.8045	Intermediate Similarity	NPD8313	Approved
0.8022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD7819	Suspended
0.7989	Intermediate Similarity	NPD3787	Discontinued
0.7988	Intermediate Similarity	NPD7411	Suspended
0.7964	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7926	Intermediate Similarity	NPD6782	Approved
0.7926	Intermediate Similarity	NPD6776	Approved
0.7926	Intermediate Similarity	NPD6780	Approved
0.7926	Intermediate Similarity	NPD6781	Approved
0.7926	Intermediate Similarity	NPD6778	Approved
0.7926	Intermediate Similarity	NPD6777	Approved
0.7926	Intermediate Similarity	NPD6779	Approved
0.7901	Intermediate Similarity	NPD2796	Approved
0.7892	Intermediate Similarity	NPD6799	Approved
0.7887	Intermediate Similarity	NPD7783	Phase 2
0.7887	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5403	Approved
0.7844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7836	Intermediate Similarity	NPD37	Approved
0.7833	Intermediate Similarity	NPD7685	Pre-registration
0.7816	Intermediate Similarity	NPD6234	Discontinued
0.7803	Intermediate Similarity	NPD4965	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7803	Intermediate Similarity	NPD4966	Approved
0.7801	Intermediate Similarity	NPD7697	Approved
0.7801	Intermediate Similarity	NPD7696	Phase 3
0.7801	Intermediate Similarity	NPD7698	Approved
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7797	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8151	Discontinued
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5401	Approved
0.7735	Intermediate Similarity	NPD7240	Approved
0.7732	Intermediate Similarity	NPD7701	Phase 2
0.7727	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1240	Approved
0.7702	Intermediate Similarity	NPD1613	Approved
0.7688	Intermediate Similarity	NPD8455	Phase 2
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7871	Phase 2
0.7668	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD6534	Approved
0.766	Intermediate Similarity	NPD6535	Approved
0.7656	Intermediate Similarity	NPD6823	Phase 2
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7636	Intermediate Similarity	NPD7266	Discontinued
0.7632	Intermediate Similarity	NPD7700	Phase 2
0.7632	Intermediate Similarity	NPD7699	Phase 2
0.7607	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD7584	Approved
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7557	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD1933	Approved
0.7525	Intermediate Similarity	NPD7801	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7514	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6190	Approved
0.7453	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD230	Phase 1
0.7439	Intermediate Similarity	NPD447	Suspended
0.7427	Intermediate Similarity	NPD2532	Approved
0.7427	Intermediate Similarity	NPD2534	Approved
0.7427	Intermediate Similarity	NPD2533	Approved
0.7421	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6212	Phase 3
0.7421	Intermediate Similarity	NPD6213	Phase 3
0.7398	Intermediate Similarity	NPD8319	Approved
0.7398	Intermediate Similarity	NPD8320	Phase 1
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2800	Approved
0.732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5953	Discontinued
0.7259	Intermediate Similarity	NPD7680	Approved
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7257	Intermediate Similarity	NPD3226	Approved
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD920	Approved
0.7235	Intermediate Similarity	NPD6674	Discontinued
0.7232	Intermediate Similarity	NPD6844	Discontinued
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3748	Approved
0.72	Intermediate Similarity	NPD7585	Approved
0.7198	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7286	Phase 2
0.7168	Intermediate Similarity	NPD7390	Discontinued
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.715	Intermediate Similarity	NPD7583	Approved
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1091	Approved
0.7118	Intermediate Similarity	NPD2344	Approved
0.7118	Intermediate Similarity	NPD2346	Discontinued
0.7113	Intermediate Similarity	NPD4360	Phase 2
0.7113	Intermediate Similarity	NPD4363	Phase 3
0.7101	Intermediate Similarity	NPD2799	Discontinued
0.7101	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7033	Discontinued
0.71	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6651	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7065	Intermediate Similarity	NPD5242	Approved
0.7056	Intermediate Similarity	NPD5353	Approved
0.7048	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7549	Discontinued
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD5006	Approved
0.7035	Intermediate Similarity	NPD1243	Approved
0.703	Intermediate Similarity	NPD6832	Phase 2
0.7028	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8059	Phase 3
0.7019	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5710	Approved
0.7011	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2861	Phase 2
0.6966	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8127	Discontinued
0.6954	Remote Similarity	NPD2309	Approved
0.6951	Remote Similarity	NPD1203	Approved
0.6946	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD6841	Approved
0.6943	Remote Similarity	NPD6842	Approved
0.6943	Remote Similarity	NPD6843	Phase 3
0.6941	Remote Similarity	NPD7097	Phase 1
0.6936	Remote Similarity	NPD1652	Phase 2
0.6933	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7422	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