NPASS Compound

Structure

NPC469661 OpenBabel07101718222D 29 31 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 -6.9282 -2.0000 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 -2.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 0.8660 -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 -0.8660 -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 2 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 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 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 1.7321 -2.0000 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 -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 2 1 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 21 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 28 1 6 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.14
Volume:	392.1
LogP:	0.136
LogD:	0.488
LogS:	-2.202
# Rotatable Bonds:	6
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	3.743
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.192
MDCK Permeability:	5.307065748638706e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.87
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	87.83546447753906%
Volume Distribution (VD):	0.813
Pgp-substrate:	8.793978691101074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.418
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	8.918
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.203
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.942
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.162
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC469661

Natural Product ID:	NPC469661
*Common Name:**	(2S,3R,4S,5S,6R)-2-[5-[2-(3,5-Dihydroxyphenyl)Ethyl]-2-Hydroxyphenoxy]-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[5-[2-(3,5-dihydroxyphenyl)ethyl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	ALURDYSHZFKTJP-OUUBHVDSSA-N
Standard InCHI:	InChI=1S/C20H24O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-7-10(3-4-14(15)24)1-2-11-5-12(22)8-13(23)6-11/h3-8,16-27H,1-2,9H2/t16-,17-,18+,19-,20-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(ccc2O)CCc2cc(O)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL109702
PubChem CID:	44339715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO88	Rheum undulatum	Species	Polygonaceae	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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[490872]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	6.0	%	PMID[490872]

☑ 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 NPC469661 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	466
0.1-0.2	1597
0.2-0.3	4546
0.3-0.4	10964
0.4-0.5	7286
0.5-0.6	4756
0.6-0.7	6700
0.7-0.8	4662
0.8-0.85	1105
0.85-0.9	460
0.9-0.95	131
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC189115
0.9779	High Similarity	NPC25292
0.9779	High Similarity	NPC473045
0.9778	High Similarity	NPC469559
0.9774	High Similarity	NPC59324
0.9774	High Similarity	NPC65530
0.9708	High Similarity	NPC475096
0.9706	High Similarity	NPC473044
0.9701	High Similarity	NPC98777
0.9701	High Similarity	NPC212770
0.9699	High Similarity	NPC242028
0.9699	High Similarity	NPC203230
0.9638	High Similarity	NPC190714
0.9638	High Similarity	NPC125755
0.9638	High Similarity	NPC99515
0.9635	High Similarity	NPC168579
0.9635	High Similarity	NPC76176
0.9635	High Similarity	NPC469313
0.9635	High Similarity	NPC138227
0.9632	High Similarity	NPC475084
0.9568	High Similarity	NPC227902
0.9568	High Similarity	NPC39657
0.9565	High Similarity	NPC161700
0.9565	High Similarity	NPC277867
0.9562	High Similarity	NPC37793
0.9562	High Similarity	NPC252169
0.95	High Similarity	NPC175976
0.9489	High Similarity	NPC5262
0.9489	High Similarity	NPC472714
0.9485	High Similarity	NPC106944
0.9481	High Similarity	NPC138738
0.9481	High Similarity	NPC470413
0.9433	High Similarity	NPC55158
0.9433	High Similarity	NPC286235
0.9433	High Similarity	NPC51328
0.9429	High Similarity	NPC473480
0.9429	High Similarity	NPC15538
0.9407	High Similarity	NPC177035
0.9407	High Similarity	NPC199459
0.9407	High Similarity	NPC52277
0.9403	High Similarity	NPC48863
0.9403	High Similarity	NPC13745
0.9403	High Similarity	NPC170694
0.9403	High Similarity	NPC251981
0.9403	High Similarity	NPC107478
0.9403	High Similarity	NPC476411
0.9398	High Similarity	NPC303422
0.9398	High Similarity	NPC85799
0.9398	High Similarity	NPC26080
0.9398	High Similarity	NPC165686
0.9362	High Similarity	NPC248132
0.9362	High Similarity	NPC130449
0.9362	High Similarity	NPC280945
0.9353	High Similarity	NPC118385
0.9353	High Similarity	NPC472713
0.9353	High Similarity	NPC187774
0.9353	High Similarity	NPC472712
0.9353	High Similarity	NPC473046
0.9328	High Similarity	NPC294166
0.9328	High Similarity	NPC215833
0.9328	High Similarity	NPC132895
0.9328	High Similarity	NPC115022
0.9328	High Similarity	NPC49074
0.9328	High Similarity	NPC69513
0.9323	High Similarity	NPC121376
0.9296	High Similarity	NPC106138
0.9281	High Similarity	NPC46092
0.9281	High Similarity	NPC470950
0.9281	High Similarity	NPC81638
0.9281	High Similarity	NPC185307
0.9275	High Similarity	NPC210192
0.927	High Similarity	NPC292487
0.9265	High Similarity	NPC269091
0.9265	High Similarity	NPC16435
0.9265	High Similarity	NPC25695
0.9265	High Similarity	NPC164857
0.9265	High Similarity	NPC302701
0.9265	High Similarity	NPC306441
0.9265	High Similarity	NPC172818
0.9259	High Similarity	NPC130496
0.9259	High Similarity	NPC187194
0.9259	High Similarity	NPC188555
0.9254	High Similarity	NPC35932
0.9254	High Similarity	NPC253105
0.9254	High Similarity	NPC162093
0.9254	High Similarity	NPC201587
0.9254	High Similarity	NPC160991
0.9254	High Similarity	NPC299144
0.9254	High Similarity	NPC7903
0.9254	High Similarity	NPC184447
0.9254	High Similarity	NPC470752
0.9254	High Similarity	NPC470270
0.9254	High Similarity	NPC16208
0.9236	High Similarity	NPC21902
0.9231	High Similarity	NPC472709
0.9231	High Similarity	NPC472710
0.9214	High Similarity	NPC129417
0.9214	High Similarity	NPC470235
0.9214	High Similarity	NPC283995
0.9209	High Similarity	NPC476356
0.9191	High Similarity	NPC238243
0.9191	High Similarity	NPC112246
0.9191	High Similarity	NPC47398
0.9191	High Similarity	NPC260898
0.9191	High Similarity	NPC94750
0.9191	High Similarity	NPC234333
0.9191	High Similarity	NPC164787
0.9191	High Similarity	NPC112939
0.9191	High Similarity	NPC470356
0.9191	High Similarity	NPC474206
0.9191	High Similarity	NPC61946
0.9191	High Similarity	NPC121812
0.9191	High Similarity	NPC470236
0.9179	High Similarity	NPC65942
0.9179	High Similarity	NPC9912
0.9179	High Similarity	NPC475067
0.9179	High Similarity	NPC472597
0.9179	High Similarity	NPC248307
0.9179	High Similarity	NPC309787
0.9173	High Similarity	NPC218003
0.9172	High Similarity	NPC150442
0.9172	High Similarity	NPC78809
0.9167	High Similarity	NPC473621
0.9149	High Similarity	NPC279298
0.9149	High Similarity	NPC22150
0.9149	High Similarity	NPC469586
0.9149	High Similarity	NPC38041
0.9149	High Similarity	NPC18979
0.9137	High Similarity	NPC472711
0.913	High Similarity	NPC22517
0.9124	High Similarity	NPC40664
0.9124	High Similarity	NPC165482
0.9124	High Similarity	NPC227503
0.9124	High Similarity	NPC230734
0.9124	High Similarity	NPC3293
0.9124	High Similarity	NPC474639
0.9124	High Similarity	NPC197723
0.9124	High Similarity	NPC138350
0.9118	High Similarity	NPC35731
0.9118	High Similarity	NPC310854
0.9118	High Similarity	NPC87696
0.9111	High Similarity	NPC126029
0.9111	High Similarity	NPC219876
0.9111	High Similarity	NPC261619
0.9111	High Similarity	NPC61477
0.9111	High Similarity	NPC185604
0.9111	High Similarity	NPC15658
0.9111	High Similarity	NPC78770
0.9104	High Similarity	NPC472024
0.9104	High Similarity	NPC472338
0.9104	High Similarity	NPC80600
0.9103	High Similarity	NPC169404
0.9103	High Similarity	NPC176186
0.9103	High Similarity	NPC53587
0.9098	High Similarity	NPC72529
0.9091	High Similarity	NPC270751
0.9091	High Similarity	NPC478237
0.9085	High Similarity	NPC112861
0.9071	High Similarity	NPC60249
0.9071	High Similarity	NPC48309
0.9065	High Similarity	NPC266197
0.9065	High Similarity	NPC291101
0.9065	High Similarity	NPC262189
0.9058	High Similarity	NPC87777
0.9058	High Similarity	NPC304152
0.9058	High Similarity	NPC262328
0.9058	High Similarity	NPC195196
0.9058	High Similarity	NPC107551
0.9058	High Similarity	NPC211549
0.9058	High Similarity	NPC326797
0.9058	High Similarity	NPC474282
0.9058	High Similarity	NPC102904
0.9058	High Similarity	NPC176051
0.9058	High Similarity	NPC474039
0.9058	High Similarity	NPC103976
0.9058	High Similarity	NPC124149
0.9058	High Similarity	NPC474390
0.9058	High Similarity	NPC134260
0.9051	High Similarity	NPC151224
0.9044	High Similarity	NPC475840
0.9044	High Similarity	NPC263064
0.9044	High Similarity	NPC11060
0.9037	High Similarity	NPC42760
0.9037	High Similarity	NPC30043
0.9037	High Similarity	NPC473412
0.9037	High Similarity	NPC470095
0.9037	High Similarity	NPC469613
0.9037	High Similarity	NPC470096
0.9037	High Similarity	NPC469698
0.9037	High Similarity	NPC268342
0.9037	High Similarity	NPC220825
0.9037	High Similarity	NPC469625
0.9037	High Similarity	NPC166168
0.9037	High Similarity	NPC268266
0.903	High Similarity	NPC307110
0.903	High Similarity	NPC218856
0.903	High Similarity	NPC170844
0.903	High Similarity	NPC3439
0.903	High Similarity	NPC248355
0.903	High Similarity	NPC270849

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 NPC469661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	847
0.2-0.3	1933
0.3-0.4	2753
0.4-0.5	1651
0.5-0.6	914
0.6-0.7	553
0.7-0.8	113
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9111	High Similarity	NPD1612	Clinical (unspecified phase)
0.9111	High Similarity	NPD1613	Approved
0.903	High Similarity	NPD3027	Phase 3
0.8815	High Similarity	NPD1529	Clinical (unspecified phase)
0.8767	High Similarity	NPD1653	Approved
0.8741	High Similarity	NPD1530	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7074	Phase 3
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD7266	Discontinued
0.8302	Intermediate Similarity	NPD7054	Approved
0.8296	Intermediate Similarity	NPD1091	Approved
0.825	Intermediate Similarity	NPD7472	Approved
0.8141	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD7228	Approved
0.8098	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6674	Discontinued
0.8086	Intermediate Similarity	NPD6797	Phase 2
0.8077	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1934	Approved
0.8052	Intermediate Similarity	NPD37	Approved
0.8037	Intermediate Similarity	NPD7251	Discontinued
0.8029	Intermediate Similarity	NPD1610	Phase 2
0.8014	Intermediate Similarity	NPD4908	Phase 1
0.8013	Intermediate Similarity	NPD4966	Approved
0.8013	Intermediate Similarity	NPD4965	Approved
0.8013	Intermediate Similarity	NPD4967	Phase 2
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7925	Intermediate Similarity	NPD7199	Phase 2
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7885	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7817	Intermediate Similarity	NPD2861	Phase 2
0.7786	Intermediate Similarity	NPD2982	Phase 2
0.7786	Intermediate Similarity	NPD2983	Phase 2
0.777	Intermediate Similarity	NPD3705	Approved
0.7716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2981	Phase 2
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD5058	Phase 3
0.7692	Intermediate Similarity	NPD3018	Phase 2
0.7681	Intermediate Similarity	NPD1357	Approved
0.7658	Intermediate Similarity	NPD2801	Approved
0.7636	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD228	Approved
0.7605	Intermediate Similarity	NPD7240	Approved
0.7586	Intermediate Similarity	NPD4625	Phase 3
0.7547	Intermediate Similarity	NPD8455	Phase 2
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4749	Approved
0.7534	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1511	Approved
0.7517	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD4536	Approved
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7467	Intermediate Similarity	NPD5588	Approved
0.7467	Intermediate Similarity	NPD5960	Phase 3
0.7453	Intermediate Similarity	NPD3882	Suspended
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7438	Intermediate Similarity	NPD2977	Approved
0.7438	Intermediate Similarity	NPD2978	Approved
0.7436	Intermediate Similarity	NPD1512	Approved
0.7432	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3620	Phase 2
0.7432	Intermediate Similarity	NPD1558	Phase 1
0.7426	Intermediate Similarity	NPD7843	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6190	Approved
0.7396	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD7157	Approved
0.7391	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2684	Approved
0.7386	Intermediate Similarity	NPD1652	Phase 2
0.7358	Intermediate Similarity	NPD4678	Approved
0.7358	Intermediate Similarity	NPD4675	Approved
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7315	Intermediate Similarity	NPD4060	Phase 1
0.7301	Intermediate Similarity	NPD7075	Discontinued
0.7297	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7263	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1375	Discontinued
0.7254	Intermediate Similarity	NPD6516	Phase 2
0.7254	Intermediate Similarity	NPD5846	Approved
0.7241	Intermediate Similarity	NPD6841	Approved
0.7241	Intermediate Similarity	NPD6842	Approved
0.7241	Intermediate Similarity	NPD6843	Phase 3
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1549	Phase 2
0.7206	Intermediate Similarity	NPD3022	Approved
0.7206	Intermediate Similarity	NPD3021	Approved
0.7198	Intermediate Similarity	NPD7680	Approved
0.7197	Intermediate Similarity	NPD7213	Phase 3
0.7197	Intermediate Similarity	NPD7212	Phase 2
0.7188	Intermediate Similarity	NPD4005	Discontinued
0.7178	Intermediate Similarity	NPD5402	Approved
0.7171	Intermediate Similarity	NPD7097	Phase 1
0.7168	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3060	Approved
0.7161	Intermediate Similarity	NPD5177	Phase 3
0.716	Intermediate Similarity	NPD3384	Approved
0.716	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD3382	Approved
0.716	Intermediate Similarity	NPD3383	Approved
0.7153	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD6671	Approved
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD5125	Phase 3
0.7133	Intermediate Similarity	NPD5126	Approved
0.7126	Intermediate Similarity	NPD6232	Discontinued
0.7124	Intermediate Similarity	NPD4108	Discontinued
0.7123	Intermediate Similarity	NPD8651	Approved
0.7117	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4628	Phase 3
0.7114	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD968	Approved
0.7108	Intermediate Similarity	NPD5494	Approved
0.7078	Intermediate Similarity	NPD3539	Phase 1
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.7059	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.7052	Intermediate Similarity	NPD7549	Discontinued
0.7051	Intermediate Similarity	NPD4162	Approved
0.7051	Intermediate Similarity	NPD4236	Phase 3
0.7051	Intermediate Similarity	NPD4237	Approved
0.7044	Intermediate Similarity	NPD4123	Phase 3
0.7044	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5735	Approved
0.7039	Intermediate Similarity	NPD4340	Discontinued
0.7039	Intermediate Similarity	NPD230	Phase 1
0.7027	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3687	Approved
0.7019	Intermediate Similarity	NPD3686	Approved
0.7012	Intermediate Similarity	NPD7819	Suspended
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD3750	Approved
0.7006	Intermediate Similarity	NPD4535	Phase 3
0.7006	Intermediate Similarity	NPD3892	Phase 2
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.7	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1242	Phase 1
0.6986	Remote Similarity	NPD2235	Phase 2
0.6986	Remote Similarity	NPD2231	Phase 2
0.6981	Remote Similarity	NPD4357	Discontinued
0.6971	Remote Similarity	NPD8053	Approved
0.6971	Remote Similarity	NPD8054	Approved
0.697	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD3454	Phase 3
0.6968	Remote Similarity	NPD6099	Approved
0.6962	Remote Similarity	NPD2677	Approved
0.6951	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.694	Remote Similarity	NPD291	Approved
0.6939	Remote Similarity	NPD3685	Discontinued
0.6939	Remote Similarity	NPD6582	Phase 2
0.6939	Remote Similarity	NPD6583	Phase 3
0.6937	Remote Similarity	NPD5401	Approved
0.6933	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5535	Approved
0.6928	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5536	Phase 2
0.6923	Remote Similarity	NPD5763	Approved
0.6918	Remote Similarity	NPD7124	Phase 2
0.6909	Remote Similarity	NPD5773	Approved
0.6909	Remote Similarity	NPD5772	Approved
0.6909	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1510	Phase 2
0.6903	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6028	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