NPASS Compound

Structure

NPC184633 OpenBabel07101718242D 33 34 0 0 1 0 0 0 0 0999 V2000 6.0622 1.5000 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 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 5.1962 -0.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -4.3301 0.5000 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -2.5981 -1.5000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 32 1 0 0 0 0 10 31 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 6 0 0 0 13 17 1 0 0 0 0 13 24 1 6 0 0 0 14 10 1 6 0 0 0 14 18 1 0 0 0 0 14 33 1 0 0 0 0 15 25 2 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 1 0 0 0 17 27 1 6 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 32 1 6 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.17
Volume:	446.96
LogP:	-0.752
LogD:	-1.763
LogS:	-1.522
# Rotatable Bonds:	12
TPSA:	206.6
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	4.297
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.836
MDCK Permeability:	6.943775224499404e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	33.30900573730469%
Volume Distribution (VD):	0.336
Pgp-substrate:	39.18568801879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.029
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.799
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.25
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC184633

Natural Product ID:	NPC184633
*Common Name:**	1-O-Mannityl-6-O-(E-Cinnamoyl)-Beta-D-Glucopyranose
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]oxan-2-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	UFFKFKUSUNAZJF-KGURTYBNSA-N
Standard InCHI:	InChI=1S/C21H30O12/c22-8-12(23)16(26)17(27)13(24)9-32-21-20(30)19(29)18(28)14(33-21)10-31-15(25)7-6-11-4-2-1-3-5-11/h1-7,12-14,16-24,26-30H,8-10H2/b7-6+/t12-,13-,14-,16-,17-,18-,19+,20-,21-/m1/s1
SMILES:	OC[C@H]([C@H]([C@@H]([C@@H](CO[C@@H]1O[C@H](COC(=O)/C=C/c2ccccc2)[C@H]([C@@H]([C@H]1O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436431
PubChem CID:	72375657
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15133218]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15706916]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24035096]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	25000.0	nM	PMID[451617]

☑ 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 NPC184633 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	221
0.1-0.2	957
0.2-0.3	2704
0.3-0.4	8242
0.4-0.5	13076
0.5-0.6	13934
0.6-0.7	2996
0.7-0.8	486
0.8-0.85	62
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC470825
0.9612	High Similarity	NPC43584
0.9524	High Similarity	NPC474641
0.9118	High Similarity	NPC469527
0.8899	High Similarity	NPC29607
0.885	High Similarity	NPC229600
0.8696	High Similarity	NPC141970
0.8696	High Similarity	NPC140561
0.8696	High Similarity	NPC52097
0.8611	High Similarity	NPC474148
0.8611	High Similarity	NPC276061
0.8609	High Similarity	NPC11724
0.8585	High Similarity	NPC37714
0.8585	High Similarity	NPC152384
0.8547	High Similarity	NPC87153
0.8547	High Similarity	NPC145287
0.8547	High Similarity	NPC162925
0.8532	High Similarity	NPC30563
0.8532	High Similarity	NPC264784
0.8522	High Similarity	NPC476872
0.8475	Intermediate Similarity	NPC83218
0.8475	Intermediate Similarity	NPC77651
0.8475	Intermediate Similarity	NPC28069
0.8475	Intermediate Similarity	NPC126991
0.8403	Intermediate Similarity	NPC35338
0.8403	Intermediate Similarity	NPC290276
0.8403	Intermediate Similarity	NPC267733
0.8403	Intermediate Similarity	NPC10121
0.8403	Intermediate Similarity	NPC276047
0.8403	Intermediate Similarity	NPC252114
0.8403	Intermediate Similarity	NPC198918
0.8403	Intermediate Similarity	NPC124878
0.8403	Intermediate Similarity	NPC114096
0.8403	Intermediate Similarity	NPC63404
0.8403	Intermediate Similarity	NPC471157
0.8403	Intermediate Similarity	NPC92283
0.8403	Intermediate Similarity	NPC10883
0.8403	Intermediate Similarity	NPC231888
0.8403	Intermediate Similarity	NPC204214
0.8365	Intermediate Similarity	NPC262826
0.8333	Intermediate Similarity	NPC45224
0.8333	Intermediate Similarity	NPC471882
0.8333	Intermediate Similarity	NPC148026
0.8333	Intermediate Similarity	NPC288416
0.8333	Intermediate Similarity	NPC471025
0.8333	Intermediate Similarity	NPC156692
0.8333	Intermediate Similarity	NPC173150
0.8333	Intermediate Similarity	NPC35288
0.8333	Intermediate Similarity	NPC471881
0.8333	Intermediate Similarity	NPC231627
0.8333	Intermediate Similarity	NPC106677
0.8333	Intermediate Similarity	NPC175333
0.8318	Intermediate Similarity	NPC47286
0.8264	Intermediate Similarity	NPC471024
0.8264	Intermediate Similarity	NPC225307
0.8264	Intermediate Similarity	NPC301857
0.8264	Intermediate Similarity	NPC226101
0.8264	Intermediate Similarity	NPC237182
0.8235	Intermediate Similarity	NPC244454
0.8197	Intermediate Similarity	NPC477294
0.8197	Intermediate Similarity	NPC253595
0.8197	Intermediate Similarity	NPC229784
0.8197	Intermediate Similarity	NPC477293
0.819	Intermediate Similarity	NPC476096
0.8148	Intermediate Similarity	NPC148060
0.813	Intermediate Similarity	NPC289415
0.813	Intermediate Similarity	NPC319995
0.813	Intermediate Similarity	NPC17567
0.8115	Intermediate Similarity	NPC146540
0.8115	Intermediate Similarity	NPC232880
0.8099	Intermediate Similarity	NPC61181
0.8099	Intermediate Similarity	NPC147032
0.8083	Intermediate Similarity	NPC57607
0.8065	Intermediate Similarity	NPC46137
0.8065	Intermediate Similarity	NPC138777
0.8065	Intermediate Similarity	NPC478255
0.8065	Intermediate Similarity	NPC254819
0.8065	Intermediate Similarity	NPC235294
0.8065	Intermediate Similarity	NPC246869
0.8065	Intermediate Similarity	NPC281798
0.8065	Intermediate Similarity	NPC225384
0.8065	Intermediate Similarity	NPC219677
0.8049	Intermediate Similarity	NPC295970
0.8033	Intermediate Similarity	NPC476873
0.8033	Intermediate Similarity	NPC103533
0.8017	Intermediate Similarity	NPC122245
0.8017	Intermediate Similarity	NPC266389
0.8017	Intermediate Similarity	NPC216605
0.8	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC136962
0.8	Intermediate Similarity	NPC473924
0.8	Intermediate Similarity	NPC474376
0.8	Intermediate Similarity	NPC475203
0.8	Intermediate Similarity	NPC37115
0.8	Intermediate Similarity	NPC473285
0.8	Intermediate Similarity	NPC472315
0.7982	Intermediate Similarity	NPC242913
0.7982	Intermediate Similarity	NPC280616
0.7982	Intermediate Similarity	NPC120217
0.7982	Intermediate Similarity	NPC171831
0.7965	Intermediate Similarity	NPC234376
0.7965	Intermediate Similarity	NPC185840
0.7961	Intermediate Similarity	NPC472319
0.7937	Intermediate Similarity	NPC322503
0.7937	Intermediate Similarity	NPC254398
0.7937	Intermediate Similarity	NPC470143
0.7937	Intermediate Similarity	NPC28637
0.7913	Intermediate Similarity	NPC313193
0.7903	Intermediate Similarity	NPC11025
0.7895	Intermediate Similarity	NPC265002
0.7874	Intermediate Similarity	NPC471883
0.7874	Intermediate Similarity	NPC886
0.7874	Intermediate Similarity	NPC34293
0.7874	Intermediate Similarity	NPC287597
0.7851	Intermediate Similarity	NPC473881
0.7833	Intermediate Similarity	NPC475328
0.7812	Intermediate Similarity	NPC263829
0.7812	Intermediate Similarity	NPC185778
0.7812	Intermediate Similarity	NPC476870
0.7805	Intermediate Similarity	NPC471026
0.7778	Intermediate Similarity	NPC175771
0.7768	Intermediate Similarity	NPC277788
0.776	Intermediate Similarity	NPC27712
0.7752	Intermediate Similarity	NPC157554
0.7752	Intermediate Similarity	NPC166180
0.7752	Intermediate Similarity	NPC471345
0.7752	Intermediate Similarity	NPC470572
0.7752	Intermediate Similarity	NPC37468
0.7752	Intermediate Similarity	NPC472132
0.7742	Intermediate Similarity	NPC230331
0.7734	Intermediate Similarity	NPC169398
0.7705	Intermediate Similarity	NPC138798
0.7705	Intermediate Similarity	NPC470815
0.7692	Intermediate Similarity	NPC260425
0.7692	Intermediate Similarity	NPC476376
0.7692	Intermediate Similarity	NPC78363
0.7664	Intermediate Similarity	NPC30361
0.7656	Intermediate Similarity	NPC136608
0.7656	Intermediate Similarity	NPC38420
0.7656	Intermediate Similarity	NPC114116
0.7634	Intermediate Similarity	NPC64141
0.7634	Intermediate Similarity	NPC49597
0.7634	Intermediate Similarity	NPC472350
0.7634	Intermediate Similarity	NPC171134
0.7634	Intermediate Similarity	NPC197316
0.7634	Intermediate Similarity	NPC328273
0.7634	Intermediate Similarity	NPC68092
0.7634	Intermediate Similarity	NPC321184
0.7634	Intermediate Similarity	NPC31745
0.7634	Intermediate Similarity	NPC476383
0.7634	Intermediate Similarity	NPC321638
0.7634	Intermediate Similarity	NPC100389
0.7634	Intermediate Similarity	NPC220942
0.7634	Intermediate Similarity	NPC220936
0.7634	Intermediate Similarity	NPC226005
0.7634	Intermediate Similarity	NPC205195
0.7634	Intermediate Similarity	NPC89105
0.7634	Intermediate Similarity	NPC81515
0.7627	Intermediate Similarity	NPC148055
0.7615	Intermediate Similarity	NPC186418
0.7615	Intermediate Similarity	NPC103409
0.7611	Intermediate Similarity	NPC20485
0.7607	Intermediate Similarity	NPC157338
0.7603	Intermediate Similarity	NPC198734
0.7603	Intermediate Similarity	NPC469412
0.7583	Intermediate Similarity	NPC14950
0.7581	Intermediate Similarity	NPC123704
0.7576	Intermediate Similarity	NPC202700
0.7568	Intermediate Similarity	NPC82426
0.7568	Intermediate Similarity	NPC91820
0.7559	Intermediate Similarity	NPC305162
0.7557	Intermediate Similarity	NPC475195
0.7557	Intermediate Similarity	NPC101686
0.7557	Intermediate Similarity	NPC65262
0.7557	Intermediate Similarity	NPC469364
0.7542	Intermediate Similarity	NPC476476
0.7538	Intermediate Similarity	NPC55040
0.7521	Intermediate Similarity	NPC60589
0.7521	Intermediate Similarity	NPC469702
0.7521	Intermediate Similarity	NPC282409
0.7521	Intermediate Similarity	NPC469708
0.752	Intermediate Similarity	NPC233559
0.752	Intermediate Similarity	NPC476971
0.752	Intermediate Similarity	NPC476972
0.7519	Intermediate Similarity	NPC476385
0.7519	Intermediate Similarity	NPC476377
0.7519	Intermediate Similarity	NPC215512
0.7519	Intermediate Similarity	NPC476442
0.7519	Intermediate Similarity	NPC46644
0.7519	Intermediate Similarity	NPC186406
0.7519	Intermediate Similarity	NPC134405
0.7519	Intermediate Similarity	NPC475513
0.7519	Intermediate Similarity	NPC47471
0.7519	Intermediate Similarity	NPC473755
0.7519	Intermediate Similarity	NPC80098
0.75	Intermediate Similarity	NPC471758
0.75	Intermediate Similarity	NPC287429
0.75	Intermediate Similarity	NPC317163
0.748	Intermediate Similarity	NPC476142
0.748	Intermediate Similarity	NPC469549

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 NPC184633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	695
0.2-0.3	1527
0.3-0.4	3378
0.4-0.5	2342
0.5-0.6	955
0.6-0.7	68
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7965	Intermediate Similarity	NPD969	Suspended
0.7717	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7266	Discontinued
0.7596	Intermediate Similarity	NPD689	Discontinued
0.7398	Intermediate Similarity	NPD1091	Approved
0.7377	Intermediate Similarity	NPD5125	Phase 3
0.7377	Intermediate Similarity	NPD5126	Approved
0.7281	Intermediate Similarity	NPD5048	Discontinued
0.7257	Intermediate Similarity	NPD6647	Phase 2
0.7238	Intermediate Similarity	NPD1282	Approved
0.6972	Remote Similarity	NPD1653	Approved
0.6923	Remote Similarity	NPD6685	Approved
0.6911	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2067	Discontinued
0.6879	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5765	Approved
0.6803	Remote Similarity	NPD6010	Discontinued
0.6777	Remote Similarity	NPD6912	Phase 3
0.6754	Remote Similarity	NPD5926	Approved
0.6733	Remote Similarity	NPD9716	Approved
0.6723	Remote Similarity	NPD1358	Approved
0.6718	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7798	Approved
0.6694	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD6190	Approved
0.6642	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2629	Approved
0.661	Remote Similarity	NPD5909	Discontinued
0.6609	Remote Similarity	NPD9495	Approved
0.6609	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1238	Approved
0.6549	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3971	Phase 1
0.6529	Remote Similarity	NPD2182	Approved
0.6525	Remote Similarity	NPD1652	Phase 2
0.651	Remote Similarity	NPD8455	Phase 2
0.65	Remote Similarity	NPD3134	Approved
0.649	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD7838	Discovery
0.6423	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD9545	Approved
0.6364	Remote Similarity	NPD4628	Phase 3
0.6349	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD290	Approved
0.629	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7097	Phase 1
0.6279	Remote Similarity	NPD7741	Discontinued
0.6273	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2066	Phase 3
0.6259	Remote Similarity	NPD5124	Phase 1
0.6259	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4340	Discontinued
0.625	Remote Similarity	NPD5291	Approved
0.625	Remote Similarity	NPD5292	Approved
0.6232	Remote Similarity	NPD6233	Phase 2
0.6231	Remote Similarity	NPD7503	Approved
0.6216	Remote Similarity	NPD5403	Approved
0.6211	Remote Similarity	NPD7685	Pre-registration
0.6204	Remote Similarity	NPD226	Approved
0.6198	Remote Similarity	NPD1237	Approved
0.6198	Remote Similarity	NPD164	Approved
0.619	Remote Similarity	NPD5401	Approved
0.619	Remote Similarity	NPD7843	Approved
0.6179	Remote Similarity	NPD9532	Phase 3
0.6165	Remote Similarity	NPD6637	Approved
0.6164	Remote Similarity	NPD7799	Discontinued
0.6164	Remote Similarity	NPD5058	Phase 3
0.6161	Remote Similarity	NPD4793	Discontinued
0.6148	Remote Similarity	NPD2626	Approved
0.6148	Remote Similarity	NPD2625	Approved
0.6148	Remote Similarity	NPD2628	Approved
0.6148	Remote Similarity	NPD2159	Approved
0.6148	Remote Similarity	NPD2160	Approved
0.6148	Remote Similarity	NPD2627	Approved
0.6143	Remote Similarity	NPD230	Phase 1
0.614	Remote Similarity	NPD9258	Approved
0.614	Remote Similarity	NPD9256	Approved
0.614	Remote Similarity	NPD6698	Approved
0.614	Remote Similarity	NPD3673	Approved
0.614	Remote Similarity	NPD46	Approved
0.614	Remote Similarity	NPD3672	Approved
0.6138	Remote Similarity	NPD2575	Approved
0.6138	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD3496	Discontinued
0.6135	Remote Similarity	NPD8313	Approved
0.6135	Remote Similarity	NPD8312	Approved
0.6132	Remote Similarity	NPD9294	Approved
0.6131	Remote Similarity	NPD2613	Approved
0.6129	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2684	Approved
0.6122	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD1202	Approved
0.6119	Remote Similarity	NPD7876	Discontinued
0.6115	Remote Similarity	NPD4404	Approved
0.6111	Remote Similarity	NPD6559	Discontinued
0.6107	Remote Similarity	NPD1357	Approved
0.6106	Remote Similarity	NPD531	Approved
0.6099	Remote Similarity	NPD6653	Approved
0.6093	Remote Similarity	NPD4380	Phase 2
0.6091	Remote Similarity	NPD9491	Approved
0.609	Remote Similarity	NPD3705	Approved
0.609	Remote Similarity	NPD422	Phase 1
0.6087	Remote Similarity	NPD3027	Phase 3
0.6074	Remote Similarity	NPD3225	Approved
0.6074	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6674	Discontinued
0.6062	Remote Similarity	NPD3818	Discontinued
0.6061	Remote Similarity	NPD5305	Approved
0.6061	Remote Similarity	NPD5306	Approved
0.6053	Remote Similarity	NPD5346	Phase 2
0.6053	Remote Similarity	NPD5347	Phase 2
0.6048	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7157	Approved
0.6043	Remote Similarity	NPD6798	Discontinued
0.6043	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5762	Approved
0.6042	Remote Similarity	NPD5763	Approved
0.6039	Remote Similarity	NPD5402	Approved
0.6033	Remote Similarity	NPD1932	Approved
0.6028	Remote Similarity	NPD1933	Approved
0.6025	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD7054	Approved
0.6017	Remote Similarity	NPD1989	Approved
0.6016	Remote Similarity	NPD9697	Approved
0.6015	Remote Similarity	NPD4106	Approved
0.6015	Remote Similarity	NPD4136	Approved
0.6015	Remote Similarity	NPD4135	Approved
0.6014	Remote Similarity	NPD6799	Approved
0.6014	Remote Similarity	NPD7033	Discontinued
0.6013	Remote Similarity	NPD37	Approved
0.6	Remote Similarity	NPD3090	Approved
0.6	Remote Similarity	NPD3089	Approved
0.6	Remote Similarity	NPD9493	Approved
0.6	Remote Similarity	NPD4967	Phase 2
0.6	Remote Similarity	NPD2571	Approved
0.6	Remote Similarity	NPD4745	Approved
0.6	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2566	Approved
0.6	Remote Similarity	NPD3087	Approved
0.6	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4746	Phase 3
0.6	Remote Similarity	NPD2424	Discontinued
0.6	Remote Similarity	NPD4062	Phase 3
0.6	Remote Similarity	NPD4966	Approved
0.6	Remote Similarity	NPD3615	Approved
0.6	Remote Similarity	NPD2574	Discontinued
0.6	Remote Similarity	NPD2573	Approved
0.6	Remote Similarity	NPD4965	Approved
0.6	Remote Similarity	NPD3088	Approved
0.6	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2570	Approved
0.6	Remote Similarity	NPD3614	Approved
0.6	Remote Similarity	NPD3616	Approved
0.5988	Remote Similarity	NPD7472	Approved
0.5988	Remote Similarity	NPD7074	Phase 3
0.5985	Remote Similarity	NPD5647	Approved
0.5984	Remote Similarity	NPD1929	Approved
0.5984	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD1930	Approved
0.5983	Remote Similarity	NPD1066	Discontinued
0.5974	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4807	Approved
0.597	Remote Similarity	NPD4806	Approved
0.5963	Remote Similarity	NPD7228	Approved
0.5962	Remote Similarity	NPD7075	Discontinued
0.5957	Remote Similarity	NPD1613	Approved
0.5957	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD6797	Phase 2
0.5944	Remote Similarity	NPD5886	Approved
0.5944	Remote Similarity	NPD41	Approved
0.5944	Remote Similarity	NPD4536	Approved
0.5944	Remote Similarity	NPD4538	Approved
0.5944	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.594	Remote Similarity	NPD5723	Approved
0.594	Remote Similarity	NPD1778	Approved
0.5932	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6049	Phase 2
0.5931	Remote Similarity	NPD6005	Phase 3
0.5931	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD6004	Phase 3
0.5931	Remote Similarity	NPD6002	Phase 3
0.5929	Remote Similarity	NPD3764	Approved
0.5929	Remote Similarity	NPD9259	Approved
0.5929	Remote Similarity	NPD9257	Approved
0.5926	Remote Similarity	NPD225	Approved
0.5926	Remote Similarity	NPD227	Approved
0.5924	Remote Similarity	NPD6234	Discontinued
0.592	Remote Similarity	NPD6406	Approved
0.5915	Remote Similarity	NPD7251	Discontinued
0.5915	Remote Similarity	NPD4686	Approved
0.5915	Remote Similarity	NPD8368	Discontinued
0.5915	Remote Similarity	NPD4684	Phase 3
0.5915	Remote Similarity	NPD4685	Phase 3

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