NPASS Compound

Structure

NPC40377 OpenBabel07101719142D 21 22 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 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 -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 -2.5981 -1.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -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 -4.3301 0.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -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 1 0 0 0 0 1 7 2 0 0 0 0 2 8 2 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 18 1 6 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.1
Volume:	278.704
LogP:	-1.228
LogD:	-0.766
LogS:	-0.618
# Rotatable Bonds:	4
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	3.591
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.117
MDCK Permeability:	5.601002339972183e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.092
Human Intestinal Absorption (HIA):	0.514
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	16.524511337280273%
Volume Distribution (VD):	0.475
Pgp-substrate:	68.37178802490234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	1.742
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.701
Carcinogencity:	0.07
Eye Corrosion:	0.004
Eye Irritation:	0.402
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC40377

Natural Product ID:	NPC40377
*Common Name:**	Salirepin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[4-hydroxy-2-(hydroxymethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Salirepin
Standard InCHIKey:	NPNFZOGKIFFKGT-UJPOAAIJSA-N
Standard InCHI:	InChI=1S/C13H18O8/c14-4-6-3-7(16)1-2-8(6)20-13-12(19)11(18)10(17)9(5-15)21-13/h1-3,9-19H,4-5H2/t9-,10-,11+,12-,13-/m1/s1
SMILES:	c1cc(c(cc1O)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468146
PubChem CID:	16681676
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23628332]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	29.7	%	PMID[533220]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	110300.0	nM	PMID[533221]

☑ 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 NPC40377 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	409
0.1-0.2	1670
0.2-0.3	4947
0.3-0.4	11159
0.4-0.5	6809
0.5-0.6	5638
0.6-0.7	8604
0.7-0.8	3061
0.8-0.85	296
0.85-0.9	93
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC97326
0.9444	High Similarity	NPC166168
0.9421	High Similarity	NPC226712
0.9231	High Similarity	NPC104167
0.9225	High Similarity	NPC87696
0.912	High Similarity	NPC470510
0.912	High Similarity	NPC12308
0.9084	High Similarity	NPC475628
0.903	High Similarity	NPC145319
0.9024	High Similarity	NPC269242
0.8984	High Similarity	NPC166040
0.8984	High Similarity	NPC218003
0.8963	High Similarity	NPC252169
0.8923	High Similarity	NPC26080
0.8923	High Similarity	NPC303422
0.8923	High Similarity	NPC165686
0.8923	High Similarity	NPC85799
0.8915	High Similarity	NPC262606
0.8906	High Similarity	NPC146540
0.8889	High Similarity	NPC164599
0.8872	High Similarity	NPC134260
0.8871	High Similarity	NPC198734
0.8871	High Similarity	NPC469412
0.8855	High Similarity	NPC115022
0.8855	High Similarity	NPC294166
0.8846	High Similarity	NPC121376
0.8837	High Similarity	NPC248355
0.8815	High Similarity	NPC210192
0.879	High Similarity	NPC469708
0.879	High Similarity	NPC60589
0.8788	High Similarity	NPC130496
0.8788	High Similarity	NPC188555
0.8779	High Similarity	NPC299144
0.8769	High Similarity	NPC472024
0.8769	High Similarity	NPC80600
0.876	High Similarity	NPC302378
0.876	High Similarity	NPC142319
0.875	High Similarity	NPC475084
0.8722	High Similarity	NPC185778
0.8722	High Similarity	NPC238243
0.8722	High Similarity	NPC79957
0.872	High Similarity	NPC473875
0.8712	High Similarity	NPC25821
0.8712	High Similarity	NPC49074
0.8705	High Similarity	NPC474422
0.8705	High Similarity	NPC227902
0.8702	High Similarity	NPC475067
0.8702	High Similarity	NPC65942
0.8702	High Similarity	NPC9912
0.8702	High Similarity	NPC248307
0.8696	High Similarity	NPC138915
0.8692	High Similarity	NPC26653
0.8692	High Similarity	NPC270849
0.8692	High Similarity	NPC307110
0.8657	High Similarity	NPC166180
0.8657	High Similarity	NPC242028
0.8657	High Similarity	NPC165482
0.8657	High Similarity	NPC3293
0.8657	High Similarity	NPC40664
0.8657	High Similarity	NPC197723
0.8657	High Similarity	NPC203230
0.8657	High Similarity	NPC138350
0.8647	High Similarity	NPC251981
0.8647	High Similarity	NPC13745
0.8647	High Similarity	NPC48863
0.8643	High Similarity	NPC92054
0.8643	High Similarity	NPC175976
0.8643	High Similarity	NPC83975
0.8643	High Similarity	NPC4958
0.8643	High Similarity	NPC140722
0.8636	High Similarity	NPC470270
0.8636	High Similarity	NPC162093
0.8623	High Similarity	NPC76176
0.8623	High Similarity	NPC138227
0.8623	High Similarity	NPC469313
0.8623	High Similarity	NPC168579
0.8623	High Similarity	NPC292443
0.8618	High Similarity	NPC175771
0.8594	High Similarity	NPC287429
0.8593	High Similarity	NPC65530
0.8593	High Similarity	NPC59324
0.8593	High Similarity	NPC262328
0.8593	High Similarity	NPC138738
0.8593	High Similarity	NPC470413
0.8593	High Similarity	NPC124149
0.8593	High Similarity	NPC87777
0.8582	High Similarity	NPC313334
0.8582	High Similarity	NPC212670
0.8582	High Similarity	NPC206264
0.8571	High Similarity	NPC132895
0.8571	High Similarity	NPC215833
0.8571	High Similarity	NPC6836
0.8571	High Similarity	NPC69513
0.8561	High Similarity	NPC475096
0.8561	High Similarity	NPC23807
0.8551	High Similarity	NPC37793
0.854	High Similarity	NPC469661
0.8537	High Similarity	NPC301321
0.8529	High Similarity	NPC98777
0.8529	High Similarity	NPC212770
0.8529	High Similarity	NPC183781
0.8529	High Similarity	NPC472151
0.8519	High Similarity	NPC186418
0.8519	High Similarity	NPC164857
0.8507	High Similarity	NPC107478
0.8507	High Similarity	NPC35731
0.8507	High Similarity	NPC470881
0.8507	High Similarity	NPC476411
0.8507	High Similarity	NPC187194
0.85	High Similarity	NPC199928
0.85	High Similarity	NPC99515
0.85	High Similarity	NPC125755
0.85	High Similarity	NPC190714
0.8496	Intermediate Similarity	NPC252833
0.8496	Intermediate Similarity	NPC269421
0.8489	Intermediate Similarity	NPC232228
0.8485	Intermediate Similarity	NPC474491
0.848	Intermediate Similarity	NPC283616
0.8478	Intermediate Similarity	NPC469559
0.8478	Intermediate Similarity	NPC472353
0.8478	Intermediate Similarity	NPC189115
0.8468	Intermediate Similarity	NPC154256
0.8468	Intermediate Similarity	NPC290470
0.8467	Intermediate Similarity	NPC106944
0.8462	Intermediate Similarity	NPC93619
0.8462	Intermediate Similarity	NPC213197
0.8455	Intermediate Similarity	NPC313193
0.8444	Intermediate Similarity	NPC470236
0.844	Intermediate Similarity	NPC15538
0.844	Intermediate Similarity	NPC41844
0.844	Intermediate Similarity	NPC473480
0.8438	Intermediate Similarity	NPC476142
0.8429	Intermediate Similarity	NPC161700
0.8429	Intermediate Similarity	NPC277867
0.8425	Intermediate Similarity	NPC475529
0.8417	Intermediate Similarity	NPC473044
0.8406	Intermediate Similarity	NPC89686
0.8406	Intermediate Similarity	NPC257095
0.8406	Intermediate Similarity	NPC186406
0.8406	Intermediate Similarity	NPC273932
0.8394	Intermediate Similarity	NPC100389
0.8382	Intermediate Similarity	NPC37468
0.8382	Intermediate Similarity	NPC103409
0.8382	Intermediate Similarity	NPC469383
0.8382	Intermediate Similarity	NPC199459
0.8382	Intermediate Similarity	NPC52277
0.8382	Intermediate Similarity	NPC177035
0.838	Intermediate Similarity	NPC280945
0.838	Intermediate Similarity	NPC96294
0.8372	Intermediate Similarity	NPC474130
0.837	Intermediate Similarity	NPC34456
0.8359	Intermediate Similarity	NPC57751
0.8359	Intermediate Similarity	NPC266045
0.8357	Intermediate Similarity	NPC473045
0.8357	Intermediate Similarity	NPC25292
0.8345	Intermediate Similarity	NPC84207
0.8345	Intermediate Similarity	NPC78809
0.8345	Intermediate Similarity	NPC5253
0.8345	Intermediate Similarity	NPC139976
0.8345	Intermediate Similarity	NPC183536
0.8345	Intermediate Similarity	NPC49542
0.8345	Intermediate Similarity	NPC34965
0.8345	Intermediate Similarity	NPC128337
0.8345	Intermediate Similarity	NPC230718
0.8333	Intermediate Similarity	NPC202700
0.8321	Intermediate Similarity	NPC195196
0.8321	Intermediate Similarity	NPC233559
0.8321	Intermediate Similarity	NPC304152
0.831	Intermediate Similarity	NPC213074
0.831	Intermediate Similarity	NPC193473
0.831	Intermediate Similarity	NPC15956
0.831	Intermediate Similarity	NPC31325
0.831	Intermediate Similarity	NPC224674
0.831	Intermediate Similarity	NPC114505
0.831	Intermediate Similarity	NPC275284
0.8309	Intermediate Similarity	NPC472337
0.8309	Intermediate Similarity	NPC55040
0.8308	Intermediate Similarity	NPC221090
0.8306	Intermediate Similarity	NPC157338
0.8298	Intermediate Similarity	NPC476301
0.8298	Intermediate Similarity	NPC472154
0.8298	Intermediate Similarity	NPC271076
0.8298	Intermediate Similarity	NPC43508
0.8295	Intermediate Similarity	NPC152722
0.8295	Intermediate Similarity	NPC46586
0.8295	Intermediate Similarity	NPC204535
0.8288	Intermediate Similarity	NPC92153
0.8288	Intermediate Similarity	NPC260604
0.8288	Intermediate Similarity	NPC279281
0.8288	Intermediate Similarity	NPC230439
0.8288	Intermediate Similarity	NPC299435
0.8288	Intermediate Similarity	NPC299761
0.8286	Intermediate Similarity	NPC478239
0.8286	Intermediate Similarity	NPC470950
0.8286	Intermediate Similarity	NPC46092
0.8286	Intermediate Similarity	NPC185307
0.8273	Intermediate Similarity	NPC108674
0.8271	Intermediate Similarity	NPC295970
0.8264	Intermediate Similarity	NPC238140
0.8264	Intermediate Similarity	NPC114740

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 NPC40377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	844
0.2-0.3	2058
0.3-0.4	2763
0.4-0.5	1585
0.5-0.6	977
0.6-0.7	535
0.7-0.8	48
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9421	High Similarity	NPD1091	Approved
0.8582	High Similarity	NPD1653	Approved
0.8222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1613	Approved
0.8033	Intermediate Similarity	NPD290	Approved
0.7985	Intermediate Similarity	NPD2861	Phase 2
0.7953	Intermediate Similarity	NPD6671	Approved
0.7926	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD968	Approved
0.7737	Intermediate Similarity	NPD3027	Phase 3
0.7669	Intermediate Similarity	NPD1610	Phase 2
0.7647	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6674	Discontinued
0.7634	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD7266	Discontinued
0.7594	Intermediate Similarity	NPD3496	Discontinued
0.7576	Intermediate Similarity	NPD1357	Approved
0.7556	Intermediate Similarity	NPD4749	Approved
0.7554	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4908	Phase 1
0.7469	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8455	Phase 2
0.7442	Intermediate Similarity	NPD7843	Approved
0.7438	Intermediate Similarity	NPD7054	Approved
0.7429	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3705	Approved
0.7405	Intermediate Similarity	NPD7157	Approved
0.7402	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD1652	Phase 2
0.7397	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD7074	Phase 3
0.7388	Intermediate Similarity	NPD1778	Approved
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7365	Intermediate Similarity	NPD5058	Phase 3
0.7357	Intermediate Similarity	NPD4625	Phase 3
0.7346	Intermediate Similarity	NPD6797	Phase 2
0.7324	Intermediate Similarity	NPD4060	Phase 1
0.7301	Intermediate Similarity	NPD7251	Discontinued
0.7301	Intermediate Similarity	NPD6559	Discontinued
0.729	Intermediate Similarity	NPD5402	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.726	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD5762	Approved
0.7256	Intermediate Similarity	NPD7808	Phase 3
0.7246	Intermediate Similarity	NPD6696	Suspended
0.7246	Intermediate Similarity	NPD8651	Approved
0.7233	Intermediate Similarity	NPD3787	Discontinued
0.7231	Intermediate Similarity	NPD228	Approved
0.7226	Intermediate Similarity	NPD2231	Phase 2
0.7226	Intermediate Similarity	NPD2235	Phase 2
0.7222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6653	Approved
0.7181	Intermediate Similarity	NPD2677	Approved
0.7172	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4538	Approved
0.7172	Intermediate Similarity	NPD4536	Approved
0.7163	Intermediate Similarity	NPD596	Approved
0.7163	Intermediate Similarity	NPD600	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD839	Approved
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD840	Approved
0.7123	Intermediate Similarity	NPD5588	Approved
0.7123	Intermediate Similarity	NPD5960	Phase 3
0.7121	Intermediate Similarity	NPD1398	Phase 1
0.7108	Intermediate Similarity	NPD8312	Approved
0.7108	Intermediate Similarity	NPD8313	Approved
0.7095	Intermediate Similarity	NPD2424	Discontinued
0.7092	Intermediate Similarity	NPD3018	Phase 2
0.7086	Intermediate Similarity	NPD1774	Approved
0.7063	Intermediate Similarity	NPD1048	Approved
0.7063	Intermediate Similarity	NPD7199	Phase 2
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD291	Approved
0.7055	Intermediate Similarity	NPD7228	Approved
0.7055	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7051	Intermediate Similarity	NPD37	Approved
0.7051	Intermediate Similarity	NPD1934	Approved
0.7044	Intermediate Similarity	NPD6234	Discontinued
0.7034	Intermediate Similarity	NPD5124	Phase 1
0.7034	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4380	Phase 2
0.7025	Intermediate Similarity	NPD4966	Approved
0.7025	Intermediate Similarity	NPD9365	Approved
0.7025	Intermediate Similarity	NPD4967	Phase 2
0.7025	Intermediate Similarity	NPD4965	Approved
0.7021	Intermediate Similarity	NPD558	Phase 2
0.7007	Intermediate Similarity	NPD5126	Approved
0.7007	Intermediate Similarity	NPD5125	Phase 3
0.7007	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD2801	Approved
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3225	Approved
0.6963	Remote Similarity	NPD7340	Approved
0.6959	Remote Similarity	NPD6032	Approved
0.6959	Remote Similarity	NPD1551	Phase 2
0.6948	Remote Similarity	NPD5403	Approved
0.6947	Remote Similarity	NPD556	Approved
0.6944	Remote Similarity	NPD6798	Discontinued
0.6933	Remote Similarity	NPD6166	Phase 2
0.6933	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3685	Discontinued
0.6929	Remote Similarity	NPD2983	Phase 2
0.6929	Remote Similarity	NPD2982	Phase 2
0.6919	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD447	Suspended
0.6913	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6005	Phase 3
0.6913	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6002	Phase 3
0.6913	Remote Similarity	NPD6004	Phase 3
0.6913	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1375	Discontinued
0.6913	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD776	Approved
0.6906	Remote Similarity	NPD1611	Approved
0.6906	Remote Similarity	NPD1535	Discovery
0.6889	Remote Similarity	NPD709	Approved
0.6887	Remote Similarity	NPD3892	Phase 2
0.6887	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4628	Phase 3
0.6887	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6516	Phase 2
0.6884	Remote Similarity	NPD5846	Approved
0.6875	Remote Similarity	NPD3179	Approved
0.6875	Remote Similarity	NPD3180	Approved
0.6875	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1549	Phase 2
0.6863	Remote Similarity	NPD1511	Approved
0.6857	Remote Similarity	NPD1608	Approved
0.6857	Remote Similarity	NPD1481	Phase 2
0.6857	Remote Similarity	NPD2981	Phase 2
0.685	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1558	Phase 1
0.6849	Remote Similarity	NPD2238	Phase 2
0.6846	Remote Similarity	NPD6099	Approved
0.6846	Remote Similarity	NPD6100	Approved
0.6846	Remote Similarity	NPD2935	Discontinued
0.6842	Remote Similarity	NPD6190	Approved
0.6842	Remote Similarity	NPD969	Suspended
0.6831	Remote Similarity	NPD1203	Approved
0.6831	Remote Similarity	NPD1794	Approved
0.6828	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7985	Registered
0.6821	Remote Similarity	NPD5177	Phase 3
0.6818	Remote Similarity	NPD5401	Approved
0.6812	Remote Similarity	NPD5585	Approved
0.6809	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5844	Phase 1
0.6803	Remote Similarity	NPD5735	Approved
0.6803	Remote Similarity	NPD4340	Discontinued
0.6794	Remote Similarity	NPD1358	Approved
0.6792	Remote Similarity	NPD2978	Approved
0.6792	Remote Similarity	NPD2977	Approved
0.6791	Remote Similarity	NPD821	Approved
0.6791	Remote Similarity	NPD1138	Approved
0.6786	Remote Similarity	NPD7685	Pre-registration
0.6783	Remote Similarity	NPD6584	Phase 3
0.6779	Remote Similarity	NPD4108	Discontinued
0.6779	Remote Similarity	NPD2156	Approved
0.6779	Remote Similarity	NPD2155	Approved
0.6779	Remote Similarity	NPD2154	Approved
0.6776	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1512	Approved
0.677	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9697	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.6753	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7213	Phase 3
0.6753	Remote Similarity	NPD7212	Phase 2
0.675	Remote Similarity	NPD3817	Phase 2
0.6744	Remote Similarity	NPD6841	Approved
0.6744	Remote Similarity	NPD6842	Approved
0.6744	Remote Similarity	NPD6843	Phase 3
0.6741	Remote Similarity	NPD5283	Phase 1
0.6739	Remote Similarity	NPD1182	Approved
0.6738	Remote Similarity	NPD9717	Approved
0.6726	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD9295	Approved
0.6719	Remote Similarity	NPD1242	Phase 1
0.6716	Remote Similarity	NPD1139	Approved
0.6716	Remote Similarity	NPD1137	Approved
0.6713	Remote Similarity	NPD2797	Approved
0.6712	Remote Similarity	NPD1336	Approved
0.6711	Remote Similarity	NPD5061	Approved
0.6711	Remote Similarity	NPD5062	Approved
0.671	Remote Similarity	NPD2505	Approved
0.671	Remote Similarity	NPD7447	Phase 1
0.671	Remote Similarity	NPD2504	Approved
0.6708	Remote Similarity	NPD3882	Suspended

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