NPASS Compound

Structure

CID310252 OpenBabel06191716122D 33 35 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 -5.1962 1.0000 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 -6.0622 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -6.9282 -0.0000 0.0000 C 0 0 0 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -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 -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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 31 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 28 2 0 0 0 0 18 33 1 0 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 22 1 0 0 0 0 21 33 1 6 0 0 0 22 31 1 1 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.15
Volume:	441.636
LogP:	-0.114
LogD:	0.103
LogS:	-1.404
# Rotatable Bonds:	9
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.199
Synthetic Accessibility Score:	3.871
Fsp3:	0.409
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.38
MDCK Permeability:	6.292743819358293e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	81.7345962524414%
Volume Distribution (VD):	0.582
Pgp-substrate:	17.15743064880371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.197
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	15.32
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.485
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.945
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.545
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: NPC310252

Natural Product ID:	NPC310252
*Common Name:**	Ternstroside A
IUPAC Name:	[(2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(3,4-dihydroxyphenyl)acetate
Synonyms:
Standard InCHIKey:	QAOKYQQABTYYAS-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H26O11/c23-10-17-19(29)20(30)21(33-18(28)9-12-2-4-14(25)16(27)8-12)22(32-17)31-6-5-11-1-3-13(24)15(26)7-11/h1-4,7-8,17,19-27,29-30H,5-6,9-10H2/t17-,19-,20+,21-,22-/m1/s1
SMILES:	c1cc(c(cc1CCO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)OC(=O)Cc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465424
PubChem CID:	16091519
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:0002207] O-glycosyl compounds

*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
NPO17348	Ternstroemia japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17067150]
NPO17348	Ternstroemia japonica	Species	Pentaphylacaceae	Eukaryota	fresh leaves	n.a.	n.a.	PMID[17067150]
NPO17348	Ternstroemia japonica	Species	Pentaphylacaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3410.0	nM	PMID[478322]
NPT1590	Tissue	Kidney	Rattus norvegicus	IC50	=	39260.0	nM	PMID[478322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1690.0	nM	PMID[478322]

☑ 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 NPC310252 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	317
0.1-0.2	1191
0.2-0.3	2968
0.3-0.4	7407
0.4-0.5	10636
0.5-0.6	6294
0.6-0.7	9494
0.7-0.8	3860
0.8-0.85	406
0.85-0.9	111
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC302583
1.0	High Similarity	NPC100558
1.0	High Similarity	NPC84789
0.9846	High Similarity	NPC123988
0.9281	High Similarity	NPC474465
0.9254	High Similarity	NPC180171
0.9254	High Similarity	NPC103398
0.9254	High Similarity	NPC158325
0.9091	High Similarity	NPC140151
0.9037	High Similarity	NPC886
0.9037	High Similarity	NPC34293
0.9037	High Similarity	NPC287597
0.9	High Similarity	NPC85565
0.8955	High Similarity	NPC476407
0.8951	High Similarity	NPC92117
0.8939	High Similarity	NPC231607
0.8939	High Similarity	NPC79715
0.8939	High Similarity	NPC108659
0.8939	High Similarity	NPC264900
0.8881	High Similarity	NPC248257
0.8881	High Similarity	NPC120621
0.8873	High Similarity	NPC473867
0.8872	High Similarity	NPC148982
0.8864	High Similarity	NPC94179
0.8857	High Similarity	NPC296643
0.8841	High Similarity	NPC260425
0.8841	High Similarity	NPC78363
0.8836	High Similarity	NPC157898
0.8806	High Similarity	NPC184092
0.8788	High Similarity	NPC123704
0.8784	High Similarity	NPC471405
0.8777	High Similarity	NPC197316
0.8777	High Similarity	NPC64141
0.8777	High Similarity	NPC171134
0.8777	High Similarity	NPC205195
0.8777	High Similarity	NPC472350
0.8777	High Similarity	NPC476383
0.8777	High Similarity	NPC68092
0.8777	High Similarity	NPC321184
0.8777	High Similarity	NPC321638
0.8777	High Similarity	NPC89105
0.8777	High Similarity	NPC81515
0.8777	High Similarity	NPC328273
0.8776	High Similarity	NPC327032
0.8776	High Similarity	NPC191046
0.8776	High Similarity	NPC194095
0.8769	High Similarity	NPC266045
0.8769	High Similarity	NPC472271
0.8768	High Similarity	NPC471345
0.875	High Similarity	NPC28776
0.875	High Similarity	NPC473138
0.8741	High Similarity	NPC469705
0.8741	High Similarity	NPC470122
0.8741	High Similarity	NPC17968
0.8731	High Similarity	NPC158673
0.8725	High Similarity	NPC187205
0.8725	High Similarity	NPC226759
0.8725	High Similarity	NPC472860
0.8716	High Similarity	NPC10205
0.8707	High Similarity	NPC16024
0.8707	High Similarity	NPC205037
0.8707	High Similarity	NPC3746
0.8707	High Similarity	NPC61152
0.8707	High Similarity	NPC44260
0.8696	High Similarity	NPC476870
0.8671	High Similarity	NPC108455
0.8667	High Similarity	NPC229784
0.8667	High Similarity	NPC477293
0.8667	High Similarity	NPC477294
0.8662	High Similarity	NPC478250
0.8652	High Similarity	NPC47471
0.8652	High Similarity	NPC476377
0.8652	High Similarity	NPC476385
0.8652	High Similarity	NPC134405
0.8647	High Similarity	NPC90318
0.8639	High Similarity	NPC134905
0.8639	High Similarity	NPC36130
0.8639	High Similarity	NPC106818
0.8621	High Similarity	NPC116229
0.8613	High Similarity	NPC473285
0.8613	High Similarity	NPC254275
0.8613	High Similarity	NPC471095
0.8613	High Similarity	NPC471066
0.8609	High Similarity	NPC239966
0.8609	High Similarity	NPC203020
0.8601	High Similarity	NPC190587
0.8601	High Similarity	NPC121573
0.8601	High Similarity	NPC22176
0.8601	High Similarity	NPC226738
0.8601	High Similarity	NPC229036
0.86	High Similarity	NPC133984
0.8593	High Similarity	NPC232880
0.8592	High Similarity	NPC471027
0.8592	High Similarity	NPC265648
0.8592	High Similarity	NPC222433
0.8592	High Similarity	NPC13818
0.8592	High Similarity	NPC206095
0.8592	High Similarity	NPC224389
0.8592	High Similarity	NPC477335
0.8592	High Similarity	NPC297517
0.8592	High Similarity	NPC35702
0.8592	High Similarity	NPC140502
0.8582	High Similarity	NPC475530
0.8582	High Similarity	NPC473799
0.8581	High Similarity	NPC245615
0.8581	High Similarity	NPC299706
0.8581	High Similarity	NPC137813
0.8581	High Similarity	NPC115466
0.8581	High Similarity	NPC61604
0.8581	High Similarity	NPC87403
0.8581	High Similarity	NPC44730
0.8562	High Similarity	NPC478242
0.8562	High Similarity	NPC111785
0.8562	High Similarity	NPC75945
0.8551	High Similarity	NPC164172
0.8543	High Similarity	NPC287872
0.8543	High Similarity	NPC74319
0.8543	High Similarity	NPC160780
0.8543	High Similarity	NPC289811
0.854	High Similarity	NPC219677
0.8531	High Similarity	NPC43158
0.8531	High Similarity	NPC269141
0.8531	High Similarity	NPC298257
0.8531	High Similarity	NPC476378
0.8531	High Similarity	NPC220664
0.8531	High Similarity	NPC476375
0.8531	High Similarity	NPC476384
0.8531	High Similarity	NPC119537
0.8531	High Similarity	NPC192831
0.8531	High Similarity	NPC205864
0.8531	High Similarity	NPC277315
0.8531	High Similarity	NPC303090
0.8531	High Similarity	NPC247032
0.8531	High Similarity	NPC472016
0.8531	High Similarity	NPC284948
0.8531	High Similarity	NPC112
0.8531	High Similarity	NPC105005
0.8531	High Similarity	NPC258469
0.8531	High Similarity	NPC476381
0.8531	High Similarity	NPC96795
0.8531	High Similarity	NPC476397
0.8531	High Similarity	NPC37331
0.8531	High Similarity	NPC264632
0.8531	High Similarity	NPC76406
0.8531	High Similarity	NPC175214
0.8531	High Similarity	NPC319628
0.8531	High Similarity	NPC40305
0.8531	High Similarity	NPC476380
0.8529	High Similarity	NPC469549
0.8521	High Similarity	NPC186406
0.8519	High Similarity	NPC476873
0.8519	High Similarity	NPC288416
0.8511	High Similarity	NPC278068
0.8511	High Similarity	NPC152942
0.8511	High Similarity	NPC220942
0.8511	High Similarity	NPC142703
0.8511	High Similarity	NPC219428
0.8511	High Similarity	NPC37250
0.8511	High Similarity	NPC302857
0.8503	High Similarity	NPC12006
0.85	High Similarity	NPC470572
0.8497	Intermediate Similarity	NPC145847
0.8493	Intermediate Similarity	NPC23677
0.8489	Intermediate Similarity	NPC106406
0.8487	Intermediate Similarity	NPC289346
0.8478	Intermediate Similarity	NPC61
0.8478	Intermediate Similarity	NPC18074
0.8478	Intermediate Similarity	NPC473924
0.8478	Intermediate Similarity	NPC5419
0.8478	Intermediate Similarity	NPC25581
0.8477	Intermediate Similarity	NPC172419
0.8477	Intermediate Similarity	NPC1913
0.8477	Intermediate Similarity	NPC238419
0.8472	Intermediate Similarity	NPC64195
0.8472	Intermediate Similarity	NPC296954
0.8472	Intermediate Similarity	NPC300894
0.8472	Intermediate Similarity	NPC141455
0.8472	Intermediate Similarity	NPC196063
0.8472	Intermediate Similarity	NPC470130
0.8467	Intermediate Similarity	NPC475484
0.8467	Intermediate Similarity	NPC38699
0.8462	Intermediate Similarity	NPC469623
0.8462	Intermediate Similarity	NPC148080
0.8451	Intermediate Similarity	NPC303683
0.8451	Intermediate Similarity	NPC26241
0.8451	Intermediate Similarity	NPC295492
0.8451	Intermediate Similarity	NPC476820
0.8451	Intermediate Similarity	NPC474875
0.8451	Intermediate Similarity	NPC274891
0.8451	Intermediate Similarity	NPC205751
0.8451	Intermediate Similarity	NPC476819
0.8442	Intermediate Similarity	NPC109990
0.844	Intermediate Similarity	NPC476376
0.8435	Intermediate Similarity	NPC476394
0.8435	Intermediate Similarity	NPC98809
0.8431	Intermediate Similarity	NPC472859
0.8431	Intermediate Similarity	NPC25389
0.8431	Intermediate Similarity	NPC311803
0.8417	Intermediate Similarity	NPC114116
0.8417	Intermediate Similarity	NPC155209

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 NPC310252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	764
0.2-0.3	1563
0.3-0.4	2840
0.4-0.5	2062
0.5-0.6	1141
0.6-0.7	455
0.7-0.8	61
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD7266	Discontinued
0.8531	High Similarity	NPD6190	Approved
0.8041	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD7685	Pre-registration
0.795	Intermediate Similarity	NPD7472	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7834	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD37	Approved
0.7712	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD4966	Approved
0.7707	Intermediate Similarity	NPD4967	Phase 2
0.7707	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7628	Intermediate Similarity	NPD1934	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.747	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3817	Phase 2
0.7389	Intermediate Similarity	NPD4380	Phase 2
0.7358	Intermediate Similarity	NPD2801	Approved
0.7349	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD943	Approved
0.7338	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD9570	Approved
0.7321	Intermediate Similarity	NPD7240	Approved
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.7315	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7266	Intermediate Similarity	NPD9545	Approved
0.7255	Intermediate Similarity	NPD8166	Discontinued
0.725	Intermediate Similarity	NPD1465	Phase 2
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7244	Intermediate Similarity	NPD1512	Approved
0.7239	Intermediate Similarity	NPD3021	Approved
0.7239	Intermediate Similarity	NPD3022	Approved
0.723	Intermediate Similarity	NPD826	Approved
0.723	Intermediate Similarity	NPD825	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7215	Intermediate Similarity	NPD3455	Phase 2
0.7214	Intermediate Similarity	NPD9268	Approved
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1091	Approved
0.716	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2629	Approved
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7095	Intermediate Similarity	NPD3764	Approved
0.7083	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD555	Phase 2
0.7047	Intermediate Similarity	NPD6663	Approved
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7473	Discontinued
0.7007	Intermediate Similarity	NPD5736	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5402	Approved
0.6982	Remote Similarity	NPD3751	Discontinued
0.6975	Remote Similarity	NPD6801	Discontinued
0.6968	Remote Similarity	NPD6674	Discontinued
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6355	Discontinued
0.6948	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3705	Approved
0.694	Remote Similarity	NPD5048	Discontinued
0.694	Remote Similarity	NPD7680	Approved
0.6939	Remote Similarity	NPD257	Approved
0.6939	Remote Similarity	NPD258	Approved
0.6933	Remote Similarity	NPD7819	Suspended
0.6933	Remote Similarity	NPD259	Phase 1
0.6933	Remote Similarity	NPD4062	Phase 3
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD3400	Discontinued
0.6914	Remote Similarity	NPD6386	Approved
0.6914	Remote Similarity	NPD6385	Approved
0.6903	Remote Similarity	NPD1549	Phase 2
0.6899	Remote Similarity	NPD6799	Approved
0.6897	Remote Similarity	NPD1481	Phase 2
0.6897	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7458	Discontinued
0.6892	Remote Similarity	NPD9569	Approved
0.6887	Remote Similarity	NPD3062	Approved
0.6887	Remote Similarity	NPD3059	Approved
0.6887	Remote Similarity	NPD3061	Approved
0.6883	Remote Similarity	NPD2935	Discontinued
0.6883	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD5403	Approved
0.6863	Remote Similarity	NPD7097	Phase 1
0.6853	Remote Similarity	NPD1357	Approved
0.6842	Remote Similarity	NPD1933	Approved
0.6828	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD8150	Discontinued
0.6818	Remote Similarity	NPD1510	Phase 2
0.681	Remote Similarity	NPD7411	Suspended
0.6806	Remote Similarity	NPD5125	Phase 3
0.6806	Remote Similarity	NPD9381	Approved
0.6806	Remote Similarity	NPD9384	Approved
0.6806	Remote Similarity	NPD5126	Approved
0.68	Remote Similarity	NPD7095	Approved
0.6797	Remote Similarity	NPD5314	Approved
0.6797	Remote Similarity	NPD6653	Approved
0.6795	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8127	Discontinued
0.6783	Remote Similarity	NPD1894	Discontinued
0.6779	Remote Similarity	NPD2861	Phase 2
0.6778	Remote Similarity	NPD6535	Approved
0.6778	Remote Similarity	NPD6534	Approved
0.6776	Remote Similarity	NPD4060	Phase 1
0.6776	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5408	Approved
0.6774	Remote Similarity	NPD5406	Approved
0.6774	Remote Similarity	NPD5404	Approved
0.6774	Remote Similarity	NPD5405	Approved
0.6763	Remote Similarity	NPD228	Approved
0.6757	Remote Similarity	NPD7435	Discontinued
0.6757	Remote Similarity	NPD3094	Phase 2
0.675	Remote Similarity	NPD3146	Approved
0.675	Remote Similarity	NPD5401	Approved
0.675	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9495	Approved
0.673	Remote Similarity	NPD5058	Phase 3
0.6727	Remote Similarity	NPD2977	Approved
0.6727	Remote Similarity	NPD2978	Approved
0.6726	Remote Similarity	NPD5494	Approved
0.6724	Remote Similarity	NPD7039	Approved
0.6724	Remote Similarity	NPD7038	Approved
0.672	Remote Similarity	NPD8319	Approved
0.672	Remote Similarity	NPD8320	Phase 1
0.6711	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3750	Approved
0.669	Remote Similarity	NPD2932	Approved
0.669	Remote Similarity	NPD3019	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD9537	Phase 1
0.6689	Remote Similarity	NPD9536	Phase 1
0.6687	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5353	Approved
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD6776	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD7700	Phase 2
0.6646	Remote Similarity	NPD6599	Discontinued
0.6642	Remote Similarity	NPD1242	Phase 1
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD2933	Approved
0.663	Remote Similarity	NPD6212	Phase 3
0.663	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6213	Phase 3
0.6626	Remote Similarity	NPD3687	Approved
0.6626	Remote Similarity	NPD3686	Approved
0.6623	Remote Similarity	NPD275	Approved
0.6623	Remote Similarity	NPD4340	Discontinued
0.6623	Remote Similarity	NPD447	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