NPASS Compound

Structure

CID123988 OpenBabel06191715482D 32 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 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 -3.4641 -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 0.0000 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 -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 -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 -5.1962 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 -6.9282 1.0000 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 -5.1962 -2.0000 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 -7.7942 1.5000 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 -6.0622 -1.5000 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 4 1 0 0 0 0 1 12 2 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 30 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 18 27 2 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 30 1 1 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.15
Volume:	432.846
LogP:	0.474
LogD:	0.55
LogS:	-1.72
# Rotatable Bonds:	9
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	3.752
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
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:	-6.235
MDCK Permeability:	7.790978997945786e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.977
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	80.82036590576172%
Volume Distribution (VD):	0.595
Pgp-substrate:	23.03156852722168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.478
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	12.969
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.922
Carcinogencity:	0.124
Eye Corrosion:	0.003
Eye Irritation:	0.115
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: NPC123988

Natural Product ID:	NPC123988
*Common Name:**	Ternstroside B
IUPAC Name:	[(2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(4-hydroxyphenyl)acetate
Synonyms:	Ternstroside B
Standard InCHIKey:	GTYGWPXLHJZXDF-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H26O10/c23-11-17-19(28)20(29)21(32-18(27)10-12-1-4-14(24)5-2-12)22(31-17)30-8-7-13-3-6-15(25)16(26)9-13/h1-6,9,17,19-26,28-29H,7-8,10-11H2/t17-,19-,20+,21-,22-/m1/s1
SMILES:	c1cc(ccc1CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1OCCc1ccc(c(c1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462808
PubChem CID:	16091520
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	=	4660.0	nM	PMID[561879]
NPT1590	Tissue	Kidney	Rattus norvegicus	IC50	=	62520.0	nM	PMID[561879]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2360.0	nM	PMID[561879]

☑ 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 NPC123988 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	303
0.1-0.2	1177
0.2-0.3	2885
0.3-0.4	7475
0.4-0.5	10855
0.5-0.6	6251
0.6-0.7	9479
0.7-0.8	3707
0.8-0.85	434
0.85-0.9	113
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC84789
0.9846	High Similarity	NPC302583
0.9846	High Similarity	NPC310252
0.9846	High Similarity	NPC100558
0.9394	High Similarity	NPC103398
0.9394	High Similarity	NPC180171
0.9394	High Similarity	NPC158325
0.9173	High Similarity	NPC34293
0.9173	High Similarity	NPC886
0.9173	High Similarity	NPC287597
0.9137	High Similarity	NPC474465
0.9091	High Similarity	NPC476407
0.9077	High Similarity	NPC108659
0.9077	High Similarity	NPC264900
0.9077	High Similarity	NPC231607
0.9077	High Similarity	NPC79715
0.9008	High Similarity	NPC148982
0.9	High Similarity	NPC94179
0.8971	High Similarity	NPC78363
0.8971	High Similarity	NPC260425
0.8951	High Similarity	NPC140151
0.8939	High Similarity	NPC184092
0.8906	High Similarity	NPC472271
0.8906	High Similarity	NPC266045
0.8905	High Similarity	NPC328273
0.8905	High Similarity	NPC321184
0.8905	High Similarity	NPC197316
0.8905	High Similarity	NPC205195
0.8905	High Similarity	NPC64141
0.8905	High Similarity	NPC89105
0.8905	High Similarity	NPC321638
0.8905	High Similarity	NPC476383
0.8905	High Similarity	NPC81515
0.8905	High Similarity	NPC68092
0.8905	High Similarity	NPC171134
0.8905	High Similarity	NPC472350
0.8897	High Similarity	NPC471345
0.8873	High Similarity	NPC28776
0.8873	High Similarity	NPC473138
0.8872	High Similarity	NPC469705
0.8872	High Similarity	NPC17968
0.8872	High Similarity	NPC470122
0.8864	High Similarity	NPC158673
0.8849	High Similarity	NPC296643
0.8846	High Similarity	NPC85565
0.8824	High Similarity	NPC476870
0.8811	High Similarity	NPC92117
0.8797	High Similarity	NPC229784
0.8797	High Similarity	NPC477294
0.8797	High Similarity	NPC477293
0.8779	High Similarity	NPC90318
0.8777	High Similarity	NPC134405
0.8777	High Similarity	NPC47471
0.8777	High Similarity	NPC476377
0.8777	High Similarity	NPC476385
0.8759	High Similarity	NPC106818
0.8741	High Similarity	NPC471066
0.8741	High Similarity	NPC471095
0.8741	High Similarity	NPC254275
0.8741	High Similarity	NPC120621
0.8741	High Similarity	NPC248257
0.8741	High Similarity	NPC473285
0.8741	High Similarity	NPC116229
0.8732	High Similarity	NPC473867
0.8722	High Similarity	NPC232880
0.8714	High Similarity	NPC222433
0.8714	High Similarity	NPC265648
0.8714	High Similarity	NPC140502
0.8705	High Similarity	NPC475530
0.8705	High Similarity	NPC473799
0.8699	High Similarity	NPC157898
0.8699	High Similarity	NPC245615
0.8699	High Similarity	NPC299706
0.8699	High Similarity	NPC115466
0.8699	High Similarity	NPC87403
0.8699	High Similarity	NPC61604
0.8681	High Similarity	NPC478242
0.8681	High Similarity	NPC111785
0.8676	High Similarity	NPC164172
0.8667	High Similarity	NPC219677
0.8652	High Similarity	NPC476384
0.8652	High Similarity	NPC298257
0.8652	High Similarity	NPC264632
0.8652	High Similarity	NPC476380
0.8652	High Similarity	NPC476375
0.8652	High Similarity	NPC476378
0.8652	High Similarity	NPC247032
0.8652	High Similarity	NPC205864
0.8652	High Similarity	NPC40305
0.8652	High Similarity	NPC476397
0.8652	High Similarity	NPC112
0.8652	High Similarity	NPC175214
0.8652	High Similarity	NPC96795
0.8652	High Similarity	NPC105005
0.8652	High Similarity	NPC476381
0.8652	High Similarity	NPC119537
0.8652	High Similarity	NPC269141
0.8652	High Similarity	NPC76406
0.8649	High Similarity	NPC471405
0.8647	High Similarity	NPC476873
0.8647	High Similarity	NPC288416
0.8643	High Similarity	NPC186406
0.8639	High Similarity	NPC191046
0.8639	High Similarity	NPC194095
0.8639	High Similarity	NPC327032
0.8636	High Similarity	NPC123704
0.8633	High Similarity	NPC220942
0.8623	High Similarity	NPC470572
0.8621	High Similarity	NPC12006
0.8613	High Similarity	NPC106406
0.8603	High Similarity	NPC25581
0.8603	High Similarity	NPC61
0.8603	High Similarity	NPC473924
0.8603	High Similarity	NPC18074
0.8603	High Similarity	NPC5419
0.8592	High Similarity	NPC196063
0.8592	High Similarity	NPC296954
0.8592	High Similarity	NPC300894
0.8592	High Similarity	NPC64195
0.8592	High Similarity	NPC141455
0.8591	High Similarity	NPC187205
0.8591	High Similarity	NPC472860
0.8591	High Similarity	NPC226759
0.8582	High Similarity	NPC469623
0.8582	High Similarity	NPC148080
0.8581	High Similarity	NPC38699
0.8581	High Similarity	NPC10205
0.8571	High Similarity	NPC205037
0.8571	High Similarity	NPC3746
0.8571	High Similarity	NPC44260
0.8571	High Similarity	NPC16024
0.8571	High Similarity	NPC61152
0.8561	High Similarity	NPC476376
0.854	High Similarity	NPC254398
0.854	High Similarity	NPC168799
0.854	High Similarity	NPC155209
0.8538	High Similarity	NPC160854
0.8538	High Similarity	NPC469704
0.8538	High Similarity	NPC201402
0.8538	High Similarity	NPC469703
0.8531	High Similarity	NPC100998
0.8531	High Similarity	NPC34927
0.8531	High Similarity	NPC34587
0.8531	High Similarity	NPC476382
0.8531	High Similarity	NPC252292
0.8531	High Similarity	NPC108455
0.8529	High Similarity	NPC198388
0.8523	High Similarity	NPC478055
0.8523	High Similarity	NPC163635
0.8521	High Similarity	NPC478239
0.8521	High Similarity	NPC478250
0.8519	High Similarity	NPC469549
0.8503	High Similarity	NPC134905
0.8503	High Similarity	NPC36130
0.8496	Intermediate Similarity	NPC126991
0.8496	Intermediate Similarity	NPC83218
0.8493	Intermediate Similarity	NPC158635
0.8493	Intermediate Similarity	NPC229882
0.8489	Intermediate Similarity	NPC177035
0.8489	Intermediate Similarity	NPC199459
0.8489	Intermediate Similarity	NPC52277
0.8483	Intermediate Similarity	NPC23677
0.8478	Intermediate Similarity	NPC471883
0.8477	Intermediate Similarity	NPC203020
0.8477	Intermediate Similarity	NPC239966
0.8473	Intermediate Similarity	NPC469686
0.8472	Intermediate Similarity	NPC229505
0.8467	Intermediate Similarity	NPC133984
0.8462	Intermediate Similarity	NPC226738
0.8462	Intermediate Similarity	NPC190587
0.8462	Intermediate Similarity	NPC232228
0.8462	Intermediate Similarity	NPC121573
0.8462	Intermediate Similarity	NPC229036
0.8462	Intermediate Similarity	NPC292443
0.8462	Intermediate Similarity	NPC22176
0.8456	Intermediate Similarity	NPC131532
0.8451	Intermediate Similarity	NPC471027
0.8451	Intermediate Similarity	NPC13818
0.8451	Intermediate Similarity	NPC206095
0.8451	Intermediate Similarity	NPC224389
0.8451	Intermediate Similarity	NPC477335
0.8451	Intermediate Similarity	NPC35702
0.8451	Intermediate Similarity	NPC157816
0.8451	Intermediate Similarity	NPC297517
0.8446	Intermediate Similarity	NPC137813
0.8446	Intermediate Similarity	NPC44730
0.8433	Intermediate Similarity	NPC471157
0.8429	Intermediate Similarity	NPC138738
0.8429	Intermediate Similarity	NPC470413
0.8429	Intermediate Similarity	NPC469696
0.8425	Intermediate Similarity	NPC75945
0.8414	Intermediate Similarity	NPC232992
0.8411	Intermediate Similarity	NPC74319
0.8411	Intermediate Similarity	NPC160780
0.8411	Intermediate Similarity	NPC289811
0.8411	Intermediate Similarity	NPC287872
0.8409	Intermediate Similarity	NPC471067
0.8394	Intermediate Similarity	NPC318799
0.8394	Intermediate Similarity	NPC65942
0.8394	Intermediate Similarity	NPC235294

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 NPC123988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	754
0.2-0.3	1531
0.3-0.4	2838
0.4-0.5	2068
0.5-0.6	1169
0.6-0.7	478
0.7-0.8	58
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
0.8905	High Similarity	NPD7266	Discontinued
0.8392	Intermediate Similarity	NPD6190	Approved
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7925	Intermediate Similarity	NPD7228	Approved
0.7905	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7054	Approved
0.7843	Intermediate Similarity	NPD37	Approved
0.784	Intermediate Similarity	NPD7685	Pre-registration
0.7826	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD7074	Phase 3
0.7815	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4965	Approved
0.7806	Intermediate Similarity	NPD4966	Approved
0.7806	Intermediate Similarity	NPD4967	Phase 2
0.7792	Intermediate Similarity	NPD8455	Phase 2
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD3027	Phase 3
0.7576	Intermediate Similarity	NPD7808	Phase 3
0.7569	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1613	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1934	Approved
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9570	Approved
0.7415	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7240	Approved
0.741	Intermediate Similarity	NPD6559	Discontinued
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7357	Intermediate Similarity	NPD9269	Phase 2
0.7351	Intermediate Similarity	NPD4628	Phase 3
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7349	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3021	Approved
0.7348	Intermediate Similarity	NPD3022	Approved
0.7329	Intermediate Similarity	NPD826	Approved
0.7329	Intermediate Similarity	NPD825	Approved
0.7308	Intermediate Similarity	NPD3455	Phase 2
0.7301	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1091	Approved
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.7233	Intermediate Similarity	NPD2801	Approved
0.7229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD8313	Approved
0.7211	Intermediate Similarity	NPD943	Approved
0.7208	Intermediate Similarity	NPD1511	Approved
0.7206	Intermediate Similarity	NPD2629	Approved
0.7192	Intermediate Similarity	NPD6798	Discontinued
0.7192	Intermediate Similarity	NPD3764	Approved
0.7183	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD555	Phase 2
0.7161	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6663	Approved
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7122	Intermediate Similarity	NPD9545	Approved
0.7115	Intermediate Similarity	NPD1512	Approved
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5736	Approved
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7081	Intermediate Similarity	NPD5402	Approved
0.7079	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7051	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6355	Discontinued
0.7042	Intermediate Similarity	NPD3705	Approved
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3882	Suspended
0.7034	Intermediate Similarity	NPD258	Approved
0.7034	Intermediate Similarity	NPD257	Approved
0.703	Intermediate Similarity	NPD6232	Discontinued
0.703	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD259	Phase 1
0.7027	Intermediate Similarity	NPD4062	Phase 3
0.7017	Intermediate Similarity	NPD7680	Approved
0.7013	Intermediate Similarity	NPD3400	Discontinued
0.7013	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD1481	Phase 2
0.6993	Remote Similarity	NPD1608	Approved
0.6986	Remote Similarity	NPD9569	Approved
0.698	Remote Similarity	NPD3062	Approved
0.698	Remote Similarity	NPD3061	Approved
0.698	Remote Similarity	NPD3059	Approved
0.6977	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2438	Suspended
0.6974	Remote Similarity	NPD2935	Discontinued
0.6962	Remote Similarity	NPD5403	Approved
0.6954	Remote Similarity	NPD7097	Phase 1
0.695	Remote Similarity	NPD1357	Approved
0.6933	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD1535	Discovery
0.6914	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7033	Discontinued
0.6905	Remote Similarity	NPD7473	Discontinued
0.6901	Remote Similarity	NPD9384	Approved
0.6901	Remote Similarity	NPD9381	Approved
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD5125	Phase 3
0.6892	Remote Similarity	NPD7095	Approved
0.6887	Remote Similarity	NPD6653	Approved
0.6887	Remote Similarity	NPD5314	Approved
0.6879	Remote Similarity	NPD1894	Discontinued
0.6871	Remote Similarity	NPD9494	Approved
0.6871	Remote Similarity	NPD2861	Phase 2
0.6867	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD8127	Discontinued
0.6864	Remote Similarity	NPD3751	Discontinued
0.6863	Remote Similarity	NPD5404	Approved
0.6863	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD5408	Approved
0.6863	Remote Similarity	NPD5406	Approved
0.6861	Remote Similarity	NPD228	Approved
0.6852	Remote Similarity	NPD6801	Discontinued
0.6849	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD9495	Approved
0.6839	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5401	Approved
0.6818	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5058	Phase 3
0.6815	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2977	Approved
0.681	Remote Similarity	NPD7819	Suspended
0.681	Remote Similarity	NPD2978	Approved
0.6803	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7038	Approved
0.6802	Remote Similarity	NPD7039	Approved
0.6797	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3750	Approved
0.6791	Remote Similarity	NPD5048	Discontinued
0.679	Remote Similarity	NPD6386	Approved
0.679	Remote Similarity	NPD6385	Approved
0.6783	Remote Similarity	NPD2932	Approved
0.6783	Remote Similarity	NPD3019	Approved
0.6783	Remote Similarity	NPD17	Approved
0.6781	Remote Similarity	NPD1283	Approved
0.6779	Remote Similarity	NPD9536	Phase 1
0.6779	Remote Similarity	NPD9537	Phase 1
0.6774	Remote Similarity	NPD1549	Phase 2
0.6772	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD7458	Discontinued
0.6755	Remote Similarity	NPD2979	Phase 3
0.6744	Remote Similarity	NPD2934	Approved
0.6744	Remote Similarity	NPD2933	Approved
0.6742	Remote Similarity	NPD1242	Phase 1
0.6712	Remote Similarity	NPD9622	Approved
0.6711	Remote Similarity	NPD275	Approved
0.6711	Remote Similarity	NPD447	Suspended
0.6711	Remote Similarity	NPD274	Approved
0.6711	Remote Similarity	NPD4340	Discontinued
0.6708	Remote Similarity	NPD3686	Approved
0.6708	Remote Similarity	NPD3687	Approved
0.6705	Remote Similarity	NPD8150	Discontinued
0.6692	Remote Similarity	NPD2860	Approved
0.6692	Remote Similarity	NPD2859	Approved
0.669	Remote Similarity	NPD1201	Approved
0.669	Remote Similarity	NPD5536	Phase 2
0.669	Remote Similarity	NPD3092	Approved
0.6688	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5958	Discontinued
0.6649	Remote Similarity	NPD7435	Discontinued
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5283	Phase 1
0.6626	Remote Similarity	NPD7028	Phase 2
0.6625	Remote Similarity	NPD4378	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