NPASS Compound

Structure

CID83975 OpenBabel06191715422D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.5981 -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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 7 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 4 1 6 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 1 0 0 0 10 11 1 0 0 0 0 10 17 1 6 0 0 0 11 13 1 0 0 0 0 11 18 1 1 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 6 0 0 0 13 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.08
Volume:	284.858
LogP:	-0.073
LogD:	-0.182
LogS:	-1.28
# Rotatable Bonds:	4
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	3.47
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.45
MDCK Permeability:	3.210299473721534e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.701
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	55.195640563964844%
Volume Distribution (VD):	0.279
Pgp-substrate:	51.11064910888672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.686
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.099
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.125
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC83975

Natural Product ID:	NPC83975
*Common Name:**	Gentisic Acid 5-O-Beta-Dglucopyranoside
IUPAC Name:	2-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
Synonyms:
Standard InCHIKey:	CBTFERBMQQAROP-BZNQNGANSA-N
Standard InCHI:	InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-5-1-2-7(15)6(3-5)12(19)20/h1-3,8-11,13-18H,4H2,(H,19,20)/t8-,9-,10+,11-,13-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(c(c2)C(=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092660
PubChem CID:	10914066
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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[569904]

☑ 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 NPC83975 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	351
0.1-0.2	1573
0.2-0.3	4001
0.3-0.4	8870
0.4-0.5	9418
0.5-0.6	4142
0.6-0.7	6485
0.7-0.8	7061
0.8-0.85	694
0.85-0.9	75
0.9-0.95	25
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC34965
0.9655	High Similarity	NPC183536
0.9521	High Similarity	NPC215811
0.9456	High Similarity	NPC279281
0.9456	High Similarity	NPC92153
0.9456	High Similarity	NPC230439
0.9456	High Similarity	NPC299761
0.9444	High Similarity	NPC4958
0.9444	High Similarity	NPC140722
0.9444	High Similarity	NPC92054
0.9324	High Similarity	NPC260604
0.9324	High Similarity	NPC299435
0.9252	High Similarity	NPC93619
0.9205	High Similarity	NPC57072
0.9205	High Similarity	NPC231475
0.9195	High Similarity	NPC470331
0.9161	High Similarity	NPC164599
0.9139	High Similarity	NPC474441
0.9139	High Similarity	NPC476026
0.9139	High Similarity	NPC474401
0.9139	High Similarity	NPC474398
0.9085	High Similarity	NPC132737
0.9085	High Similarity	NPC217950
0.9067	High Similarity	NPC185103
0.9048	High Similarity	NPC302989
0.9028	High Similarity	NPC31081
0.9028	High Similarity	NPC245219
0.9028	High Similarity	NPC65833
0.8966	High Similarity	NPC242756
0.891	High Similarity	NPC280923
0.8889	High Similarity	NPC177742
0.8859	High Similarity	NPC22137
0.8851	High Similarity	NPC474422
0.8846	High Similarity	NPC127415
0.8846	High Similarity	NPC475183
0.879	High Similarity	NPC472130
0.879	High Similarity	NPC472131
0.8782	High Similarity	NPC22324
0.8774	High Similarity	NPC328093
0.8767	High Similarity	NPC145319
0.8742	High Similarity	NPC131874
0.8734	High Similarity	NPC475174
0.8718	High Similarity	NPC71780
0.871	High Similarity	NPC287872
0.871	High Similarity	NPC74319
0.8693	High Similarity	NPC472128
0.8693	High Similarity	NPC472127
0.8688	High Similarity	NPC280385
0.8679	High Similarity	NPC116745
0.8671	High Similarity	NPC178281
0.8667	High Similarity	NPC23084
0.8667	High Similarity	NPC218685
0.8662	High Similarity	NPC56735
0.8662	High Similarity	NPC61594
0.8645	High Similarity	NPC43638
0.8643	High Similarity	NPC40377
0.8643	High Similarity	NPC146540
0.8634	High Similarity	NPC254540
0.8634	High Similarity	NPC172807
0.8634	High Similarity	NPC211594
0.8634	High Similarity	NPC472386
0.8627	High Similarity	NPC310661
0.8627	High Similarity	NPC105827
0.8627	High Similarity	NPC259767
0.8627	High Similarity	NPC88484
0.8625	High Similarity	NPC472133
0.8609	High Similarity	NPC199335
0.8609	High Similarity	NPC111785
0.8608	High Similarity	NPC17432
0.8608	High Similarity	NPC147596
0.8608	High Similarity	NPC94777
0.8608	High Similarity	NPC88043
0.8599	High Similarity	NPC311803
0.8599	High Similarity	NPC472859
0.8599	High Similarity	NPC25389
0.859	High Similarity	NPC279732
0.8589	High Similarity	NPC472992
0.8589	High Similarity	NPC472991
0.8581	High Similarity	NPC261866
0.8581	High Similarity	NPC127406
0.858	High Similarity	NPC470438
0.8571	High Similarity	NPC194095
0.8571	High Similarity	NPC149011
0.8571	High Similarity	NPC199079
0.8571	High Similarity	NPC210808
0.8571	High Similarity	NPC34287
0.8571	High Similarity	NPC471416
0.8571	High Similarity	NPC43434
0.8571	High Similarity	NPC105511
0.8571	High Similarity	NPC204937
0.8571	High Similarity	NPC44558
0.8571	High Similarity	NPC80098
0.8571	High Similarity	NPC472129
0.8571	High Similarity	NPC191046
0.8571	High Similarity	NPC327032
0.8562	High Similarity	NPC36130
0.8562	High Similarity	NPC45618
0.8562	High Similarity	NPC134905
0.8562	High Similarity	NPC146792
0.8562	High Similarity	NPC58716
0.8562	High Similarity	NPC190217
0.8553	High Similarity	NPC99216
0.8553	High Similarity	NPC205054
0.8553	High Similarity	NPC165720
0.8553	High Similarity	NPC182350
0.8544	High Similarity	NPC146837
0.8544	High Similarity	NPC212099
0.8544	High Similarity	NPC101116
0.8544	High Similarity	NPC90905
0.8544	High Similarity	NPC4013
0.8544	High Similarity	NPC278329
0.8537	High Similarity	NPC476618
0.8537	High Similarity	NPC476619
0.8537	High Similarity	NPC476622
0.8537	High Similarity	NPC476623
0.8537	High Similarity	NPC476620
0.8537	High Similarity	NPC476621
0.8537	High Similarity	NPC472387
0.8535	High Similarity	NPC119125
0.8535	High Similarity	NPC166277
0.8531	High Similarity	NPC269421
0.8528	High Similarity	NPC115760
0.8528	High Similarity	NPC477848
0.8528	High Similarity	NPC237435
0.8528	High Similarity	NPC43211
0.8528	High Similarity	NPC264735
0.8528	High Similarity	NPC49344
0.8528	High Similarity	NPC210094
0.8528	High Similarity	NPC135277
0.8528	High Similarity	NPC101191
0.8526	High Similarity	NPC60966
0.8526	High Similarity	NPC258035
0.8526	High Similarity	NPC156457
0.8526	High Similarity	NPC313163
0.8526	High Similarity	NPC197896
0.8526	High Similarity	NPC161749
0.8519	High Similarity	NPC9002
0.8519	High Similarity	NPC288152
0.8519	High Similarity	NPC257011
0.8519	High Similarity	NPC205076
0.8519	High Similarity	NPC307518
0.8519	High Similarity	NPC137871
0.8519	High Similarity	NPC48773
0.8516	High Similarity	NPC99233
0.8516	High Similarity	NPC10205
0.8511	High Similarity	NPC198487
0.8509	High Similarity	NPC471457
0.8509	High Similarity	NPC469931
0.8509	High Similarity	NPC475942
0.8509	High Similarity	NPC186807
0.8509	High Similarity	NPC93337
0.8509	High Similarity	NPC45638
0.8509	High Similarity	NPC472381
0.8509	High Similarity	NPC58053
0.8509	High Similarity	NPC472383
0.8509	High Similarity	NPC105025
0.8509	High Similarity	NPC112755
0.8509	High Similarity	NPC201292
0.8509	High Similarity	NPC226294
0.8509	High Similarity	NPC170675
0.8506	High Similarity	NPC121001
0.8506	High Similarity	NPC259182
0.85	High Similarity	NPC70441
0.85	High Similarity	NPC99957
0.85	High Similarity	NPC181616
0.8497	Intermediate Similarity	NPC213723
0.8497	Intermediate Similarity	NPC106025
0.8497	Intermediate Similarity	NPC213382
0.8497	Intermediate Similarity	NPC477240
0.8497	Intermediate Similarity	NPC473966
0.8497	Intermediate Similarity	NPC214454
0.8497	Intermediate Similarity	NPC191154
0.8497	Intermediate Similarity	NPC164527
0.8491	Intermediate Similarity	NPC168822
0.8483	Intermediate Similarity	NPC185778
0.8481	Intermediate Similarity	NPC472994
0.8481	Intermediate Similarity	NPC195685
0.8481	Intermediate Similarity	NPC210961
0.8481	Intermediate Similarity	NPC477628
0.8481	Intermediate Similarity	NPC477629
0.8481	Intermediate Similarity	NPC270675
0.8481	Intermediate Similarity	NPC282169
0.8476	Intermediate Similarity	NPC472385
0.8476	Intermediate Similarity	NPC472384
0.8476	Intermediate Similarity	NPC198324
0.8476	Intermediate Similarity	NPC211532
0.8476	Intermediate Similarity	NPC268533
0.8476	Intermediate Similarity	NPC472382
0.8476	Intermediate Similarity	NPC233994
0.8476	Intermediate Similarity	NPC472380
0.8471	Intermediate Similarity	NPC73511
0.8471	Intermediate Similarity	NPC160780
0.8471	Intermediate Similarity	NPC43761
0.8471	Intermediate Similarity	NPC289811
0.8467	Intermediate Similarity	NPC138915
0.8466	Intermediate Similarity	NPC88560
0.8466	Intermediate Similarity	NPC172033
0.8466	Intermediate Similarity	NPC175230
0.8462	Intermediate Similarity	NPC265480
0.8462	Intermediate Similarity	NPC149368

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 NPC83975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	858
0.2-0.3	1925
0.3-0.4	2630
0.4-0.5	1834
0.5-0.6	1063
0.6-0.7	375
0.7-0.8	146
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8528	High Similarity	NPD4338	Clinical (unspecified phase)
0.8526	High Similarity	NPD4381	Clinical (unspecified phase)
0.8516	High Similarity	NPD5402	Approved
0.8366	Intermediate Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8253	Intermediate Similarity	NPD8312	Approved
0.8253	Intermediate Similarity	NPD8313	Approved
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8219	Intermediate Similarity	NPD447	Suspended
0.8171	Intermediate Similarity	NPD7054	Approved
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1091	Approved
0.8121	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8065	Intermediate Similarity	NPD5403	Approved
0.8042	Intermediate Similarity	NPD1203	Approved
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7958	Intermediate Similarity	NPD9717	Approved
0.7952	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7935	Intermediate Similarity	NPD5401	Approved
0.7911	Intermediate Similarity	NPD4380	Phase 2
0.7875	Intermediate Similarity	NPD2801	Approved
0.7852	Intermediate Similarity	NPD1933	Approved
0.7812	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.777	Intermediate Similarity	NPD411	Approved
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6799	Approved
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7733	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7669	Intermediate Similarity	NPD3882	Suspended
0.7665	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6166	Phase 2
0.7665	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7819	Suspended
0.7654	Intermediate Similarity	NPD8455	Phase 2
0.7643	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD1019	Discontinued
0.7602	Intermediate Similarity	NPD7685	Pre-registration
0.7589	Intermediate Similarity	NPD9493	Approved
0.7582	Intermediate Similarity	NPD7435	Discontinued
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD1512	Approved
0.7544	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD7411	Suspended
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7516	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD7266	Discontinued
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7432	Intermediate Similarity	NPD6823	Phase 2
0.7425	Intermediate Similarity	NPD5494	Approved
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6190	Approved
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7783	Phase 2
0.7378	Intermediate Similarity	NPD6844	Discontinued
0.7375	Intermediate Similarity	NPD2534	Approved
0.7375	Intermediate Similarity	NPD2532	Approved
0.7375	Intermediate Similarity	NPD2533	Approved
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2799	Discontinued
0.7349	Intermediate Similarity	NPD7768	Phase 2
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3750	Approved
0.734	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.7329	Intermediate Similarity	NPD3496	Discontinued
0.732	Intermediate Similarity	NPD1240	Approved
0.7308	Intermediate Similarity	NPD2796	Approved
0.7297	Intermediate Similarity	NPD7696	Phase 3
0.7297	Intermediate Similarity	NPD7697	Approved
0.7297	Intermediate Similarity	NPD7698	Approved
0.7289	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD7228	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.726	Intermediate Similarity	NPD1778	Approved
0.7258	Intermediate Similarity	NPD7870	Phase 2
0.7258	Intermediate Similarity	NPD7871	Phase 2
0.7255	Intermediate Similarity	NPD6233	Phase 2
0.7251	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7241	Intermediate Similarity	NPD9545	Approved
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.7226	Intermediate Similarity	NPD1607	Approved
0.7209	Intermediate Similarity	NPD7473	Discontinued
0.7208	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1613	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3749	Approved
0.7191	Intermediate Similarity	NPD8150	Discontinued
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6212	Phase 3
0.7182	Intermediate Similarity	NPD6213	Phase 3
0.7178	Intermediate Similarity	NPD920	Approved
0.7178	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7176	Intermediate Similarity	NPD6959	Discontinued
0.717	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD5647	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD3225	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7115	Intermediate Similarity	NPD6653	Approved
0.7114	Intermediate Similarity	NPD1481	Phase 2
0.7114	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD8151	Discontinued
0.7105	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD2797	Approved
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7076	Intermediate Similarity	NPD1247	Approved
0.7071	Intermediate Similarity	NPD9263	Approved
0.7071	Intermediate Similarity	NPD9267	Approved
0.7071	Intermediate Similarity	NPD9264	Approved
0.7059	Intermediate Similarity	NPD919	Approved
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7047	Intermediate Similarity	NPD422	Phase 1
0.7047	Intermediate Similarity	NPD1535	Discovery
0.7045	Intermediate Similarity	NPD5953	Discontinued
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7037	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD520	Approved
0.7025	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD7584	Approved
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2861	Phase 2
0.6988	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD943	Approved
0.6984	Remote Similarity	NPD8320	Phase 1
0.6984	Remote Similarity	NPD8319	Approved
0.697	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3268	Approved
0.6962	Remote Similarity	NPD7097	Phase 1
0.6962	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2800	Approved
0.6957	Remote Similarity	NPD1243	Approved
0.6951	Remote Similarity	NPD4662	Approved
0.6951	Remote Similarity	NPD4661	Approved
0.695	Remote Similarity	NPD290	Approved
0.6948	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2344	Approved
0.6937	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5710	Approved
0.6936	Remote Similarity	NPD5711	Approved
0.6932	Remote Similarity	NPD7286	Phase 2
0.6918	Remote Similarity	NPD6671	Approved
0.6913	Remote Similarity	NPD17	Approved

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