NPASS Compound

Structure

CID185838 OpenBabel06191715562D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 2.5981 -1.5000 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 -0.0000 -3.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -2.5981 -1.5000 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 0.8660 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 N 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.17
Volume:	333.059
LogP:	2.483
LogD:	2.942
LogS:	-1.964
# Rotatable Bonds:	4
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.941
Synthetic Accessibility Score:	2.581
Fsp3:	0.368
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:	-4.559
MDCK Permeability:	1.7639922589296475e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.481
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.467

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	67.57552337646484%
Volume Distribution (VD):	2.296
Pgp-substrate:	18.003358840942383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.194
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.22
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.758
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	13.196
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.648
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.617
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC185838

Natural Product ID:	NPC185838
*Common Name:**	4-[(6,7-Dimethoxy-2-Methyl-3,4-Dihydro-1H-Isoquinolin-1-Yl)Methyl]Phenol
IUPAC Name:	4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]phenol
Synonyms:	D,L-Armepavine
Standard InCHIKey:	ZBKFZIUKXTWQTP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3
SMILES:	COc1cc2c(cc1OC)CCN(C2Cc1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451722
PubChem CID:	98348
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2957	Papaver caucasicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2957	Papaver caucasicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2957	Papaver caucasicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30631	Rhamnus frangula	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30157	Euonymus europaeua	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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	3
Ki	2
Others	7
Potency	8

Activity Type	# Activity
Individual Protein	7
Others	9
Protein Family	2
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[470646]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[470646]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[470646]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[470646]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[470646]
NPT968	Protein Family	Adrenergic receptor alpha-1	Rattus norvegicus	Ki	=	7244.36	nM	PMID[470645]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Ki	=	9549.93	nM	PMID[470645]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	208929.61	nM	PMID[470645]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	=	114815.36	nM	PMID[470645]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	44668.4	nM	PMID[470646]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	25118.9	nM	PMID[470646]
NPT2	Others	Unspecified		Potency	n.a.	2909.3	nM	PMID[470646]
NPT2	Others	Unspecified		Inhibition	=	18.2	%	PMID[470647]
NPT2	Others	Unspecified		Inhibition	=	7.5	%	PMID[470647]
NPT27	Others	Unspecified		Inhibition	=	82.0	%	PMID[470647]
NPT27	Others	Unspecified		Inhibition	=	86.0	%	PMID[470647]
NPT2	Others	Unspecified		IC50	=	25600.0	nM	PMID[470647]
NPT2	Others	Unspecified		Inhibition	=	80.3	%	PMID[470647]
NPT2	Others	Unspecified		Inhibition	=	50.4	%	PMID[470647]
NPT2	Others	Unspecified		Inhibition	=	34.0	%	PMID[470647]

☑ 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 NPC185838 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	254
0.1-0.2	1622
0.2-0.3	8591
0.3-0.4	9159
0.4-0.5	5917
0.5-0.6	11595
0.6-0.7	4183
0.7-0.8	931
0.8-0.85	247
0.85-0.9	118
0.9-0.95	65
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC191376
0.9855	High Similarity	NPC321505
0.9855	High Similarity	NPC179825
0.9784	High Similarity	NPC476571
0.9784	High Similarity	NPC428
0.9784	High Similarity	NPC24233
0.9784	High Similarity	NPC135538
0.9784	High Similarity	NPC147390
0.9784	High Similarity	NPC246587
0.9712	High Similarity	NPC476151
0.9632	High Similarity	NPC314682
0.9574	High Similarity	NPC103379
0.9574	High Similarity	NPC477565
0.9574	High Similarity	NPC60538
0.9574	High Similarity	NPC207824
0.9562	High Similarity	NPC188163
0.9562	High Similarity	NPC474915
0.9562	High Similarity	NPC213206
0.9562	High Similarity	NPC328750
0.9507	High Similarity	NPC151895
0.9507	High Similarity	NPC192768
0.9507	High Similarity	NPC97221
0.9507	High Similarity	NPC88249
0.9507	High Similarity	NPC220858
0.9441	High Similarity	NPC277669
0.9441	High Similarity	NPC76213
0.9379	High Similarity	NPC2413
0.9379	High Similarity	NPC204828
0.9379	High Similarity	NPC110416
0.9379	High Similarity	NPC39701
0.9379	High Similarity	NPC276588
0.9379	High Similarity	NPC207757
0.9379	High Similarity	NPC189266
0.9379	High Similarity	NPC193949
0.9379	High Similarity	NPC127674
0.9379	High Similarity	NPC249797
0.9379	High Similarity	NPC172765
0.9379	High Similarity	NPC184026
0.9379	High Similarity	NPC278799
0.9379	High Similarity	NPC5238
0.9379	High Similarity	NPC54379
0.9379	High Similarity	NPC295691
0.9379	High Similarity	NPC469817
0.9286	High Similarity	NPC476567
0.9286	High Similarity	NPC136860
0.9286	High Similarity	NPC128019
0.9178	High Similarity	NPC477564
0.9178	High Similarity	NPC2295
0.9161	High Similarity	NPC476144
0.9161	High Similarity	NPC210437
0.9161	High Similarity	NPC51957
0.9161	High Similarity	NPC106295
0.9161	High Similarity	NPC16107
0.913	High Similarity	NPC301050
0.913	High Similarity	NPC131204
0.9128	High Similarity	NPC166014
0.9128	High Similarity	NPC27410
0.911	High Similarity	NPC82285
0.911	High Similarity	NPC133011
0.9103	High Similarity	NPC274026
0.9097	High Similarity	NPC475959
0.9097	High Similarity	NPC7467
0.906	High Similarity	NPC111485
0.9054	High Similarity	NPC147091
0.898	High Similarity	NPC26601
0.8971	High Similarity	NPC160193
0.8951	High Similarity	NPC294249
0.8947	High Similarity	NPC238530
0.8947	High Similarity	NPC276944
0.8947	High Similarity	NPC232514
0.8912	High Similarity	NPC326316
0.8912	High Similarity	NPC81733
0.8889	High Similarity	NPC317272
0.8889	High Similarity	NPC13916
0.8889	High Similarity	NPC268503
0.8889	High Similarity	NPC130926
0.8889	High Similarity	NPC42549
0.8889	High Similarity	NPC250846
0.8889	High Similarity	NPC240841
0.8889	High Similarity	NPC256012
0.8889	High Similarity	NPC264850
0.8882	High Similarity	NPC324144
0.8851	High Similarity	NPC37272
0.8831	High Similarity	NPC117188
0.8831	High Similarity	NPC205421
0.8831	High Similarity	NPC12053
0.8831	High Similarity	NPC474931
0.8831	High Similarity	NPC306555
0.8831	High Similarity	NPC298979
0.8831	High Similarity	NPC145832
0.8831	High Similarity	NPC81218
0.8831	High Similarity	NPC158376
0.8824	High Similarity	NPC136508
0.8824	High Similarity	NPC134858
0.8824	High Similarity	NPC253043
0.8824	High Similarity	NPC196447
0.8824	High Similarity	NPC121275
0.8824	High Similarity	NPC78222
0.8824	High Similarity	NPC24465
0.8824	High Similarity	NPC4138
0.8824	High Similarity	NPC477563
0.8824	High Similarity	NPC306843
0.8824	High Similarity	NPC212794
0.8824	High Similarity	NPC96603
0.8824	High Similarity	NPC13504
0.8824	High Similarity	NPC172403
0.8824	High Similarity	NPC284183
0.88	High Similarity	NPC186063
0.8794	High Similarity	NPC253429
0.8794	High Similarity	NPC193528
0.8784	High Similarity	NPC476568
0.8776	High Similarity	NPC92541
0.8776	High Similarity	NPC219162
0.8774	High Similarity	NPC204908
0.8774	High Similarity	NPC83198
0.8766	High Similarity	NPC35627
0.8766	High Similarity	NPC476573
0.8766	High Similarity	NPC81247
0.8758	High Similarity	NPC233650
0.8758	High Similarity	NPC1229
0.875	High Similarity	NPC205167
0.875	High Similarity	NPC249274
0.8733	High Similarity	NPC41178
0.8733	High Similarity	NPC216459
0.8733	High Similarity	NPC138487
0.8725	High Similarity	NPC233029
0.8725	High Similarity	NPC210148
0.871	High Similarity	NPC210140
0.8693	High Similarity	NPC60186
0.8684	High Similarity	NPC92191
0.8684	High Similarity	NPC59028
0.8675	High Similarity	NPC146288
0.8675	High Similarity	NPC247639
0.8675	High Similarity	NPC25084
0.8654	High Similarity	NPC66573
0.8639	High Similarity	NPC144863
0.8639	High Similarity	NPC90844
0.8639	High Similarity	NPC95075
0.8639	High Similarity	NPC253883
0.8627	High Similarity	NPC97072
0.8627	High Similarity	NPC215829
0.8618	High Similarity	NPC476572
0.8618	High Similarity	NPC475326
0.8609	High Similarity	NPC325871
0.8609	High Similarity	NPC99659
0.8609	High Similarity	NPC80129
0.8609	High Similarity	NPC187022
0.8608	High Similarity	NPC152680
0.8608	High Similarity	NPC190783
0.8608	High Similarity	NPC232386
0.8601	High Similarity	NPC170170
0.8601	High Similarity	NPC219233
0.8601	High Similarity	NPC211468
0.8599	High Similarity	NPC168753
0.8599	High Similarity	NPC118274
0.8599	High Similarity	NPC109925
0.859	High Similarity	NPC150879
0.8581	High Similarity	NPC130941
0.8553	High Similarity	NPC126519
0.8553	High Similarity	NPC31311
0.8553	High Similarity	NPC234392
0.8553	High Similarity	NPC170503
0.8553	High Similarity	NPC203784
0.8544	High Similarity	NPC239775
0.8544	High Similarity	NPC108434
0.8544	High Similarity	NPC475215
0.8542	High Similarity	NPC323123
0.8535	High Similarity	NPC470324
0.8533	High Similarity	NPC476579
0.8521	High Similarity	NPC11147
0.8511	High Similarity	NPC160692
0.8506	High Similarity	NPC477559
0.8506	High Similarity	NPC160298
0.8506	High Similarity	NPC306902
0.8506	High Similarity	NPC266753
0.8506	High Similarity	NPC232924
0.85	High Similarity	NPC241704
0.8491	Intermediate Similarity	NPC477020
0.8491	Intermediate Similarity	NPC66341
0.8491	Intermediate Similarity	NPC192135
0.8491	Intermediate Similarity	NPC2314
0.8487	Intermediate Similarity	NPC78733
0.8483	Intermediate Similarity	NPC470925
0.8481	Intermediate Similarity	NPC26240
0.8481	Intermediate Similarity	NPC69712
0.8481	Intermediate Similarity	NPC477562
0.8477	Intermediate Similarity	NPC148898
0.8462	Intermediate Similarity	NPC169743
0.8462	Intermediate Similarity	NPC7018
0.8447	Intermediate Similarity	NPC320223
0.8447	Intermediate Similarity	NPC114364
0.8442	Intermediate Similarity	NPC216816
0.8442	Intermediate Similarity	NPC477080
0.844	Intermediate Similarity	NPC118419
0.8438	Intermediate Similarity	NPC229166
0.8438	Intermediate Similarity	NPC128560
0.8438	Intermediate Similarity	NPC199465
0.8408	Intermediate Similarity	NPC124657
0.8397	Intermediate Similarity	NPC475393
0.8395	Intermediate Similarity	NPC32154

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 NPC185838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	747
0.2-0.3	1032
0.3-0.4	1610
0.4-0.5	2651
0.5-0.6	1868
0.6-0.7	770
0.7-0.8	257
0.8-0.85	26
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9562	High Similarity	NPD4664	Clinical (unspecified phase)
0.9161	High Similarity	NPD4584	Approved
0.8912	High Similarity	NPD4017	Approved
0.8819	High Similarity	NPD5241	Discontinued
0.8792	High Similarity	NPD4772	Phase 2
0.8792	High Similarity	NPD4773	Phase 2
0.8766	High Similarity	NPD4010	Discontinued
0.8758	High Similarity	NPD7201	Clinical (unspecified phase)
0.8649	High Similarity	NPD3640	Phase 3
0.8649	High Similarity	NPD3641	Approved
0.8649	High Similarity	NPD3639	Approved
0.8609	High Similarity	NPD7298	Approved
0.8553	High Similarity	NPD6818	Clinical (unspecified phase)
0.8535	High Similarity	NPD2898	Approved
0.8523	High Similarity	NPD6030	Approved
0.8523	High Similarity	NPD6031	Approved
0.8506	High Similarity	NPD7832	Clinical (unspecified phase)
0.8506	High Similarity	NPD7833	Phase 2
0.8506	High Similarity	NPD7831	Phase 2
0.85	High Similarity	NPD5718	Phase 2
0.8429	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2421	Approved
0.8322	Intermediate Similarity	NPD2420	Approved
0.8293	Intermediate Similarity	NPD8053	Approved
0.8293	Intermediate Similarity	NPD8054	Approved
0.8276	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD3845	Phase 1
0.8227	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD27	Approved
0.8187	Intermediate Similarity	NPD2489	Approved
0.8182	Intermediate Similarity	NPD2674	Phase 3
0.8176	Intermediate Similarity	NPD6071	Discontinued
0.8176	Intermediate Similarity	NPD5177	Phase 3
0.816	Intermediate Similarity	NPD6297	Approved
0.8141	Intermediate Similarity	NPD2563	Approved
0.8141	Intermediate Similarity	NPD2560	Approved
0.8137	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2969	Approved
0.8125	Intermediate Similarity	NPD2970	Approved
0.8089	Intermediate Similarity	NPD6788	Approved
0.8086	Intermediate Similarity	NPD8099	Discontinued
0.8086	Intermediate Similarity	NPD8252	Approved
0.8086	Intermediate Similarity	NPD8251	Approved
0.8082	Intermediate Similarity	NPD6895	Approved
0.8082	Intermediate Similarity	NPD6896	Approved
0.8079	Intermediate Similarity	NPD3124	Discontinued
0.8063	Intermediate Similarity	NPD3051	Approved
0.8054	Intermediate Similarity	NPD3060	Approved
0.8037	Intermediate Similarity	NPD8156	Discontinued
0.8027	Intermediate Similarity	NPD1753	Discontinued
0.8	Intermediate Similarity	NPD7802	Discontinued
0.8	Intermediate Similarity	NPD6107	Approved
0.7986	Intermediate Similarity	NPD3145	Approved
0.7986	Intermediate Similarity	NPD3144	Approved
0.7973	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6851	Approved
0.7964	Intermediate Similarity	NPD6853	Approved
0.795	Intermediate Similarity	NPD4166	Phase 2
0.7947	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5978	Approved
0.7911	Intermediate Similarity	NPD5977	Approved
0.7895	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD3109	Approved
0.7877	Intermediate Similarity	NPD3110	Approved
0.7842	Intermediate Similarity	NPD2667	Approved
0.7842	Intermediate Similarity	NPD2668	Approved
0.7829	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD4475	Approved
0.7808	Intermediate Similarity	NPD4474	Approved
0.7801	Intermediate Similarity	NPD2232	Approved
0.7801	Intermediate Similarity	NPD2230	Approved
0.7801	Intermediate Similarity	NPD2233	Approved
0.7778	Intermediate Similarity	NPD3635	Approved
0.7778	Intermediate Similarity	NPD3636	Approved
0.7778	Intermediate Similarity	NPD3637	Approved
0.777	Intermediate Similarity	NPD4093	Discontinued
0.7762	Intermediate Similarity	NPD3055	Approved
0.7762	Intermediate Similarity	NPD3053	Approved
0.7736	Intermediate Similarity	NPD2978	Approved
0.7736	Intermediate Similarity	NPD2977	Approved
0.7722	Intermediate Similarity	NPD7110	Phase 1
0.7722	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7906	Approved
0.7712	Intermediate Similarity	NPD3692	Discontinued
0.7711	Intermediate Similarity	NPD5313	Approved
0.7711	Intermediate Similarity	NPD5312	Approved
0.7707	Intermediate Similarity	NPD4005	Discontinued
0.7702	Intermediate Similarity	NPD4055	Discovery
0.7697	Intermediate Similarity	NPD4236	Phase 3
0.7697	Intermediate Similarity	NPD4237	Approved
0.7697	Intermediate Similarity	NPD4162	Approved
0.7692	Intermediate Similarity	NPD7310	Approved
0.7692	Intermediate Similarity	NPD4577	Approved
0.7692	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7312	Approved
0.7692	Intermediate Similarity	NPD4578	Approved
0.7692	Intermediate Similarity	NPD7311	Approved
0.7692	Intermediate Similarity	NPD7313	Approved
0.7677	Intermediate Similarity	NPD1424	Approved
0.7677	Intermediate Similarity	NPD4123	Phase 3
0.7671	Intermediate Similarity	NPD5155	Approved
0.7671	Intermediate Similarity	NPD5156	Approved
0.7662	Intermediate Similarity	NPD7124	Phase 2
0.7657	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6331	Phase 2
0.7647	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7309	Approved
0.764	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4481	Phase 3
0.7635	Intermediate Similarity	NPD2238	Phase 2
0.7628	Intermediate Similarity	NPD6090	Discontinued
0.7622	Intermediate Similarity	NPD1669	Approved
0.7619	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3595	Approved
0.7603	Intermediate Similarity	NPD3594	Approved
0.7603	Intermediate Similarity	NPD2606	Approved
0.7603	Intermediate Similarity	NPD2605	Approved
0.7595	Intermediate Similarity	NPD824	Approved
0.7593	Intermediate Similarity	NPD5604	Discontinued
0.7588	Intermediate Similarity	NPD7280	Phase 3
0.7588	Intermediate Similarity	NPD7281	Phase 3
0.7586	Intermediate Similarity	NPD6584	Phase 3
0.7586	Intermediate Similarity	NPD7905	Discontinued
0.758	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6687	Approved
0.7576	Intermediate Similarity	NPD6688	Approved
0.7571	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4663	Approved
0.7532	Intermediate Similarity	NPD6748	Discontinued
0.7532	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2488	Approved
0.7529	Intermediate Similarity	NPD2490	Approved
0.7517	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4103	Phase 2
0.7517	Intermediate Similarity	NPD4098	Discontinued
0.7516	Intermediate Similarity	NPD5773	Approved
0.7516	Intermediate Similarity	NPD7153	Discontinued
0.7516	Intermediate Similarity	NPD7037	Approved
0.7516	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5772	Approved
0.7514	Intermediate Similarity	NPD7291	Discontinued
0.75	Intermediate Similarity	NPD2161	Phase 2
0.75	Intermediate Similarity	NPD4659	Approved
0.7485	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4083	Discontinued
0.7468	Intermediate Similarity	NPD44	Approved
0.7468	Intermediate Similarity	NPD6364	Approved
0.7468	Intermediate Similarity	NPD2122	Discontinued
0.7464	Intermediate Similarity	NPD5283	Phase 1
0.7456	Intermediate Similarity	NPD3920	Phase 2
0.7456	Intermediate Similarity	NPD7479	Phase 2
0.7453	Intermediate Similarity	NPD5720	Discontinued
0.7453	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5311	Approved
0.7448	Intermediate Similarity	NPD5310	Approved
0.7447	Intermediate Similarity	NPD5304	Approved
0.7447	Intermediate Similarity	NPD5303	Approved
0.7438	Intermediate Similarity	NPD6875	Approved
0.7438	Intermediate Similarity	NPD4678	Approved
0.7438	Intermediate Similarity	NPD4675	Approved
0.7438	Intermediate Similarity	NPD6876	Approved
0.7429	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD823	Approved
0.7417	Intermediate Similarity	NPD817	Approved
0.7394	Intermediate Similarity	NPD5677	Discontinued
0.7389	Intermediate Similarity	NPD7598	Phase 2
0.7383	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6582	Phase 2
0.7379	Intermediate Similarity	NPD6583	Phase 3
0.7379	Intermediate Similarity	NPD1420	Approved
0.7379	Intermediate Similarity	NPD1421	Approved
0.7375	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5160	Discontinued
0.7361	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1914	Approved
0.7355	Intermediate Similarity	NPD2460	Phase 3
0.7355	Intermediate Similarity	NPD2458	Approved
0.7355	Intermediate Similarity	NPD2459	Approved
0.7343	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2874	Phase 2
0.7341	Intermediate Similarity	NPD6618	Phase 2
0.7338	Intermediate Similarity	NPD2228	Approved
0.7338	Intermediate Similarity	NPD3656	Approved
0.7338	Intermediate Similarity	NPD2229	Approved
0.7338	Intermediate Similarity	NPD2234	Approved
0.7337	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3531	Approved
0.7333	Intermediate Similarity	NPD3532	Approved
0.7333	Intermediate Similarity	NPD3530	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