NPASS Compound

Structure

CID188163 OpenBabel06191715572D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 2.5981 -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 -3.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -4.3301 -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 -0.5000 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 0.0000 -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 -2.0000 0.0000 C 0 0 1 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 0.8660 -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 -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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 10 1 1 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.19
Volume:	376.442
LogP:	2.599
LogD:	3.089
LogS:	-2.97
# Rotatable Bonds:	6
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.583
Fsp3:	0.429
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:	-4.829
MDCK Permeability:	3.8274756661849096e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	65.43547821044922%
Volume Distribution (VD):	1.642
Pgp-substrate:	22.089038848876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.958
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	11.294
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.736
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.438
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC188163

Natural Product ID:	NPC188163
*Common Name:**	(1S)-1-[(3,4-Dimethoxyphenyl)Methyl]-6,7-Dimethoxy-2-Methyl-3,4-Dihydro-1H-Isoquinoline
IUPAC Name:	(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms:
Standard InCHIKey:	KGPAYJZAMGEDIQ-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
SMILES:	COc1cc(ccc1OC)C[C@@H]1N(C)CCc2c1cc(OC)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519894
PubChem CID:	73397
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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19966	Dendrobium amplum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO260	Cyclacanthia bellae	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23007	Horsfieldia glabra	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17383	Cyperus nipponicus	Species	Cyperaceae	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
AC50	1
Potency	5

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	316.2	nM	PMID[522979]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	6309.6	nM	PMID[522979]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	12589.3	nM	PMID[522980]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[522979]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	6309.57	nM	PMID[522979]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[522979]

☑ 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 NPC188163 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	290
0.1-0.2	1607
0.2-0.3	9168
0.3-0.4	8545
0.4-0.5	6779
0.5-0.6	11809
0.6-0.7	3415
0.7-0.8	687
0.8-0.85	214
0.85-0.9	115
0.9-0.95	58
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474915
1.0	High Similarity	NPC328750
1.0	High Similarity	NPC213206
0.9924	High Similarity	NPC314682
0.9704	High Similarity	NPC476567
0.9704	High Similarity	NPC128019
0.9704	High Similarity	NPC136860
0.9565	High Similarity	NPC106295
0.9565	High Similarity	NPC16107
0.9565	High Similarity	NPC210437
0.9565	High Similarity	NPC51957
0.9565	High Similarity	NPC476144
0.9562	High Similarity	NPC185838
0.9496	High Similarity	NPC147390
0.9496	High Similarity	NPC246587
0.9496	High Similarity	NPC428
0.9496	High Similarity	NPC475959
0.9496	High Similarity	NPC476571
0.9496	High Similarity	NPC135538
0.9496	High Similarity	NPC7467
0.9496	High Similarity	NPC24233
0.9424	High Similarity	NPC321505
0.9424	High Similarity	NPC191376
0.9424	High Similarity	NPC179825
0.9286	High Similarity	NPC476151
0.9242	High Similarity	NPC160193
0.9225	High Similarity	NPC97221
0.9225	High Similarity	NPC151895
0.9225	High Similarity	NPC220858
0.9225	High Similarity	NPC88249
0.9225	High Similarity	NPC192768
0.9161	High Similarity	NPC81733
0.9161	High Similarity	NPC476568
0.9161	High Similarity	NPC326316
0.9155	High Similarity	NPC207824
0.9155	High Similarity	NPC477565
0.9155	High Similarity	NPC60538
0.9155	High Similarity	NPC103379
0.9143	High Similarity	NPC130926
0.9103	High Similarity	NPC207757
0.9103	High Similarity	NPC295691
0.9103	High Similarity	NPC39701
0.9103	High Similarity	NPC469817
0.9103	High Similarity	NPC172765
0.9103	High Similarity	NPC193949
0.9103	High Similarity	NPC189266
0.9103	High Similarity	NPC54379
0.9103	High Similarity	NPC2413
0.9103	High Similarity	NPC278799
0.9103	High Similarity	NPC216459
0.9103	High Similarity	NPC184026
0.9103	High Similarity	NPC204828
0.9103	High Similarity	NPC110416
0.9103	High Similarity	NPC249797
0.9103	High Similarity	NPC41178
0.9103	High Similarity	NPC5238
0.9103	High Similarity	NPC138487
0.9103	High Similarity	NPC127674
0.9103	High Similarity	NPC276588
0.9097	High Similarity	NPC210148
0.9097	High Similarity	NPC233029
0.9091	High Similarity	NPC172403
0.9051	High Similarity	NPC253429
0.9041	High Similarity	NPC25084
0.9041	High Similarity	NPC247639
0.9041	High Similarity	NPC146288
0.9028	High Similarity	NPC277669
0.9028	High Similarity	NPC76213
0.9021	High Similarity	NPC92541
0.9021	High Similarity	NPC219162
0.898	High Similarity	NPC476572
0.8973	High Similarity	NPC325871
0.8973	High Similarity	NPC99659
0.8973	High Similarity	NPC80129
0.8973	High Similarity	NPC187022
0.8951	High Similarity	NPC130941
0.8912	High Similarity	NPC234392
0.8912	High Similarity	NPC31311
0.8905	High Similarity	NPC11147
0.8897	High Similarity	NPC476579
0.8881	High Similarity	NPC90844
0.8881	High Similarity	NPC144863
0.8881	High Similarity	NPC95075
0.8881	High Similarity	NPC253883
0.8828	High Similarity	NPC274026
0.8792	High Similarity	NPC216816
0.8792	High Similarity	NPC111485
0.8784	High Similarity	NPC170503
0.8784	High Similarity	NPC126519
0.8784	High Similarity	NPC203784
0.8776	High Similarity	NPC477564
0.8776	High Similarity	NPC2295
0.8759	High Similarity	NPC160692
0.8742	High Similarity	NPC475393
0.8733	High Similarity	NPC266753
0.8733	High Similarity	NPC166014
0.8733	High Similarity	NPC160298
0.8733	High Similarity	NPC306902
0.8733	High Similarity	NPC27410
0.8733	High Similarity	NPC232924
0.8733	High Similarity	NPC477559
0.8723	High Similarity	NPC470925
0.8716	High Similarity	NPC244112
0.8716	High Similarity	NPC78733
0.8716	High Similarity	NPC93593
0.8707	High Similarity	NPC82285
0.8707	High Similarity	NPC133011
0.8707	High Similarity	NPC148898
0.8705	High Similarity	NPC131204
0.8705	High Similarity	NPC7018
0.8705	High Similarity	NPC301050
0.8686	High Similarity	NPC118419
0.8684	High Similarity	NPC232514
0.8684	High Similarity	NPC276944
0.8684	High Similarity	NPC238530
0.8667	High Similarity	NPC477080
0.8658	High Similarity	NPC147091
0.8627	High Similarity	NPC476432
0.8627	High Similarity	NPC256012
0.8627	High Similarity	NPC268503
0.8627	High Similarity	NPC317272
0.8627	High Similarity	NPC24264
0.8627	High Similarity	NPC240841
0.8627	High Similarity	NPC13916
0.8627	High Similarity	NPC264850
0.8627	High Similarity	NPC250846
0.8627	High Similarity	NPC42549
0.8618	High Similarity	NPC324144
0.8618	High Similarity	NPC233650
0.8581	High Similarity	NPC26601
0.8581	High Similarity	NPC37272
0.8581	High Similarity	NPC470924
0.8571	High Similarity	NPC474931
0.8571	High Similarity	NPC306555
0.8571	High Similarity	NPC158376
0.8571	High Similarity	NPC145832
0.8571	High Similarity	NPC81218
0.8571	High Similarity	NPC247389
0.8571	High Similarity	NPC117188
0.8571	High Similarity	NPC205421
0.8571	High Similarity	NPC12053
0.8562	High Similarity	NPC306843
0.8562	High Similarity	NPC16805
0.8562	High Similarity	NPC225774
0.8562	High Similarity	NPC78222
0.8562	High Similarity	NPC13504
0.8562	High Similarity	NPC96603
0.8562	High Similarity	NPC167546
0.8562	High Similarity	NPC4138
0.8562	High Similarity	NPC253043
0.8562	High Similarity	NPC284183
0.8562	High Similarity	NPC477563
0.8562	High Similarity	NPC121275
0.8562	High Similarity	NPC136508
0.8562	High Similarity	NPC196447
0.8562	High Similarity	NPC24465
0.8562	High Similarity	NPC302527
0.8562	High Similarity	NPC134858
0.8562	High Similarity	NPC212794
0.8543	High Similarity	NPC92191
0.8543	High Similarity	NPC59028
0.8543	High Similarity	NPC118804
0.8542	High Similarity	NPC294249
0.8533	High Similarity	NPC186063
0.8516	High Similarity	NPC83198
0.8516	High Similarity	NPC204908
0.8514	High Similarity	NPC85747
0.8514	High Similarity	NPC8337
0.8506	High Similarity	NPC219341
0.8487	Intermediate Similarity	NPC205167
0.8467	Intermediate Similarity	NPC76079
0.8456	Intermediate Similarity	NPC476580
0.8452	Intermediate Similarity	NPC150879
0.8452	Intermediate Similarity	NPC210140
0.8452	Intermediate Similarity	NPC298979
0.8452	Intermediate Similarity	NPC210918
0.8446	Intermediate Similarity	NPC223125
0.844	Intermediate Similarity	NPC231884
0.844	Intermediate Similarity	NPC167944
0.844	Intermediate Similarity	NPC42793
0.8431	Intermediate Similarity	NPC60186
0.8421	Intermediate Similarity	NPC106786
0.8411	Intermediate Similarity	NPC180756
0.8411	Intermediate Similarity	NPC323443
0.8408	Intermediate Similarity	NPC276890
0.8408	Intermediate Similarity	NPC227060
0.8408	Intermediate Similarity	NPC76682
0.8408	Intermediate Similarity	NPC10908
0.8408	Intermediate Similarity	NPC115284
0.8408	Intermediate Similarity	NPC317145
0.8408	Intermediate Similarity	NPC198498
0.8408	Intermediate Similarity	NPC63646
0.8408	Intermediate Similarity	NPC317439
0.8397	Intermediate Similarity	NPC241055
0.8397	Intermediate Similarity	NPC66573
0.8387	Intermediate Similarity	NPC304659
0.8387	Intermediate Similarity	NPC35627
0.8387	Intermediate Similarity	NPC81247
0.8387	Intermediate Similarity	NPC86144
0.8387	Intermediate Similarity	NPC476573

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 NPC188163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	755
0.2-0.3	1009
0.3-0.4	1630
0.4-0.5	2687
0.5-0.6	1875
0.6-0.7	740
0.7-0.8	219
0.8-0.85	29
0.85-0.9	15
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4664	Clinical (unspecified phase)
0.9565	High Similarity	NPD4584	Approved
0.9161	High Similarity	NPD4017	Approved
0.8973	High Similarity	NPD7298	Approved
0.8889	High Similarity	NPD3641	Approved
0.8889	High Similarity	NPD6030	Approved
0.8889	High Similarity	NPD6031	Approved
0.8889	High Similarity	NPD3639	Approved
0.8889	High Similarity	NPD3640	Phase 3
0.875	High Similarity	NPD5718	Phase 2
0.8676	High Similarity	NPD2669	Clinical (unspecified phase)
0.8649	High Similarity	NPD4773	Phase 2
0.8649	High Similarity	NPD4772	Phase 2
0.8618	High Similarity	NPD7201	Clinical (unspecified phase)
0.8542	High Similarity	NPD5241	Discontinued
0.8511	High Similarity	NPD6029	Clinical (unspecified phase)
0.8511	High Similarity	NPD6028	Clinical (unspecified phase)
0.8506	High Similarity	NPD4010	Discontinued
0.8467	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD6896	Approved
0.844	Intermediate Similarity	NPD6895	Approved
0.8408	Intermediate Similarity	NPD8099	Discontinued
0.8408	Intermediate Similarity	NPD8252	Approved
0.8408	Intermediate Similarity	NPD8251	Approved
0.8354	Intermediate Similarity	NPD8156	Discontinued
0.8323	Intermediate Similarity	NPD6107	Approved
0.8323	Intermediate Similarity	NPD7802	Discontinued
0.8301	Intermediate Similarity	NPD6788	Approved
0.8299	Intermediate Similarity	NPD3124	Discontinued
0.8289	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD2898	Approved
0.8163	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4166	Phase 2
0.8146	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6297	Approved
0.8129	Intermediate Similarity	NPD7833	Phase 2
0.8129	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7831	Phase 2
0.8117	Intermediate Similarity	NPD5977	Approved
0.8117	Intermediate Similarity	NPD5978	Approved
0.8113	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD3110	Approved
0.8099	Intermediate Similarity	NPD3109	Approved
0.8049	Intermediate Similarity	NPD8054	Approved
0.8049	Intermediate Similarity	NPD8053	Approved
0.8039	Intermediate Similarity	NPD7110	Phase 1
0.8039	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4474	Approved
0.8028	Intermediate Similarity	NPD4475	Approved
0.8012	Intermediate Similarity	NPD5313	Approved
0.8012	Intermediate Similarity	NPD5312	Approved
0.8	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7124	Phase 2
0.7973	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6853	Approved
0.7939	Intermediate Similarity	NPD6851	Approved
0.7937	Intermediate Similarity	NPD4481	Phase 3
0.7933	Intermediate Similarity	NPD2421	Approved
0.7933	Intermediate Similarity	NPD2420	Approved
0.7925	Intermediate Similarity	NPD6071	Discontinued
0.7925	Intermediate Similarity	NPD3051	Approved
0.7905	Intermediate Similarity	NPD5177	Phase 3
0.7895	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2560	Approved
0.7885	Intermediate Similarity	NPD2563	Approved
0.7881	Intermediate Similarity	NPD1424	Approved
0.7875	Intermediate Similarity	NPD2969	Approved
0.7875	Intermediate Similarity	NPD6688	Approved
0.7875	Intermediate Similarity	NPD2970	Approved
0.7875	Intermediate Similarity	NPD6687	Approved
0.7867	Intermediate Similarity	NPD3845	Phase 1
0.7829	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2489	Approved
0.7826	Intermediate Similarity	NPD27	Approved
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7801	Intermediate Similarity	NPD7905	Discontinued
0.7786	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4162	Approved
0.7785	Intermediate Similarity	NPD3060	Approved
0.7785	Intermediate Similarity	NPD4055	Discovery
0.7778	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2674	Phase 3
0.7748	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6875	Approved
0.7742	Intermediate Similarity	NPD6876	Approved
0.7733	Intermediate Similarity	NPD6748	Discontinued
0.7733	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4098	Discontinued
0.7703	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7291	Discontinued
0.7688	Intermediate Similarity	NPD5677	Discontinued
0.7681	Intermediate Similarity	NPD2667	Approved
0.7681	Intermediate Similarity	NPD2668	Approved
0.7677	Intermediate Similarity	NPD4005	Discontinued
0.7667	Intermediate Similarity	NPD4237	Approved
0.7667	Intermediate Similarity	NPD4236	Phase 3
0.7665	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5720	Discontinued
0.7636	Intermediate Similarity	NPD3920	Phase 2
0.7635	Intermediate Similarity	NPD1753	Discontinued
0.763	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6618	Phase 2
0.7619	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1420	Approved
0.7589	Intermediate Similarity	NPD1669	Approved
0.7589	Intermediate Similarity	NPD1421	Approved
0.7586	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5109	Approved
0.7586	Intermediate Similarity	NPD5110	Phase 2
0.7586	Intermediate Similarity	NPD3145	Approved
0.7586	Intermediate Similarity	NPD5111	Phase 2
0.7586	Intermediate Similarity	NPD3144	Approved
0.7582	Intermediate Similarity	NPD7598	Phase 2
0.7574	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7281	Phase 3
0.756	Intermediate Similarity	NPD7280	Phase 3
0.7558	Intermediate Similarity	NPD3922	Approved
0.7558	Intermediate Similarity	NPD3921	Approved
0.7558	Intermediate Similarity	NPD3924	Approved
0.7558	Intermediate Similarity	NPD3923	Approved
0.7543	Intermediate Similarity	NPD4420	Approved
0.7534	Intermediate Similarity	NPD3530	Approved
0.7534	Intermediate Similarity	NPD3531	Approved
0.7534	Intermediate Similarity	NPD3532	Approved
0.7532	Intermediate Similarity	NPD4123	Phase 3
0.7518	Intermediate Similarity	NPD2230	Approved
0.7518	Intermediate Similarity	NPD2233	Approved
0.7518	Intermediate Similarity	NPD2232	Approved
0.7516	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD2986	Phase 2
0.75	Intermediate Similarity	NPD5754	Discontinued
0.75	Intermediate Similarity	NPD2653	Approved
0.75	Intermediate Similarity	NPD8095	Phase 1
0.75	Intermediate Similarity	NPD2989	Phase 2
0.75	Intermediate Similarity	NPD2492	Phase 1
0.7485	Intermediate Similarity	NPD7906	Approved
0.7484	Intermediate Similarity	NPD2978	Approved
0.7484	Intermediate Similarity	NPD2977	Approved
0.7483	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2595	Approved
0.7482	Intermediate Similarity	NPD2594	Approved
0.7468	Intermediate Similarity	NPD6385	Approved
0.7468	Intermediate Similarity	NPD6386	Approved
0.7456	Intermediate Similarity	NPD7310	Approved
0.7456	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2968	Approved
0.7456	Intermediate Similarity	NPD7312	Approved
0.7456	Intermediate Similarity	NPD2971	Approved
0.7456	Intermediate Similarity	NPD7311	Approved
0.7456	Intermediate Similarity	NPD7313	Approved
0.7451	Intermediate Similarity	NPD3692	Discontinued
0.745	Intermediate Similarity	NPD6111	Discontinued
0.7436	Intermediate Similarity	NPD5976	Discontinued
0.7436	Intermediate Similarity	NPD4727	Phase 1
0.7434	Intermediate Similarity	NPD44	Approved
0.7434	Intermediate Similarity	NPD6364	Approved
0.7421	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3656	Approved
0.7412	Intermediate Similarity	NPD7309	Approved
0.7403	Intermediate Similarity	NPD2120	Phase 2
0.7399	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4210	Discontinued
0.7386	Intermediate Similarity	NPD7034	Discontinued
0.7381	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3636	Approved
0.7379	Intermediate Similarity	NPD3635	Approved
0.7379	Intermediate Similarity	NPD3637	Approved
0.7375	Intermediate Similarity	NPD5773	Approved
0.7375	Intermediate Similarity	NPD4585	Approved
0.7375	Intermediate Similarity	NPD5772	Approved
0.7374	Intermediate Similarity	NPD5005	Approved
0.7374	Intermediate Similarity	NPD5006	Approved
0.7372	Intermediate Similarity	NPD6090	Discontinued
0.7368	Intermediate Similarity	NPD7153	Discontinued
0.7365	Intermediate Similarity	NPD2238	Phase 2
0.7361	Intermediate Similarity	NPD3055	Approved
0.7361	Intermediate Similarity	NPD3053	Approved
0.7358	Intermediate Similarity	NPD6873	Phase 2
0.7357	Intermediate Similarity	NPD3444	Approved
0.7357	Intermediate Similarity	NPD6382	Discontinued
0.7357	Intermediate Similarity	NPD3443	Approved
0.7357	Intermediate Similarity	NPD3445	Approved
0.7357	Intermediate Similarity	NPD4093	Discontinued
0.7353	Intermediate Similarity	NPD4578	Approved
0.7353	Intermediate Similarity	NPD4577	Approved
0.7351	Intermediate Similarity	NPD2161	Phase 2
0.7349	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5604	Discontinued
0.7342	Intermediate Similarity	NPD6357	Discontinued
0.7338	Intermediate Similarity	NPD5160	Discontinued
0.7338	Intermediate Similarity	NPD3301	Approved
0.7333	Intermediate Similarity	NPD4083	Discontinued
0.7329	Intermediate Similarity	NPD5967	Approved
0.7326	Intermediate Similarity	NPD4663	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