NPASS Compound

Structure

CID114124 OpenBabel06191715472D 28 30 0 0 0 0 0 0 0 0999 V2000 0.8660 -4.5000 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 2.5981 3.5000 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 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 3.4641 -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 -2.5000 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 4.3301 0.5000 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 3.4641 -0.0000 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 0.8660 -1.5000 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 4.3301 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 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 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 -4.0000 0.0000 N 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 3.4641 3.0000 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 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.19
Volume:	399.891
LogP:	3.165
LogD:	3.164
LogS:	-3.477
# Rotatable Bonds:	8
TPSA:	58.18
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	2.545
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.883
MDCK Permeability:	2.1972495233057998e-05
Pgp-inhibitor:	0.317
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	75.3016586303711%
Volume Distribution (VD):	1.278
Pgp-substrate:	21.044008255004883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.637
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	6.728
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.871
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.345
Skin Sensitization:	0.93
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC114124

Natural Product ID:	NPC114124
*Common Name:**	Thalicpureine
IUPAC Name:	N-methyl-2-(2,3,4,6,7-pentamethoxyphenanthren-1-yl)ethanamine
Synonyms:	Thalicpureine
Standard InCHIKey:	VMIFHEUVQQHIOK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H27NO5/c1-23-10-9-15-14-8-7-13-11-17(24-2)18(25-3)12-16(13)19(14)21(27-5)22(28-6)20(15)26-4/h7-8,11-12,23H,9-10H2,1-6H3
SMILES:	CNCCc1c2ccc3cc(c(cc3c2c(c(c1OC)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464772
PubChem CID:	10430190
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003332] 6,6a-secoaporphines

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[9599253]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868142]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	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	12

Activity Type	# Activity
CELL-LINE	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	33.6	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	3.9	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	41.9	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	55.5	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	74.2	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	78.8	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	83.7	%	PMID[496839]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	82.4	%	PMID[496839]

☑ 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 NPC114124 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	357
0.1-0.2	1782
0.2-0.3	8097
0.3-0.4	10515
0.4-0.5	5280
0.5-0.6	8752
0.6-0.7	6482
0.7-0.8	1290
0.8-0.85	121
0.85-0.9	19
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8917	High Similarity	NPC204947
0.8774	High Similarity	NPC7393
0.8742	High Similarity	NPC211296
0.8671	High Similarity	NPC149337
0.8671	High Similarity	NPC471983
0.8598	High Similarity	NPC474507
0.8545	High Similarity	NPC32413
0.8545	High Similarity	NPC474506
0.8537	High Similarity	NPC23219
0.8531	High Similarity	NPC262641
0.85	High Similarity	NPC193853
0.85	High Similarity	NPC56887
0.85	High Similarity	NPC223077
0.8485	Intermediate Similarity	NPC470879
0.8485	Intermediate Similarity	NPC258695
0.8477	Intermediate Similarity	NPC145304
0.8476	Intermediate Similarity	NPC112575
0.8476	Intermediate Similarity	NPC173416
0.8476	Intermediate Similarity	NPC148709
0.8476	Intermediate Similarity	NPC476577
0.8438	Intermediate Similarity	NPC209377
0.8421	Intermediate Similarity	NPC473934
0.8408	Intermediate Similarity	NPC170503
0.8408	Intermediate Similarity	NPC203784
0.8408	Intermediate Similarity	NPC126519
0.8392	Intermediate Similarity	NPC471986
0.8344	Intermediate Similarity	NPC244112
0.8344	Intermediate Similarity	NPC123323
0.8322	Intermediate Similarity	NPC266006
0.8313	Intermediate Similarity	NPC60186
0.8267	Intermediate Similarity	NPC275061
0.8267	Intermediate Similarity	NPC243996
0.8267	Intermediate Similarity	NPC132804
0.8267	Intermediate Similarity	NPC220344
0.8263	Intermediate Similarity	NPC475479
0.8263	Intermediate Similarity	NPC243454
0.8242	Intermediate Similarity	NPC477020
0.8242	Intermediate Similarity	NPC192135
0.8242	Intermediate Similarity	NPC66341
0.8239	Intermediate Similarity	NPC476572
0.8235	Intermediate Similarity	NPC57036
0.8232	Intermediate Similarity	NPC477562
0.8232	Intermediate Similarity	NPC6152
0.8232	Intermediate Similarity	NPC26240
0.8232	Intermediate Similarity	NPC69712
0.8228	Intermediate Similarity	NPC325871
0.8228	Intermediate Similarity	NPC99659
0.8214	Intermediate Similarity	NPC239584
0.8212	Intermediate Similarity	NPC308768
0.8212	Intermediate Similarity	NPC12668
0.8205	Intermediate Similarity	NPC265473
0.8205	Intermediate Similarity	NPC276665
0.82	Intermediate Similarity	NPC230919
0.82	Intermediate Similarity	NPC56329
0.82	Intermediate Similarity	NPC22902
0.82	Intermediate Similarity	NPC242715
0.82	Intermediate Similarity	NPC266453
0.82	Intermediate Similarity	NPC200935
0.8187	Intermediate Similarity	NPC186546
0.8187	Intermediate Similarity	NPC476576
0.8182	Intermediate Similarity	NPC105513
0.8182	Intermediate Similarity	NPC239775
0.8182	Intermediate Similarity	NPC19520
0.8182	Intermediate Similarity	NPC149090
0.816	Intermediate Similarity	NPC195392
0.8146	Intermediate Similarity	NPC243759
0.8146	Intermediate Similarity	NPC105847
0.8146	Intermediate Similarity	NPC218131
0.8137	Intermediate Similarity	NPC119649
0.8137	Intermediate Similarity	NPC230956
0.8137	Intermediate Similarity	NPC205255
0.8137	Intermediate Similarity	NPC235143
0.8137	Intermediate Similarity	NPC271388
0.8133	Intermediate Similarity	NPC30632
0.8125	Intermediate Similarity	NPC79328
0.8121	Intermediate Similarity	NPC168753
0.8121	Intermediate Similarity	NPC118274
0.8105	Intermediate Similarity	NPC175838
0.8105	Intermediate Similarity	NPC183709
0.8103	Intermediate Similarity	NPC256124
0.8086	Intermediate Similarity	NPC79402
0.8086	Intermediate Similarity	NPC80759
0.8084	Intermediate Similarity	NPC329969
0.8079	Intermediate Similarity	NPC210086
0.8079	Intermediate Similarity	NPC151656
0.8075	Intermediate Similarity	NPC221864
0.8067	Intermediate Similarity	NPC200557
0.8067	Intermediate Similarity	NPC69029
0.8067	Intermediate Similarity	NPC108198
0.8067	Intermediate Similarity	NPC158142
0.8067	Intermediate Similarity	NPC294884
0.8067	Intermediate Similarity	NPC241241
0.8067	Intermediate Similarity	NPC10314
0.8063	Intermediate Similarity	NPC190931
0.805	Intermediate Similarity	NPC475557
0.8049	Intermediate Similarity	NPC35627
0.8049	Intermediate Similarity	NPC476573
0.8049	Intermediate Similarity	NPC86144
0.8049	Intermediate Similarity	NPC304659
0.8049	Intermediate Similarity	NPC68328
0.8049	Intermediate Similarity	NPC81247
0.8046	Intermediate Similarity	NPC117717
0.8042	Intermediate Similarity	NPC298486
0.8038	Intermediate Similarity	NPC326316
0.8038	Intermediate Similarity	NPC81733
0.8025	Intermediate Similarity	NPC92541
0.8025	Intermediate Similarity	NPC219162
0.8014	Intermediate Similarity	NPC291847
0.8013	Intermediate Similarity	NPC202846
0.8013	Intermediate Similarity	NPC205442
0.8013	Intermediate Similarity	NPC143139
0.8012	Intermediate Similarity	NPC302275
0.8	Intermediate Similarity	NPC125649
0.7974	Intermediate Similarity	NPC34431
0.7974	Intermediate Similarity	NPC165026
0.7974	Intermediate Similarity	NPC295719
0.7974	Intermediate Similarity	NPC73505
0.7974	Intermediate Similarity	NPC323204
0.7964	Intermediate Similarity	NPC317439
0.7964	Intermediate Similarity	NPC198498
0.7964	Intermediate Similarity	NPC227060
0.7964	Intermediate Similarity	NPC76682
0.7964	Intermediate Similarity	NPC276890
0.7964	Intermediate Similarity	NPC115284
0.7964	Intermediate Similarity	NPC317145
0.7964	Intermediate Similarity	NPC10908
0.7964	Intermediate Similarity	NPC63646
0.7962	Intermediate Similarity	NPC130941
0.795	Intermediate Similarity	NPC29647
0.7947	Intermediate Similarity	NPC111655
0.7947	Intermediate Similarity	NPC313081
0.7941	Intermediate Similarity	NPC267408
0.7939	Intermediate Similarity	NPC13916
0.7939	Intermediate Similarity	NPC476432
0.7939	Intermediate Similarity	NPC264850
0.7939	Intermediate Similarity	NPC24264
0.7937	Intermediate Similarity	NPC2295
0.7937	Intermediate Similarity	NPC477564
0.7931	Intermediate Similarity	NPC11296
0.7931	Intermediate Similarity	NPC82457
0.7931	Intermediate Similarity	NPC281581
0.7931	Intermediate Similarity	NPC175890
0.7931	Intermediate Similarity	NPC48490
0.7931	Intermediate Similarity	NPC274661
0.7927	Intermediate Similarity	NPC189470
0.7917	Intermediate Similarity	NPC12424
0.7917	Intermediate Similarity	NPC129518
0.7917	Intermediate Similarity	NPC41376
0.7917	Intermediate Similarity	NPC251580
0.7917	Intermediate Similarity	NPC474051
0.7911	Intermediate Similarity	NPC60538
0.7911	Intermediate Similarity	NPC207824
0.7908	Intermediate Similarity	NPC79622
0.7908	Intermediate Similarity	NPC212942
0.7908	Intermediate Similarity	NPC29868
0.7907	Intermediate Similarity	NPC135772
0.7901	Intermediate Similarity	NPC195766
0.7901	Intermediate Similarity	NPC206736
0.7898	Intermediate Similarity	NPC90844
0.7898	Intermediate Similarity	NPC253883
0.7898	Intermediate Similarity	NPC144863
0.7898	Intermediate Similarity	NPC95075
0.7895	Intermediate Similarity	NPC477561
0.7895	Intermediate Similarity	NPC257269
0.7895	Intermediate Similarity	NPC476574
0.7895	Intermediate Similarity	NPC155442
0.7895	Intermediate Similarity	NPC312918
0.7892	Intermediate Similarity	NPC306555
0.7892	Intermediate Similarity	NPC12053
0.7892	Intermediate Similarity	NPC145832
0.7892	Intermediate Similarity	NPC474931
0.7892	Intermediate Similarity	NPC81218
0.7892	Intermediate Similarity	NPC247389
0.7892	Intermediate Similarity	NPC158376
0.7892	Intermediate Similarity	NPC117188
0.7892	Intermediate Similarity	NPC150879
0.7892	Intermediate Similarity	NPC205421
0.7886	Intermediate Similarity	NPC60295
0.7886	Intermediate Similarity	NPC191132
0.7881	Intermediate Similarity	NPC160697
0.7879	Intermediate Similarity	NPC24465
0.7879	Intermediate Similarity	NPC477563
0.7879	Intermediate Similarity	NPC96603
0.7879	Intermediate Similarity	NPC16805
0.7879	Intermediate Similarity	NPC212794
0.7879	Intermediate Similarity	NPC302527
0.7879	Intermediate Similarity	NPC13504
0.7879	Intermediate Similarity	NPC225774
0.7879	Intermediate Similarity	NPC167546
0.7879	Intermediate Similarity	NPC78222
0.7879	Intermediate Similarity	NPC196447
0.7879	Intermediate Similarity	NPC306843
0.7879	Intermediate Similarity	NPC253043
0.7879	Intermediate Similarity	NPC136508
0.787	Intermediate Similarity	NPC477558
0.7867	Intermediate Similarity	NPC228843
0.7867	Intermediate Similarity	NPC160692
0.7861	Intermediate Similarity	NPC16357
0.7861	Intermediate Similarity	NPC302245
0.7861	Intermediate Similarity	NPC95426

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 NPC114124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	868
0.2-0.3	1134
0.3-0.4	2509
0.4-0.5	2311
0.5-0.6	1306
0.6-0.7	669
0.7-0.8	135
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8129	Intermediate Similarity	NPD1424	Approved
0.8117	Intermediate Similarity	NPD7124	Phase 2
0.8075	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4585	Approved
0.8038	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD8099	Discontinued
0.7964	Intermediate Similarity	NPD8252	Approved
0.7964	Intermediate Similarity	NPD8251	Approved
0.7963	Intermediate Similarity	NPD6788	Approved
0.7922	Intermediate Similarity	NPD3060	Approved
0.7917	Intermediate Similarity	NPD8156	Discontinued
0.7911	Intermediate Similarity	NPD6031	Approved
0.7911	Intermediate Similarity	NPD6030	Approved
0.7857	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4055	Discovery
0.7785	Intermediate Similarity	NPD4584	Approved
0.7736	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4005	Discontinued
0.7692	Intermediate Similarity	NPD4162	Approved
0.7688	Intermediate Similarity	NPD5976	Discontinued
0.7669	Intermediate Similarity	NPD7298	Approved
0.7662	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8053	Approved
0.7644	Intermediate Similarity	NPD8054	Approved
0.7616	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5718	Phase 2
0.76	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6895	Approved
0.7597	Intermediate Similarity	NPD6896	Approved
0.7597	Intermediate Similarity	NPD6111	Discontinued
0.7545	Intermediate Similarity	NPD5709	Phase 3
0.7532	Intermediate Similarity	NPD2653	Approved
0.7515	Intermediate Similarity	NPD3051	Approved
0.75	Intermediate Similarity	NPD4666	Phase 3
0.7484	Intermediate Similarity	NPD5241	Discontinued
0.7455	Intermediate Similarity	NPD3383	Approved
0.7455	Intermediate Similarity	NPD3384	Approved
0.7455	Intermediate Similarity	NPD3382	Approved
0.7452	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4481	Phase 3
0.7414	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3489	Phase 3
0.7383	Intermediate Similarity	NPD1669	Approved
0.7375	Intermediate Similarity	NPD2677	Approved
0.7368	Intermediate Similarity	NPD2970	Approved
0.7368	Intermediate Similarity	NPD2969	Approved
0.7365	Intermediate Similarity	NPD2563	Approved
0.7365	Intermediate Similarity	NPD2560	Approved
0.7358	Intermediate Similarity	NPD5177	Phase 3
0.7349	Intermediate Similarity	NPD5720	Discontinued
0.7329	Intermediate Similarity	NPD3845	Phase 1
0.7329	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD3686	Approved
0.7317	Intermediate Similarity	NPD3687	Approved
0.7312	Intermediate Similarity	NPD7466	Approved
0.7312	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2977	Approved
0.7305	Intermediate Similarity	NPD2978	Approved
0.7303	Intermediate Similarity	NPD3018	Phase 2
0.7301	Intermediate Similarity	NPD1351	Approved
0.7301	Intermediate Similarity	NPD1350	Approved
0.7301	Intermediate Similarity	NPD1349	Approved
0.7296	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2238	Phase 2
0.7289	Intermediate Similarity	NPD5090	Approved
0.7289	Intermediate Similarity	NPD5089	Approved
0.7289	Intermediate Similarity	NPD6072	Discontinued
0.7279	Intermediate Similarity	NPD3049	Approved
0.7278	Intermediate Similarity	NPD7833	Phase 2
0.7278	Intermediate Similarity	NPD7831	Phase 2
0.7278	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7039	Approved
0.7273	Intermediate Similarity	NPD7038	Approved
0.7273	Intermediate Similarity	NPD4017	Approved
0.7256	Intermediate Similarity	NPD4727	Phase 1
0.7247	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7447	Phase 1
0.7232	Intermediate Similarity	NPD7549	Discontinued
0.7229	Intermediate Similarity	NPD4678	Approved
0.7229	Intermediate Similarity	NPD4675	Approved
0.7226	Intermediate Similarity	NPD3530	Approved
0.7226	Intermediate Similarity	NPD4475	Approved
0.7226	Intermediate Similarity	NPD3532	Approved
0.7226	Intermediate Similarity	NPD3531	Approved
0.7226	Intermediate Similarity	NPD4474	Approved
0.7225	Intermediate Similarity	NPD27	Approved
0.7225	Intermediate Similarity	NPD2489	Approved
0.7222	Intermediate Similarity	NPD7906	Approved
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7215	Intermediate Similarity	NPD2156	Approved
0.7215	Intermediate Similarity	NPD2154	Approved
0.7215	Intermediate Similarity	NPD2155	Approved
0.7209	Intermediate Similarity	NPD6071	Discontinued
0.7209	Intermediate Similarity	NPD6232	Discontinued
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7205	Intermediate Similarity	NPD6331	Phase 2
0.7202	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6042	Phase 2
0.72	Intermediate Similarity	NPD42	Phase 2
0.72	Intermediate Similarity	NPD2981	Phase 2
0.7197	Intermediate Similarity	NPD2568	Approved
0.7197	Intermediate Similarity	NPD4097	Suspended
0.7197	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5677	Discontinued
0.7191	Intermediate Similarity	NPD4577	Approved
0.7191	Intermediate Similarity	NPD4578	Approved
0.7179	Intermediate Similarity	NPD3110	Approved
0.7179	Intermediate Similarity	NPD3109	Approved
0.7178	Intermediate Similarity	NPD7598	Phase 2
0.7178	Intermediate Similarity	NPD7213	Phase 3
0.7178	Intermediate Similarity	NPD7212	Phase 2
0.7172	Intermediate Similarity	NPD593	Approved
0.7172	Intermediate Similarity	NPD595	Approved
0.717	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4663	Approved
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2200	Suspended
0.7152	Intermediate Similarity	NPD2982	Phase 2
0.7152	Intermediate Similarity	NPD2983	Phase 2
0.7151	Intermediate Similarity	NPD8095	Phase 1
0.7151	Intermediate Similarity	NPD7802	Discontinued
0.7143	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7020	Approved
0.7134	Intermediate Similarity	NPD7019	Approved
0.7115	Intermediate Similarity	NPD6405	Approved
0.7115	Intermediate Similarity	NPD6407	Approved
0.7114	Intermediate Similarity	NPD2554	Approved
0.7114	Intermediate Similarity	NPD2556	Approved
0.7107	Intermediate Similarity	NPD4108	Discontinued
0.7095	Intermediate Similarity	NPD7313	Approved
0.7095	Intermediate Similarity	NPD7310	Approved
0.7095	Intermediate Similarity	NPD7312	Approved
0.7095	Intermediate Similarity	NPD2971	Approved
0.7095	Intermediate Similarity	NPD2968	Approved
0.7095	Intermediate Similarity	NPD7311	Approved
0.7086	Intermediate Similarity	NPD7473	Discontinued
0.7083	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7110	Phase 1
0.7073	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3059	Approved
0.707	Intermediate Similarity	NPD3061	Approved
0.707	Intermediate Similarity	NPD3062	Approved
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7056	Intermediate Similarity	NPD7309	Approved
0.7052	Intermediate Similarity	NPD6107	Approved
0.7048	Intermediate Similarity	NPD3641	Approved
0.7048	Intermediate Similarity	NPD3640	Phase 3
0.7048	Intermediate Similarity	NPD3639	Approved
0.7037	Intermediate Similarity	NPD4236	Phase 3
0.7037	Intermediate Similarity	NPD4237	Approved
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7032	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3158	Phase 1
0.703	Intermediate Similarity	NPD3157	Approved
0.7024	Intermediate Similarity	NPD6876	Approved
0.7024	Intermediate Similarity	NPD6875	Approved
0.7022	Intermediate Similarity	NPD6297	Approved
0.7019	Intermediate Similarity	NPD1375	Discontinued
0.7013	Intermediate Similarity	NPD7905	Discontinued
0.7012	Intermediate Similarity	NPD3122	Phase 3
0.7006	Intermediate Similarity	NPD4210	Discontinued
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD2667	Approved
0.6994	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6746	Phase 2
0.6993	Remote Similarity	NPD5310	Approved
0.6993	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2922	Phase 1
0.6993	Remote Similarity	NPD5311	Approved
0.6981	Remote Similarity	NPD5314	Approved
0.6975	Remote Similarity	NPD7153	Discontinued
0.6974	Remote Similarity	NPD2233	Approved
0.6974	Remote Similarity	NPD2232	Approved
0.6974	Remote Similarity	NPD2230	Approved
0.6971	Remote Similarity	NPD5242	Approved
0.697	Remote Similarity	NPD2420	Approved
0.697	Remote Similarity	NPD1774	Approved
0.697	Remote Similarity	NPD5297	Approved
0.697	Remote Similarity	NPD2421	Approved
0.6968	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3597	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