NPASS Compound

Structure

CID7467 OpenBabel06191715332D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 -2.5981 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 1.7321 -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 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 -0.8660 -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 1 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 -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 -1.7321 0.0000 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 2.5981 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 0.0000 1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 7 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 1 1 6 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.19
Volume:	385.181
LogP:	3.47
LogD:	3.305
LogS:	-2.905
# Rotatable Bonds:	4
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.816
Synthetic Accessibility Score:	3.243
Fsp3:	0.455
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:	-5.165
MDCK Permeability:	2.336283250770066e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	80.43504333496094%
Volume Distribution (VD):	1.51
Pgp-substrate:	8.325843811035156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.458
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	10.588
Half-life (T1/2):	0.507

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.125
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC7467

Natural Product ID:	NPC7467
*Common Name:**	Corydaline
IUPAC Name:	(13S,13aR)-2,3,9,10-tetramethoxy-13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
Synonyms:	(+)-Corydaline
Standard InCHIKey:	VRSRXLJTYQVOHC-YEJXKQKISA-N
Standard InCHI:	InChI=1S/C22H27NO4/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23/h6-7,10-11,13,21H,8-9,12H2,1-5H3/t13-,21+/m0/s1
SMILES:	C[C@H]1c2ccc(c(c2CN2CCc3cc(c(cc3[C@@H]12)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2165401
PubChem CID:	101301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785434]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17311	Penicillium vulpinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29441	Eremophila oppositifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29490	Taxillus yadoriki	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29086	Dovyalis hebecarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29246	Ixeris repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29347	Hydnum aurantiacum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29206	Lycopodium chinense	Species	Lycopodiaceae	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	12
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	10
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	13.9	%	PMID[479495]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[479498]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-0.53	%	PMID[479495]
NPT27	Others	Unspecified		log Pe	=	-4.93	n.a.	PMID[479496]
NPT2	Others	Unspecified		Inhibition	=	12.7	%	PMID[479497]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	19952.62	nM	PMID[479498]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	50118.72	nM	PMID[479498]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	15848.93	nM	PMID[479498]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	50118.72	nM	PMID[479498]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	25118.86	nM	PMID[479498]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	39810.72	nM	PMID[479498]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	25118.86	nM	PMID[479498]
NPT25484	SINGLE PROTEIN	Sterol 14-alpha demethylase	Trypanosoma cruzi (strain CL Brener)	IC50	=	79432.82	nM	PMID[479498]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	19952.62	nM	PMID[479498]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2511.89	nM	PMID[479498]

☑ 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 NPC7467 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	323
0.1-0.2	1658
0.2-0.3	8917
0.3-0.4	8923
0.4-0.5	6530
0.5-0.6	11964
0.6-0.7	3428
0.7-0.8	520
0.8-0.85	255
0.85-0.9	124
0.9-0.95	46
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC16107
0.9928	High Similarity	NPC51957
0.9928	High Similarity	NPC210437
0.9928	High Similarity	NPC106295
0.9928	High Similarity	NPC476144
0.964	High Similarity	NPC128019
0.964	High Similarity	NPC136860
0.964	High Similarity	NPC476567
0.9521	High Similarity	NPC146288
0.9496	High Similarity	NPC474915
0.9496	High Similarity	NPC213206
0.9496	High Similarity	NPC328750
0.9496	High Similarity	NPC188163
0.9452	High Similarity	NPC469817
0.9452	High Similarity	NPC2413
0.9452	High Similarity	NPC278799
0.9452	High Similarity	NPC39701
0.9452	High Similarity	NPC127674
0.9452	High Similarity	NPC189266
0.9452	High Similarity	NPC5238
0.9452	High Similarity	NPC193949
0.9452	High Similarity	NPC184026
0.9452	High Similarity	NPC41178
0.9452	High Similarity	NPC276588
0.9452	High Similarity	NPC249797
0.9452	High Similarity	NPC207757
0.9452	High Similarity	NPC54379
0.9452	High Similarity	NPC138487
0.9452	High Similarity	NPC204828
0.9452	High Similarity	NPC216459
0.9452	High Similarity	NPC295691
0.9452	High Similarity	NPC110416
0.9452	High Similarity	NPC172765
0.9424	High Similarity	NPC314682
0.9257	High Similarity	NPC234392
0.9257	High Similarity	NPC31311
0.9236	High Similarity	NPC476151
0.9178	High Similarity	NPC97221
0.9178	High Similarity	NPC151895
0.9178	High Similarity	NPC220858
0.9178	High Similarity	NPC192768
0.9178	High Similarity	NPC88249
0.9116	High Similarity	NPC326316
0.9116	High Similarity	NPC81733
0.911	High Similarity	NPC477565
0.911	High Similarity	NPC103379
0.9097	High Similarity	NPC185838
0.906	High Similarity	NPC187022
0.906	High Similarity	NPC80129
0.9054	High Similarity	NPC233029
0.9054	High Similarity	NPC210148
0.9041	High Similarity	NPC246587
0.9041	High Similarity	NPC428
0.9041	High Similarity	NPC476571
0.9041	High Similarity	NPC24233
0.9041	High Similarity	NPC135538
0.9041	High Similarity	NPC475959
0.9041	High Similarity	NPC147390
0.902	High Similarity	NPC232514
0.902	High Similarity	NPC238530
0.902	High Similarity	NPC276944
0.9	High Similarity	NPC25084
0.9	High Similarity	NPC247639
0.898	High Similarity	NPC92541
0.8973	High Similarity	NPC321505
0.8973	High Similarity	NPC179825
0.8973	High Similarity	NPC191376
0.8961	High Similarity	NPC13916
0.8961	High Similarity	NPC264850
0.894	High Similarity	NPC476572
0.8933	High Similarity	NPC325871
0.8933	High Similarity	NPC99659
0.8896	High Similarity	NPC24465
0.8882	High Similarity	NPC216816
0.8859	High Similarity	NPC476579
0.8859	High Similarity	NPC476568
0.8844	High Similarity	NPC144863
0.8836	High Similarity	NPC130926
0.8808	High Similarity	NPC93593
0.8777	High Similarity	NPC160193
0.8758	High Similarity	NPC111485
0.875	High Similarity	NPC126519
0.875	High Similarity	NPC170503
0.875	High Similarity	NPC203784
0.8742	High Similarity	NPC477564
0.8742	High Similarity	NPC2295
0.8734	High Similarity	NPC198498
0.8734	High Similarity	NPC115284
0.8734	High Similarity	NPC317439
0.8734	High Similarity	NPC76682
0.8734	High Similarity	NPC227060
0.8734	High Similarity	NPC317145
0.8734	High Similarity	NPC63646
0.8734	High Similarity	NPC10908
0.8734	High Similarity	NPC276890
0.8725	High Similarity	NPC219162
0.8725	High Similarity	NPC207824
0.8725	High Similarity	NPC60538
0.871	High Similarity	NPC475393
0.8701	High Similarity	NPC27410
0.8701	High Similarity	NPC232924
0.8701	High Similarity	NPC477559
0.8701	High Similarity	NPC266753
0.8701	High Similarity	NPC166014
0.8701	High Similarity	NPC160298
0.8701	High Similarity	NPC306902
0.8684	High Similarity	NPC244112
0.8679	High Similarity	NPC2314
0.8679	High Similarity	NPC12424
0.8679	High Similarity	NPC129518
0.8679	High Similarity	NPC41376
0.8679	High Similarity	NPC251580
0.8658	High Similarity	NPC130941
0.8654	High Similarity	NPC284183
0.8654	High Similarity	NPC4138
0.8654	High Similarity	NPC121275
0.8636	High Similarity	NPC477080
0.8633	High Similarity	NPC172403
0.8611	High Similarity	NPC253429
0.8609	High Similarity	NPC277669
0.8609	High Similarity	NPC76213
0.8599	High Similarity	NPC268503
0.8599	High Similarity	NPC256012
0.8599	High Similarity	NPC317272
0.8599	High Similarity	NPC24264
0.8599	High Similarity	NPC240841
0.8599	High Similarity	NPC42549
0.8599	High Similarity	NPC476432
0.8599	High Similarity	NPC250846
0.8591	High Similarity	NPC253883
0.8591	High Similarity	NPC95075
0.8591	High Similarity	NPC90844
0.859	High Similarity	NPC324144
0.8571	High Similarity	NPC241704
0.8571	High Similarity	NPC293093
0.8571	High Similarity	NPC222524
0.8553	High Similarity	NPC37272
0.8553	High Similarity	NPC470924
0.8544	High Similarity	NPC81218
0.8544	High Similarity	NPC145832
0.8544	High Similarity	NPC247389
0.8544	High Similarity	NPC117188
0.8544	High Similarity	NPC205421
0.8544	High Similarity	NPC158376
0.8544	High Similarity	NPC474931
0.8544	High Similarity	NPC12053
0.8544	High Similarity	NPC306555
0.8543	High Similarity	NPC274026
0.8535	High Similarity	NPC253043
0.8535	High Similarity	NPC136508
0.8535	High Similarity	NPC477563
0.8535	High Similarity	NPC196447
0.8535	High Similarity	NPC302527
0.8535	High Similarity	NPC13504
0.8535	High Similarity	NPC225774
0.8535	High Similarity	NPC78222
0.8535	High Similarity	NPC212794
0.8535	High Similarity	NPC306843
0.8535	High Similarity	NPC167546
0.8535	High Similarity	NPC16805
0.8535	High Similarity	NPC96603
0.8526	High Similarity	NPC60186
0.8491	Intermediate Similarity	NPC83198
0.8491	Intermediate Similarity	NPC66573
0.8491	Intermediate Similarity	NPC204908
0.8481	Intermediate Similarity	NPC219341
0.8472	Intermediate Similarity	NPC11147
0.8466	Intermediate Similarity	NPC475479
0.8466	Intermediate Similarity	NPC243454
0.8466	Intermediate Similarity	NPC32154
0.8442	Intermediate Similarity	NPC78733
0.8438	Intermediate Similarity	NPC109925
0.8435	Intermediate Similarity	NPC470925
0.8431	Intermediate Similarity	NPC148898
0.8431	Intermediate Similarity	NPC133011
0.8431	Intermediate Similarity	NPC82285
0.8428	Intermediate Similarity	NPC210918
0.8428	Intermediate Similarity	NPC298979
0.8415	Intermediate Similarity	NPC239584
0.8405	Intermediate Similarity	NPC148693
0.8405	Intermediate Similarity	NPC118633
0.8405	Intermediate Similarity	NPC294790
0.8397	Intermediate Similarity	NPC118804
0.8397	Intermediate Similarity	NPC106786
0.8387	Intermediate Similarity	NPC180756
0.8387	Intermediate Similarity	NPC147091
0.8387	Intermediate Similarity	NPC323443
0.8375	Intermediate Similarity	NPC241055
0.8365	Intermediate Similarity	NPC476573
0.8365	Intermediate Similarity	NPC35627
0.8365	Intermediate Similarity	NPC304659
0.8365	Intermediate Similarity	NPC81247
0.8365	Intermediate Similarity	NPC86144
0.8364	Intermediate Similarity	NPC73492
0.8364	Intermediate Similarity	NPC222661
0.8364	Intermediate Similarity	NPC182052
0.8364	Intermediate Similarity	NPC90998
0.8364	Intermediate Similarity	NPC42663
0.8364	Intermediate Similarity	NPC311973
0.8364	Intermediate Similarity	NPC290582

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 NPC7467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	752
0.2-0.3	1040
0.3-0.4	1724
0.4-0.5	2683
0.5-0.6	1818
0.6-0.7	688
0.7-0.8	205
0.8-0.85	20
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9928	High Similarity	NPD4584	Approved
0.9496	High Similarity	NPD4664	Clinical (unspecified phase)
0.906	High Similarity	NPD7298	Approved
0.8851	High Similarity	NPD3639	Approved
0.8851	High Similarity	NPD3641	Approved
0.8851	High Similarity	NPD3640	Phase 3
0.8742	High Similarity	NPD4772	Phase 2
0.8742	High Similarity	NPD4773	Phase 2
0.8741	High Similarity	NPD6028	Clinical (unspecified phase)
0.8741	High Similarity	NPD6029	Clinical (unspecified phase)
0.8734	High Similarity	NPD8251	Approved
0.8734	High Similarity	NPD8099	Discontinued
0.8734	High Similarity	NPD8252	Approved
0.8733	High Similarity	NPD4017	Approved
0.8679	High Similarity	NPD8156	Discontinued
0.8477	Intermediate Similarity	NPD6031	Approved
0.8477	Intermediate Similarity	NPD6030	Approved
0.8418	Intermediate Similarity	NPD6107	Approved
0.84	Intermediate Similarity	NPD3124	Discontinued
0.8397	Intermediate Similarity	NPD6788	Approved
0.8364	Intermediate Similarity	NPD8054	Approved
0.8364	Intermediate Similarity	NPD8053	Approved
0.8354	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD5718	Phase 2
0.8252	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6896	Approved
0.8163	Intermediate Similarity	NPD6895	Approved
0.8146	Intermediate Similarity	NPD5241	Discontinued
0.8146	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD4010	Discontinued
0.8137	Intermediate Similarity	NPD4166	Phase 2
0.811	Intermediate Similarity	NPD5312	Approved
0.811	Intermediate Similarity	NPD5313	Approved
0.8105	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7802	Discontinued
0.8056	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7598	Phase 2
0.8038	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4481	Phase 3
0.8037	Intermediate Similarity	NPD2898	Approved
0.8025	Intermediate Similarity	NPD3051	Approved
0.8014	Intermediate Similarity	NPD4475	Approved
0.8014	Intermediate Similarity	NPD4474	Approved
0.8	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7831	Phase 2
0.8	Intermediate Similarity	NPD7833	Phase 2
0.7988	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2970	Approved
0.7975	Intermediate Similarity	NPD2969	Approved
0.7959	Intermediate Similarity	NPD3109	Approved
0.7959	Intermediate Similarity	NPD3110	Approved
0.7947	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD27	Approved
0.7927	Intermediate Similarity	NPD2489	Approved
0.7922	Intermediate Similarity	NPD2421	Approved
0.7922	Intermediate Similarity	NPD2420	Approved
0.7898	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5177	Phase 3
0.7875	Intermediate Similarity	NPD5978	Approved
0.7875	Intermediate Similarity	NPD5977	Approved
0.7871	Intermediate Similarity	NPD1424	Approved
0.7857	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6748	Discontinued
0.7821	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6071	Discontinued
0.7799	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7110	Phase 1
0.7798	Intermediate Similarity	NPD6297	Approved
0.7797	Intermediate Similarity	NPD8095	Phase 1
0.7792	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2560	Approved
0.7764	Intermediate Similarity	NPD2563	Approved
0.7742	Intermediate Similarity	NPD7124	Phase 2
0.7727	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6618	Phase 2
0.7669	Intermediate Similarity	NPD4055	Discovery
0.7655	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6687	Approved
0.7651	Intermediate Similarity	NPD6688	Approved
0.7628	Intermediate Similarity	NPD3845	Phase 1
0.7628	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6853	Approved
0.7616	Intermediate Similarity	NPD6851	Approved
0.7613	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4098	Discontinued
0.7586	Intermediate Similarity	NPD7291	Discontinued
0.7558	Intermediate Similarity	NPD7313	Approved
0.7558	Intermediate Similarity	NPD7312	Approved
0.7558	Intermediate Similarity	NPD7311	Approved
0.7558	Intermediate Similarity	NPD7310	Approved
0.7558	Intermediate Similarity	NPD2971	Approved
0.7558	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2968	Approved
0.7554	Intermediate Similarity	NPD5283	Phase 1
0.7552	Intermediate Similarity	NPD2668	Approved
0.7552	Intermediate Similarity	NPD2667	Approved
0.7548	Intermediate Similarity	NPD4162	Approved
0.7547	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2233	Approved
0.7517	Intermediate Similarity	NPD2230	Approved
0.7517	Intermediate Similarity	NPD2232	Approved
0.7516	Intermediate Similarity	NPD6876	Approved
0.7516	Intermediate Similarity	NPD6875	Approved
0.7514	Intermediate Similarity	NPD7309	Approved
0.75	Intermediate Similarity	NPD5754	Discontinued
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7906	Approved
0.7484	Intermediate Similarity	NPD6090	Discontinued
0.7467	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4578	Approved
0.7457	Intermediate Similarity	NPD7280	Phase 3
0.7457	Intermediate Similarity	NPD4577	Approved
0.7457	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7281	Phase 3
0.7444	Intermediate Similarity	NPD4420	Approved
0.7436	Intermediate Similarity	NPD3060	Approved
0.7436	Intermediate Similarity	NPD4237	Approved
0.7436	Intermediate Similarity	NPD4236	Phase 3
0.7432	Intermediate Similarity	NPD7905	Discontinued
0.7429	Intermediate Similarity	NPD4663	Approved
0.7417	Intermediate Similarity	NPD2674	Phase 3
0.7417	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1753	Discontinued
0.7399	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5005	Approved
0.7377	Intermediate Similarity	NPD5006	Approved
0.7371	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2238	Phase 2
0.7365	Intermediate Similarity	NPD5677	Discontinued
0.7351	Intermediate Similarity	NPD5110	Phase 2
0.7351	Intermediate Similarity	NPD3145	Approved
0.7351	Intermediate Similarity	NPD3144	Approved
0.7351	Intermediate Similarity	NPD5111	Phase 2
0.7351	Intermediate Similarity	NPD5109	Approved
0.7346	Intermediate Similarity	NPD4005	Discontinued
0.7342	Intermediate Similarity	NPD3692	Discontinued
0.7342	Intermediate Similarity	NPD5160	Discontinued
0.7338	Intermediate Similarity	NPD2200	Suspended
0.7329	Intermediate Similarity	NPD2122	Discontinued
0.7329	Intermediate Similarity	NPD5976	Discontinued
0.7329	Intermediate Similarity	NPD4727	Phase 1
0.7326	Intermediate Similarity	NPD3920	Phase 2
0.7317	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5720	Discontinued
0.731	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7400	Phase 3
0.7303	Intermediate Similarity	NPD2490	Approved
0.7303	Intermediate Similarity	NPD3530	Approved
0.7303	Intermediate Similarity	NPD3532	Approved
0.7303	Intermediate Similarity	NPD3531	Approved
0.7303	Intermediate Similarity	NPD2488	Approved
0.7301	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7034	Discontinued
0.7284	Intermediate Similarity	NPD4210	Discontinued
0.7278	Intermediate Similarity	NPD6331	Phase 2
0.7273	Intermediate Similarity	NPD2653	Approved
0.7273	Intermediate Similarity	NPD4585	Approved
0.7263	Intermediate Similarity	NPD3922	Approved
0.7263	Intermediate Similarity	NPD3921	Approved
0.7263	Intermediate Similarity	NPD3923	Approved
0.7263	Intermediate Similarity	NPD3924	Approved
0.7241	Intermediate Similarity	NPD3445	Approved
0.7241	Intermediate Similarity	NPD3443	Approved
0.7241	Intermediate Similarity	NPD3444	Approved
0.7239	Intermediate Similarity	NPD6357	Discontinued
0.723	Intermediate Similarity	NPD1669	Approved
0.723	Intermediate Similarity	NPD1421	Approved
0.723	Intermediate Similarity	NPD1420	Approved
0.7226	Intermediate Similarity	NPD6111	Discontinued
0.7222	Intermediate Similarity	NPD1914	Approved
0.7215	Intermediate Similarity	NPD44	Approved
0.7215	Intermediate Similarity	NPD6364	Approved
0.7211	Intermediate Similarity	NPD3816	Phase 1
0.7211	Intermediate Similarity	NPD3815	Phase 1
0.7207	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4123	Phase 3
0.7197	Intermediate Similarity	NPD3656	Approved
0.7184	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2922	Phase 1
0.7179	Intermediate Similarity	NPD2156	Approved
0.7179	Intermediate Similarity	NPD2154	Approved
0.7179	Intermediate Similarity	NPD2155	Approved
0.7172	Intermediate Similarity	NPD2486	Discontinued
0.7171	Intermediate Similarity	NPD5156	Approved
0.7171	Intermediate Similarity	NPD5155	Approved
0.7169	Intermediate Similarity	NPD5773	Approved
0.7169	Intermediate Similarity	NPD2977	Approved
0.7169	Intermediate Similarity	NPD5772	Approved
0.7169	Intermediate Similarity	NPD2978	Approved
0.7161	Intermediate Similarity	NPD2492	Phase 1
0.7161	Intermediate Similarity	NPD2989	Phase 2
0.7161	Intermediate Similarity	NPD2986	Phase 2
0.716	Intermediate Similarity	NPD6037	Discontinued
0.7152	Intermediate Similarity	NPD3635	Approved
0.7152	Intermediate Similarity	NPD6873	Phase 2

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