NPASS Compound

Structure

CID79213 OpenBabel06191715412D 27 30 0 0 0 0 0 0 0 0999 V2000 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1222 5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 5.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3902 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3902 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1222 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 5.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.16
Volume:	373.179
LogP:	3.46
LogD:	3.305
LogS:	-3.933
# Rotatable Bonds:	4
TPSA:	72.26
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	2.7
Fsp3:	0.19
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:	-5.248
MDCK Permeability:	1.6265197700704448e-05
Pgp-inhibitor:	0.086
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	86.64513397216797%
Volume Distribution (VD):	1.044
Pgp-substrate:	9.085114479064941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.416
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.582
CYP2D6-inhibitor:	0.513
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.486
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	7.778
Half-life (T1/2):	0.491

ADMET: Toxicity

hERG Blockers:	0.929
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.716
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.123
Carcinogencity:	0.908
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC79213

Natural Product ID:	NPC79213
*Common Name:**	Kealiinine B
IUPAC Name:	6,7-dimethoxy-4-(4-methoxyphenyl)-1-methylbenzo[f]benzimidazol-2-amine
Synonyms:
Standard InCHIKey:	ADAJQGCVARDFOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H21N3O3/c1-24-16-9-13-10-17(26-3)18(27-4)11-15(13)19(20(16)23-21(24)22)12-5-7-14(25-2)8-6-12/h5-11H,1-4H3,(H2,22,23)
SMILES:	Cn1c2cc3cc(c(cc3c(c3ccc(cc3)OC)c2[nH]c1=N)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2441625
PubChem CID:	23248790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193030]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165143]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822294]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25256628]
NPO644	Pestalotiopsis theae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27731995]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29648818]
NPO29255	Salvia chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30370766]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28861	Cladonia graciliformis	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29509	Leucetta chagosensis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28968	Teucrium flavum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29434	Centaurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29255	Salvia chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29238	Heterocondylus vitalbae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17683	Cryptocarya moschata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29473	Amycolatopsis mediterranei	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29124	Argemone squarrosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24421.1	Agave salmiana var. ferox	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29065	Hypoxis rooperi	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29470	Anhalonium fissuratum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO644	Pestalotiopsis theae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29025	Streptomyces nojiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29043	Hypoxylon oceanicum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	28800.0	nM	PMID[470515]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4400.0	nM	PMID[470516]

☑ 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 NPC79213 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	840
0.1-0.2	6222
0.2-0.3	11384
0.3-0.4	11565
0.4-0.5	8402
0.5-0.6	3193
0.6-0.7	936
0.7-0.8	150
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC25897
0.9341	High Similarity	NPC261388
0.8222	Intermediate Similarity	NPC285941
0.8054	Intermediate Similarity	NPC249405
0.7989	Intermediate Similarity	NPC190461
0.7935	Intermediate Similarity	NPC287588
0.7914	Intermediate Similarity	NPC276674
0.7914	Intermediate Similarity	NPC33902
0.7884	Intermediate Similarity	NPC312531
0.7807	Intermediate Similarity	NPC179704
0.7789	Intermediate Similarity	NPC474904
0.7778	Intermediate Similarity	NPC24954
0.7771	Intermediate Similarity	NPC13397
0.7744	Intermediate Similarity	NPC212163
0.7737	Intermediate Similarity	NPC320088
0.7665	Intermediate Similarity	NPC295676
0.755	Intermediate Similarity	NPC156728
0.755	Intermediate Similarity	NPC244606
0.7487	Intermediate Similarity	NPC302001
0.7419	Intermediate Similarity	NPC471604
0.7416	Intermediate Similarity	NPC219162
0.7398	Intermediate Similarity	NPC78284
0.7371	Intermediate Similarity	NPC477186
0.7368	Intermediate Similarity	NPC265383
0.7363	Intermediate Similarity	NPC203784
0.7363	Intermediate Similarity	NPC126519
0.7363	Intermediate Similarity	NPC170503
0.7353	Intermediate Similarity	NPC207873
0.7353	Intermediate Similarity	NPC100573
0.7337	Intermediate Similarity	NPC193906
0.7337	Intermediate Similarity	NPC23080
0.7333	Intermediate Similarity	NPC326316
0.7333	Intermediate Similarity	NPC81733
0.733	Intermediate Similarity	NPC260118
0.7323	Intermediate Similarity	NPC162653
0.7303	Intermediate Similarity	NPC253883
0.7303	Intermediate Similarity	NPC90844
0.7303	Intermediate Similarity	NPC95075
0.7292	Intermediate Similarity	NPC311936
0.7292	Intermediate Similarity	NPC215747
0.7292	Intermediate Similarity	NPC192939
0.7273	Intermediate Similarity	NPC86144
0.7273	Intermediate Similarity	NPC304659
0.7263	Intermediate Similarity	NPC130941
0.7254	Intermediate Similarity	NPC119579
0.7253	Intermediate Similarity	NPC292003
0.7243	Intermediate Similarity	NPC232924
0.7243	Intermediate Similarity	NPC477559
0.7243	Intermediate Similarity	NPC266753
0.7243	Intermediate Similarity	NPC306902
0.7243	Intermediate Similarity	NPC160298
0.7234	Intermediate Similarity	NPC85482
0.7216	Intermediate Similarity	NPC28425
0.7166	Intermediate Similarity	NPC189470
0.7164	Intermediate Similarity	NPC17677
0.7157	Intermediate Similarity	NPC296742
0.7143	Intermediate Similarity	NPC69213
0.7143	Intermediate Similarity	NPC219170
0.7143	Intermediate Similarity	NPC180253
0.7136	Intermediate Similarity	NPC308943
0.7136	Intermediate Similarity	NPC222561
0.7135	Intermediate Similarity	NPC476572
0.7128	Intermediate Similarity	NPC225774
0.7128	Intermediate Similarity	NPC276060
0.7127	Intermediate Similarity	NPC92541
0.712	Intermediate Similarity	NPC99659
0.712	Intermediate Similarity	NPC325871
0.712	Intermediate Similarity	NPC244112
0.7107	Intermediate Similarity	NPC224293
0.7104	Intermediate Similarity	NPC26601
0.7102	Intermediate Similarity	NPC314682
0.7101	Intermediate Similarity	NPC90185
0.7097	Intermediate Similarity	NPC315498
0.7097	Intermediate Similarity	NPC230942
0.709	Intermediate Similarity	NPC81247
0.709	Intermediate Similarity	NPC476432
0.709	Intermediate Similarity	NPC24264
0.709	Intermediate Similarity	NPC219341
0.709	Intermediate Similarity	NPC476573
0.709	Intermediate Similarity	NPC35627
0.7071	Intermediate Similarity	NPC112676
0.7068	Intermediate Similarity	NPC6152
0.7062	Intermediate Similarity	NPC188163
0.7062	Intermediate Similarity	NPC213206
0.7062	Intermediate Similarity	NPC474915
0.7062	Intermediate Similarity	NPC55470
0.7062	Intermediate Similarity	NPC470925
0.7062	Intermediate Similarity	NPC328750
0.7059	Intermediate Similarity	NPC166014
0.7059	Intermediate Similarity	NPC27410
0.7056	Intermediate Similarity	NPC21425
0.7053	Intermediate Similarity	NPC247389
0.7053	Intermediate Similarity	NPC298979
0.7044	Intermediate Similarity	NPC5374
0.7037	Intermediate Similarity	NPC16805
0.7037	Intermediate Similarity	NPC302527
0.7037	Intermediate Similarity	NPC167546
0.7027	Intermediate Similarity	NPC76079
0.702	Intermediate Similarity	NPC22928
0.7017	Intermediate Similarity	NPC144863
0.7016	Intermediate Similarity	NPC241055
0.7	Intermediate Similarity	NPC145304
0.6995	Remote Similarity	NPC71124
0.6991	Remote Similarity	NPC280272
0.6989	Remote Similarity	NPC186063
0.6984	Remote Similarity	NPC233650
0.6979	Remote Similarity	NPC152212
0.6978	Remote Similarity	NPC475959
0.6976	Remote Similarity	NPC471489
0.6965	Remote Similarity	NPC254957
0.6963	Remote Similarity	NPC204947
0.6963	Remote Similarity	NPC210918
0.6957	Remote Similarity	NPC475147
0.6952	Remote Similarity	NPC199667
0.6947	Remote Similarity	NPC134858
0.6947	Remote Similarity	NPC168409
0.694	Remote Similarity	NPC60538
0.694	Remote Similarity	NPC207824
0.6939	Remote Similarity	NPC267408
0.6934	Remote Similarity	NPC149471
0.6934	Remote Similarity	NPC271215
0.6931	Remote Similarity	NPC29472
0.6931	Remote Similarity	NPC247251
0.6923	Remote Similarity	NPC112575
0.6923	Remote Similarity	NPC85613
0.6907	Remote Similarity	NPC477020
0.6907	Remote Similarity	NPC66341
0.6907	Remote Similarity	NPC192135
0.6906	Remote Similarity	NPC185838
0.6905	Remote Similarity	NPC473181
0.6904	Remote Similarity	NPC32413
0.6904	Remote Similarity	NPC474506
0.6901	Remote Similarity	NPC298449
0.6895	Remote Similarity	NPC324144
0.6895	Remote Similarity	NPC475393
0.6891	Remote Similarity	NPC69712
0.6891	Remote Similarity	NPC26240
0.6891	Remote Similarity	NPC477562
0.6891	Remote Similarity	NPC312872
0.689	Remote Similarity	NPC193777
0.6889	Remote Similarity	NPC476567
0.6889	Remote Similarity	NPC128019
0.6889	Remote Similarity	NPC136860
0.6888	Remote Similarity	NPC23219
0.6887	Remote Similarity	NPC251160
0.6875	Remote Similarity	NPC150879
0.6875	Remote Similarity	NPC210140
0.6875	Remote Similarity	NPC81218
0.6875	Remote Similarity	NPC11147
0.6875	Remote Similarity	NPC12053
0.6875	Remote Similarity	NPC158376
0.6875	Remote Similarity	NPC145832
0.6875	Remote Similarity	NPC117188
0.6875	Remote Similarity	NPC205421
0.6875	Remote Similarity	NPC474931
0.6875	Remote Similarity	NPC306555
0.6872	Remote Similarity	NPC188420
0.6872	Remote Similarity	NPC477558
0.6865	Remote Similarity	NPC277669
0.6865	Remote Similarity	NPC76213
0.6861	Remote Similarity	NPC473182
0.6859	Remote Similarity	NPC78222
0.6859	Remote Similarity	NPC13504
0.6859	Remote Similarity	NPC253043
0.6859	Remote Similarity	NPC212794
0.6859	Remote Similarity	NPC306843
0.6859	Remote Similarity	NPC96603
0.6859	Remote Similarity	NPC196447
0.6859	Remote Similarity	NPC477563
0.6859	Remote Similarity	NPC136508
0.6856	Remote Similarity	NPC19520
0.6856	Remote Similarity	NPC149090
0.6853	Remote Similarity	NPC258695
0.6853	Remote Similarity	NPC470879
0.6848	Remote Similarity	NPC211296
0.6845	Remote Similarity	NPC80129
0.6845	Remote Similarity	NPC93593
0.6845	Remote Similarity	NPC187022
0.684	Remote Similarity	NPC208284
0.6837	Remote Similarity	NPC283810
0.6837	Remote Similarity	NPC5167
0.6834	Remote Similarity	NPC135772
0.6832	Remote Similarity	NPC133140
0.6832	Remote Similarity	NPC294244
0.6832	Remote Similarity	NPC195268
0.6831	Remote Similarity	NPC51957
0.6831	Remote Similarity	NPC210437
0.6831	Remote Similarity	NPC476144
0.6831	Remote Similarity	NPC106295
0.6831	Remote Similarity	NPC16107
0.6831	Remote Similarity	NPC179825
0.6831	Remote Similarity	NPC321505
0.6831	Remote Similarity	NPC191376
0.6827	Remote Similarity	NPC207971
0.6825	Remote Similarity	NPC201697
0.6825	Remote Similarity	NPC475133
0.6818	Remote Similarity	NPC312918
0.6818	Remote Similarity	NPC227908
0.6818	Remote Similarity	NPC477561
0.6818	Remote Similarity	NPC155442

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 NPC79213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	736
0.2-0.3	783
0.3-0.4	1895
0.4-0.5	2549
0.5-0.6	2012
0.6-0.7	670
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8222	Intermediate Similarity	NPD5810	Discontinued
0.7795	Intermediate Similarity	NPD6612	Phase 2
0.7717	Intermediate Similarity	NPD7032	Approved
0.7716	Intermediate Similarity	NPD3515	Approved
0.7716	Intermediate Similarity	NPD3516	Approved
0.7713	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1909	Discontinued
0.7429	Intermediate Similarity	NPD3301	Approved
0.7407	Intermediate Similarity	NPD7479	Phase 2
0.7343	Intermediate Similarity	NPD4356	Discontinued
0.7333	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3983	Phase 3
0.7268	Intermediate Similarity	NPD5658	Approved
0.7264	Intermediate Similarity	NPD3290	Approved
0.7264	Intermediate Similarity	NPD3289	Phase 3
0.7263	Intermediate Similarity	NPD5600	Discontinued
0.7249	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4083	Discontinued
0.7222	Intermediate Similarity	NPD7262	Phase 1
0.7184	Intermediate Similarity	NPD4859	Phase 1
0.7182	Intermediate Similarity	NPD2883	Discontinued
0.7129	Intermediate Similarity	NPD7225	Discontinued
0.7112	Intermediate Similarity	NPD4796	Discontinued
0.7097	Intermediate Similarity	NPD19	Approved
0.7097	Intermediate Similarity	NPD1742	Approved
0.7097	Intermediate Similarity	NPD1743	Approved
0.7071	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3920	Phase 2
0.7043	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6030	Approved
0.7033	Intermediate Similarity	NPD6031	Approved
0.7028	Intermediate Similarity	NPD8149	Discontinued
0.702	Intermediate Similarity	NPD3349	Phase 2
0.701	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3634	Approved
0.7	Intermediate Similarity	NPD3633	Approved
0.6984	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4598	Approved
0.6966	Remote Similarity	NPD4597	Approved
0.6965	Remote Similarity	NPD6526	Approved
0.6965	Remote Similarity	NPD3631	Phase 3
0.6959	Remote Similarity	NPD7278	Phase 2
0.6959	Remote Similarity	NPD7279	Phase 2
0.695	Remote Similarity	NPD5641	Discontinued
0.6946	Remote Similarity	NPD7034	Discontinued
0.6927	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5530	Phase 1
0.6919	Remote Similarity	NPD6340	Approved
0.6919	Remote Similarity	NPD6339	Approved
0.6912	Remote Similarity	NPD5071	Phase 2
0.6902	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6037	Discontinued
0.6891	Remote Similarity	NPD5938	Phase 3
0.6888	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6357	Discontinued
0.6863	Remote Similarity	NPD6527	Approved
0.6861	Remote Similarity	NPD4080	Discontinued
0.6856	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7298	Approved
0.6832	Remote Similarity	NPD3921	Approved
0.6832	Remote Similarity	NPD3924	Approved
0.6832	Remote Similarity	NPD3922	Approved
0.6832	Remote Similarity	NPD3923	Approved
0.6831	Remote Similarity	NPD4584	Approved
0.6821	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5930	Phase 3
0.682	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6230	Discontinued
0.6812	Remote Similarity	NPD6238	Discontinued
0.6788	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5241	Discontinued
0.6758	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5720	Discontinued
0.6753	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2917	Approved
0.6748	Remote Similarity	NPD6877	Discontinued
0.6746	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD3592	Approved
0.6745	Remote Similarity	NPD3591	Approved
0.6743	Remote Similarity	NPD5718	Phase 2
0.6736	Remote Similarity	NPD4166	Phase 2
0.6735	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3964	Approved
0.6721	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6738	Phase 2
0.672	Remote Similarity	NPD6737	Phase 2
0.6719	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5561	Approved
0.6713	Remote Similarity	NPD5562	Approved
0.6699	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3763	Approved
0.6684	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4017	Approved
0.6683	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4511	Phase 1
0.6649	Remote Similarity	NPD5183	Approved
0.6649	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5186	Approved
0.6637	Remote Similarity	NPD7922	Phase 1
0.6635	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7125	Discontinued
0.6632	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4996	Approved
0.6622	Remote Similarity	NPD4995	Approved
0.6616	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1954	Phase 1
0.6606	Remote Similarity	NPD8311	Discontinued
0.6603	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6493	Phase 3
0.6601	Remote Similarity	NPD3398	Discontinued
0.6598	Remote Similarity	NPD6457	Approved
0.6597	Remote Similarity	NPD6063	Approved
0.6593	Remote Similarity	NPD4885	Approved
0.6591	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4917	Discontinued
0.6588	Remote Similarity	NPD3804	Discontinued
0.658	Remote Similarity	NPD2190	Approved
0.6579	Remote Similarity	NPD1769	Discontinued
0.6578	Remote Similarity	NPD4925	Approved
0.6574	Remote Similarity	NPD3816	Phase 1
0.6574	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3815	Phase 1
0.657	Remote Similarity	NPD2804	Phase 1
0.657	Remote Similarity	NPD5582	Discontinued
0.6562	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6788	Approved
0.6558	Remote Similarity	NPD5645	Phase 3
0.6557	Remote Similarity	NPD4795	Phase 2
0.6553	Remote Similarity	NPD5150	Phase 2
0.6552	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6760	Discontinued
0.6535	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7831	Phase 2
0.6528	Remote Similarity	NPD7833	Phase 2
0.6526	Remote Similarity	NPD1440	Discontinued
0.6526	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5754	Discontinued
0.6522	Remote Similarity	NPD4418	Discontinued
0.6522	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5903	Approved
0.6514	Remote Similarity	NPD5902	Approved
0.6509	Remote Similarity	NPD6473	Phase 1
0.6505	Remote Similarity	NPD2421	Approved
0.6505	Remote Similarity	NPD7598	Phase 2
0.6505	Remote Similarity	NPD2420	Approved
0.6504	Remote Similarity	NPD6968	Phase 2
0.6504	Remote Similarity	NPD6969	Phase 2
0.65	Remote Similarity	NPD6297	Approved
0.6498	Remote Similarity	NPD6742	Phase 2
0.6498	Remote Similarity	NPD6743	Phase 2
0.6498	Remote Similarity	NPD2794	Discontinued
0.6497	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7222	Phase 2
0.6495	Remote Similarity	NPD7453	Approved
0.6495	Remote Similarity	NPD7452	Approved
0.6494	Remote Similarity	NPD5905	Phase 1
0.6491	Remote Similarity	NPD6723	Discontinued
0.6489	Remote Similarity	NPD3640	Phase 3
0.6489	Remote Similarity	NPD3641	Approved
0.6489	Remote Similarity	NPD3639	Approved
0.6488	Remote Similarity	NPD2843	Phase 2
0.6488	Remote Similarity	NPD2845	Phase 2
0.6486	Remote Similarity	NPD7726	Phase 1
0.6483	Remote Similarity	NPD6244	Phase 3
0.6483	Remote Similarity	NPD6243	Phase 3
0.6482	Remote Similarity	NPD5670	Approved
0.6481	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.648	Remote Similarity	NPD3051	Approved
0.6471	Remote Similarity	NPD6501	Approved
0.6471	Remote Similarity	NPD6500	Approved
0.6465	Remote Similarity	NPD2189	Approved
0.6465	Remote Similarity	NPD2187	Approved
0.6464	Remote Similarity	NPD6895	Approved
0.6464	Remote Similarity	NPD6896	Approved
0.6461	Remote Similarity	NPD1039	Discontinued
0.6458	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7085	Approved
0.6452	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3845	Phase 1
0.645	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6245	Phase 2
0.6447	Remote Similarity	NPD3975	Discontinued
0.6445	Remote Similarity	NPD6810	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