NPASS Compound

Structure

CID247251 OpenBabel06191716052D 28 30 0 0 0 0 0 0 0 0999 V2000 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3212 -3.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3975 -5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6270 -3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8838 -4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 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 -2.0917 -5.1727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5780 -3.8344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1896 -4.5546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 25 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:	383.18
Volume:	393.162
LogP:	2.16
LogD:	2.356
LogS:	-3.565
# Rotatable Bonds:	7
TPSA:	92.49
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	2.781
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.749
MDCK Permeability:	5.283298833091976e-06
Pgp-inhibitor:	0.036
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.098
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	92.40188598632812%
Volume Distribution (VD):	0.65
Pgp-substrate:	8.280125617980957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.224
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.301
CYP2D6-inhibitor:	0.376
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.5
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	8.507
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.473
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.696
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.598
Maximum Recommended Daily Dose:	0.417
Skin Sensitization:	0.099
Carcinogencity:	0.715
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC247251

Natural Product ID:	NPC247251
*Common Name:**	Naamine G
IUPAC Name:	4-[[2-amino-5-[(4-methoxyphenyl)methyl]-3-methylimidazol-4-yl]methyl]-2,6-dimethoxyphenol
Synonyms:	Naamine G
Standard InCHIKey:	DMFFDOWRZFDQGT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H25N3O4/c1-24-17(10-14-11-18(27-3)20(25)19(12-14)28-4)16(23-21(24)22)9-13-5-7-15(26-2)8-6-13/h5-8,11-12,25H,9-10H2,1-4H3,(H2,22,23)
SMILES:	COc1ccc(cc1)Cc1[nH]c(=N)n(c1Cc1cc(OC)c(c(c1)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488195
PubChem CID:	11153300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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]
NPO644	Pestalotiopsis theae	Species	Sporocadaceae	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]
NPO29043	Hypoxylon oceanicum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29025	Streptomyces nojiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO29065	Hypoxis rooperi	Species	Hypoxidaceae	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]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	29.0	%	PMID[545367]
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	46.0	%	PMID[545367]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	10.0	%	PMID[545367]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	IZ	=	20.0	mm	PMID[545367]

☑ 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 NPC247251 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	507
0.1-0.2	3352
0.2-0.3	13762
0.3-0.4	4281
0.4-0.5	13069
0.5-0.6	7087
0.6-0.7	598
0.7-0.8	31
0.8-0.85	3
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8535	High Similarity	NPC13397
0.8491	Intermediate Similarity	NPC292003
0.8467	Intermediate Similarity	NPC237227
0.8065	Intermediate Similarity	NPC296898
0.7927	Intermediate Similarity	NPC475557
0.7895	Intermediate Similarity	NPC262641
0.7803	Intermediate Similarity	NPC228040
0.7784	Intermediate Similarity	NPC235628
0.7748	Intermediate Similarity	NPC17943
0.7748	Intermediate Similarity	NPC193544
0.7748	Intermediate Similarity	NPC208950
0.7748	Intermediate Similarity	NPC472093
0.7748	Intermediate Similarity	NPC298757
0.7748	Intermediate Similarity	NPC116907
0.7748	Intermediate Similarity	NPC203133
0.7748	Intermediate Similarity	NPC57490
0.7748	Intermediate Similarity	NPC251855
0.7748	Intermediate Similarity	NPC233410
0.7748	Intermediate Similarity	NPC117214
0.7748	Intermediate Similarity	NPC475169
0.7748	Intermediate Similarity	NPC221077
0.7697	Intermediate Similarity	NPC78974
0.7697	Intermediate Similarity	NPC28730
0.7697	Intermediate Similarity	NPC18924
0.7697	Intermediate Similarity	NPC103823
0.7697	Intermediate Similarity	NPC214406
0.7697	Intermediate Similarity	NPC44748
0.7697	Intermediate Similarity	NPC223136
0.7697	Intermediate Similarity	NPC127402
0.7677	Intermediate Similarity	NPC214869
0.7667	Intermediate Similarity	NPC262253
0.7667	Intermediate Similarity	NPC71579
0.7667	Intermediate Similarity	NPC473411
0.7647	Intermediate Similarity	NPC74817
0.7647	Intermediate Similarity	NPC82679
0.7647	Intermediate Similarity	NPC159968
0.7647	Intermediate Similarity	NPC236791
0.7647	Intermediate Similarity	NPC210355
0.7647	Intermediate Similarity	NPC124452
0.7647	Intermediate Similarity	NPC293054
0.7647	Intermediate Similarity	NPC282000
0.7647	Intermediate Similarity	NPC246620
0.7647	Intermediate Similarity	NPC169474
0.7647	Intermediate Similarity	NPC127587
0.7647	Intermediate Similarity	NPC324112
0.7632	Intermediate Similarity	NPC234400
0.7632	Intermediate Similarity	NPC299584
0.7632	Intermediate Similarity	NPC60885
0.7632	Intermediate Similarity	NPC265483
0.7632	Intermediate Similarity	NPC82483
0.7616	Intermediate Similarity	NPC13916
0.7616	Intermediate Similarity	NPC282496
0.7616	Intermediate Similarity	NPC228922
0.7616	Intermediate Similarity	NPC233526
0.7616	Intermediate Similarity	NPC136319
0.7616	Intermediate Similarity	NPC264850
0.7616	Intermediate Similarity	NPC197757
0.7613	Intermediate Similarity	NPC114102
0.761	Intermediate Similarity	NPC299583
0.7597	Intermediate Similarity	NPC470213
0.7597	Intermediate Similarity	NPC206615
0.7597	Intermediate Similarity	NPC186843
0.7597	Intermediate Similarity	NPC98631
0.7582	Intermediate Similarity	NPC76451
0.7566	Intermediate Similarity	NPC105513
0.756	Intermediate Similarity	NPC107602
0.7558	Intermediate Similarity	NPC24465
0.755	Intermediate Similarity	NPC41562
0.7548	Intermediate Similarity	NPC10225
0.7548	Intermediate Similarity	NPC52029
0.7548	Intermediate Similarity	NPC170844
0.7548	Intermediate Similarity	NPC58164
0.7548	Intermediate Similarity	NPC195749
0.7548	Intermediate Similarity	NPC35961
0.7548	Intermediate Similarity	NPC476968
0.7547	Intermediate Similarity	NPC41473
0.7547	Intermediate Similarity	NPC160607
0.7547	Intermediate Similarity	NPC312770
0.7547	Intermediate Similarity	NPC14600
0.7547	Intermediate Similarity	NPC204848
0.7545	Intermediate Similarity	NPC114124
0.7543	Intermediate Similarity	NPC254053
0.7533	Intermediate Similarity	NPC166759
0.7532	Intermediate Similarity	NPC291847
0.7529	Intermediate Similarity	NPC204908
0.7529	Intermediate Similarity	NPC329837
0.7529	Intermediate Similarity	NPC83198
0.7528	Intermediate Similarity	NPC474507
0.7516	Intermediate Similarity	NPC105925
0.75	Intermediate Similarity	NPC299221
0.75	Intermediate Similarity	NPC126836
0.75	Intermediate Similarity	NPC95168
0.75	Intermediate Similarity	NPC51840
0.75	Intermediate Similarity	NPC13020
0.75	Intermediate Similarity	NPC473934
0.75	Intermediate Similarity	NPC140359
0.75	Intermediate Similarity	NPC472338
0.75	Intermediate Similarity	NPC311680
0.75	Intermediate Similarity	NPC234488
0.7485	Intermediate Similarity	NPC76213
0.7485	Intermediate Similarity	NPC277669
0.7484	Intermediate Similarity	NPC154866
0.7484	Intermediate Similarity	NPC155838
0.7484	Intermediate Similarity	NPC28765
0.7468	Intermediate Similarity	NPC158331
0.7468	Intermediate Similarity	NPC471391
0.7468	Intermediate Similarity	NPC471390
0.7467	Intermediate Similarity	NPC10932
0.7467	Intermediate Similarity	NPC61516
0.7467	Intermediate Similarity	NPC474565
0.7467	Intermediate Similarity	NPC232084
0.7467	Intermediate Similarity	NPC247364
0.7455	Intermediate Similarity	NPC277857
0.7455	Intermediate Similarity	NPC115144
0.7452	Intermediate Similarity	NPC470096
0.7452	Intermediate Similarity	NPC472597
0.7452	Intermediate Similarity	NPC470095
0.7452	Intermediate Similarity	NPC474017
0.7451	Intermediate Similarity	NPC228972
0.7451	Intermediate Similarity	NPC206487
0.7451	Intermediate Similarity	NPC5796
0.7451	Intermediate Similarity	NPC122792
0.7438	Intermediate Similarity	NPC193528
0.7436	Intermediate Similarity	NPC470633
0.7436	Intermediate Similarity	NPC228769
0.7436	Intermediate Similarity	NPC212015
0.7434	Intermediate Similarity	NPC298486
0.7432	Intermediate Similarity	NPC11296
0.7432	Intermediate Similarity	NPC48490
0.7432	Intermediate Similarity	NPC175890
0.7432	Intermediate Similarity	NPC82457
0.7432	Intermediate Similarity	NPC274661
0.7421	Intermediate Similarity	NPC287745
0.7419	Intermediate Similarity	NPC252131
0.7419	Intermediate Similarity	NPC153990
0.7419	Intermediate Similarity	NPC236760
0.7419	Intermediate Similarity	NPC470699
0.7419	Intermediate Similarity	NPC251571
0.7419	Intermediate Similarity	NPC186898
0.7419	Intermediate Similarity	NPC266555
0.7416	Intermediate Similarity	NPC148709
0.7416	Intermediate Similarity	NPC476577
0.7416	Intermediate Similarity	NPC173416
0.7414	Intermediate Similarity	NPC286790
0.7414	Intermediate Similarity	NPC188120
0.7414	Intermediate Similarity	NPC53146
0.7412	Intermediate Similarity	NPC37205
0.7412	Intermediate Similarity	NPC160931
0.741	Intermediate Similarity	NPC428
0.741	Intermediate Similarity	NPC246587
0.741	Intermediate Similarity	NPC476571
0.741	Intermediate Similarity	NPC135538
0.741	Intermediate Similarity	NPC147390
0.741	Intermediate Similarity	NPC24233
0.7405	Intermediate Similarity	NPC16208
0.7405	Intermediate Similarity	NPC184447
0.7405	Intermediate Similarity	NPC35932
0.7405	Intermediate Similarity	NPC6451
0.7405	Intermediate Similarity	NPC175067
0.7405	Intermediate Similarity	NPC160991
0.7405	Intermediate Similarity	NPC201587
0.7405	Intermediate Similarity	NPC204215
0.7405	Intermediate Similarity	NPC253105
0.7405	Intermediate Similarity	NPC7903
0.7401	Intermediate Similarity	NPC190783
0.7401	Intermediate Similarity	NPC232386
0.7401	Intermediate Similarity	NPC152680
0.74	Intermediate Similarity	NPC226629
0.74	Intermediate Similarity	NPC20674
0.7396	Intermediate Similarity	NPC477564
0.7396	Intermediate Similarity	NPC2295
0.7391	Intermediate Similarity	NPC60295
0.7391	Intermediate Similarity	NPC191132
0.7389	Intermediate Similarity	NPC326599
0.7389	Intermediate Similarity	NPC63574
0.7389	Intermediate Similarity	NPC329595
0.7386	Intermediate Similarity	NPC84086
0.7386	Intermediate Similarity	NPC121115
0.7375	Intermediate Similarity	NPC99572
0.7375	Intermediate Similarity	NPC126409
0.7372	Intermediate Similarity	NPC266691
0.7368	Intermediate Similarity	NPC75713
0.7368	Intermediate Similarity	NPC49341
0.7365	Intermediate Similarity	NPC60538
0.7365	Intermediate Similarity	NPC207824
0.7358	Intermediate Similarity	NPC229442
0.7358	Intermediate Similarity	NPC168059
0.7358	Intermediate Similarity	NPC475840
0.7358	Intermediate Similarity	NPC32778
0.7355	Intermediate Similarity	NPC181361
0.7355	Intermediate Similarity	NPC301713
0.7355	Intermediate Similarity	NPC223953
0.7349	Intermediate Similarity	NPC321505
0.7349	Intermediate Similarity	NPC191376
0.7349	Intermediate Similarity	NPC179825
0.7345	Intermediate Similarity	NPC239775
0.7342	Intermediate Similarity	NPC45715
0.7342	Intermediate Similarity	NPC12275
0.7342	Intermediate Similarity	NPC474356
0.7342	Intermediate Similarity	NPC232275

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 NPC247251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	692
0.2-0.3	839
0.3-0.4	1857
0.4-0.5	3147
0.5-0.6	2025
0.6-0.7	311
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.795	Intermediate Similarity	NPD1349	Approved
0.795	Intermediate Similarity	NPD1351	Approved
0.795	Intermediate Similarity	NPD1350	Approved
0.7911	Intermediate Similarity	NPD3060	Approved
0.7725	Intermediate Similarity	NPD2977	Approved
0.7725	Intermediate Similarity	NPD2978	Approved
0.7669	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7124	Phase 2
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7545	Intermediate Similarity	NPD4675	Approved
0.7545	Intermediate Similarity	NPD4678	Approved
0.7516	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4162	Approved
0.7455	Intermediate Similarity	NPD1424	Approved
0.7418	Intermediate Similarity	NPD4157	Discontinued
0.7416	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3053	Approved
0.7403	Intermediate Similarity	NPD3055	Approved
0.7386	Intermediate Similarity	NPD3489	Phase 3
0.7338	Intermediate Similarity	NPD5310	Approved
0.7338	Intermediate Similarity	NPD5311	Approved
0.7312	Intermediate Similarity	NPD5314	Approved
0.7312	Intermediate Similarity	NPD2568	Approved
0.7296	Intermediate Similarity	NPD3059	Approved
0.7296	Intermediate Similarity	NPD3061	Approved
0.7296	Intermediate Similarity	NPD3062	Approved
0.7289	Intermediate Similarity	NPD4357	Discontinued
0.7278	Intermediate Similarity	NPD5718	Phase 2
0.7278	Intermediate Similarity	NPD4005	Discontinued
0.7261	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4236	Phase 3
0.7256	Intermediate Similarity	NPD4237	Approved
0.7253	Intermediate Similarity	NPD8054	Approved
0.7253	Intermediate Similarity	NPD8053	Approved
0.7246	Intermediate Similarity	NPD4123	Phase 3
0.7246	Intermediate Similarity	NPD3158	Phase 1
0.7246	Intermediate Similarity	NPD3157	Approved
0.7233	Intermediate Similarity	NPD2674	Phase 3
0.7219	Intermediate Similarity	NPD3686	Approved
0.7219	Intermediate Similarity	NPD3687	Approved
0.7216	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5241	Discontinued
0.716	Intermediate Similarity	NPD6896	Approved
0.716	Intermediate Similarity	NPD6895	Approved
0.716	Intermediate Similarity	NPD6030	Approved
0.716	Intermediate Similarity	NPD6031	Approved
0.716	Intermediate Similarity	NPD6111	Discontinued
0.7126	Intermediate Similarity	NPD6788	Approved
0.7125	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5773	Approved
0.711	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5772	Approved
0.7093	Intermediate Similarity	NPD6072	Discontinued
0.7081	Intermediate Similarity	NPD1558	Phase 1
0.7079	Intermediate Similarity	NPD4083	Discontinued
0.7076	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2219	Phase 1
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD597	Approved
0.7063	Intermediate Similarity	NPD601	Approved
0.7063	Intermediate Similarity	NPD3145	Approved
0.7063	Intermediate Similarity	NPD3144	Approved
0.7063	Intermediate Similarity	NPD598	Approved
0.7044	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1375	Discontinued
0.7025	Intermediate Similarity	NPD9619	Approved
0.7025	Intermediate Similarity	NPD9621	Approved
0.7025	Intermediate Similarity	NPD9620	Approved
0.7019	Intermediate Similarity	NPD1136	Approved
0.7019	Intermediate Similarity	NPD1132	Approved
0.7019	Intermediate Similarity	NPD1130	Approved
0.7011	Intermediate Similarity	NPD4585	Approved
0.7	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3054	Approved
0.6994	Remote Similarity	NPD2653	Approved
0.6994	Remote Similarity	NPD3052	Approved
0.6989	Remote Similarity	NPD4055	Discovery
0.6988	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7125	Discontinued
0.6981	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2238	Phase 2
0.6975	Remote Similarity	NPD1613	Approved
0.6957	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1039	Discontinued
0.6954	Remote Similarity	NPD5720	Discontinued
0.6946	Remote Similarity	NPD5177	Phase 3
0.6943	Remote Similarity	NPD2982	Phase 2
0.6943	Remote Similarity	NPD2983	Phase 2
0.6941	Remote Similarity	NPD3536	Discontinued
0.6931	Remote Similarity	NPD3634	Approved
0.6931	Remote Similarity	NPD3633	Approved
0.6928	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5267	Discontinued
0.6915	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5604	Discontinued
0.689	Remote Similarity	NPD817	Approved
0.689	Remote Similarity	NPD823	Approved
0.6886	Remote Similarity	NPD7153	Discontinued
0.6882	Remote Similarity	NPD5297	Approved
0.6879	Remote Similarity	NPD2981	Phase 2
0.6875	Remote Similarity	NPD2560	Approved
0.6875	Remote Similarity	NPD2563	Approved
0.6875	Remote Similarity	NPD3018	Phase 2
0.6868	Remote Similarity	NPD8099	Discontinued
0.6868	Remote Similarity	NPD8251	Approved
0.6868	Remote Similarity	NPD8252	Approved
0.6867	Remote Similarity	NPD228	Approved
0.6867	Remote Similarity	NPD2161	Phase 2
0.6867	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2677	Approved
0.6857	Remote Similarity	NPD7298	Approved
0.6856	Remote Similarity	NPD6612	Phase 2
0.6851	Remote Similarity	NPD2489	Approved
0.6851	Remote Similarity	NPD27	Approved
0.6842	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7447	Phase 1
0.6839	Remote Similarity	NPD1009	Approved
0.6831	Remote Similarity	NPD8156	Discontinued
0.6816	Remote Similarity	NPD5677	Discontinued
0.6813	Remote Similarity	NPD602	Approved
0.6813	Remote Similarity	NPD859	Approved
0.6813	Remote Similarity	NPD858	Approved
0.6813	Remote Similarity	NPD599	Approved
0.6811	Remote Similarity	NPD7038	Approved
0.6811	Remote Similarity	NPD7039	Approved
0.6807	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6331	Phase 2
0.6802	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7526	Approved
0.6802	Remote Similarity	NPD52	Approved
0.6802	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2970	Approved
0.6796	Remote Similarity	NPD2969	Approved
0.6795	Remote Similarity	NPD2667	Approved
0.6795	Remote Similarity	NPD2668	Approved
0.6784	Remote Similarity	NPD7213	Phase 3
0.6784	Remote Similarity	NPD1774	Approved
0.6784	Remote Similarity	NPD7212	Phase 2
0.6772	Remote Similarity	NPD7906	Approved
0.6766	Remote Similarity	NPD4206	Approved
0.6763	Remote Similarity	NPD5976	Discontinued
0.6763	Remote Similarity	NPD2122	Discontinued
0.6761	Remote Similarity	NPD3384	Approved
0.6761	Remote Similarity	NPD3383	Approved
0.6761	Remote Similarity	NPD3382	Approved
0.6748	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4584	Approved
0.6744	Remote Similarity	NPD6419	Discontinued
0.674	Remote Similarity	NPD6071	Discontinued
0.674	Remote Similarity	NPD3051	Approved
0.674	Remote Similarity	NPD4010	Discontinued
0.6738	Remote Similarity	NPD7313	Approved
0.6738	Remote Similarity	NPD7311	Approved
0.6738	Remote Similarity	NPD7310	Approved
0.6738	Remote Similarity	NPD4577	Approved
0.6738	Remote Similarity	NPD4578	Approved
0.6738	Remote Similarity	NPD7312	Approved
0.6737	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7263	Phase 2
0.673	Remote Similarity	NPD9622	Approved
0.673	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4666	Phase 3
0.6721	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4663	Approved
0.6711	Remote Similarity	NPD9379	Approved
0.6711	Remote Similarity	NPD9377	Approved
0.6706	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5090	Approved
0.6705	Remote Similarity	NPD1440	Discontinued
0.6705	Remote Similarity	NPD5089	Approved
0.6704	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7833	Phase 2
0.6704	Remote Similarity	NPD7831	Phase 2
0.6703	Remote Similarity	NPD5242	Approved
0.6702	Remote Similarity	NPD7309	Approved
0.6701	Remote Similarity	NPD3515	Approved
0.6701	Remote Similarity	NPD3516	Approved
0.6688	Remote Similarity	NPD9384	Approved
0.6688	Remote Similarity	NPD9381	Approved
0.6687	Remote Similarity	NPD3180	Approved
0.6687	Remote Similarity	NPD3179	Approved
0.6686	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3560	Approved
0.6685	Remote Similarity	NPD3558	Approved
0.6685	Remote Similarity	NPD3557	Approved
0.6685	Remote Similarity	NPD3556	Approved
0.6684	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3473	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