NPASS Compound

Structure

CID264379 OpenBabel06191716062D 22 23 0 0 0 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 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 -2.5981 1.5000 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 -3.4641 -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 -1.7321 -0.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Br 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 -2.5981 -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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	619.65
Volume:	340.557
LogP:	6.499
LogD:	3.493
LogS:	-8.544
# Rotatable Bonds:	4
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	2.648
Fsp3:	0.143
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826
MDCK Permeability:	1.8128437659470364e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	101.0285415649414%
Volume Distribution (VD):	4.461
Pgp-substrate:	9.342754364013672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.83
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	1.071
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.911
Carcinogencity:	0.052
Eye Corrosion:	0.274
Eye Irritation:	0.949
Respiratory Toxicity:	0.748

Download Data

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

Natural Product: NPC264379

Natural Product ID:	NPC264379
*Common Name:**	1,2,3-Tribromo-4-(3,5-Dibromo-2-Methoxyphenoxy)-5-Methoxybenzene
IUPAC Name:	1,2,3-tribromo-4-(3,5-dibromo-2-methoxyphenoxy)-5-methoxybenzene
Synonyms:
Standard InCHIKey:	MXPHINKLSXPVGO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H9Br5O3/c1-20-9-5-7(16)11(18)12(19)14(9)22-10-4-6(15)3-8(17)13(10)21-2/h3-5H,1-2H3
SMILES:	COc1cc(Br)c(c(c1Oc1cc(Br)cc(c1OC)Br)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL150603
PubChem CID:	21637537
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	Eukaryota	n.a.	Palau	n.a.	PMID[15043436]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17311456]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25863431]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27399938]
NPO40870	Lamellodysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27399938]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31990554]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19028	Dysidea granulosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	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	1
MIC	7
Others	6

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	9
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT41	Individual Protein	Aldose reductase	Homo sapiens	Inhibition	=	0.0	%	PMID[528127]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.0	mm	PMID[528128]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[528130]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50.0	ug.mL-1	PMID[528130]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MNTD	=	50.0	ug ml-1	PMID[528130]

☑ 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 NPC264379 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	824
0.1-0.2	6714
0.2-0.3	14263
0.3-0.4	5567
0.4-0.5	11285
0.5-0.6	3675
0.6-0.7	313
0.7-0.8	6
0.8-0.85	4
0.85-0.9	20
0.9-0.95	18
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC71186
0.9815	High Similarity	NPC221301
0.9725	High Similarity	NPC162294
0.9304	High Similarity	NPC173511
0.9304	High Similarity	NPC88733
0.9217	High Similarity	NPC170824
0.9145	High Similarity	NPC81149
0.9145	High Similarity	NPC230013
0.9145	High Similarity	NPC197576
0.9145	High Similarity	NPC68350
0.9145	High Similarity	NPC131940
0.913	High Similarity	NPC63317
0.913	High Similarity	NPC41232
0.9068	High Similarity	NPC163019
0.9068	High Similarity	NPC1744
0.9052	High Similarity	NPC226737
0.9052	High Similarity	NPC299939
0.9052	High Similarity	NPC153580
0.8974	High Similarity	NPC40302
0.8974	High Similarity	NPC137922
0.8957	High Similarity	NPC104124
0.8898	High Similarity	NPC175520
0.8898	High Similarity	NPC159866
0.8898	High Similarity	NPC97157
0.8898	High Similarity	NPC25134
0.8898	High Similarity	NPC64130
0.8898	High Similarity	NPC295879
0.8879	High Similarity	NPC86007
0.8879	High Similarity	NPC44270
0.8814	High Similarity	NPC235166
0.8814	High Similarity	NPC474375
0.8793	High Similarity	NPC191194
0.8729	High Similarity	NPC196371
0.8729	High Similarity	NPC47769
0.8629	High Similarity	NPC178301
0.8624	High Similarity	NPC319933
0.84	Intermediate Similarity	NPC206183
0.84	Intermediate Similarity	NPC222684
0.816	Intermediate Similarity	NPC45728
0.7717	Intermediate Similarity	NPC236265
0.7591	Intermediate Similarity	NPC8577
0.7591	Intermediate Similarity	NPC286337
0.7431	Intermediate Similarity	NPC206876
0.7156	Intermediate Similarity	NPC125306
0.7094	Intermediate Similarity	NPC314803
0.7029	Intermediate Similarity	NPC245386
0.7027	Intermediate Similarity	NPC135103
0.7	Intermediate Similarity	NPC271942
0.693	Remote Similarity	NPC318429
0.6912	Remote Similarity	NPC195902
0.6897	Remote Similarity	NPC114325
0.6889	Remote Similarity	NPC280736
0.6885	Remote Similarity	NPC41594
0.6861	Remote Similarity	NPC226493
0.6861	Remote Similarity	NPC160081
0.6829	Remote Similarity	NPC258171
0.6824	Remote Similarity	NPC152947
0.6788	Remote Similarity	NPC85049
0.6752	Remote Similarity	NPC475466
0.6741	Remote Similarity	NPC220311
0.6739	Remote Similarity	NPC70485
0.6739	Remote Similarity	NPC11449
0.6736	Remote Similarity	NPC89341
0.6713	Remote Similarity	NPC160932
0.6697	Remote Similarity	NPC124576
0.6696	Remote Similarity	NPC23837
0.6694	Remote Similarity	NPC310905
0.6694	Remote Similarity	NPC12714
0.6667	Remote Similarity	NPC474535
0.6643	Remote Similarity	NPC303011
0.6642	Remote Similarity	NPC13004
0.6623	Remote Similarity	NPC475697
0.6618	Remote Similarity	NPC110131
0.6614	Remote Similarity	NPC55300
0.6614	Remote Similarity	NPC245552
0.6599	Remote Similarity	NPC109346
0.6593	Remote Similarity	NPC474169
0.6593	Remote Similarity	NPC473572
0.6585	Remote Similarity	NPC292792
0.6579	Remote Similarity	NPC252149
0.6573	Remote Similarity	NPC213471
0.6562	Remote Similarity	NPC165646
0.6544	Remote Similarity	NPC272463
0.6533	Remote Similarity	NPC473608
0.6532	Remote Similarity	NPC307875
0.6529	Remote Similarity	NPC132725
0.6522	Remote Similarity	NPC122359
0.6522	Remote Similarity	NPC78061
0.6522	Remote Similarity	NPC159987
0.6519	Remote Similarity	NPC116562
0.6519	Remote Similarity	NPC229213
0.6512	Remote Similarity	NPC165106
0.6512	Remote Similarity	NPC471488
0.6512	Remote Similarity	NPC303522
0.6493	Remote Similarity	NPC472596
0.648	Remote Similarity	NPC232654
0.6466	Remote Similarity	NPC47422
0.6466	Remote Similarity	NPC38483
0.6463	Remote Similarity	NPC79076
0.6463	Remote Similarity	NPC135349
0.6463	Remote Similarity	NPC78530
0.6457	Remote Similarity	NPC54543
0.6439	Remote Similarity	NPC76915
0.6439	Remote Similarity	NPC151617
0.6439	Remote Similarity	NPC86947
0.6429	Remote Similarity	NPC227894
0.6423	Remote Similarity	NPC137117
0.6414	Remote Similarity	NPC168680
0.6412	Remote Similarity	NPC475815
0.6412	Remote Similarity	NPC473264
0.6412	Remote Similarity	NPC47194
0.641	Remote Similarity	NPC302546
0.6406	Remote Similarity	NPC473358
0.6404	Remote Similarity	NPC319826
0.6403	Remote Similarity	NPC474147
0.6403	Remote Similarity	NPC473708
0.64	Remote Similarity	NPC17537
0.6397	Remote Similarity	NPC261661
0.6397	Remote Similarity	NPC71090
0.6395	Remote Similarity	NPC474850
0.6395	Remote Similarity	NPC474851
0.6391	Remote Similarity	NPC277460
0.6385	Remote Similarity	NPC33244
0.6377	Remote Similarity	NPC142776
0.6369	Remote Similarity	NPC38980
0.6364	Remote Similarity	NPC9341
0.6364	Remote Similarity	NPC303993
0.6364	Remote Similarity	NPC123948
0.6364	Remote Similarity	NPC81067
0.6364	Remote Similarity	NPC163560
0.6351	Remote Similarity	NPC184632
0.635	Remote Similarity	NPC470887
0.635	Remote Similarity	NPC105999
0.635	Remote Similarity	NPC279379
0.635	Remote Similarity	NPC84606
0.6343	Remote Similarity	NPC214289
0.6336	Remote Similarity	NPC94217
0.6333	Remote Similarity	NPC71629
0.6333	Remote Similarity	NPC296085
0.6331	Remote Similarity	NPC475361
0.6331	Remote Similarity	NPC134219
0.6331	Remote Similarity	NPC43706
0.6328	Remote Similarity	NPC36108
0.6328	Remote Similarity	NPC233731
0.6328	Remote Similarity	NPC7097
0.6328	Remote Similarity	NPC165386
0.6328	Remote Similarity	NPC246358
0.6328	Remote Similarity	NPC127326
0.6325	Remote Similarity	NPC157213
0.6324	Remote Similarity	NPC145780
0.6324	Remote Similarity	NPC127389
0.6324	Remote Similarity	NPC290451
0.6316	Remote Similarity	NPC9248
0.6316	Remote Similarity	NPC293619
0.6316	Remote Similarity	NPC185738
0.6316	Remote Similarity	NPC280001
0.6311	Remote Similarity	NPC313918
0.6304	Remote Similarity	NPC114901
0.6304	Remote Similarity	NPC213414
0.6304	Remote Similarity	NPC74478
0.6304	Remote Similarity	NPC293701
0.6304	Remote Similarity	NPC48990
0.6304	Remote Similarity	NPC94276
0.6304	Remote Similarity	NPC109822
0.6303	Remote Similarity	NPC475396
0.6301	Remote Similarity	NPC156356
0.6299	Remote Similarity	NPC124712
0.6299	Remote Similarity	NPC194034
0.629	Remote Similarity	NPC300166
0.629	Remote Similarity	NPC51633
0.6284	Remote Similarity	NPC250597
0.6279	Remote Similarity	NPC179309
0.6279	Remote Similarity	NPC137685
0.6277	Remote Similarity	NPC47790
0.6277	Remote Similarity	NPC219444
0.6271	Remote Similarity	NPC177844
0.6271	Remote Similarity	NPC8002
0.6271	Remote Similarity	NPC259134
0.6271	Remote Similarity	NPC99886
0.6269	Remote Similarity	NPC159916
0.6269	Remote Similarity	NPC470626
0.6269	Remote Similarity	NPC228907
0.6269	Remote Similarity	NPC474040
0.6269	Remote Similarity	NPC124916
0.6269	Remote Similarity	NPC474214
0.626	Remote Similarity	NPC307039
0.626	Remote Similarity	NPC471576
0.6259	Remote Similarity	NPC194519
0.625	Remote Similarity	NPC76412
0.625	Remote Similarity	NPC471495
0.625	Remote Similarity	NPC205850
0.625	Remote Similarity	NPC276195
0.625	Remote Similarity	NPC244890
0.6241	Remote Similarity	NPC196034
0.6241	Remote Similarity	NPC150929
0.624	Remote Similarity	NPC192596
0.6233	Remote Similarity	NPC224663
0.6231	Remote Similarity	NPC257124
0.6231	Remote Similarity	NPC156840
0.6231	Remote Similarity	NPC203924

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 NPC264379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	644
0.1-0.2	1395
0.2-0.3	3251
0.3-0.4	2301
0.4-0.5	1167
0.5-0.6	368
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7119	Intermediate Similarity	NPD291	Approved
0.693	Remote Similarity	NPD9365	Approved
0.6897	Remote Similarity	NPD9296	Approved
0.672	Remote Similarity	NPD556	Approved
0.6512	Remote Similarity	NPD5283	Phase 1
0.6439	Remote Similarity	NPD1102	Approved
0.6439	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1103	Approved
0.6349	Remote Similarity	NPD968	Approved
0.6325	Remote Similarity	NPD9295	Approved
0.632	Remote Similarity	NPD9501	Approved
0.6316	Remote Similarity	NPD5536	Phase 2
0.6299	Remote Similarity	NPD290	Approved
0.6269	Remote Similarity	NPD7534	Approved
0.6269	Remote Similarity	NPD7533	Approved
0.625	Remote Similarity	NPD2684	Approved
0.6231	Remote Similarity	NPD228	Approved
0.6222	Remote Similarity	NPD1797	Approved
0.6222	Remote Similarity	NPD1798	Approved
0.6172	Remote Similarity	NPD9552	Approved
0.6131	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD915	Approved
0.6127	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD9244	Approved
0.6061	Remote Similarity	NPD769	Approved
0.6061	Remote Similarity	NPD5535	Approved
0.6061	Remote Similarity	NPD7843	Approved
0.6047	Remote Similarity	NPD1358	Approved
0.6043	Remote Similarity	NPD2981	Phase 2
0.6031	Remote Similarity	NPD2673	Approved
0.6031	Remote Similarity	NPD2671	Approved
0.6028	Remote Similarity	NPD1318	Phase 2
0.6	Remote Similarity	NPD3532	Approved
0.6	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2982	Phase 2
0.6	Remote Similarity	NPD3530	Approved
0.6	Remote Similarity	NPD3531	Approved
0.6	Remote Similarity	NPD2983	Phase 2
0.597	Remote Similarity	NPD9299	Approved
0.5957	Remote Similarity	NPD2922	Phase 1
0.5954	Remote Similarity	NPD5451	Approved
0.5942	Remote Similarity	NPD6516	Phase 2
0.5942	Remote Similarity	NPD5846	Approved
0.5926	Remote Similarity	NPD2557	Approved
0.5926	Remote Similarity	NPD7157	Approved
0.5923	Remote Similarity	NPD5374	Approved
0.5923	Remote Similarity	NPD9624	Approved
0.5923	Remote Similarity	NPD5373	Approved
0.5918	Remote Similarity	NPD1933	Approved
0.5915	Remote Similarity	NPD9549	Phase 2
0.5915	Remote Similarity	NPD4010	Discontinued
0.5896	Remote Similarity	NPD1241	Discontinued
0.5891	Remote Similarity	NPD9697	Approved
0.5882	Remote Similarity	NPD3596	Phase 2
0.5879	Remote Similarity	NPD6687	Approved
0.5879	Remote Similarity	NPD6688	Approved
0.587	Remote Similarity	NPD5585	Approved
0.587	Remote Similarity	NPD1357	Approved
0.5857	Remote Similarity	NPD3705	Approved
0.585	Remote Similarity	NPD1558	Phase 1
0.5846	Remote Similarity	NPD3134	Approved
0.5839	Remote Similarity	NPD2296	Approved
0.5833	Remote Similarity	NPD3018	Phase 2
0.5833	Remote Similarity	NPD2250	Discontinued
0.5833	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD821	Approved
0.5809	Remote Similarity	NPD191	Approved
0.5804	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD1182	Approved
0.5797	Remote Similarity	NPD1548	Phase 1
0.5797	Remote Similarity	NPD6581	Approved
0.5797	Remote Similarity	NPD6580	Approved
0.5793	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD4870	Approved
0.5755	Remote Similarity	NPD3049	Approved
0.5755	Remote Similarity	NPD3444	Approved
0.5755	Remote Similarity	NPD6382	Discontinued
0.5755	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD2595	Approved
0.5755	Remote Similarity	NPD3445	Approved
0.5755	Remote Similarity	NPD2594	Approved
0.5755	Remote Similarity	NPD3443	Approved
0.5753	Remote Similarity	NPD3027	Phase 3
0.5743	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD1613	Approved
0.5741	Remote Similarity	NPD4288	Approved
0.5724	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2556	Approved
0.5714	Remote Similarity	NPD2554	Approved
0.5714	Remote Similarity	NPD5718	Phase 2
0.5714	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5109	Approved
0.5714	Remote Similarity	NPD5110	Phase 2
0.5714	Remote Similarity	NPD5111	Phase 2
0.5714	Remote Similarity	NPD17	Approved
0.5696	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD6671	Approved
0.5683	Remote Similarity	NPD2486	Discontinued
0.5683	Remote Similarity	NPD1894	Discontinued
0.5676	Remote Similarity	NPD481	Phase 3
0.5676	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD3447	Discontinued
0.5664	Remote Similarity	NPD4359	Approved
0.5664	Remote Similarity	NPD6582	Phase 2
0.5664	Remote Similarity	NPD6583	Phase 3
0.5658	Remote Similarity	NPD3454	Phase 3
0.5649	Remote Similarity	NPD4162	Approved
0.5634	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD1611	Approved
0.5634	Remote Similarity	NPD1610	Phase 2
0.5634	Remote Similarity	NPD776	Approved
0.5634	Remote Similarity	NPD1091	Approved
0.5613	Remote Similarity	NPD6331	Phase 2
0.5613	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD254	Approved
0.5608	Remote Similarity	NPD6798	Discontinued
0.5604	Remote Similarity	NPD8095	Phase 1
0.5603	Remote Similarity	NPD2107	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