NPASS Compound

Structure

CID221301 OpenBabel06191716012D 21 22 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -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 0.0000 -0.0000 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 -5.1962 -2.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	541.74
Volume:	321.274
LogP:	6.135
LogD:	3.205
LogS:	-7.723
# Rotatable Bonds:	4
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	2.391
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:	-5.004
MDCK Permeability:	1.722392516967375e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.793
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443
Plasma Protein Binding (PPB):	99.26956939697266%
Volume Distribution (VD):	3.92
Pgp-substrate:	6.854031085968018%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.417
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.185
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	0.863
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.246
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.763
Carcinogencity:	0.111
Eye Corrosion:	0.261
Eye Irritation:	0.939
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC221301

Natural Product ID:	NPC221301
*Common Name:**	1,5-Dibromo-2-(3,5-Dibromo-2-Methoxyphenoxy)-3-Methoxybenzene
IUPAC Name:	1,5-dibromo-2-(3,5-dibromo-2-methoxyphenoxy)-3-methoxybenzene
Synonyms:
Standard InCHIKey:	RUJCIUYVRUQTQY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10Br4O3/c1-19-11-5-7(15)4-10(18)14(11)21-12-6-8(16)3-9(17)13(12)20-2/h3-6H,1-2H3
SMILES:	COc1cc(Br)cc(c1Oc1cc(Br)cc(c1OC)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221215
PubChem CID:	11978812
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]
NPO24471	Dysidea dendyi	Species	Dysideidae	Eukaryota	n.a.	Australian	n.a.	PMID[11434317]
NPO24471	Dysidea dendyi	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193037]
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]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	Niphates recondita	Weizhou Island, Beibuwan Bay, Guangxi,China	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387683]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28530828]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31265296]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32966070]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514013]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO5958	Senegalia modesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12364	Polyides rotundus	Species	Polyideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12931	Carex pumila	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8395.1	Crepis foetida subsp. rhoeadifolia	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8857	Hydnum repandum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9977	Polygonum sieboldi	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28504	Calothrix brevissima	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6781	Senecio acanthifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13038	Fomes hartigii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8225	Salvia karabachensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12586	Tapirira guianensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10944	Mantella baroni	Species	Mantellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2453	Stachybotrys chartarum	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12708	Rothia indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24471	Dysidea dendyi	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	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]
NPO2431	Penicilliopsis zonata	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3308	Calycadenia fremontii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7116	Monachosorum henryi	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9355	Polygonatum orientale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9147	Frasera albomarginata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5472	Spongia foliascens	Species	Spongiidae	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
Others	4

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.0	mm	PMID[488350]
NPT2	Others	Unspecified		IC50	=	137000.0	nM	PMID[488352]

☑ 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 NPC221301 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	793
0.1-0.2	6366
0.2-0.3	14501
0.3-0.4	5361
0.4-0.5	11028
0.5-0.6	4164
0.6-0.7	426
0.7-0.8	8
0.8-0.85	5
0.85-0.9	30
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC162294
0.9815	High Similarity	NPC264379
0.9636	High Similarity	NPC71186
0.9381	High Similarity	NPC170824
0.913	High Similarity	NPC173511
0.913	High Similarity	NPC88733
0.9115	High Similarity	NPC104124
0.9035	High Similarity	NPC44270
0.9035	High Similarity	NPC86007
0.8974	High Similarity	NPC197576
0.8974	High Similarity	NPC68350
0.8974	High Similarity	NPC81149
0.8974	High Similarity	NPC230013
0.8974	High Similarity	NPC131940
0.8966	High Similarity	NPC235166
0.8957	High Similarity	NPC41232
0.8957	High Similarity	NPC63317
0.8898	High Similarity	NPC1744
0.8898	High Similarity	NPC163019
0.8879	High Similarity	NPC153580
0.8879	High Similarity	NPC299939
0.8879	High Similarity	NPC226737
0.8879	High Similarity	NPC196371
0.8879	High Similarity	NPC47769
0.8803	High Similarity	NPC40302
0.8803	High Similarity	NPC137922
0.8785	High Similarity	NPC319933
0.8729	High Similarity	NPC295879
0.8729	High Similarity	NPC64130
0.8729	High Similarity	NPC25134
0.8729	High Similarity	NPC97157
0.8729	High Similarity	NPC159866
0.8729	High Similarity	NPC175520
0.8644	High Similarity	NPC474375
0.8621	High Similarity	NPC191194
0.8468	Intermediate Similarity	NPC178301
0.8293	Intermediate Similarity	NPC45728
0.824	Intermediate Similarity	NPC222684
0.824	Intermediate Similarity	NPC206183
0.7704	Intermediate Similarity	NPC286337
0.7704	Intermediate Similarity	NPC8577
0.757	Intermediate Similarity	NPC206876
0.7559	Intermediate Similarity	NPC236265
0.729	Intermediate Similarity	NPC125306
0.7217	Intermediate Similarity	NPC314803
0.7054	Intermediate Similarity	NPC318429
0.7018	Intermediate Similarity	NPC114325
0.7015	Intermediate Similarity	NPC195902
0.7	Intermediate Similarity	NPC41594
0.6992	Remote Similarity	NPC280736
0.6942	Remote Similarity	NPC258171
0.6918	Remote Similarity	NPC152947
0.6892	Remote Similarity	NPC135103
0.6884	Remote Similarity	NPC245386
0.6857	Remote Similarity	NPC271942
0.6838	Remote Similarity	NPC70485
0.6838	Remote Similarity	NPC11449
0.6822	Remote Similarity	NPC124576
0.6818	Remote Similarity	NPC23837
0.6807	Remote Similarity	NPC310905
0.6807	Remote Similarity	NPC12714
0.672	Remote Similarity	NPC245552
0.672	Remote Similarity	NPC55300
0.6716	Remote Similarity	NPC110131
0.6715	Remote Similarity	NPC226493
0.6715	Remote Similarity	NPC160081
0.6696	Remote Similarity	NPC252149
0.6694	Remote Similarity	NPC292792
0.6692	Remote Similarity	NPC474169
0.6692	Remote Similarity	NPC473572
0.6667	Remote Similarity	NPC165646
0.6667	Remote Similarity	NPC213471
0.6642	Remote Similarity	NPC85049
0.6642	Remote Similarity	NPC272463
0.6639	Remote Similarity	NPC132725
0.6639	Remote Similarity	NPC307875
0.6618	Remote Similarity	NPC78061
0.6618	Remote Similarity	NPC159987
0.6618	Remote Similarity	NPC122359
0.6617	Remote Similarity	NPC116562
0.6617	Remote Similarity	NPC229213
0.6614	Remote Similarity	NPC471488
0.6614	Remote Similarity	NPC165106
0.6614	Remote Similarity	NPC303522
0.6597	Remote Similarity	NPC89341
0.6593	Remote Similarity	NPC220311
0.6591	Remote Similarity	NPC472596
0.6585	Remote Similarity	NPC232654
0.6581	Remote Similarity	NPC475466
0.6579	Remote Similarity	NPC47422
0.6573	Remote Similarity	NPC160932
0.6565	Remote Similarity	NPC38483
0.656	Remote Similarity	NPC54543
0.6552	Remote Similarity	NPC78530
0.6552	Remote Similarity	NPC135349
0.6538	Remote Similarity	NPC76915
0.6538	Remote Similarity	NPC151617
0.6538	Remote Similarity	NPC86947
0.6536	Remote Similarity	NPC474535
0.6532	Remote Similarity	NPC227894
0.6522	Remote Similarity	NPC302546
0.6518	Remote Similarity	NPC319826
0.6512	Remote Similarity	NPC475815
0.6512	Remote Similarity	NPC47194
0.6512	Remote Similarity	NPC473264
0.6508	Remote Similarity	NPC473358
0.6504	Remote Similarity	NPC17537
0.65	Remote Similarity	NPC303011
0.6496	Remote Similarity	NPC13004
0.6496	Remote Similarity	NPC474147
0.6496	Remote Similarity	NPC473708
0.6494	Remote Similarity	NPC475697
0.6493	Remote Similarity	NPC71090
0.6493	Remote Similarity	NPC261661
0.6489	Remote Similarity	NPC277460
0.6484	Remote Similarity	NPC33244
0.6483	Remote Similarity	NPC474851
0.6483	Remote Similarity	NPC474850
0.6463	Remote Similarity	NPC109346
0.6462	Remote Similarity	NPC123948
0.6462	Remote Similarity	NPC81067
0.6462	Remote Similarity	NPC9341
0.6454	Remote Similarity	NPC303993
0.6452	Remote Similarity	NPC38980
0.6444	Remote Similarity	NPC279379
0.6444	Remote Similarity	NPC105999
0.6444	Remote Similarity	NPC470887
0.6439	Remote Similarity	NPC214289
0.6438	Remote Similarity	NPC184632
0.6435	Remote Similarity	NPC157213
0.6434	Remote Similarity	NPC94217
0.6429	Remote Similarity	NPC233731
0.6429	Remote Similarity	NPC165386
0.6429	Remote Similarity	NPC246358
0.6429	Remote Similarity	NPC127326
0.6429	Remote Similarity	NPC7097
0.6429	Remote Similarity	NPC36108
0.6423	Remote Similarity	NPC475361
0.6423	Remote Similarity	NPC43706
0.6419	Remote Similarity	NPC296085
0.6419	Remote Similarity	NPC71629
0.6418	Remote Similarity	NPC290451
0.6418	Remote Similarity	NPC145780
0.6418	Remote Similarity	NPC127389
0.6417	Remote Similarity	NPC313918
0.6412	Remote Similarity	NPC293619
0.6412	Remote Similarity	NPC280001
0.6412	Remote Similarity	NPC185738
0.6412	Remote Similarity	NPC9248
0.64	Remote Similarity	NPC124712
0.64	Remote Similarity	NPC194034
0.64	Remote Similarity	NPC473608
0.6397	Remote Similarity	NPC48990
0.6397	Remote Similarity	NPC109822
0.6397	Remote Similarity	NPC74478
0.6397	Remote Similarity	NPC213414
0.6397	Remote Similarity	NPC293701
0.6397	Remote Similarity	NPC114901
0.6397	Remote Similarity	NPC94276
0.6393	Remote Similarity	NPC300166
0.6393	Remote Similarity	NPC51633
0.6389	Remote Similarity	NPC156356
0.638	Remote Similarity	NPC475396
0.6379	Remote Similarity	NPC177844
0.6379	Remote Similarity	NPC8002
0.6379	Remote Similarity	NPC259134
0.6379	Remote Similarity	NPC99886
0.6378	Remote Similarity	NPC179309
0.6378	Remote Similarity	NPC137685
0.637	Remote Similarity	NPC250597
0.6364	Remote Similarity	NPC470626
0.6364	Remote Similarity	NPC474040
0.6364	Remote Similarity	NPC307039
0.6364	Remote Similarity	NPC471576
0.6364	Remote Similarity	NPC124916
0.6364	Remote Similarity	NPC474214
0.6364	Remote Similarity	NPC159916
0.6364	Remote Similarity	NPC228907
0.635	Remote Similarity	NPC194519
0.6349	Remote Similarity	NPC471495
0.6343	Remote Similarity	NPC276195
0.6343	Remote Similarity	NPC205850
0.6341	Remote Similarity	NPC192596
0.6333	Remote Similarity	NPC76412
0.6331	Remote Similarity	NPC196034
0.6328	Remote Similarity	NPC195873
0.6328	Remote Similarity	NPC8547
0.6328	Remote Similarity	NPC156840
0.6328	Remote Similarity	NPC139617
0.6328	Remote Similarity	NPC78918
0.6328	Remote Similarity	NPC257124
0.6328	Remote Similarity	NPC173746
0.6328	Remote Similarity	NPC203924
0.6327	Remote Similarity	NPC79076
0.6325	Remote Similarity	NPC71853
0.632	Remote Similarity	NPC326801
0.6316	Remote Similarity	NPC15805
0.6316	Remote Similarity	NPC475961
0.6316	Remote Similarity	NPC474320
0.6316	Remote Similarity	NPC310338

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 NPC221301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	624
0.1-0.2	1357
0.2-0.3	3222
0.3-0.4	2312
0.4-0.5	1186
0.5-0.6	421
0.6-0.7	27
0.7-0.8	1
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
0.7241	Intermediate Similarity	NPD291	Approved
0.7054	Intermediate Similarity	NPD9365	Approved
0.7018	Intermediate Similarity	NPD9296	Approved
0.6829	Remote Similarity	NPD556	Approved
0.6614	Remote Similarity	NPD5283	Phase 1
0.6538	Remote Similarity	NPD1102	Approved
0.6538	Remote Similarity	NPD1103	Approved
0.6538	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD968	Approved
0.6435	Remote Similarity	NPD9295	Approved
0.6423	Remote Similarity	NPD9501	Approved
0.6412	Remote Similarity	NPD5536	Phase 2
0.64	Remote Similarity	NPD290	Approved
0.6364	Remote Similarity	NPD7533	Approved
0.6364	Remote Similarity	NPD7534	Approved
0.6349	Remote Similarity	NPD2684	Approved
0.6328	Remote Similarity	NPD228	Approved
0.6316	Remote Similarity	NPD1797	Approved
0.6316	Remote Similarity	NPD1798	Approved
0.627	Remote Similarity	NPD9552	Approved
0.6222	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD915	Approved
0.6214	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.616	Remote Similarity	NPD9244	Approved
0.6154	Remote Similarity	NPD5535	Approved
0.6154	Remote Similarity	NPD7843	Approved
0.6154	Remote Similarity	NPD769	Approved
0.6142	Remote Similarity	NPD1358	Approved
0.6131	Remote Similarity	NPD2981	Phase 2
0.6124	Remote Similarity	NPD2673	Approved
0.6124	Remote Similarity	NPD2671	Approved
0.6115	Remote Similarity	NPD1318	Phase 2
0.6087	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2982	Phase 2
0.6087	Remote Similarity	NPD2983	Phase 2
0.6084	Remote Similarity	NPD3531	Approved
0.6084	Remote Similarity	NPD3530	Approved
0.6084	Remote Similarity	NPD3532	Approved
0.6061	Remote Similarity	NPD9299	Approved
0.6047	Remote Similarity	NPD5451	Approved
0.6043	Remote Similarity	NPD2922	Phase 1
0.6029	Remote Similarity	NPD5846	Approved
0.6029	Remote Similarity	NPD6516	Phase 2
0.6016	Remote Similarity	NPD5373	Approved
0.6016	Remote Similarity	NPD9624	Approved
0.6016	Remote Similarity	NPD5374	Approved
0.6015	Remote Similarity	NPD2557	Approved
0.6015	Remote Similarity	NPD7157	Approved
0.6	Remote Similarity	NPD1933	Approved
0.6	Remote Similarity	NPD9549	Phase 2
0.5988	Remote Similarity	NPD4010	Discontinued
0.5985	Remote Similarity	NPD1241	Discontinued
0.5984	Remote Similarity	NPD9697	Approved
0.597	Remote Similarity	NPD3596	Phase 2
0.5956	Remote Similarity	NPD5585	Approved
0.5956	Remote Similarity	NPD1357	Approved
0.5951	Remote Similarity	NPD6687	Approved
0.5951	Remote Similarity	NPD6688	Approved
0.5942	Remote Similarity	NPD3705	Approved
0.5938	Remote Similarity	NPD3134	Approved
0.5931	Remote Similarity	NPD1558	Phase 1
0.5915	Remote Similarity	NPD3018	Phase 2
0.5915	Remote Similarity	NPD2250	Discontinued
0.5915	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD2296	Approved
0.5909	Remote Similarity	NPD821	Approved
0.5896	Remote Similarity	NPD191	Approved
0.5887	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1548	Phase 1
0.5882	Remote Similarity	NPD6580	Approved
0.5882	Remote Similarity	NPD6581	Approved
0.5882	Remote Similarity	NPD1182	Approved
0.5878	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4870	Approved
0.5839	Remote Similarity	NPD3049	Approved
0.5839	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD3443	Approved
0.5839	Remote Similarity	NPD2595	Approved
0.5839	Remote Similarity	NPD2594	Approved
0.5839	Remote Similarity	NPD3444	Approved
0.5839	Remote Similarity	NPD6382	Discontinued
0.5839	Remote Similarity	NPD3445	Approved
0.5833	Remote Similarity	NPD3027	Phase 3
0.5822	Remote Similarity	NPD1613	Approved
0.5822	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD4288	Approved
0.5804	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD2556	Approved
0.5797	Remote Similarity	NPD2554	Approved
0.5797	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD17	Approved
0.5793	Remote Similarity	NPD5111	Phase 2
0.5793	Remote Similarity	NPD5718	Phase 2
0.5793	Remote Similarity	NPD5109	Approved
0.5793	Remote Similarity	NPD5110	Phase 2
0.5778	Remote Similarity	NPD6671	Approved
0.5769	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD1894	Discontinued
0.5766	Remote Similarity	NPD2486	Discontinued
0.5755	Remote Similarity	NPD3447	Discontinued
0.5753	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD481	Phase 3
0.5745	Remote Similarity	NPD6582	Phase 2
0.5745	Remote Similarity	NPD6583	Phase 3
0.5745	Remote Similarity	NPD4359	Approved
0.5733	Remote Similarity	NPD3454	Phase 3
0.5724	Remote Similarity	NPD4162	Approved
0.5714	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1091	Approved
0.5714	Remote Similarity	NPD776	Approved
0.5714	Remote Similarity	NPD1610	Phase 2
0.5714	Remote Similarity	NPD1611	Approved
0.5693	Remote Similarity	NPD254	Approved
0.5686	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6331	Phase 2
0.5685	Remote Similarity	NPD6798	Discontinued
0.5683	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD1840	Phase 2
0.5674	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD1608	Approved
0.5672	Remote Similarity	NPD2496	Approved
0.5672	Remote Similarity	NPD2497	Approved
0.5667	Remote Similarity	NPD8095	Phase 1
0.5664	Remote Similarity	NPD4098	Discontinued
0.5662	Remote Similarity	NPD709	Approved
0.5646	Remote Similarity	NPD6233	Phase 2
0.5646	Remote Similarity	NPD4062	Phase 3
0.5643	Remote Similarity	NPD3294	Phase 2
0.5634	Remote Similarity	NPD2429	Approved
0.5634	Remote Similarity	NPD6540	Phase 3
0.5634	Remote Similarity	NPD5327	Phase 3
0.5634	Remote Similarity	NPD2428	Approved
0.5634	Remote Similarity	NPD6539	Approved
0.5634	Remote Similarity	NPD6543	Approved
0.5634	Remote Similarity	NPD6542	Approved
0.5634	Remote Similarity	NPD4129	Approved
0.563	Remote Similarity	NPD592	Approved
0.563	Remote Similarity	NPD594	Approved
0.563	Remote Similarity	NPD9069	Phase 1
0.5629	Remote Similarity	NPD729	Discontinued
0.5625	Remote Similarity	NPD6584	Phase 3
0.5616	Remote Similarity	NPD7095	Approved
0.5612	Remote Similarity	NPD1651	Approved
0.5608	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD3620	Phase 2
0.5608	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD4060	Phase 1
0.5603	Remote Similarity	NPD1535	Discovery
0.56	Remote Similarity	NPD6895	Approved
0.56	Remote Similarity	NPD6896	Approved

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