NPASS Compound

Structure

NPC245386 OpenBabel07101718242D 23 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 -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 -3.0000 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 -4.3301 -2.5000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -5.1962 -4.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -5.1962 0.0000 0.0000 O 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 -6.9282 -1.0000 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 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 7 1 0 0 0 0 2 6 2 0 0 0 0 2 8 1 0 0 0 0 3 5 1 0 0 0 0 3 23 1 0 0 0 0 4 6 1 0 0 0 0 4 23 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 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:	573.73
Volume:	338.854
LogP:	4.862
LogD:	3.055
LogS:	-4.001
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	3.141
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995
MDCK Permeability:	1.47412329170038e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.956
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	100.4588394165039%
Volume Distribution (VD):	1.049
Pgp-substrate:	1.1968938112258911%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.255
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	1.532
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.97
Carcinogencity:	0.046
Eye Corrosion:	0.012
Eye Irritation:	0.941
Respiratory Toxicity:	0.142

Download Data

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

Natural Product: NPC245386

Natural Product ID:	NPC245386
*Common Name:**	Bis(2,3-Dibromo-4,5-Dihydroxybenzyl)Ether
IUPAC Name:	3,4-dibromo-5-[(2,3-dibromo-4,5-dihydroxyphenyl)methoxymethyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	NVINDBOUFPDPNZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10Br4O5/c15-9-5(1-7(19)13(21)11(9)17)3-23-4-6-2-8(20)14(22)12(18)10(6)16/h1-2,19-22H,3-4H2
SMILES:	c1c(COCc2cc(c(c(c2Br)Br)O)O)c(c(c(c1O)O)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491516
PubChem CID:	10053921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497936]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	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	7
MIC	9

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	19500.0	nM	PMID[551415]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	8600.0	nM	PMID[551415]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21400.0	nM	PMID[551415]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	1900.0	nM	PMID[551415]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	20700.0	nM	PMID[551415]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	28060.0	nM	PMID[551417]
NPT2	Others	Unspecified		IC50	=	98.0	nM	PMID[551416]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[551417]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[551417]

☑ 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 NPC245386 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	603
0.1-0.2	2577
0.2-0.3	10225
0.3-0.4	10396
0.4-0.5	5871
0.5-0.6	9795
0.6-0.7	3008
0.7-0.8	181
0.8-0.85	15
0.85-0.9	16
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC271942
0.9531	High Similarity	NPC226493
0.9531	High Similarity	NPC160081
0.9453	High Similarity	NPC85049
0.9403	High Similarity	NPC89341
0.9398	High Similarity	NPC160932
0.9237	High Similarity	NPC303011
0.9197	High Similarity	NPC109346
0.9037	High Similarity	NPC156356
0.9023	High Similarity	NPC163560
0.9	High Similarity	NPC473708
0.9	High Similarity	NPC474147
0.8992	High Similarity	NPC220311
0.8984	High Similarity	NPC474169
0.8984	High Similarity	NPC473572
0.8923	High Similarity	NPC43706
0.8915	High Similarity	NPC137117
0.8906	High Similarity	NPC47790
0.8906	High Similarity	NPC229213
0.8788	High Similarity	NPC150929
0.8759	High Similarity	NPC168680
0.8722	High Similarity	NPC474614
0.8686	High Similarity	NPC224663
0.8636	High Similarity	NPC134219
0.8603	High Similarity	NPC244890
0.8571	High Similarity	NPC13004
0.8483	Intermediate Similarity	NPC152947
0.845	Intermediate Similarity	NPC38483
0.8385	Intermediate Similarity	NPC474146
0.8359	Intermediate Similarity	NPC79844
0.831	Intermediate Similarity	NPC118794
0.8271	Intermediate Similarity	NPC84606
0.8261	Intermediate Similarity	NPC300678
0.8258	Intermediate Similarity	NPC136543
0.8195	Intermediate Similarity	NPC219444
0.8182	Intermediate Similarity	NPC227976
0.8148	Intermediate Similarity	NPC142776
0.8108	Intermediate Similarity	NPC7398
0.8092	Intermediate Similarity	NPC475697
0.8026	Intermediate Similarity	NPC474535
0.8014	Intermediate Similarity	NPC312155
0.7914	Intermediate Similarity	NPC474536
0.7905	Intermediate Similarity	NPC88896
0.7801	Intermediate Similarity	NPC43613
0.7727	Intermediate Similarity	NPC50782
0.7647	Intermediate Similarity	NPC470414
0.7635	Intermediate Similarity	NPC184632
0.763	Intermediate Similarity	NPC117759
0.7586	Intermediate Similarity	NPC199089
0.758	Intermediate Similarity	NPC38980
0.7569	Intermediate Similarity	NPC471328
0.7566	Intermediate Similarity	NPC473608
0.7535	Intermediate Similarity	NPC105702
0.7482	Intermediate Similarity	NPC473451
0.7464	Intermediate Similarity	NPC88733
0.7464	Intermediate Similarity	NPC173511
0.7462	Intermediate Similarity	NPC471495
0.7445	Intermediate Similarity	NPC63317
0.7445	Intermediate Similarity	NPC41232
0.7444	Intermediate Similarity	NPC471488
0.7429	Intermediate Similarity	NPC131747
0.7429	Intermediate Similarity	NPC257682
0.7429	Intermediate Similarity	NPC146355
0.7426	Intermediate Similarity	NPC191194
0.7405	Intermediate Similarity	NPC54543
0.7391	Intermediate Similarity	NPC471486
0.7391	Intermediate Similarity	NPC153580
0.7391	Intermediate Similarity	NPC226737
0.7391	Intermediate Similarity	NPC170824
0.7391	Intermediate Similarity	NPC299939
0.7386	Intermediate Similarity	NPC178097
0.7361	Intermediate Similarity	NPC178301
0.7357	Intermediate Similarity	NPC68350
0.7357	Intermediate Similarity	NPC131940
0.7357	Intermediate Similarity	NPC81149
0.7357	Intermediate Similarity	NPC230013
0.7357	Intermediate Similarity	NPC197576
0.7348	Intermediate Similarity	NPC473358
0.7348	Intermediate Similarity	NPC471487
0.7338	Intermediate Similarity	NPC137922
0.7338	Intermediate Similarity	NPC40302
0.7338	Intermediate Similarity	NPC147654
0.7324	Intermediate Similarity	NPC58607
0.7324	Intermediate Similarity	NPC178284
0.7324	Intermediate Similarity	NPC191037
0.732	Intermediate Similarity	NPC113862
0.7313	Intermediate Similarity	NPC471485
0.7299	Intermediate Similarity	NPC275519
0.7299	Intermediate Similarity	NPC104124
0.7292	Intermediate Similarity	NPC222684
0.7292	Intermediate Similarity	NPC206183
0.7286	Intermediate Similarity	NPC97157
0.7286	Intermediate Similarity	NPC25134
0.7286	Intermediate Similarity	NPC64130
0.7286	Intermediate Similarity	NPC175520
0.7286	Intermediate Similarity	NPC159866
0.7286	Intermediate Similarity	NPC295879
0.7286	Intermediate Similarity	NPC296202
0.7273	Intermediate Similarity	NPC147821
0.7273	Intermediate Similarity	NPC41706
0.7273	Intermediate Similarity	NPC111247
0.7273	Intermediate Similarity	NPC163332
0.7273	Intermediate Similarity	NPC118787
0.7273	Intermediate Similarity	NPC183181
0.7273	Intermediate Similarity	NPC473372
0.7273	Intermediate Similarity	NPC319625
0.7273	Intermediate Similarity	NPC292056
0.7254	Intermediate Similarity	NPC194519
0.7246	Intermediate Similarity	NPC477803
0.7246	Intermediate Similarity	NPC86007
0.7246	Intermediate Similarity	NPC320987
0.7246	Intermediate Similarity	NPC226629
0.7246	Intermediate Similarity	NPC181969
0.7246	Intermediate Similarity	NPC44270
0.7234	Intermediate Similarity	NPC105999
0.7234	Intermediate Similarity	NPC212541
0.7234	Intermediate Similarity	NPC471693
0.7222	Intermediate Similarity	NPC252307
0.7222	Intermediate Similarity	NPC128208
0.7222	Intermediate Similarity	NPC55113
0.7222	Intermediate Similarity	NPC45774
0.7222	Intermediate Similarity	NPC184733
0.7222	Intermediate Similarity	NPC474178
0.7222	Intermediate Similarity	NPC245826
0.7222	Intermediate Similarity	NPC129570
0.7222	Intermediate Similarity	NPC11258
0.7222	Intermediate Similarity	NPC21867
0.7222	Intermediate Similarity	NPC72529
0.7222	Intermediate Similarity	NPC282703
0.7214	Intermediate Similarity	NPC7830
0.7214	Intermediate Similarity	NPC470804
0.7214	Intermediate Similarity	NPC474375
0.7194	Intermediate Similarity	NPC35071
0.7194	Intermediate Similarity	NPC148615
0.7194	Intermediate Similarity	NPC177475
0.7188	Intermediate Similarity	NPC305490
0.7188	Intermediate Similarity	NPC223393
0.7185	Intermediate Similarity	NPC264558
0.7185	Intermediate Similarity	NPC33244
0.7183	Intermediate Similarity	NPC109822
0.7183	Intermediate Similarity	NPC94276
0.7183	Intermediate Similarity	NPC213414
0.7174	Intermediate Similarity	NPC255675
0.7172	Intermediate Similarity	NPC5851
0.7172	Intermediate Similarity	NPC86030
0.7163	Intermediate Similarity	NPC209567
0.7154	Intermediate Similarity	NPC471511
0.7154	Intermediate Similarity	NPC12278
0.7153	Intermediate Similarity	NPC122359
0.7153	Intermediate Similarity	NPC5428
0.7153	Intermediate Similarity	NPC118533
0.7153	Intermediate Similarity	NPC221049
0.7153	Intermediate Similarity	NPC165045
0.7153	Intermediate Similarity	NPC78061
0.7153	Intermediate Similarity	NPC159987
0.7152	Intermediate Similarity	NPC135103
0.7143	Intermediate Similarity	NPC196371
0.7143	Intermediate Similarity	NPC474135
0.7143	Intermediate Similarity	NPC47769
0.7133	Intermediate Similarity	NPC148627
0.7132	Intermediate Similarity	NPC120280
0.7132	Intermediate Similarity	NPC94217
0.7123	Intermediate Similarity	NPC42300
0.7123	Intermediate Similarity	NPC257582
0.7123	Intermediate Similarity	NPC153739
0.7123	Intermediate Similarity	NPC241522
0.7123	Intermediate Similarity	NPC174495
0.7123	Intermediate Similarity	NPC64201
0.7123	Intermediate Similarity	NPC187998
0.7123	Intermediate Similarity	NPC145305
0.7123	Intermediate Similarity	NPC92164
0.7123	Intermediate Similarity	NPC77040
0.7123	Intermediate Similarity	NPC11449
0.7123	Intermediate Similarity	NPC242807
0.7122	Intermediate Similarity	NPC141791
0.7122	Intermediate Similarity	NPC263386
0.7113	Intermediate Similarity	NPC136319
0.7113	Intermediate Similarity	NPC84086
0.7107	Intermediate Similarity	NPC294870
0.7105	Intermediate Similarity	NPC250597
0.7103	Intermediate Similarity	NPC472968
0.7103	Intermediate Similarity	NPC214553
0.7101	Intermediate Similarity	NPC293619
0.7092	Intermediate Similarity	NPC472271
0.7092	Intermediate Similarity	NPC145780
0.709	Intermediate Similarity	NPC226401
0.709	Intermediate Similarity	NPC120982
0.709	Intermediate Similarity	NPC174096
0.709	Intermediate Similarity	NPC79793
0.709	Intermediate Similarity	NPC147634
0.7083	Intermediate Similarity	NPC45728
0.7075	Intermediate Similarity	NPC27843
0.7075	Intermediate Similarity	NPC472597
0.7075	Intermediate Similarity	NPC42760
0.7075	Intermediate Similarity	NPC158079
0.7075	Intermediate Similarity	NPC309787
0.7075	Intermediate Similarity	NPC470096
0.7075	Intermediate Similarity	NPC161557
0.7075	Intermediate Similarity	NPC268342
0.7075	Intermediate Similarity	NPC318799

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 NPC245386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	485
0.1-0.2	1101
0.2-0.3	2689
0.3-0.4	2728
0.4-0.5	1371
0.5-0.6	712
0.6-0.7	63
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
0.7055	Intermediate Similarity	NPD3027	Phase 3
0.7034	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1613	Approved
0.6986	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD228	Approved
0.6894	Remote Similarity	NPD9244	Approved
0.6889	Remote Similarity	NPD3021	Approved
0.6889	Remote Similarity	NPD3022	Approved
0.6766	Remote Similarity	NPD4010	Discontinued
0.6645	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD230	Phase 1
0.6645	Remote Similarity	NPD7266	Discontinued
0.6644	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1558	Phase 1
0.6544	Remote Similarity	NPD968	Approved
0.6541	Remote Similarity	NPD1242	Phase 1
0.6483	Remote Similarity	NPD9381	Approved
0.6483	Remote Similarity	NPD9384	Approved
0.6478	Remote Similarity	NPD6190	Approved
0.6467	Remote Similarity	NPD2861	Phase 2
0.6458	Remote Similarity	NPD1548	Phase 1
0.6454	Remote Similarity	NPD5283	Phase 1
0.6407	Remote Similarity	NPD4288	Approved
0.6395	Remote Similarity	NPD1610	Phase 2
0.6395	Remote Similarity	NPD3705	Approved
0.6364	Remote Similarity	NPD3062	Approved
0.6364	Remote Similarity	NPD3059	Approved
0.6364	Remote Similarity	NPD3061	Approved
0.6309	Remote Similarity	NPD9622	Approved
0.6309	Remote Similarity	NPD2983	Phase 2
0.6309	Remote Similarity	NPD2982	Phase 2
0.6296	Remote Similarity	NPD1511	Approved
0.6288	Remote Similarity	NPD2934	Approved
0.6288	Remote Similarity	NPD2933	Approved
0.6282	Remote Similarity	NPD5314	Approved
0.6268	Remote Similarity	NPD9379	Approved
0.6268	Remote Similarity	NPD9377	Approved
0.6258	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3620	Phase 2
0.6258	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3018	Phase 2
0.6242	Remote Similarity	NPD2981	Phase 2
0.6241	Remote Similarity	NPD2859	Approved
0.6241	Remote Similarity	NPD2860	Approved
0.6222	Remote Similarity	NPD3020	Approved
0.622	Remote Similarity	NPD1512	Approved
0.6209	Remote Similarity	NPD4908	Phase 1
0.619	Remote Similarity	NPD1357	Approved
0.619	Remote Similarity	NPD1934	Approved
0.6184	Remote Similarity	NPD9620	Approved
0.6184	Remote Similarity	NPD9619	Approved
0.6184	Remote Similarity	NPD9621	Approved
0.6174	Remote Similarity	NPD1091	Approved
0.6164	Remote Similarity	NPD5536	Phase 2
0.6159	Remote Similarity	NPD4123	Phase 3
0.6154	Remote Similarity	NPD4060	Phase 1
0.6154	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3060	Approved
0.6149	Remote Similarity	NPD6688	Approved
0.6149	Remote Similarity	NPD6687	Approved
0.6145	Remote Similarity	NPD1653	Approved
0.6144	Remote Similarity	NPD9494	Approved
0.6129	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD1182	Approved
0.6122	Remote Similarity	NPD9545	Approved
0.6099	Remote Similarity	NPD2684	Approved
0.6093	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6584	Phase 3
0.6065	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD2801	Approved
0.6053	Remote Similarity	NPD5311	Approved
0.6053	Remote Similarity	NPD5310	Approved
0.6051	Remote Similarity	NPD943	Approved
0.6049	Remote Similarity	NPD4236	Phase 3
0.6049	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4237	Approved
0.6042	Remote Similarity	NPD7843	Approved
0.6032	Remote Similarity	NPD8095	Phase 1
0.6028	Remote Similarity	NPD290	Approved
0.6027	Remote Similarity	NPD6671	Approved
0.6027	Remote Similarity	NPD7157	Approved
0.6026	Remote Similarity	NPD601	Approved
0.6026	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD597	Approved
0.6026	Remote Similarity	NPD598	Approved
0.6026	Remote Similarity	NPD9269	Phase 2
0.6023	Remote Similarity	NPD2296	Approved
0.6013	Remote Similarity	NPD3053	Approved
0.6013	Remote Similarity	NPD3094	Phase 2
0.6013	Remote Similarity	NPD3055	Approved
0.6012	Remote Similarity	NPD6234	Discontinued
0.6012	Remote Similarity	NPD8166	Discontinued
0.6	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1169	Approved
0.5988	Remote Similarity	NPD3882	Suspended
0.5987	Remote Similarity	NPD1132	Approved
0.5987	Remote Similarity	NPD2674	Phase 3
0.5987	Remote Similarity	NPD1136	Approved
0.5987	Remote Similarity	NPD1130	Approved
0.5976	Remote Similarity	NPD4678	Approved
0.5976	Remote Similarity	NPD4675	Approved
0.5975	Remote Similarity	NPD817	Approved
0.5975	Remote Similarity	NPD823	Approved
0.5969	Remote Similarity	NPD111	Approved
0.5965	Remote Similarity	NPD2978	Approved
0.5965	Remote Similarity	NPD2977	Approved
0.5962	Remote Similarity	NPD9718	Approved
0.596	Remote Similarity	NPD1535	Discovery
0.596	Remote Similarity	NPD3092	Approved
0.5949	Remote Similarity	NPD826	Approved
0.5949	Remote Similarity	NPD825	Approved
0.5942	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4538	Approved
0.5938	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4536	Approved
0.5933	Remote Similarity	NPD5846	Approved
0.5933	Remote Similarity	NPD6516	Phase 2
0.5928	Remote Similarity	NPD2184	Approved
0.5928	Remote Similarity	NPD2183	Approved
0.5926	Remote Similarity	NPD9296	Approved
0.5926	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD1375	Discontinued
0.5924	Remote Similarity	NPD3145	Approved
0.5924	Remote Similarity	NPD3764	Approved
0.5924	Remote Similarity	NPD3144	Approved
0.5921	Remote Similarity	NPD1608	Approved
0.5921	Remote Similarity	NPD2235	Phase 2
0.5921	Remote Similarity	NPD1481	Phase 2
0.5921	Remote Similarity	NPD1840	Phase 2
0.5921	Remote Similarity	NPD2231	Phase 2
0.5917	Remote Similarity	NPD3455	Phase 2
0.5912	Remote Similarity	NPD555	Phase 2
0.5912	Remote Similarity	NPD4340	Discontinued
0.5901	Remote Similarity	NPD5588	Approved
0.5901	Remote Similarity	NPD5960	Phase 3
0.5899	Remote Similarity	NPD940	Approved
0.5899	Remote Similarity	NPD846	Approved
0.5897	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6582	Phase 2
0.5882	Remote Similarity	NPD844	Approved
0.5882	Remote Similarity	NPD6583	Phase 3
0.5882	Remote Similarity	NPD4749	Approved
0.5879	Remote Similarity	NPD2677	Approved
0.5879	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD9570	Approved
0.586	Remote Similarity	NPD7095	Approved
0.586	Remote Similarity	NPD4287	Approved
0.586	Remote Similarity	NPD4625	Phase 3
0.5855	Remote Similarity	NPD422	Phase 1
0.5854	Remote Similarity	NPD6674	Discontinued
0.5854	Remote Similarity	NPD4162	Approved
0.5844	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD8651	Approved
0.5843	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6166	Phase 2
0.5843	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD288	Approved
0.5833	Remote Similarity	NPD4750	Phase 3
0.5833	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD3540	Phase 1
0.5828	Remote Similarity	NPD1778	Approved
0.5823	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD821	Approved
0.5818	Remote Similarity	NPD4628	Phase 3
0.5814	Remote Similarity	NPD37	Approved
0.5813	Remote Similarity	NPD5735	Approved
0.5808	Remote Similarity	NPD4357	Discontinued
0.5805	Remote Similarity	NPD4965	Approved
0.5805	Remote Similarity	NPD4966	Approved
0.5805	Remote Similarity	NPD4967	Phase 2
0.5804	Remote Similarity	NPD1358	Approved
0.5802	Remote Similarity	NPD1510	Phase 2
0.58	Remote Similarity	NPD1894	Discontinued
0.58	Remote Similarity	NPD3091	Approved
0.5799	Remote Similarity	NPD2122	Discontinued
0.5789	Remote Similarity	NPD3496	Discontinued
0.5786	Remote Similarity	NPD6233	Phase 2
0.5786	Remote Similarity	NPD259	Phase 1
0.5786	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD291	Approved
0.5783	Remote Similarity	NPD2219	Phase 1
0.578	Remote Similarity	NPD1465	Phase 2
0.5778	Remote Similarity	NPD3818	Discontinued
0.5778	Remote Similarity	NPD7228	Approved
0.5774	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD257	Approved
0.5769	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD258	Approved
0.5767	Remote Similarity	NPD3539	Phase 1
0.5765	Remote Similarity	NPD3687	Approved
0.5765	Remote Similarity	NPD3686	Approved
0.5762	Remote Similarity	NPD5585	Approved
0.5762	Remote Similarity	NPD9268	Approved
0.5761	Remote Similarity	NPD3337	Discontinued

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