NPASS Compound

Structure

CID71186 OpenBabel06191715412D 23 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -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 -1.7321 0.0000 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 0.8660 1.5000 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 -2.5981 -0.5000 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 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 -4.3301 -0.5000 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 2.5981 -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 -2.5981 -1.5000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 5 1 0 0 0 0 4 7 2 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 23 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	487.27
Volume:	518.459
LogP:	5.56
LogD:	4.807
LogS:	-4.188
# Rotatable Bonds:	1
TPSA:	75.63
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	7.24
Fsp3:	0.548
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.038
MDCK Permeability:	6.43636958557181e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.639
Plasma Protein Binding (PPB):	94.13138580322266%
Volume Distribution (VD):	1.947
Pgp-substrate:	4.046148777008057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.335
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.236
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.977
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	2.459
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.634
Human Hepatotoxicity (H-HT):	0.682
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.669
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.12
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC71186

Natural Product ID:	NPC71186
*Common Name:**	1,2,3,4-Tetrabromo-5-(3,5-Dibromo-2-Methoxyphenoxy)-6-Methoxybenzene
IUPAC Name:	1,2,3,4-tetrabromo-5-(3,5-dibromo-2-methoxyphenoxy)-6-methoxybenzene
Synonyms:
Standard InCHIKey:	CNBWUPDUFTVCLE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8Br6O3/c1-21-12-6(16)3-5(15)4-7(12)23-14-11(20)9(18)8(17)10(19)13(14)22-2/h3-4H,1-2H3
SMILES:	COc1c(cc(cc1Br)Br)Oc1c(Br)c(Br)c(c(c1OC)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL148842
PubChem CID:	23247448
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]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
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]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	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]
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]
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]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	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]
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]

☑ 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	5

Activity Type	# Activity
Individual Protein	1
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[534201]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.0	mm	PMID[534202]

☑ 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 NPC71186 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	873
0.1-0.2	7029
0.2-0.3	14017
0.3-0.4	5779
0.4-0.5	11420
0.5-0.6	3311
0.6-0.7	210
0.7-0.8	8
0.8-0.85	6
0.85-0.9	20
0.9-0.95	17
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC264379
0.9636	High Similarity	NPC221301
0.955	High Similarity	NPC162294
0.9316	High Similarity	NPC230013
0.9316	High Similarity	NPC197576
0.9316	High Similarity	NPC131940
0.9316	High Similarity	NPC68350
0.9316	High Similarity	NPC81149
0.9145	High Similarity	NPC88733
0.9145	High Similarity	NPC137922
0.9145	High Similarity	NPC173511
0.9145	High Similarity	NPC40302
0.9068	High Similarity	NPC64130
0.9068	High Similarity	NPC159866
0.9068	High Similarity	NPC25134
0.9068	High Similarity	NPC175520
0.9068	High Similarity	NPC295879
0.9068	High Similarity	NPC97157
0.906	High Similarity	NPC170824
0.8983	High Similarity	NPC474375
0.8974	High Similarity	NPC41232
0.8974	High Similarity	NPC63317
0.8917	High Similarity	NPC1744
0.8917	High Similarity	NPC163019
0.8898	High Similarity	NPC47769
0.8898	High Similarity	NPC226737
0.8898	High Similarity	NPC153580
0.8898	High Similarity	NPC196371
0.8898	High Similarity	NPC299939
0.8803	High Similarity	NPC104124
0.8729	High Similarity	NPC86007
0.8729	High Similarity	NPC44270
0.8667	High Similarity	NPC235166
0.8644	High Similarity	NPC191194
0.8492	Intermediate Similarity	NPC178301
0.8468	Intermediate Similarity	NPC319933
0.8268	Intermediate Similarity	NPC222684
0.8268	Intermediate Similarity	NPC206183
0.8031	Intermediate Similarity	NPC45728
0.7874	Intermediate Similarity	NPC236265
0.7482	Intermediate Similarity	NPC286337
0.7482	Intermediate Similarity	NPC8577
0.7297	Intermediate Similarity	NPC206876
0.7162	Intermediate Similarity	NPC135103
0.7143	Intermediate Similarity	NPC271942
0.7027	Intermediate Similarity	NPC125306
0.6975	Remote Similarity	NPC314803
0.6959	Remote Similarity	NPC152947
0.6929	Remote Similarity	NPC245386
0.6923	Remote Similarity	NPC475466
0.6812	Remote Similarity	NPC195902
0.681	Remote Similarity	NPC318429
0.6788	Remote Similarity	NPC13004
0.6788	Remote Similarity	NPC280736
0.6786	Remote Similarity	NPC303011
0.678	Remote Similarity	NPC114325
0.6774	Remote Similarity	NPC41594
0.6763	Remote Similarity	NPC160081
0.6763	Remote Similarity	NPC226493
0.672	Remote Similarity	NPC258171
0.6691	Remote Similarity	NPC85049
0.6644	Remote Similarity	NPC89341
0.6643	Remote Similarity	NPC70485
0.6643	Remote Similarity	NPC11449
0.6642	Remote Similarity	NPC220311
0.6621	Remote Similarity	NPC160932
0.6585	Remote Similarity	NPC12714
0.6585	Remote Similarity	NPC310905
0.6581	Remote Similarity	NPC474535
0.6579	Remote Similarity	NPC23837
0.6577	Remote Similarity	NPC124576
0.6552	Remote Similarity	NPC168680
0.6547	Remote Similarity	NPC474147
0.6547	Remote Similarity	NPC473708
0.6538	Remote Similarity	NPC475697
0.6522	Remote Similarity	NPC110131
0.6512	Remote Similarity	NPC55300
0.6512	Remote Similarity	NPC245552
0.651	Remote Similarity	NPC109346
0.6496	Remote Similarity	NPC474169
0.6496	Remote Similarity	NPC84606
0.6496	Remote Similarity	NPC473572
0.6483	Remote Similarity	NPC213471
0.648	Remote Similarity	NPC292792
0.6475	Remote Similarity	NPC134219
0.6475	Remote Similarity	NPC43706
0.6466	Remote Similarity	NPC252149
0.6462	Remote Similarity	NPC165646
0.6449	Remote Similarity	NPC272463
0.6447	Remote Similarity	NPC473608
0.6429	Remote Similarity	NPC307875
0.6429	Remote Similarity	NPC122359
0.6429	Remote Similarity	NPC159987
0.6429	Remote Similarity	NPC78061
0.6423	Remote Similarity	NPC116562
0.6423	Remote Similarity	NPC132725
0.6423	Remote Similarity	NPC229213
0.6423	Remote Similarity	NPC219444
0.6412	Remote Similarity	NPC303522
0.6412	Remote Similarity	NPC471488
0.6412	Remote Similarity	NPC165106
0.6397	Remote Similarity	NPC472596
0.6378	Remote Similarity	NPC232654
0.6376	Remote Similarity	NPC79076
0.6376	Remote Similarity	NPC135349
0.6376	Remote Similarity	NPC78530
0.637	Remote Similarity	NPC38483
0.6357	Remote Similarity	NPC54543
0.6356	Remote Similarity	NPC47422
0.6343	Remote Similarity	NPC86947
0.6343	Remote Similarity	NPC151617
0.6343	Remote Similarity	NPC76915
0.6331	Remote Similarity	NPC137117
0.6328	Remote Similarity	NPC227894
0.6316	Remote Similarity	NPC473264
0.6316	Remote Similarity	NPC50782
0.6316	Remote Similarity	NPC475815
0.6316	Remote Similarity	NPC47194
0.6309	Remote Similarity	NPC474851
0.6309	Remote Similarity	NPC474850
0.6308	Remote Similarity	NPC473358
0.6304	Remote Similarity	NPC261661
0.6304	Remote Similarity	NPC71090
0.6303	Remote Similarity	NPC302546
0.6299	Remote Similarity	NPC17537
0.6296	Remote Similarity	NPC277460
0.6293	Remote Similarity	NPC319826
0.6289	Remote Similarity	NPC38980
0.6288	Remote Similarity	NPC33244
0.6286	Remote Similarity	NPC142776
0.6276	Remote Similarity	NPC303993
0.6276	Remote Similarity	NPC163560
0.6269	Remote Similarity	NPC9341
0.6269	Remote Similarity	NPC123948
0.6269	Remote Similarity	NPC81067
0.6267	Remote Similarity	NPC184632
0.6259	Remote Similarity	NPC470887
0.6259	Remote Similarity	NPC105999
0.6259	Remote Similarity	NPC279379
0.625	Remote Similarity	NPC71629
0.625	Remote Similarity	NPC214289
0.625	Remote Similarity	NPC296085
0.6241	Remote Similarity	NPC94217
0.6241	Remote Similarity	NPC475361
0.6232	Remote Similarity	NPC290451
0.6232	Remote Similarity	NPC145780
0.6232	Remote Similarity	NPC127389
0.6231	Remote Similarity	NPC165386
0.6231	Remote Similarity	NPC36108
0.6231	Remote Similarity	NPC246358
0.6231	Remote Similarity	NPC127326
0.6231	Remote Similarity	NPC7097
0.6231	Remote Similarity	NPC233731
0.6228	Remote Similarity	NPC475396
0.6222	Remote Similarity	NPC293619
0.6222	Remote Similarity	NPC185738
0.6222	Remote Similarity	NPC280001
0.6222	Remote Similarity	NPC9248
0.6218	Remote Similarity	NPC157213
0.6216	Remote Similarity	NPC156356
0.6214	Remote Similarity	NPC94276
0.6214	Remote Similarity	NPC48990
0.6214	Remote Similarity	NPC109822
0.6214	Remote Similarity	NPC114901
0.6214	Remote Similarity	NPC293701
0.6214	Remote Similarity	NPC74478
0.6214	Remote Similarity	NPC213414
0.621	Remote Similarity	NPC313918
0.6202	Remote Similarity	NPC124712
0.6202	Remote Similarity	NPC194034
0.62	Remote Similarity	NPC250597
0.619	Remote Similarity	NPC51633
0.619	Remote Similarity	NPC300166
0.6187	Remote Similarity	NPC47790
0.6183	Remote Similarity	NPC137685
0.6183	Remote Similarity	NPC179309
0.6176	Remote Similarity	NPC474040
0.6176	Remote Similarity	NPC228907
0.6176	Remote Similarity	NPC470626
0.6176	Remote Similarity	NPC159916
0.6176	Remote Similarity	NPC474214
0.6176	Remote Similarity	NPC124916
0.617	Remote Similarity	NPC194519
0.6169	Remote Similarity	NPC76412
0.6167	Remote Similarity	NPC177844
0.6167	Remote Similarity	NPC99886
0.6167	Remote Similarity	NPC259134
0.6167	Remote Similarity	NPC8002
0.6164	Remote Similarity	NPC244890
0.616	Remote Similarity	NPC471576
0.616	Remote Similarity	NPC307039
0.6159	Remote Similarity	NPC276195
0.6159	Remote Similarity	NPC205850
0.6154	Remote Similarity	NPC471495
0.6154	Remote Similarity	NPC150929
0.6154	Remote Similarity	NPC196034
0.6149	Remote Similarity	NPC224663
0.6145	Remote Similarity	NPC469979
0.6145	Remote Similarity	NPC226001
0.6142	Remote Similarity	NPC192596

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 NPC71186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	667
0.1-0.2	1425
0.2-0.3	3294
0.3-0.4	2271
0.4-0.5	1148
0.5-0.6	329
0.6-0.7	16
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
0.7	Intermediate Similarity	NPD291	Approved
0.681	Remote Similarity	NPD9365	Approved
0.678	Remote Similarity	NPD9296	Approved
0.6614	Remote Similarity	NPD556	Approved
0.6412	Remote Similarity	NPD5283	Phase 1
0.6343	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1102	Approved
0.6343	Remote Similarity	NPD1103	Approved
0.625	Remote Similarity	NPD968	Approved
0.6222	Remote Similarity	NPD5536	Phase 2
0.622	Remote Similarity	NPD9501	Approved
0.6218	Remote Similarity	NPD9295	Approved
0.6202	Remote Similarity	NPD290	Approved
0.6176	Remote Similarity	NPD7534	Approved
0.6176	Remote Similarity	NPD7533	Approved
0.6154	Remote Similarity	NPD2684	Approved
0.6136	Remote Similarity	NPD228	Approved
0.6131	Remote Similarity	NPD1797	Approved
0.6131	Remote Similarity	NPD1798	Approved
0.6077	Remote Similarity	NPD9552	Approved
0.6043	Remote Similarity	NPD915	Approved
0.6043	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5535	Approved
0.597	Remote Similarity	NPD7843	Approved
0.597	Remote Similarity	NPD769	Approved
0.5969	Remote Similarity	NPD9244	Approved
0.5957	Remote Similarity	NPD2981	Phase 2
0.5954	Remote Similarity	NPD1358	Approved
0.5944	Remote Similarity	NPD1318	Phase 2
0.594	Remote Similarity	NPD2673	Approved
0.594	Remote Similarity	NPD2671	Approved
0.5918	Remote Similarity	NPD3530	Approved
0.5918	Remote Similarity	NPD3531	Approved
0.5918	Remote Similarity	NPD3532	Approved
0.5915	Remote Similarity	NPD2982	Phase 2
0.5915	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD2983	Phase 2
0.5882	Remote Similarity	NPD9299	Approved
0.5874	Remote Similarity	NPD2922	Phase 1
0.5865	Remote Similarity	NPD5451	Approved
0.5857	Remote Similarity	NPD5846	Approved
0.5857	Remote Similarity	NPD6516	Phase 2
0.5843	Remote Similarity	NPD4010	Discontinued
0.5839	Remote Similarity	NPD1933	Approved
0.5839	Remote Similarity	NPD2557	Approved
0.5839	Remote Similarity	NPD7157	Approved
0.5833	Remote Similarity	NPD5374	Approved
0.5833	Remote Similarity	NPD9624	Approved
0.5833	Remote Similarity	NPD5373	Approved
0.5833	Remote Similarity	NPD9549	Phase 2
0.5809	Remote Similarity	NPD1241	Discontinued
0.5808	Remote Similarity	NPD6687	Approved
0.5808	Remote Similarity	NPD6688	Approved
0.5802	Remote Similarity	NPD9697	Approved
0.5797	Remote Similarity	NPD3596	Phase 2
0.5786	Remote Similarity	NPD1357	Approved
0.5786	Remote Similarity	NPD5585	Approved
0.5775	Remote Similarity	NPD3705	Approved
0.5772	Remote Similarity	NPD1558	Phase 1
0.5767	Remote Similarity	NPD2296	Approved
0.5758	Remote Similarity	NPD3134	Approved
0.5753	Remote Similarity	NPD3018	Phase 2
0.5753	Remote Similarity	NPD2250	Discontinued
0.5753	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD821	Approved
0.5725	Remote Similarity	NPD191	Approved
0.5724	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1182	Approved
0.5714	Remote Similarity	NPD1548	Phase 1
0.5714	Remote Similarity	NPD6581	Approved
0.5714	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6580	Approved
0.5705	Remote Similarity	NPD4870	Approved
0.5676	Remote Similarity	NPD3027	Phase 3
0.5674	Remote Similarity	NPD3443	Approved
0.5674	Remote Similarity	NPD2595	Approved
0.5674	Remote Similarity	NPD3445	Approved
0.5674	Remote Similarity	NPD2594	Approved
0.5674	Remote Similarity	NPD6382	Discontinued
0.5674	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD3444	Approved
0.5674	Remote Similarity	NPD3049	Approved
0.5671	Remote Similarity	NPD4288	Approved
0.5667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD1613	Approved
0.5646	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5718	Phase 2
0.5638	Remote Similarity	NPD5110	Phase 2
0.5638	Remote Similarity	NPD5111	Phase 2
0.5638	Remote Similarity	NPD5109	Approved
0.5634	Remote Similarity	NPD2554	Approved
0.5634	Remote Similarity	NPD2556	Approved
0.5634	Remote Similarity	NPD17	Approved
0.5634	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6671	Approved
0.5603	Remote Similarity	NPD2486	Discontinued
0.5603	Remote Similarity	NPD1894	Discontinued
0.56	Remote Similarity	NPD481	Phase 3
0.56	Remote Similarity	NPD1726	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