NPASS Compound

Structure

CID88733 OpenBabel06191715422D 21 22 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 -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 -1.7321 -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 0.8660 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 -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 20 1 0 0 0 0 2 5 2 0 0 0 0 2 7 1 0 0 0 0 3 5 1 0 0 0 0 3 8 2 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	605.63
Volume:	323.261
LogP:	6.151
LogD:	2.997
LogS:	-7.868
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	2.702
Fsp3:	0.077
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:	-4.795
MDCK Permeability:	1.6470807167934254e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.131

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	101.62181091308594%
Volume Distribution (VD):	4.425
Pgp-substrate:	7.609351634979248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	1.009
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.91
Carcinogencity:	0.063
Eye Corrosion:	0.454
Eye Irritation:	0.955
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC88733

Natural Product ID:	NPC88733
*Common Name:**	2,4-Dibromo-6-(2,3,4-Tribromo-6-Methoxyphenoxy)Phenol
IUPAC Name:	2,4-dibromo-6-(2,3,4-tribromo-6-methoxyphenoxy)phenol
Synonyms:
Standard InCHIKey:	SVUMJBJGTXAECH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H7Br5O3/c1-20-9-4-6(15)10(17)11(18)13(9)21-8-3-5(14)2-7(16)12(8)19/h2-4,19H,1H3
SMILES:	COc1cc(c(c(c1Oc1cc(cc(c1O)Br)Br)Br)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220286
PubChem CID:	11410931
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]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
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]
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]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	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]
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]
NPO8481	Phyllospongia dendyi	Species	Thorectidae	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]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Organism	4

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[532813]

☑ 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 NPC88733 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	754
0.1-0.2	5886
0.2-0.3	14865
0.3-0.4	5190
0.4-0.5	9804
0.5-0.6	5381
0.6-0.7	749
0.7-0.8	16
0.8-0.85	5
0.85-0.9	4
0.9-0.95	15
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173511
0.9828	High Similarity	NPC197576
0.9828	High Similarity	NPC68350
0.9828	High Similarity	NPC81149
0.9828	High Similarity	NPC230013
0.9828	High Similarity	NPC131940
0.9825	High Similarity	NPC63317
0.9825	High Similarity	NPC41232
0.9739	High Similarity	NPC170824
0.9739	High Similarity	NPC299939
0.9739	High Similarity	NPC153580
0.9739	High Similarity	NPC226737
0.9655	High Similarity	NPC137922
0.9655	High Similarity	NPC40302
0.9649	High Similarity	NPC104124
0.9573	High Similarity	NPC175520
0.9573	High Similarity	NPC97157
0.9573	High Similarity	NPC159866
0.9573	High Similarity	NPC295879
0.9573	High Similarity	NPC25134
0.9573	High Similarity	NPC64130
0.9565	High Similarity	NPC44270
0.9565	High Similarity	NPC86007
0.9487	High Similarity	NPC474375
0.9478	High Similarity	NPC191194
0.9402	High Similarity	NPC47769
0.9402	High Similarity	NPC196371
0.9304	High Similarity	NPC264379
0.9268	High Similarity	NPC178301
0.9145	High Similarity	NPC71186
0.913	High Similarity	NPC221301
0.9052	High Similarity	NPC162294
0.9032	High Similarity	NPC222684
0.9032	High Similarity	NPC206183
0.879	High Similarity	NPC45728
0.8629	High Similarity	NPC1744
0.8629	High Similarity	NPC163019
0.8387	Intermediate Similarity	NPC235166
0.8174	Intermediate Similarity	NPC319933
0.8029	Intermediate Similarity	NPC8577
0.7607	Intermediate Similarity	NPC314803
0.7464	Intermediate Similarity	NPC245386
0.7429	Intermediate Similarity	NPC271942
0.7414	Intermediate Similarity	NPC475466
0.7414	Intermediate Similarity	NPC114325
0.7299	Intermediate Similarity	NPC226493
0.7299	Intermediate Similarity	NPC160081
0.7273	Intermediate Similarity	NPC286337
0.7239	Intermediate Similarity	NPC236265
0.723	Intermediate Similarity	NPC152947
0.7226	Intermediate Similarity	NPC85049
0.7206	Intermediate Similarity	NPC13004
0.7185	Intermediate Similarity	NPC220311
0.7153	Intermediate Similarity	NPC89341
0.7133	Intermediate Similarity	NPC160932
0.7071	Intermediate Similarity	NPC303011
0.7059	Intermediate Similarity	NPC474535
0.7047	Intermediate Similarity	NPC473608
0.7037	Intermediate Similarity	NPC473572
0.7037	Intermediate Similarity	NPC474169
0.7016	Intermediate Similarity	NPC307875
0.7013	Intermediate Similarity	NPC475697
0.7007	Intermediate Similarity	NPC109346
0.6963	Remote Similarity	NPC229213
0.6957	Remote Similarity	NPC252149
0.6929	Remote Similarity	NPC11449
0.6917	Remote Similarity	NPC38483
0.6897	Remote Similarity	NPC206876
0.6894	Remote Similarity	NPC151617
0.6894	Remote Similarity	NPC86947
0.6894	Remote Similarity	NPC76915
0.6884	Remote Similarity	NPC134219
0.6875	Remote Similarity	NPC213471
0.6864	Remote Similarity	NPC318429
0.6861	Remote Similarity	NPC137117
0.6838	Remote Similarity	NPC219444
0.6838	Remote Similarity	NPC47790
0.6835	Remote Similarity	NPC474147
0.6835	Remote Similarity	NPC473708
0.6828	Remote Similarity	NPC168680
0.6812	Remote Similarity	NPC142776
0.6803	Remote Similarity	NPC250597
0.6797	Remote Similarity	NPC233731
0.6797	Remote Similarity	NPC246358
0.6797	Remote Similarity	NPC7097
0.6797	Remote Similarity	NPC36108
0.6791	Remote Similarity	NPC214289
0.6788	Remote Similarity	NPC84606
0.6783	Remote Similarity	NPC319826
0.6783	Remote Similarity	NPC163560
0.6772	Remote Similarity	NPC124712
0.6767	Remote Similarity	NPC9248
0.6767	Remote Similarity	NPC293619
0.6765	Remote Similarity	NPC290451
0.6765	Remote Similarity	NPC127389
0.6765	Remote Similarity	NPC145780
0.6763	Remote Similarity	NPC43706
0.6757	Remote Similarity	NPC184632
0.6752	Remote Similarity	NPC38980
0.6742	Remote Similarity	NPC50782
0.6739	Remote Similarity	NPC74478
0.6718	Remote Similarity	NPC33244
0.6718	Remote Similarity	NPC471488
0.6716	Remote Similarity	NPC470626
0.6714	Remote Similarity	NPC78061
0.6714	Remote Similarity	NPC122359
0.6714	Remote Similarity	NPC159987
0.6712	Remote Similarity	NPC156356
0.6693	Remote Similarity	NPC232654
0.6693	Remote Similarity	NPC41594
0.6692	Remote Similarity	NPC8547
0.6692	Remote Similarity	NPC173746
0.6692	Remote Similarity	NPC195873
0.6692	Remote Similarity	NPC257124
0.6692	Remote Similarity	NPC139617
0.6692	Remote Similarity	NPC78918
0.6692	Remote Similarity	NPC156840
0.6691	Remote Similarity	NPC205850
0.6691	Remote Similarity	NPC205213
0.6691	Remote Similarity	NPC194519
0.6667	Remote Similarity	NPC310338
0.6667	Remote Similarity	NPC244890
0.6667	Remote Similarity	NPC281298
0.6667	Remote Similarity	NPC54543
0.6667	Remote Similarity	NPC94217
0.6667	Remote Similarity	NPC150929
0.6667	Remote Similarity	NPC303993
0.6645	Remote Similarity	NPC135103
0.6644	Remote Similarity	NPC224663
0.6643	Remote Similarity	NPC17837
0.6643	Remote Similarity	NPC191037
0.6643	Remote Similarity	NPC304630
0.6643	Remote Similarity	NPC178284
0.6643	Remote Similarity	NPC58607
0.6638	Remote Similarity	NPC125306
0.662	Remote Similarity	NPC474536
0.6619	Remote Similarity	NPC293701
0.6619	Remote Similarity	NPC114901
0.6619	Remote Similarity	NPC48990
0.6618	Remote Similarity	NPC227217
0.6618	Remote Similarity	NPC165133
0.6618	Remote Similarity	NPC242885
0.6618	Remote Similarity	NPC117780
0.6618	Remote Similarity	NPC95614
0.6618	Remote Similarity	NPC232084
0.6618	Remote Similarity	NPC56214
0.6618	Remote Similarity	NPC232316
0.6618	Remote Similarity	NPC61516
0.6618	Remote Similarity	NPC247364
0.6618	Remote Similarity	NPC10932
0.6615	Remote Similarity	NPC473358
0.6596	Remote Similarity	NPC210355
0.6596	Remote Similarity	NPC216836
0.6596	Remote Similarity	NPC147821
0.6596	Remote Similarity	NPC163332
0.6596	Remote Similarity	NPC292056
0.6596	Remote Similarity	NPC118787
0.6596	Remote Similarity	NPC183181
0.6596	Remote Similarity	NPC111247
0.6596	Remote Similarity	NPC41706
0.6596	Remote Similarity	NPC319625
0.6594	Remote Similarity	NPC228875
0.6594	Remote Similarity	NPC105147
0.6594	Remote Similarity	NPC126216
0.6585	Remote Similarity	NPC469979
0.6585	Remote Similarity	NPC226001
0.6577	Remote Similarity	NPC474851
0.6577	Remote Similarity	NPC474850
0.6571	Remote Similarity	NPC87113
0.6569	Remote Similarity	NPC14007
0.6569	Remote Similarity	NPC224814
0.6569	Remote Similarity	NPC109083
0.6569	Remote Similarity	NPC269843
0.6569	Remote Similarity	NPC207613
0.6569	Remote Similarity	NPC60962
0.6569	Remote Similarity	NPC189844
0.6567	Remote Similarity	NPC79844
0.6565	Remote Similarity	NPC55300
0.6555	Remote Similarity	NPC157213
0.6549	Remote Similarity	NPC226661
0.6547	Remote Similarity	NPC192810
0.6547	Remote Similarity	NPC105999
0.6547	Remote Similarity	NPC317769
0.6547	Remote Similarity	NPC31344
0.6545	Remote Similarity	NPC473462
0.6545	Remote Similarity	NPC126128
0.6545	Remote Similarity	NPC207819
0.6545	Remote Similarity	NPC110454
0.6545	Remote Similarity	NPC298981
0.6544	Remote Similarity	NPC117759
0.6536	Remote Similarity	NPC178097
0.6522	Remote Similarity	NPC473853
0.6522	Remote Similarity	NPC38996
0.6522	Remote Similarity	NPC343720
0.6522	Remote Similarity	NPC470212
0.6522	Remote Similarity	NPC113865
0.6522	Remote Similarity	NPC54872
0.6522	Remote Similarity	NPC262156
0.6522	Remote Similarity	NPC184651
0.6522	Remote Similarity	NPC160380

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 NPC88733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	593
0.1-0.2	1502
0.2-0.3	3214
0.3-0.4	2242
0.4-0.5	1204
0.5-0.6	373
0.6-0.7	20
0.7-0.8	2
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
0.7414	Intermediate Similarity	NPD9296	Approved
0.719	Intermediate Similarity	NPD291	Approved
0.6864	Remote Similarity	NPD9365	Approved
0.6692	Remote Similarity	NPD228	Approved
0.6691	Remote Similarity	NPD915	Approved
0.6667	Remote Similarity	NPD556	Approved
0.6562	Remote Similarity	NPD968	Approved
0.6555	Remote Similarity	NPD9295	Approved
0.6429	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD9299	Approved
0.6406	Remote Similarity	NPD9244	Approved
0.6385	Remote Similarity	NPD290	Approved
0.628	Remote Similarity	NPD4010	Discontinued
0.6279	Remote Similarity	NPD9501	Approved
0.626	Remote Similarity	NPD9552	Approved
0.6259	Remote Similarity	NPD1558	Phase 1
0.625	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2684	Approved
0.6207	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD1797	Approved
0.6187	Remote Similarity	NPD1798	Approved
0.6164	Remote Similarity	NPD3027	Phase 3
0.6149	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1613	Approved
0.6103	Remote Similarity	NPD5283	Phase 1
0.6066	Remote Similarity	NPD9094	Approved
0.6043	Remote Similarity	NPD1102	Approved
0.6043	Remote Similarity	NPD1103	Approved
0.6043	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7843	Approved
0.6012	Remote Similarity	NPD2296	Approved
0.6	Remote Similarity	NPD1548	Phase 1
0.5957	Remote Similarity	NPD1357	Approved
0.5933	Remote Similarity	NPD3620	Phase 2
0.5933	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5536	Phase 2
0.5918	Remote Similarity	NPD9494	Approved
0.5915	Remote Similarity	NPD6516	Phase 2
0.5915	Remote Similarity	NPD5846	Approved
0.5899	Remote Similarity	NPD7157	Approved
0.5899	Remote Similarity	NPD6671	Approved
0.589	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7534	Approved
0.5887	Remote Similarity	NPD7533	Approved
0.5862	Remote Similarity	NPD6582	Phase 2
0.5862	Remote Similarity	NPD6583	Phase 3
0.5833	Remote Similarity	NPD1091	Approved
0.5833	Remote Similarity	NPD1610	Phase 2
0.5828	Remote Similarity	NPD4060	Phase 1
0.5826	Remote Similarity	NPD9087	Approved
0.5811	Remote Similarity	NPD2250	Discontinued
0.5809	Remote Similarity	NPD3022	Approved
0.5809	Remote Similarity	NPD3021	Approved
0.58	Remote Similarity	NPD3145	Approved
0.58	Remote Similarity	NPD3144	Approved
0.5797	Remote Similarity	NPD821	Approved
0.5786	Remote Similarity	NPD191	Approved
0.5772	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD155	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD9088	Approved
0.5762	Remote Similarity	NPD2674	Phase 3
0.5753	Remote Similarity	NPD2982	Phase 2
0.5753	Remote Similarity	NPD2983	Phase 2
0.5743	Remote Similarity	NPD6584	Phase 3
0.5724	Remote Similarity	NPD1535	Discovery
0.5723	Remote Similarity	NPD4288	Approved
0.5705	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5695	Remote Similarity	NPD6798	Discontinued
0.5685	Remote Similarity	NPD1481	Phase 2
0.5685	Remote Similarity	NPD2981	Phase 2
0.5683	Remote Similarity	NPD769	Approved
0.5683	Remote Similarity	NPD5535	Approved
0.5676	Remote Similarity	NPD1318	Phase 2
0.5667	Remote Similarity	NPD4908	Phase 1
0.5664	Remote Similarity	NPD1894	Discontinued
0.5662	Remote Similarity	NPD1358	Approved
0.5659	Remote Similarity	NPD2934	Approved
0.5659	Remote Similarity	NPD2933	Approved
0.5658	Remote Similarity	NPD6233	Phase 2
0.5658	Remote Similarity	NPD4062	Phase 3
0.5658	Remote Similarity	NPD3532	Approved
0.5658	Remote Similarity	NPD3530	Approved
0.5658	Remote Similarity	NPD3531	Approved
0.5652	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD2671	Approved
0.5652	Remote Similarity	NPD2673	Approved
0.5638	Remote Similarity	NPD5647	Approved
0.5633	Remote Similarity	NPD4162	Approved
0.563	Remote Similarity	NPD9697	Approved
0.5629	Remote Similarity	NPD7095	Approved
0.5621	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.562	Remote Similarity	NPD9093	Approved
0.5616	Remote Similarity	NPD422	Phase 1
0.5615	Remote Similarity	NPD2859	Approved
0.5615	Remote Similarity	NPD2860	Approved
0.5608	Remote Similarity	NPD2922	Phase 1
0.5602	Remote Similarity	NPD1934	Approved
0.56	Remote Similarity	NPD3018	Phase 2
0.56	Remote Similarity	NPD2861	Phase 2

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