NPASS Compound

Structure

NPC168680 OpenBabel07101718312D 25 26 0 0 0 0 0 0 0 0999 V2000 5.8377 3.3704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 -0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 -0.4815 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 2.5019 -0.4815 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 -0.9630 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.6716 0.9630 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 -1.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6716 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 25 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	665.65
Volume:	375.434
LogP:	5.967
LogD:	2.727
LogS:	-2.962
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	3.498
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	1.6541940567549318e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.072

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	101.79593658447266%
Volume Distribution (VD):	0.628
Pgp-substrate:	2.079040765762329%

ADMET: Metabolism

CYP1A2-inhibitor:	0.404
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.499
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	0.846
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.95
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.879
Respiratory Toxicity:	0.298

Download Data

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

Natural Product: NPC168680

Natural Product ID:	NPC168680
*Common Name:**	4-(2,5-Dibromo-3,4-Dihydroxy-6-(Methoxymethyl)Benzyl)-3,5,6-Tribromobenzene-1,2-Diol
IUPAC Name:	3,6-dibromo-4-(methoxymethyl)-5-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	RDFIGQFCAYWQNC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H11Br5O5/c1-25-3-6-4(8(17)12(21)14(23)10(6)19)2-5-7(16)11(20)15(24)13(22)9(5)18/h21-24H,2-3H2,1H3
SMILES:	COCc1c(Cc2c(Br)c(O)c(c(c2Br)Br)O)c(Br)c(c(c1Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228909
PubChem CID:	16757396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO6092	Symphyocladia latiuscula	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	10500.0	nM	PMID[476305]

☑ 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 NPC168680 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	564
0.1-0.2	2634
0.2-0.3	10541
0.3-0.4	11079
0.4-0.5	8231
0.5-0.6	8385
0.6-0.7	1207
0.7-0.8	32
0.8-0.85	11
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC303011
0.9191	High Similarity	NPC160932
0.9154	High Similarity	NPC134219
0.9118	High Similarity	NPC271942
0.9058	High Similarity	NPC89341
0.9	High Similarity	NPC109346
0.8923	High Similarity	NPC84606
0.8846	High Similarity	NPC219444
0.8759	High Similarity	NPC245386
0.8686	High Similarity	NPC163560
0.8571	High Similarity	NPC156356
0.855	High Similarity	NPC227976
0.8529	High Similarity	NPC85049
0.8519	High Similarity	NPC13004
0.8467	Intermediate Similarity	NPC226493
0.8467	Intermediate Similarity	NPC160081
0.8444	Intermediate Similarity	NPC43706
0.8394	Intermediate Similarity	NPC474614
0.8382	Intermediate Similarity	NPC474147
0.8382	Intermediate Similarity	NPC473708
0.8369	Intermediate Similarity	NPC224663
0.8235	Intermediate Similarity	NPC220311
0.8231	Intermediate Similarity	NPC50782
0.8129	Intermediate Similarity	NPC105702
0.8029	Intermediate Similarity	NPC137117
0.8015	Intermediate Similarity	NPC229213
0.7958	Intermediate Similarity	NPC300678
0.7956	Intermediate Similarity	NPC474169
0.7956	Intermediate Similarity	NPC473572
0.7947	Intermediate Similarity	NPC7398
0.7929	Intermediate Similarity	NPC150929
0.7902	Intermediate Similarity	NPC244890
0.7883	Intermediate Similarity	NPC47790
0.7867	Intermediate Similarity	NPC113862
0.7829	Intermediate Similarity	NPC152947
0.7794	Intermediate Similarity	NPC474146
0.7724	Intermediate Similarity	NPC312155
0.7721	Intermediate Similarity	NPC38483
0.7707	Intermediate Similarity	NPC475697
0.7676	Intermediate Similarity	NPC55113
0.7651	Intermediate Similarity	NPC118794
0.7643	Intermediate Similarity	NPC474535
0.7632	Intermediate Similarity	NPC88896
0.7517	Intermediate Similarity	NPC43613
0.7438	Intermediate Similarity	NPC38980
0.7429	Intermediate Similarity	NPC136543
0.7372	Intermediate Similarity	NPC79844
0.7343	Intermediate Similarity	NPC142776
0.7297	Intermediate Similarity	NPC471328
0.7279	Intermediate Similarity	NPC110800
0.7234	Intermediate Similarity	NPC470414
0.7233	Intermediate Similarity	NPC135103
0.7153	Intermediate Similarity	NPC471488
0.7143	Intermediate Similarity	NPC474536
0.7113	Intermediate Similarity	NPC471486
0.7111	Intermediate Similarity	NPC54543
0.7032	Intermediate Similarity	NPC184632
0.7029	Intermediate Similarity	NPC471485
0.7029	Intermediate Similarity	NPC33244
0.6966	Remote Similarity	NPC68350
0.6966	Remote Similarity	NPC81149
0.6966	Remote Similarity	NPC197576
0.6966	Remote Similarity	NPC230013
0.6966	Remote Similarity	NPC131940
0.6934	Remote Similarity	NPC473358
0.6892	Remote Similarity	NPC106511
0.6875	Remote Similarity	NPC473608
0.6857	Remote Similarity	NPC94217
0.6853	Remote Similarity	NPC117759
0.6849	Remote Similarity	NPC473451
0.6828	Remote Similarity	NPC173511
0.6828	Remote Similarity	NPC474375
0.6828	Remote Similarity	NPC88733
0.6828	Remote Similarity	NPC40302
0.6828	Remote Similarity	NPC137922
0.6803	Remote Similarity	NPC257682
0.6803	Remote Similarity	NPC146355
0.6803	Remote Similarity	NPC131747
0.6803	Remote Similarity	NPC236265
0.6788	Remote Similarity	NPC471495
0.6781	Remote Similarity	NPC175520
0.6781	Remote Similarity	NPC25134
0.6781	Remote Similarity	NPC159866
0.6781	Remote Similarity	NPC295879
0.6781	Remote Similarity	NPC97157
0.6781	Remote Similarity	NPC64130
0.6779	Remote Similarity	NPC118533
0.6779	Remote Similarity	NPC165045
0.6779	Remote Similarity	NPC5428
0.6769	Remote Similarity	NPC475466
0.6759	Remote Similarity	NPC170824
0.6757	Remote Similarity	NPC148627
0.6755	Remote Similarity	NPC178301
0.6753	Remote Similarity	NPC199089
0.6735	Remote Similarity	NPC84086
0.6735	Remote Similarity	NPC105999
0.6735	Remote Similarity	NPC471693
0.6733	Remote Similarity	NPC11258
0.6733	Remote Similarity	NPC45774
0.6733	Remote Similarity	NPC472968
0.6733	Remote Similarity	NPC184733
0.6733	Remote Similarity	NPC129570
0.6733	Remote Similarity	NPC128208
0.6733	Remote Similarity	NPC282703
0.6733	Remote Similarity	NPC21867
0.6711	Remote Similarity	NPC312341
0.6708	Remote Similarity	NPC178097
0.6691	Remote Similarity	NPC471487
0.669	Remote Similarity	NPC41232
0.669	Remote Similarity	NPC472071
0.669	Remote Similarity	NPC472893
0.669	Remote Similarity	NPC63317
0.6688	Remote Similarity	NPC311256
0.6688	Remote Similarity	NPC471942
0.6667	Remote Similarity	NPC59239
0.6667	Remote Similarity	NPC21563
0.6667	Remote Similarity	NPC474135
0.6667	Remote Similarity	NPC226514
0.6667	Remote Similarity	NPC303144
0.6667	Remote Similarity	NPC85488
0.6645	Remote Similarity	NPC126836
0.6645	Remote Similarity	NPC153739
0.6645	Remote Similarity	NPC470351
0.6645	Remote Similarity	NPC11449
0.6645	Remote Similarity	NPC174495
0.6645	Remote Similarity	NPC143483
0.6645	Remote Similarity	NPC257582
0.6645	Remote Similarity	NPC187998
0.6645	Remote Similarity	NPC470350
0.6645	Remote Similarity	NPC42300
0.6645	Remote Similarity	NPC64201
0.6645	Remote Similarity	NPC92164
0.6645	Remote Similarity	NPC77040
0.6645	Remote Similarity	NPC99795
0.6645	Remote Similarity	NPC242807
0.6645	Remote Similarity	NPC241522
0.6645	Remote Similarity	NPC145305
0.6644	Remote Similarity	NPC226737
0.6644	Remote Similarity	NPC47769
0.6644	Remote Similarity	NPC299939
0.6644	Remote Similarity	NPC153580
0.6644	Remote Similarity	NPC196371
0.6629	Remote Similarity	NPC249113
0.6623	Remote Similarity	NPC245826
0.6623	Remote Similarity	NPC474178
0.6623	Remote Similarity	NPC307050
0.6623	Remote Similarity	NPC252307
0.6623	Remote Similarity	NPC277458
0.6622	Remote Similarity	NPC136319
0.6622	Remote Similarity	NPC280704
0.6621	Remote Similarity	NPC477803
0.6621	Remote Similarity	NPC181969
0.6621	Remote Similarity	NPC320987
0.662	Remote Similarity	NPC120280
0.6619	Remote Similarity	NPC473372
0.661	Remote Similarity	NPC129885
0.6604	Remote Similarity	NPC79076
0.6603	Remote Similarity	NPC133025
0.6603	Remote Similarity	NPC234952
0.6601	Remote Similarity	NPC27843
0.6601	Remote Similarity	NPC78575
0.6601	Remote Similarity	NPC40432
0.6601	Remote Similarity	NPC277804
0.6601	Remote Similarity	NPC115207
0.6601	Remote Similarity	NPC15543
0.6601	Remote Similarity	NPC474017
0.6601	Remote Similarity	NPC161557
0.6601	Remote Similarity	NPC158079
0.6601	Remote Similarity	NPC228346
0.6601	Remote Similarity	NPC7171
0.6601	Remote Similarity	NPC158078
0.66	Remote Similarity	NPC58607
0.66	Remote Similarity	NPC76451
0.66	Remote Similarity	NPC178284
0.66	Remote Similarity	NPC191037
0.6597	Remote Similarity	NPC293619
0.6581	Remote Similarity	NPC160697
0.6581	Remote Similarity	NPC56764
0.6581	Remote Similarity	NPC555
0.6581	Remote Similarity	NPC188378
0.6581	Remote Similarity	NPC276026
0.6581	Remote Similarity	NPC289258
0.6581	Remote Similarity	NPC206737
0.6581	Remote Similarity	NPC7515
0.6581	Remote Similarity	NPC469659
0.6579	Remote Similarity	NPC475875
0.6579	Remote Similarity	NPC222684
0.6579	Remote Similarity	NPC170844
0.6579	Remote Similarity	NPC206183
0.6579	Remote Similarity	NPC476968
0.6577	Remote Similarity	NPC206487
0.6577	Remote Similarity	NPC5796
0.6577	Remote Similarity	NPC213414
0.6575	Remote Similarity	NPC227217
0.6575	Remote Similarity	NPC35071
0.6575	Remote Similarity	NPC117780
0.6575	Remote Similarity	NPC232316
0.6575	Remote Similarity	NPC148615
0.6575	Remote Similarity	NPC165133
0.6575	Remote Similarity	NPC95614

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 NPC168680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	1327
0.2-0.3	3134
0.3-0.4	2527
0.4-0.5	1251
0.5-0.6	414
0.6-0.7	10
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
0.6647	Remote Similarity	NPD4010	Discontinued
0.6618	Remote Similarity	NPD9244	Approved
0.6579	Remote Similarity	NPD3027	Phase 3
0.65	Remote Similarity	NPD3022	Approved
0.65	Remote Similarity	NPD3021	Approved
0.6346	Remote Similarity	NPD1613	Approved
0.6346	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD228	Approved
0.6139	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3620	Phase 2
0.6105	Remote Similarity	NPD4288	Approved
0.6096	Remote Similarity	NPD5283	Phase 1
0.6053	Remote Similarity	NPD3705	Approved
0.6012	Remote Similarity	NPD7266	Discontinued
0.5974	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD6674	Discontinued
0.5938	Remote Similarity	NPD4060	Phase 1
0.5938	Remote Similarity	NPD1558	Phase 1
0.5924	Remote Similarity	NPD2861	Phase 2
0.5901	Remote Similarity	NPD230	Phase 1
0.5897	Remote Similarity	NPD3094	Phase 2
0.5878	Remote Similarity	NPD1398	Phase 1
0.5866	Remote Similarity	NPD6688	Approved
0.5866	Remote Similarity	NPD6687	Approved
0.5857	Remote Similarity	NPD3020	Approved
0.5855	Remote Similarity	NPD8095	Phase 1
0.5851	Remote Similarity	NPD4287	Approved
0.5844	Remote Similarity	NPD3092	Approved
0.5844	Remote Similarity	NPD1610	Phase 2
0.5843	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD2296	Approved
0.5819	Remote Similarity	NPD6234	Discontinued
0.5817	Remote Similarity	NPD9381	Approved
0.5817	Remote Similarity	NPD9384	Approved
0.5786	Remote Similarity	NPD4908	Phase 1
0.5782	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD9622	Approved
0.5765	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD7340	Approved
0.5755	Remote Similarity	NPD2859	Approved
0.5755	Remote Similarity	NPD2860	Approved
0.5741	Remote Similarity	NPD3062	Approved
0.5741	Remote Similarity	NPD3059	Approved
0.5741	Remote Similarity	NPD3061	Approved
0.5714	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD37	Approved
0.5714	Remote Similarity	NPD8166	Discontinued
0.5714	Remote Similarity	NPD1934	Approved
0.5705	Remote Similarity	NPD7635	Approved
0.5704	Remote Similarity	NPD1242	Phase 1
0.5686	Remote Similarity	NPD3091	Approved
0.5686	Remote Similarity	NPD1548	Phase 1
0.5683	Remote Similarity	NPD2934	Approved
0.5683	Remote Similarity	NPD2933	Approved
0.5682	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6190	Approved
0.5671	Remote Similarity	NPD5314	Approved
0.5669	Remote Similarity	NPD2983	Phase 2
0.5669	Remote Similarity	NPD2982	Phase 2
0.566	Remote Similarity	NPD9620	Approved
0.566	Remote Similarity	NPD9619	Approved
0.566	Remote Similarity	NPD9621	Approved
0.5655	Remote Similarity	NPD3060	Approved
0.5652	Remote Similarity	NPD4625	Phase 3
0.5652	Remote Similarity	NPD9718	Approved
0.564	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD1283	Approved
0.5633	Remote Similarity	NPD6696	Suspended
0.5632	Remote Similarity	NPD4005	Discontinued
0.5625	Remote Similarity	NPD3018	Phase 2
0.5618	Remote Similarity	NPD4965	Approved
0.5618	Remote Similarity	NPD4967	Phase 2
0.5618	Remote Similarity	NPD4966	Approved
0.5617	Remote Similarity	NPD5109	Approved
0.5617	Remote Similarity	NPD5110	Phase 2
0.5617	Remote Similarity	NPD3764	Approved
0.5617	Remote Similarity	NPD5111	Phase 2
0.5617	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD968	Approved
0.5614	Remote Similarity	NPD1511	Approved
0.5613	Remote Similarity	NPD5126	Approved
0.5613	Remote Similarity	NPD5125	Phase 3
0.561	Remote Similarity	NPD5735	Approved
0.5605	Remote Similarity	NPD2981	Phase 2
0.5602	Remote Similarity	NPD1169	Approved
0.56	Remote Similarity	NPD9379	Approved
0.56	Remote Similarity	NPD9377	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