NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	337.88
Volume:	218.846
LogP:	2.52
LogD:	2.221
LogS:	-3.09
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	2.587
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.65
MDCK Permeability:	1.729102041281294e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.41
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	97.07306671142578%
Volume Distribution (VD):	0.405
Pgp-substrate:	6.15191125869751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.715
CYP1A2-substrate:	0.568
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.32
CYP2C9-inhibitor:	0.354
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	2.099
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.837
Carcinogencity:	0.11
Eye Corrosion:	0.079
Eye Irritation:	0.684
Respiratory Toxicity:	0.288

Download Data

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

Natural Product: NPC259017

Natural Product ID:	NPC259017
*Common Name:**	Subereaphenol B
IUPAC Name:	methyl 2-(3,5-dibromo-2,4-dihydroxyphenyl)acetate
Synonyms:	subereaphenol B
Standard InCHIKey:	RMRNQYDAEAONQT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8Br2O4/c1-15-6(12)3-4-2-5(10)9(14)7(11)8(4)13/h2,13-14H,3H2,1H3
SMILES:	COC(=O)Cc1cc(c(c(c1O)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447693
PubChem CID:	25016148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	red sea	n.a.	PMID[18656986]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[21542602]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542602]
NPO29034	Suberea mollis	Species	Aplysinellidae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	5.0	mm	PMID[499352]

☑ 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 NPC259017 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	360
0.1-0.2	1854
0.2-0.3	6003
0.3-0.4	14283
0.4-0.5	5261
0.5-0.6	10957
0.6-0.7	3866
0.7-0.8	108
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.873	High Similarity	NPC180207
0.8372	Intermediate Similarity	NPC471486
0.8244	Intermediate Similarity	NPC116562
0.7832	Intermediate Similarity	NPC81137
0.7817	Intermediate Similarity	NPC471237
0.7817	Intermediate Similarity	NPC177967
0.7762	Intermediate Similarity	NPC197766
0.7762	Intermediate Similarity	NPC471236
0.7752	Intermediate Similarity	NPC471488
0.7606	Intermediate Similarity	NPC471328
0.7548	Intermediate Similarity	NPC305490
0.7537	Intermediate Similarity	NPC100395
0.7518	Intermediate Similarity	NPC105999
0.7481	Intermediate Similarity	NPC33244
0.7465	Intermediate Similarity	NPC198249
0.7464	Intermediate Similarity	NPC213414
0.7442	Intermediate Similarity	NPC54543
0.7432	Intermediate Similarity	NPC184632
0.7429	Intermediate Similarity	NPC209959
0.7424	Intermediate Similarity	NPC94217
0.7394	Intermediate Similarity	NPC11449
0.7386	Intermediate Similarity	NPC235033
0.7386	Intermediate Similarity	NPC73132
0.7386	Intermediate Similarity	NPC471235
0.7385	Intermediate Similarity	NPC473358
0.7385	Intermediate Similarity	NPC471487
0.7381	Intermediate Similarity	NPC13426
0.7361	Intermediate Similarity	NPC244890
0.7357	Intermediate Similarity	NPC95309
0.7333	Intermediate Similarity	NPC209486
0.7333	Intermediate Similarity	NPC40649
0.7319	Intermediate Similarity	NPC296202
0.7315	Intermediate Similarity	NPC147137
0.7308	Intermediate Similarity	NPC473372
0.7286	Intermediate Similarity	NPC262671
0.7286	Intermediate Similarity	NPC201728
0.7254	Intermediate Similarity	NPC293453
0.7246	Intermediate Similarity	NPC7830
0.7244	Intermediate Similarity	NPC294870
0.7231	Intermediate Similarity	NPC471495
0.7226	Intermediate Similarity	NPC294037
0.7222	Intermediate Similarity	NPC219892
0.7222	Intermediate Similarity	NPC189823
0.7222	Intermediate Similarity	NPC52472
0.7219	Intermediate Similarity	NPC270848
0.7219	Intermediate Similarity	NPC272868
0.7219	Intermediate Similarity	NPC122599
0.7218	Intermediate Similarity	NPC223004
0.7218	Intermediate Similarity	NPC98543
0.7211	Intermediate Similarity	NPC223616
0.7206	Intermediate Similarity	NPC241089
0.7203	Intermediate Similarity	NPC478071
0.719	Intermediate Similarity	NPC178097
0.7183	Intermediate Similarity	NPC122359
0.7183	Intermediate Similarity	NPC159987
0.7183	Intermediate Similarity	NPC78061
0.7174	Intermediate Similarity	NPC149246
0.7174	Intermediate Similarity	NPC146642
0.7172	Intermediate Similarity	NPC307289
0.7172	Intermediate Similarity	NPC476389
0.7172	Intermediate Similarity	NPC243404
0.7164	Intermediate Similarity	NPC276111
0.7164	Intermediate Similarity	NPC118288
0.7161	Intermediate Similarity	NPC470710
0.7153	Intermediate Similarity	NPC307732
0.7153	Intermediate Similarity	NPC158222
0.7153	Intermediate Similarity	NPC42292
0.7153	Intermediate Similarity	NPC161617
0.7152	Intermediate Similarity	NPC474535
0.7143	Intermediate Similarity	NPC80027
0.7143	Intermediate Similarity	NPC245561
0.7133	Intermediate Similarity	NPC41263
0.7132	Intermediate Similarity	NPC13495
0.7123	Intermediate Similarity	NPC153783
0.7122	Intermediate Similarity	NPC215392
0.7107	Intermediate Similarity	NPC475697
0.7103	Intermediate Similarity	NPC474753
0.7103	Intermediate Similarity	NPC264145
0.7101	Intermediate Similarity	NPC159525
0.7099	Intermediate Similarity	NPC31274
0.7092	Intermediate Similarity	NPC145134
0.7092	Intermediate Similarity	NPC6888
0.7071	Intermediate Similarity	NPC91105
0.7071	Intermediate Similarity	NPC475192
0.7071	Intermediate Similarity	NPC297193
0.7067	Intermediate Similarity	NPC471819
0.7063	Intermediate Similarity	NPC128428
0.7063	Intermediate Similarity	NPC305518
0.7059	Intermediate Similarity	NPC83718
0.7034	Intermediate Similarity	NPC469929
0.7034	Intermediate Similarity	NPC247477
0.7034	Intermediate Similarity	NPC17840
0.7027	Intermediate Similarity	NPC180905
0.7027	Intermediate Similarity	NPC182496
0.7021	Intermediate Similarity	NPC65761
0.7021	Intermediate Similarity	NPC472029
0.702	Intermediate Similarity	NPC183642
0.702	Intermediate Similarity	NPC310370
0.702	Intermediate Similarity	NPC118794
0.7015	Intermediate Similarity	NPC48525
0.7015	Intermediate Similarity	NPC17693
0.7014	Intermediate Similarity	NPC79332
0.7008	Intermediate Similarity	NPC280869
0.7007	Intermediate Similarity	NPC1321
0.7007	Intermediate Similarity	NPC156124
0.7007	Intermediate Similarity	NPC121259
0.7007	Intermediate Similarity	NPC304929
0.7007	Intermediate Similarity	NPC230349
0.7	Intermediate Similarity	NPC143427
0.7	Intermediate Similarity	NPC224273
0.7	Intermediate Similarity	NPC303737
0.7	Intermediate Similarity	NPC73532
0.7	Intermediate Similarity	NPC242895
0.7	Intermediate Similarity	NPC196976
0.7	Intermediate Similarity	NPC19174
0.7	Intermediate Similarity	NPC267552
0.7	Intermediate Similarity	NPC115159
0.7	Intermediate Similarity	NPC45438
0.7	Intermediate Similarity	NPC226275
0.698	Remote Similarity	NPC158481
0.698	Remote Similarity	NPC475955
0.698	Remote Similarity	NPC156892
0.698	Remote Similarity	NPC474726
0.698	Remote Similarity	NPC235115
0.6974	Remote Similarity	NPC90411
0.6972	Remote Similarity	NPC137117
0.6966	Remote Similarity	NPC212379
0.6966	Remote Similarity	NPC69235
0.6966	Remote Similarity	NPC85049
0.6963	Remote Similarity	NPC148969
0.6963	Remote Similarity	NPC62546
0.6963	Remote Similarity	NPC162113
0.6959	Remote Similarity	NPC175943
0.6959	Remote Similarity	NPC474394
0.6957	Remote Similarity	NPC273282
0.6957	Remote Similarity	NPC474890
0.6957	Remote Similarity	NPC161943
0.6954	Remote Similarity	NPC275356
0.695	Remote Similarity	NPC225710
0.695	Remote Similarity	NPC32032
0.695	Remote Similarity	NPC229213
0.695	Remote Similarity	NPC67300
0.695	Remote Similarity	NPC133909
0.695	Remote Similarity	NPC309765
0.6947	Remote Similarity	NPC317592
0.6934	Remote Similarity	NPC131192
0.6934	Remote Similarity	NPC128825
0.6933	Remote Similarity	NPC135837
0.6933	Remote Similarity	NPC70380
0.6933	Remote Similarity	NPC149372
0.6933	Remote Similarity	NPC474849
0.6933	Remote Similarity	NPC194579
0.6933	Remote Similarity	NPC65837
0.6933	Remote Similarity	NPC71256
0.6933	Remote Similarity	NPC178467
0.6933	Remote Similarity	NPC474771
0.6929	Remote Similarity	NPC165197
0.6929	Remote Similarity	NPC297186
0.6929	Remote Similarity	NPC260000
0.6923	Remote Similarity	NPC173608
0.6923	Remote Similarity	NPC10926
0.6923	Remote Similarity	NPC475733
0.6918	Remote Similarity	NPC470987
0.6918	Remote Similarity	NPC21378
0.6918	Remote Similarity	NPC147757
0.6918	Remote Similarity	NPC160081
0.6918	Remote Similarity	NPC247779
0.6918	Remote Similarity	NPC226493
0.6918	Remote Similarity	NPC12694
0.6917	Remote Similarity	NPC234639
0.6917	Remote Similarity	NPC326187
0.6913	Remote Similarity	NPC278375
0.6913	Remote Similarity	NPC18646
0.6912	Remote Similarity	NPC221870
0.6912	Remote Similarity	NPC115803
0.6903	Remote Similarity	NPC97188
0.6901	Remote Similarity	NPC473572
0.6901	Remote Similarity	NPC474169
0.6897	Remote Similarity	NPC24869
0.6897	Remote Similarity	NPC473744
0.6897	Remote Similarity	NPC80694
0.6897	Remote Similarity	NPC186098
0.6897	Remote Similarity	NPC470981
0.6897	Remote Similarity	NPC150929
0.6892	Remote Similarity	NPC48036
0.6892	Remote Similarity	NPC37299
0.6892	Remote Similarity	NPC180261
0.6887	Remote Similarity	NPC148738
0.6887	Remote Similarity	NPC191835
0.6887	Remote Similarity	NPC475974
0.6887	Remote Similarity	NPC33144
0.6887	Remote Similarity	NPC327612
0.6887	Remote Similarity	NPC472403
0.6887	Remote Similarity	NPC73078
0.6887	Remote Similarity	NPC319870
0.6887	Remote Similarity	NPC94248
0.6887	Remote Similarity	NPC9121
0.6887	Remote Similarity	NPC221046
0.6887	Remote Similarity	NPC212693
0.6887	Remote Similarity	NPC177307

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 NPC259017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1048
0.2-0.3	2159
0.3-0.4	3136
0.4-0.5	1680
0.5-0.6	701
0.6-0.7	96
0.7-0.8	3
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
0.7571	Intermediate Similarity	NPD9718	Approved
0.7484	Intermediate Similarity	NPD4288	Approved
0.7076	Intermediate Similarity	NPD4287	Approved
0.7031	Intermediate Similarity	NPD940	Approved
0.7031	Intermediate Similarity	NPD846	Approved
0.7007	Intermediate Similarity	NPD230	Phase 1
0.695	Remote Similarity	NPD9269	Phase 2
0.6934	Remote Similarity	NPD9493	Approved
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9268	Approved
0.6842	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9545	Approved
0.6794	Remote Similarity	NPD9244	Approved
0.6767	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD422	Phase 1
0.6728	Remote Similarity	NPD2296	Approved
0.6716	Remote Similarity	NPD74	Approved
0.6716	Remote Similarity	NPD9266	Approved
0.6711	Remote Similarity	NPD1240	Approved
0.6645	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD9267	Approved
0.6642	Remote Similarity	NPD9264	Approved
0.6642	Remote Similarity	NPD9263	Approved
0.6623	Remote Similarity	NPD1607	Approved
0.66	Remote Similarity	NPD943	Approved
0.6596	Remote Similarity	NPD1759	Phase 1
0.6582	Remote Similarity	NPD2533	Approved
0.6582	Remote Similarity	NPD2534	Approved
0.6582	Remote Similarity	NPD2532	Approved
0.6538	Remote Similarity	NPD3750	Approved
0.6536	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1510	Phase 2
0.6536	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1758	Phase 1
0.65	Remote Similarity	NPD255	Approved
0.65	Remote Similarity	NPD256	Approved
0.6494	Remote Similarity	NPD1551	Phase 2
0.6494	Remote Similarity	NPD2935	Discontinued
0.6483	Remote Similarity	NPD9717	Approved
0.6483	Remote Similarity	NPD1481	Phase 2
0.6463	Remote Similarity	NPD1164	Approved
0.6452	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1242	Phase 1
0.6429	Remote Similarity	NPD1169	Approved
0.6429	Remote Similarity	NPD9281	Approved
0.6423	Remote Similarity	NPD4750	Phase 3
0.6414	Remote Similarity	NPD1535	Discovery
0.641	Remote Similarity	NPD1549	Phase 2
0.6375	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1548	Phase 1
0.6358	Remote Similarity	NPD1296	Phase 2
0.6358	Remote Similarity	NPD3764	Approved
0.6351	Remote Similarity	NPD1203	Approved
0.6343	Remote Similarity	NPD9261	Approved
0.6341	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD9568	Approved
0.6335	Remote Similarity	NPD2184	Approved
0.6335	Remote Similarity	NPD2183	Approved
0.6329	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6799	Approved
0.6288	Remote Similarity	NPD9495	Approved
0.6287	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5405	Approved
0.6282	Remote Similarity	NPD5408	Approved
0.6282	Remote Similarity	NPD5406	Approved
0.6282	Remote Similarity	NPD5404	Approved
0.6275	Remote Similarity	NPD468	Phase 1
0.6266	Remote Similarity	NPD2800	Approved
0.626	Remote Similarity	NPD1809	Phase 2
0.625	Remote Similarity	NPD1894	Discontinued
0.6242	Remote Similarity	NPD7411	Suspended
0.6242	Remote Similarity	NPD2797	Approved
0.6234	Remote Similarity	NPD447	Suspended
0.6218	Remote Similarity	NPD3748	Approved
0.6211	Remote Similarity	NPD7390	Discontinued
0.6211	Remote Similarity	NPD1511	Approved
0.6209	Remote Similarity	NPD520	Approved
0.6205	Remote Similarity	NPD37	Approved
0.6199	Remote Similarity	NPD6232	Discontinued
0.6194	Remote Similarity	NPD6651	Approved
0.619	Remote Similarity	NPD7768	Phase 2
0.619	Remote Similarity	NPD1610	Phase 2
0.6183	Remote Similarity	NPD2934	Approved
0.6183	Remote Similarity	NPD2933	Approved
0.6174	Remote Similarity	NPD1283	Approved
0.6173	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2801	Approved
0.6164	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7075	Discontinued
0.6149	Remote Similarity	NPD1608	Approved
0.6144	Remote Similarity	NPD6798	Discontinued
0.6144	Remote Similarity	NPD3268	Approved
0.6139	Remote Similarity	NPD6005	Phase 3
0.6139	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6004	Phase 3
0.6139	Remote Similarity	NPD6002	Phase 3
0.6139	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2859	Approved
0.6136	Remote Similarity	NPD2860	Approved
0.6135	Remote Similarity	NPD1512	Approved
0.6133	Remote Similarity	NPD1470	Approved
0.6129	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5124	Phase 1
0.6125	Remote Similarity	NPD3400	Discontinued
0.6122	Remote Similarity	NPD3847	Discontinued
0.6118	Remote Similarity	NPD6234	Discontinued
0.6118	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4908	Phase 1
0.6111	Remote Similarity	NPD111	Approved
0.6111	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD1934	Approved
0.6107	Remote Similarity	NPD845	Approved
0.6105	Remote Similarity	NPD1161	Approved
0.6104	Remote Similarity	NPD6233	Phase 2
0.6104	Remote Similarity	NPD259	Phase 1
0.6098	Remote Similarity	NPD920	Approved
0.6095	Remote Similarity	NPD4967	Phase 2
0.6095	Remote Similarity	NPD4965	Approved
0.6095	Remote Similarity	NPD4966	Approved
0.6093	Remote Similarity	NPD258	Approved
0.6093	Remote Similarity	NPD257	Approved
0.6093	Remote Similarity	NPD1019	Discontinued
0.6092	Remote Similarity	NPD7473	Discontinued
0.6087	Remote Similarity	NPD6190	Approved
0.6084	Remote Similarity	NPD4380	Phase 2
0.6084	Remote Similarity	NPD6599	Discontinued
0.6081	Remote Similarity	NPD1201	Approved
0.608	Remote Similarity	NPD9491	Approved
0.6076	Remote Similarity	NPD9570	Approved
0.6076	Remote Similarity	NPD6100	Approved
0.6076	Remote Similarity	NPD6099	Approved
0.6074	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7819	Suspended
0.6071	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1465	Phase 2
0.6067	Remote Similarity	NPD3225	Approved
0.6065	Remote Similarity	NPD825	Approved
0.6065	Remote Similarity	NPD826	Approved
0.6062	Remote Similarity	NPD1652	Phase 2
0.6062	Remote Similarity	NPD1243	Approved
0.6061	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD3749	Approved
0.6058	Remote Similarity	NPD164	Approved
0.6054	Remote Similarity	NPD1778	Approved
0.6053	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD2313	Discontinued
0.6039	Remote Similarity	NPD411	Approved
0.6039	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3817	Phase 2
0.6026	Remote Similarity	NPD6355	Discontinued
0.6026	Remote Similarity	NPD555	Phase 2
0.6015	Remote Similarity	NPD844	Approved
0.6014	Remote Similarity	NPD1241	Discontinued
0.6013	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD6832	Phase 2
0.6013	Remote Similarity	NPD7033	Discontinued
0.6013	Remote Similarity	NPD2799	Discontinued
0.6013	Remote Similarity	NPD4308	Phase 3
0.6012	Remote Similarity	NPD6801	Discontinued
0.6012	Remote Similarity	NPD5710	Approved
0.6012	Remote Similarity	NPD5711	Approved
0.6	Remote Similarity	NPD6663	Approved
0.6	Remote Similarity	NPD5403	Approved
0.6	Remote Similarity	NPD3020	Approved
0.6	Remote Similarity	NPD9256	Approved
0.6	Remote Similarity	NPD9258	Approved
0.6	Remote Similarity	NPD3882	Suspended
0.5986	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD642	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5401	Approved
0.5975	Remote Similarity	NPD2796	Approved
0.5974	Remote Similarity	NPD3136	Phase 2
0.5974	Remote Similarity	NPD3027	Phase 3
0.5973	Remote Similarity	NPD1281	Approved
0.597	Remote Similarity	NPD288	Approved
0.5965	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD2654	Approved
0.5962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1613	Approved
0.596	Remote Similarity	NPD196	Phase 1
0.5949	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD454	Approved
0.5948	Remote Similarity	NPD9569	Approved
0.5948	Remote Similarity	NPD5736	Approved
0.5946	Remote Similarity	NPD2932	Approved
0.5946	Remote Similarity	NPD4626	Approved
0.5946	Remote Similarity	NPD17	Approved
0.5946	Remote Similarity	NPD3019	Approved
0.5943	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5402	Approved
0.5932	Remote Similarity	NPD7286	Phase 2
0.5926	Remote Similarity	NPD4628	Phase 3
0.5923	Remote Similarity	NPD800	Approved
0.5921	Remote Similarity	NPD3266	Approved
0.5921	Remote Similarity	NPD3267	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