NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	295.87
Volume:	178.1
LogP:	2.051
LogD:	1.644
LogS:	-2.621
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	2.764
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788
MDCK Permeability:	1.3803020010527689e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.522
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	96.95726776123047%
Volume Distribution (VD):	1.012
Pgp-substrate:	7.505465984344482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.722
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.425
CYP2D6-inhibitor:	0.187
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	5.325
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.943
Carcinogencity:	0.162
Eye Corrosion:	0.115
Eye Irritation:	0.969
Respiratory Toxicity:	0.265

Download Data

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

Natural Product: NPC47790

Natural Product ID:	NPC47790
*Common Name:**	Lanosol
IUPAC Name:	3,4-dibromo-5-(hydroxymethyl)benzene-1,2-diol
Synonyms:	Lanosol
Standard InCHIKey:	GKZCMEUEEFOXIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H6Br2O3/c8-5-3(2-10)1-4(11)7(12)6(5)9/h1,10-12H,2H2
SMILES:	OCc1cc(O)c(c(c1Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253482
PubChem CID:	78659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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]
NPO32930	polysiphonia lanosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387639]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
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	3
MIC	10

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	18300.0	nM	PMID[508063]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	20400.0	nM	PMID[508063]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[508062]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	50.0	ug.mL-1	PMID[508062]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	=	50.0	ug.mL-1	PMID[508062]
NPT2	Others	Unspecified		IC50	=	89000.0	nM	PMID[508064]

☑ 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 NPC47790 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	666
0.1-0.2	3067
0.2-0.3	13716
0.3-0.4	7651
0.4-0.5	9514
0.5-0.6	6618
0.6-0.7	1364
0.7-0.8	59
0.8-0.85	14
0.85-0.9	18
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC137117
0.9402	High Similarity	NPC474146
0.9391	High Similarity	NPC79844
0.9268	High Similarity	NPC85049
0.9194	High Similarity	NPC160081
0.9194	High Similarity	NPC226493
0.9187	High Similarity	NPC150929
0.916	High Similarity	NPC227976
0.9127	High Similarity	NPC163560
0.8906	High Similarity	NPC245386
0.881	High Similarity	NPC474614
0.879	High Similarity	NPC220311
0.872	High Similarity	NPC43706
0.8699	High Similarity	NPC229213
0.8651	High Similarity	NPC474147
0.8651	High Similarity	NPC473708
0.864	High Similarity	NPC142776
0.8636	High Similarity	NPC160932
0.8629	High Similarity	NPC473572
0.8629	High Similarity	NPC474169
0.8626	High Similarity	NPC224663
0.8618	High Similarity	NPC136543
0.8571	High Similarity	NPC134219
0.8561	High Similarity	NPC271942
0.8538	High Similarity	NPC244890
0.8507	High Similarity	NPC89341
0.8504	High Similarity	NPC13004
0.85	High Similarity	NPC50782
0.8374	Intermediate Similarity	NPC38483
0.8372	Intermediate Similarity	NPC474536
0.8321	Intermediate Similarity	NPC109346
0.8321	Intermediate Similarity	NPC300678
0.8271	Intermediate Similarity	NPC199089
0.8182	Intermediate Similarity	NPC303011
0.8148	Intermediate Similarity	NPC156356
0.811	Intermediate Similarity	NPC219444
0.8102	Intermediate Similarity	NPC118794
0.808	Intermediate Similarity	NPC117759
0.8047	Intermediate Similarity	NPC84606
0.7926	Intermediate Similarity	NPC312155
0.7883	Intermediate Similarity	NPC168680
0.7817	Intermediate Similarity	NPC88896
0.7778	Intermediate Similarity	NPC152947
0.7778	Intermediate Similarity	NPC474135
0.7744	Intermediate Similarity	NPC214553
0.7731	Intermediate Similarity	NPC12278
0.7704	Intermediate Similarity	NPC43613
0.7687	Intermediate Similarity	NPC105702
0.7612	Intermediate Similarity	NPC55113
0.7586	Intermediate Similarity	NPC473608
0.7574	Intermediate Similarity	NPC110800
0.7563	Intermediate Similarity	NPC110764
0.7542	Intermediate Similarity	NPC131587
0.748	Intermediate Similarity	NPC471495
0.7467	Intermediate Similarity	NPC474535
0.7464	Intermediate Similarity	NPC471328
0.7417	Intermediate Similarity	NPC475697
0.736	Intermediate Similarity	NPC473358
0.736	Intermediate Similarity	NPC471487
0.7323	Intermediate Similarity	NPC471485
0.7323	Intermediate Similarity	NPC76400
0.7323	Intermediate Similarity	NPC471488
0.7311	Intermediate Similarity	NPC109955
0.7297	Intermediate Similarity	NPC7398
0.7292	Intermediate Similarity	NPC184632
0.7288	Intermediate Similarity	NPC107522
0.728	Intermediate Similarity	NPC473372
0.728	Intermediate Similarity	NPC54543
0.7266	Intermediate Similarity	NPC94217
0.7213	Intermediate Similarity	NPC477802
0.7213	Intermediate Similarity	NPC477801
0.7188	Intermediate Similarity	NPC33244
0.7162	Intermediate Similarity	NPC178097
0.7143	Intermediate Similarity	NPC62258
0.7143	Intermediate Similarity	NPC471486
0.7143	Intermediate Similarity	NPC55617
0.7143	Intermediate Similarity	NPC71266
0.7132	Intermediate Similarity	NPC120280
0.7103	Intermediate Similarity	NPC250597
0.7094	Intermediate Similarity	NPC312304
0.7094	Intermediate Similarity	NPC300478
0.7087	Intermediate Similarity	NPC147634
0.7087	Intermediate Similarity	NPC226401
0.7087	Intermediate Similarity	NPC79793
0.7087	Intermediate Similarity	NPC174096
0.7087	Intermediate Similarity	NPC120982
0.7073	Intermediate Similarity	NPC196479
0.7054	Intermediate Similarity	NPC264558
0.7049	Intermediate Similarity	NPC223393
0.7045	Intermediate Similarity	NPC15350
0.704	Intermediate Similarity	NPC19149
0.7031	Intermediate Similarity	NPC179002
0.7031	Intermediate Similarity	NPC257430
0.7031	Intermediate Similarity	NPC187583
0.7023	Intermediate Similarity	NPC221049
0.7016	Intermediate Similarity	NPC471511
0.7016	Intermediate Similarity	NPC120719
0.6992	Remote Similarity	NPC320987
0.6992	Remote Similarity	NPC181969
0.6984	Remote Similarity	NPC176527
0.696	Remote Similarity	NPC239291
0.694	Remote Similarity	NPC169207
0.694	Remote Similarity	NPC115627
0.694	Remote Similarity	NPC177475
0.694	Remote Similarity	NPC472071
0.694	Remote Similarity	NPC118522
0.694	Remote Similarity	NPC180207
0.694	Remote Similarity	NPC148615
0.694	Remote Similarity	NPC35071
0.6929	Remote Similarity	NPC34864
0.6929	Remote Similarity	NPC105727
0.6929	Remote Similarity	NPC114392
0.6929	Remote Similarity	NPC58427
0.6917	Remote Similarity	NPC255675
0.6917	Remote Similarity	NPC475466
0.6917	Remote Similarity	NPC191194
0.6917	Remote Similarity	NPC63126
0.6911	Remote Similarity	NPC130103
0.6905	Remote Similarity	NPC477814
0.6899	Remote Similarity	NPC78918
0.6899	Remote Similarity	NPC268032
0.6899	Remote Similarity	NPC139617
0.6883	Remote Similarity	NPC294870
0.688	Remote Similarity	NPC52087
0.688	Remote Similarity	NPC79672
0.6879	Remote Similarity	NPC473724
0.6866	Remote Similarity	NPC477803
0.6866	Remote Similarity	NPC100395
0.686	Remote Similarity	NPC313650
0.6838	Remote Similarity	NPC173511
0.6838	Remote Similarity	NPC476343
0.6838	Remote Similarity	NPC88733
0.6838	Remote Similarity	NPC266045
0.6838	Remote Similarity	NPC470804
0.6831	Remote Similarity	NPC259017
0.6831	Remote Similarity	NPC158078
0.6815	Remote Similarity	NPC63317
0.6815	Remote Similarity	NPC38980
0.6815	Remote Similarity	NPC41232
0.6813	Remote Similarity	NPC191557
0.6807	Remote Similarity	NPC300017
0.6797	Remote Similarity	NPC233835
0.6794	Remote Similarity	NPC59387
0.6788	Remote Similarity	NPC209567
0.678	Remote Similarity	NPC104216
0.6772	Remote Similarity	NPC1075
0.6772	Remote Similarity	NPC1786
0.6772	Remote Similarity	NPC294902
0.6769	Remote Similarity	NPC156840
0.6769	Remote Similarity	NPC173746
0.6769	Remote Similarity	NPC8547
0.6769	Remote Similarity	NPC257124
0.6765	Remote Similarity	NPC153580
0.6765	Remote Similarity	NPC470414
0.6765	Remote Similarity	NPC226737
0.6765	Remote Similarity	NPC299939
0.6752	Remote Similarity	NPC305490
0.6748	Remote Similarity	NPC88420
0.6748	Remote Similarity	NPC474073
0.6744	Remote Similarity	NPC233731
0.6744	Remote Similarity	NPC36108
0.6744	Remote Similarity	NPC254833
0.6744	Remote Similarity	NPC7097
0.6744	Remote Similarity	NPC246358
0.6744	Remote Similarity	NPC473524
0.6744	Remote Similarity	NPC228343
0.6742	Remote Similarity	NPC217472
0.6742	Remote Similarity	NPC115803
0.6741	Remote Similarity	NPC135961
0.6739	Remote Similarity	NPC230013
0.6739	Remote Similarity	NPC81149
0.6739	Remote Similarity	NPC131940
0.6739	Remote Similarity	NPC473451
0.6739	Remote Similarity	NPC197576
0.6739	Remote Similarity	NPC68350
0.6739	Remote Similarity	NPC220598
0.6739	Remote Similarity	NPC165375
0.6728	Remote Similarity	NPC288747
0.6724	Remote Similarity	NPC319826
0.6716	Remote Similarity	NPC164386
0.6715	Remote Similarity	NPC49341
0.6715	Remote Similarity	NPC40302
0.6715	Remote Similarity	NPC137922
0.6694	Remote Similarity	NPC325292
0.6694	Remote Similarity	NPC138117
0.6692	Remote Similarity	NPC222084
0.6692	Remote Similarity	NPC4665
0.6692	Remote Similarity	NPC472893
0.6691	Remote Similarity	NPC229401
0.6667	Remote Similarity	NPC95381
0.6667	Remote Similarity	NPC64130
0.6667	Remote Similarity	NPC25134
0.6667	Remote Similarity	NPC226514
0.6667	Remote Similarity	NPC295879
0.6667	Remote Similarity	NPC148969
0.6667	Remote Similarity	NPC104124
0.6667	Remote Similarity	NPC159866
0.6667	Remote Similarity	NPC175520
0.6667	Remote Similarity	NPC296202
0.6667	Remote Similarity	NPC97157

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 NPC47790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	565
0.1-0.2	1167
0.2-0.3	3107
0.3-0.4	2572
0.4-0.5	1307
0.5-0.6	382
0.6-0.7	48
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
0.7583	Intermediate Similarity	NPD9244	Approved
0.7087	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9381	Approved
0.694	Remote Similarity	NPD9384	Approved
0.6769	Remote Similarity	NPD228	Approved
0.6744	Remote Similarity	NPD3021	Approved
0.6744	Remote Similarity	NPD3022	Approved
0.6739	Remote Similarity	NPD9622	Approved
0.6596	Remote Similarity	NPD9620	Approved
0.6596	Remote Similarity	NPD9621	Approved
0.6596	Remote Similarity	NPD9619	Approved
0.6591	Remote Similarity	NPD9379	Approved
0.6591	Remote Similarity	NPD9377	Approved
0.6508	Remote Similarity	NPD1242	Phase 1
0.6458	Remote Similarity	NPD3027	Phase 3
0.6441	Remote Similarity	NPD111	Approved
0.6429	Remote Similarity	NPD9269	Phase 2
0.6414	Remote Similarity	NPD601	Approved
0.6414	Remote Similarity	NPD598	Approved
0.6414	Remote Similarity	NPD597	Approved
0.637	Remote Similarity	NPD1130	Approved
0.637	Remote Similarity	NPD1136	Approved
0.637	Remote Similarity	NPD1132	Approved
0.6327	Remote Similarity	NPD3061	Approved
0.6327	Remote Similarity	NPD3059	Approved
0.6327	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1613	Approved
0.6327	Remote Similarity	NPD3062	Approved
0.6281	Remote Similarity	NPD9094	Approved
0.625	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD817	Approved
0.6242	Remote Similarity	NPD4010	Discontinued
0.6242	Remote Similarity	NPD823	Approved
0.6242	Remote Similarity	NPD5314	Approved
0.6241	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.624	Remote Similarity	NPD2934	Approved
0.624	Remote Similarity	NPD2933	Approved
0.624	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD9718	Approved
0.6207	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD940	Approved
0.6202	Remote Similarity	NPD846	Approved
0.619	Remote Similarity	NPD2860	Approved
0.619	Remote Similarity	NPD844	Approved
0.619	Remote Similarity	NPD2859	Approved
0.6174	Remote Similarity	NPD230	Phase 1
0.6172	Remote Similarity	NPD3020	Approved
0.6164	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD9268	Approved
0.6143	Remote Similarity	NPD1357	Approved
0.6142	Remote Similarity	NPD288	Approved
0.6127	Remote Similarity	NPD3092	Approved
0.6118	Remote Similarity	NPD9570	Approved
0.6078	Remote Similarity	NPD7266	Discontinued
0.6069	Remote Similarity	NPD3094	Phase 2
0.6042	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD9618	Approved
0.6014	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD9614	Approved
0.6	Remote Similarity	NPD4750	Phase 3
0.6	Remote Similarity	NPD5311	Approved
0.6	Remote Similarity	NPD5310	Approved
0.6	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3620	Phase 2
0.5986	Remote Similarity	NPD9494	Approved
0.5974	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.597	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD3055	Approved
0.5959	Remote Similarity	NPD3053	Approved
0.5957	Remote Similarity	NPD3091	Approved
0.5948	Remote Similarity	NPD1169	Approved
0.5938	Remote Similarity	NPD1809	Phase 2
0.5926	Remote Similarity	NPD2684	Approved
0.5924	Remote Similarity	NPD6190	Approved
0.5918	Remote Similarity	NPD257	Approved
0.5918	Remote Similarity	NPD258	Approved
0.5903	Remote Similarity	NPD3705	Approved
0.5897	Remote Similarity	NPD9294	Approved
0.5896	Remote Similarity	NPD968	Approved
0.5894	Remote Similarity	NPD825	Approved
0.5894	Remote Similarity	NPD1558	Phase 1
0.5894	Remote Similarity	NPD943	Approved
0.5894	Remote Similarity	NPD826	Approved
0.5887	Remote Similarity	NPD9615	Approved
0.5887	Remote Similarity	NPD856	Approved
0.5887	Remote Similarity	NPD9616	Approved
0.5887	Remote Similarity	NPD317	Approved
0.5887	Remote Similarity	NPD318	Approved
0.5887	Remote Similarity	NPD9613	Approved
0.5887	Remote Similarity	NPD16	Approved
0.5878	Remote Similarity	NPD9569	Approved
0.5859	Remote Similarity	NPD9296	Approved
0.5855	Remote Similarity	NPD555	Phase 2
0.5852	Remote Similarity	NPD290	Approved
0.5847	Remote Similarity	NPD9088	Approved
0.5846	Remote Similarity	NPD9273	Approved
0.5845	Remote Similarity	NPD316	Approved
0.5844	Remote Similarity	NPD651	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD9093	Approved
0.5828	Remote Similarity	NPD2674	Phase 3
0.5828	Remote Similarity	NPD259	Phase 1
0.5827	Remote Similarity	NPD5283	Phase 1
0.5823	Remote Similarity	NPD302	Approved
0.58	Remote Similarity	NPD9537	Phase 1
0.58	Remote Similarity	NPD9536	Phase 1
0.5789	Remote Similarity	NPD9500	Approved
0.5785	Remote Similarity	NPD9089	Approved
0.5781	Remote Similarity	NPD845	Approved
0.5778	Remote Similarity	NPD1444	Approved
0.5778	Remote Similarity	NPD1445	Approved
0.5776	Remote Similarity	NPD9087	Approved
0.5772	Remote Similarity	NPD2861	Phase 2
0.5764	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD3145	Approved
0.5762	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD3144	Approved
0.5755	Remote Similarity	NPD7843	Approved
0.5746	Remote Similarity	NPD9608	Approved
0.5746	Remote Similarity	NPD9610	Approved
0.5745	Remote Similarity	NPD7157	Approved
0.5734	Remote Similarity	NPD9545	Approved
0.5734	Remote Similarity	NPD1548	Phase 1
0.5714	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD1653	Approved
0.5705	Remote Similarity	NPD599	Approved
0.5705	Remote Similarity	NPD858	Approved
0.5705	Remote Similarity	NPD859	Approved
0.5705	Remote Similarity	NPD602	Approved
0.5696	Remote Similarity	NPD3060	Approved
0.5689	Remote Similarity	NPD4288	Approved
0.5685	Remote Similarity	NPD1610	Phase 2
0.5685	Remote Similarity	NPD1091	Approved
0.5683	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD2184	Approved
0.5679	Remote Similarity	NPD2183	Approved
0.5655	Remote Similarity	NPD3095	Discontinued
0.5652	Remote Similarity	NPD1792	Phase 2
0.5649	Remote Similarity	NPD275	Approved
0.5649	Remote Similarity	NPD274	Approved
0.5646	Remote Similarity	NPD2562	Approved
0.5646	Remote Similarity	NPD2561	Approved
0.5643	Remote Similarity	NPD7635	Approved
0.564	Remote Similarity	NPD6687	Approved
0.564	Remote Similarity	NPD6688	Approved
0.5634	Remote Similarity	NPD6671	Approved
0.562	Remote Similarity	NPD2342	Discontinued
0.5617	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD2568	Approved
0.5608	Remote Similarity	NPD4659	Approved
0.5608	Remote Similarity	NPD2982	Phase 2
0.5608	Remote Similarity	NPD2983	Phase 2
0.5603	Remote Similarity	NPD2228	Approved
0.5603	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD2229	Approved
0.5603	Remote Similarity	NPD2234	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