NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.1
Volume:	182.631
LogP:	1.5
LogD:	1.298
LogS:	-0.971
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.195
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.318
MDCK Permeability:	1.644305302761495e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.75
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	61.66155242919922%
Volume Distribution (VD):	2.108
Pgp-substrate:	33.70490264892578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.7
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.697
CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.202
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	14.461
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.563
Carcinogencity:	0.343
Eye Corrosion:	0.283
Eye Irritation:	0.977
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC325292

Natural Product ID:	NPC325292
*Common Name:**	4-(3-Hydroxybutyl)Phenol
IUPAC Name:	4-(3-hydroxybutyl)phenol
Synonyms:
Standard InCHIKey:	SFUCGABQOMYVJW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-8,11-12H,2-3H2,1H3
SMILES:	CC(CCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL108014
PubChem CID:	97790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	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
Others	6
Potency	5

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[533752]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	19952.6	nM	PMID[533753]
NPT4	Individual Protein	Large T antigen	Simian virus 40	IC50	n.a.	25380.0	nM	PMID[533753]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[533753]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	1412.5	nM	PMID[533753]
NPT2	Others	Unspecified		IC50	=	8460.0	nM	PMID[533753]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	414.7	nM	PMID[533753]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	293.6	nM	PMID[533753]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	13.09	%	PMID[533754]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	11.83	%	PMID[533754]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	-4.87	%	PMID[533754]
NPT2	Others	Unspecified		Percent Effect	=	11.18	%	PMID[533755]
NPT2	Others	Unspecified		Percent Effect	=	-4.294	%	PMID[533755]
NPT2	Others	Unspecified		Percent Effect	=	23.7	%	PMID[533755]

☑ 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 NPC325292 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	189
0.1-0.2	1403
0.2-0.3	5166
0.3-0.4	13193
0.4-0.5	6984
0.5-0.6	9546
0.6-0.7	4746
0.7-0.8	1155
0.8-0.85	202
0.85-0.9	77
0.9-0.95	32
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138117
0.9775	High Similarity	NPC313650
0.977	High Similarity	NPC300017
0.954	High Similarity	NPC104216
0.9425	High Similarity	NPC23167
0.9326	High Similarity	NPC300478
0.9318	High Similarity	NPC113460
0.9318	High Similarity	NPC25493
0.931	High Similarity	NPC197783
0.9247	High Similarity	NPC51333
0.9247	High Similarity	NPC132078
0.9247	High Similarity	NPC216468
0.9247	High Similarity	NPC78119
0.9247	High Similarity	NPC128723
0.9213	High Similarity	NPC123273
0.9213	High Similarity	NPC280347
0.9213	High Similarity	NPC258219
0.9213	High Similarity	NPC318325
0.9213	High Similarity	NPC242240
0.9213	High Similarity	NPC177420
0.9195	High Similarity	NPC175313
0.9195	High Similarity	NPC248817
0.9149	High Similarity	NPC213730
0.914	High Similarity	NPC474073
0.9111	High Similarity	NPC55561
0.908	High Similarity	NPC124436
0.908	High Similarity	NPC265146
0.9053	High Similarity	NPC40258
0.9053	High Similarity	NPC7686
0.9053	High Similarity	NPC91461
0.9011	High Similarity	NPC45040
0.9011	High Similarity	NPC304541
0.8989	High Similarity	NPC184169
0.8989	High Similarity	NPC407
0.8989	High Similarity	NPC307235
0.8969	High Similarity	NPC154899
0.8969	High Similarity	NPC233396
0.8925	High Similarity	NPC26244
0.8901	High Similarity	NPC47950
0.8901	High Similarity	NPC312304
0.8889	High Similarity	NPC27974
0.8878	High Similarity	NPC92623
0.8878	High Similarity	NPC135464
0.8876	High Similarity	NPC155393
0.8854	High Similarity	NPC101025
0.8854	High Similarity	NPC471578
0.8854	High Similarity	NPC110764
0.8842	High Similarity	NPC100870
0.883	High Similarity	NPC473388
0.8817	High Similarity	NPC128062
0.8817	High Similarity	NPC316301
0.8817	High Similarity	NPC27323
0.8817	High Similarity	NPC151715
0.8804	High Similarity	NPC204210
0.8804	High Similarity	NPC270547
0.8804	High Similarity	NPC155908
0.8791	High Similarity	NPC98772
0.8764	High Similarity	NPC286904
0.875	High Similarity	NPC174911
0.875	High Similarity	NPC294741
0.8737	High Similarity	NPC260000
0.8736	High Similarity	NPC87299
0.8736	High Similarity	NPC103326
0.8736	High Similarity	NPC99394
0.8736	High Similarity	NPC329319
0.8723	High Similarity	NPC286006
0.8723	High Similarity	NPC274678
0.8723	High Similarity	NPC8392
0.871	High Similarity	NPC181709
0.87	High Similarity	NPC317305
0.8673	High Similarity	NPC12278
0.8646	High Similarity	NPC80027
0.8646	High Similarity	NPC280869
0.8646	High Similarity	NPC92730
0.8646	High Similarity	NPC131587
0.8646	High Similarity	NPC171843
0.8621	High Similarity	NPC117180
0.8602	High Similarity	NPC306074
0.86	High Similarity	NPC251306
0.8587	High Similarity	NPC70436
0.8586	High Similarity	NPC471350
0.8571	High Similarity	NPC471228
0.8571	High Similarity	NPC305205
0.8571	High Similarity	NPC62351
0.8571	High Similarity	NPC235762
0.8557	High Similarity	NPC130103
0.8556	High Similarity	NPC150837
0.8542	High Similarity	NPC109955
0.8542	High Similarity	NPC107619
0.8542	High Similarity	NPC77492
0.8542	High Similarity	NPC225464
0.8539	High Similarity	NPC304538
0.8529	High Similarity	NPC63345
0.8515	High Similarity	NPC262365
0.8511	High Similarity	NPC3358
0.8511	High Similarity	NPC162314
0.8511	High Similarity	NPC306884
0.8511	High Similarity	NPC55903
0.8511	High Similarity	NPC147284
0.8511	High Similarity	NPC94139
0.8511	High Similarity	NPC210497
0.8495	Intermediate Similarity	NPC192
0.8485	Intermediate Similarity	NPC38079
0.8485	Intermediate Similarity	NPC475225
0.8485	Intermediate Similarity	NPC108875
0.8454	Intermediate Similarity	NPC252821
0.8454	Intermediate Similarity	NPC245561
0.8454	Intermediate Similarity	NPC122005
0.8438	Intermediate Similarity	NPC82664
0.8438	Intermediate Similarity	NPC202986
0.8438	Intermediate Similarity	NPC216520
0.8438	Intermediate Similarity	NPC283711
0.8438	Intermediate Similarity	NPC292730
0.8438	Intermediate Similarity	NPC132271
0.8431	Intermediate Similarity	NPC62258
0.8431	Intermediate Similarity	NPC145638
0.8431	Intermediate Similarity	NPC290566
0.8431	Intermediate Similarity	NPC326187
0.8431	Intermediate Similarity	NPC55617
0.8421	Intermediate Similarity	NPC32977
0.8421	Intermediate Similarity	NPC245187
0.8421	Intermediate Similarity	NPC152415
0.8421	Intermediate Similarity	NPC81010
0.8416	Intermediate Similarity	NPC305603
0.8416	Intermediate Similarity	NPC61033
0.8404	Intermediate Similarity	NPC231150
0.84	Intermediate Similarity	NPC470393
0.8384	Intermediate Similarity	NPC304638
0.8384	Intermediate Similarity	NPC196479
0.8367	Intermediate Similarity	NPC253746
0.8367	Intermediate Similarity	NPC52472
0.8367	Intermediate Similarity	NPC225506
0.8365	Intermediate Similarity	NPC228425
0.8351	Intermediate Similarity	NPC152097
0.8351	Intermediate Similarity	NPC88420
0.8351	Intermediate Similarity	NPC32674
0.835	Intermediate Similarity	NPC475018
0.835	Intermediate Similarity	NPC120982
0.835	Intermediate Similarity	NPC252544
0.835	Intermediate Similarity	NPC79793
0.835	Intermediate Similarity	NPC44732
0.835	Intermediate Similarity	NPC174096
0.835	Intermediate Similarity	NPC321252
0.835	Intermediate Similarity	NPC226401
0.835	Intermediate Similarity	NPC147634
0.8333	Intermediate Similarity	NPC144682
0.8333	Intermediate Similarity	NPC107522
0.8333	Intermediate Similarity	NPC31274
0.8317	Intermediate Similarity	NPC113457
0.8316	Intermediate Similarity	NPC271440
0.8316	Intermediate Similarity	NPC29373
0.83	Intermediate Similarity	NPC120719
0.83	Intermediate Similarity	NPC323810
0.8283	Intermediate Similarity	NPC51633
0.828	Intermediate Similarity	NPC19680
0.8269	Intermediate Similarity	NPC308689
0.8269	Intermediate Similarity	NPC257430
0.8269	Intermediate Similarity	NPC177576
0.8269	Intermediate Similarity	NPC179002
0.8269	Intermediate Similarity	NPC187583
0.8265	Intermediate Similarity	NPC260775
0.8252	Intermediate Similarity	NPC265211
0.8252	Intermediate Similarity	NPC474272
0.8252	Intermediate Similarity	NPC306045
0.8252	Intermediate Similarity	NPC473524
0.8247	Intermediate Similarity	NPC259512
0.8247	Intermediate Similarity	NPC312132
0.8235	Intermediate Similarity	NPC474352
0.8235	Intermediate Similarity	NPC66834
0.8229	Intermediate Similarity	NPC76938
0.8229	Intermediate Similarity	NPC289769
0.8222	Intermediate Similarity	NPC172984
0.8218	Intermediate Similarity	NPC8302
0.8218	Intermediate Similarity	NPC303141
0.8218	Intermediate Similarity	NPC138942
0.8211	Intermediate Similarity	NPC321956
0.8208	Intermediate Similarity	NPC12656
0.82	Intermediate Similarity	NPC178902
0.82	Intermediate Similarity	NPC470202
0.82	Intermediate Similarity	NPC168829
0.82	Intermediate Similarity	NPC135784
0.82	Intermediate Similarity	NPC192596
0.819	Intermediate Similarity	NPC42911
0.819	Intermediate Similarity	NPC473521
0.819	Intermediate Similarity	NPC290353
0.819	Intermediate Similarity	NPC48525
0.819	Intermediate Similarity	NPC153795
0.8182	Intermediate Similarity	NPC130756
0.8182	Intermediate Similarity	NPC72729
0.8182	Intermediate Similarity	NPC129373
0.8182	Intermediate Similarity	NPC12931
0.8182	Intermediate Similarity	NPC155847
0.8182	Intermediate Similarity	NPC248396
0.8182	Intermediate Similarity	NPC166761
0.8182	Intermediate Similarity	NPC48730
0.8182	Intermediate Similarity	NPC211885
0.8182	Intermediate Similarity	NPC70677
0.8182	Intermediate Similarity	NPC289381
0.8163	Intermediate Similarity	NPC475078
0.8163	Intermediate Similarity	NPC79241

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 NPC325292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	969
0.2-0.3	1458
0.3-0.4	2855
0.4-0.5	1981
0.5-0.6	1092
0.6-0.7	484
0.7-0.8	95
0.8-0.85	11
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD111	Approved
0.9022	High Similarity	NPD2933	Approved
0.9022	High Similarity	NPD2934	Approved
0.8925	High Similarity	NPD2860	Approved
0.8925	High Similarity	NPD2859	Approved
0.8817	High Similarity	NPD1432	Clinical (unspecified phase)
0.8646	High Similarity	NPD3020	Approved
0.8469	Intermediate Similarity	NPD846	Approved
0.8469	Intermediate Similarity	NPD940	Approved
0.8431	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD844	Approved
0.8333	Intermediate Similarity	NPD1809	Phase 2
0.8316	Intermediate Similarity	NPD845	Approved
0.8247	Intermediate Similarity	NPD288	Approved
0.8182	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD9294	Approved
0.8119	Intermediate Similarity	NPD9610	Approved
0.8119	Intermediate Similarity	NPD9608	Approved
0.8	Intermediate Similarity	NPD1242	Phase 1
0.7982	Intermediate Similarity	NPD856	Approved
0.7982	Intermediate Similarity	NPD317	Approved
0.7982	Intermediate Similarity	NPD318	Approved
0.7982	Intermediate Similarity	NPD16	Approved
0.7981	Intermediate Similarity	NPD2684	Approved
0.7925	Intermediate Similarity	NPD228	Approved
0.7909	Intermediate Similarity	NPD3091	Approved
0.7905	Intermediate Similarity	NPD3021	Approved
0.7905	Intermediate Similarity	NPD3022	Approved
0.7885	Intermediate Similarity	NPD290	Approved
0.787	Intermediate Similarity	NPD9614	Approved
0.787	Intermediate Similarity	NPD9618	Approved
0.7822	Intermediate Similarity	NPD3028	Approved
0.7816	Intermediate Similarity	NPD9087	Approved
0.7788	Intermediate Similarity	NPD968	Approved
0.7778	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD821	Approved
0.7685	Intermediate Similarity	NPD7843	Approved
0.7667	Intermediate Similarity	NPD9088	Approved
0.7658	Intermediate Similarity	NPD9616	Approved
0.7658	Intermediate Similarity	NPD9615	Approved
0.7658	Intermediate Similarity	NPD9613	Approved
0.7632	Intermediate Similarity	NPD3092	Approved
0.7624	Intermediate Similarity	NPD9273	Approved
0.7619	Intermediate Similarity	NPD1444	Approved
0.7619	Intermediate Similarity	NPD1445	Approved
0.7615	Intermediate Similarity	NPD2229	Approved
0.7615	Intermediate Similarity	NPD2234	Approved
0.7615	Intermediate Similarity	NPD2228	Approved
0.7611	Intermediate Similarity	NPD9384	Approved
0.7611	Intermediate Similarity	NPD9381	Approved
0.7589	Intermediate Similarity	NPD316	Approved
0.7565	Intermediate Similarity	NPD2562	Approved
0.7565	Intermediate Similarity	NPD2561	Approved
0.7523	Intermediate Similarity	NPD9377	Approved
0.7523	Intermediate Similarity	NPD9379	Approved
0.75	Intermediate Similarity	NPD9622	Approved
0.75	Intermediate Similarity	NPD4659	Approved
0.7477	Intermediate Similarity	NPD256	Approved
0.7477	Intermediate Similarity	NPD7157	Approved
0.7477	Intermediate Similarity	NPD255	Approved
0.7456	Intermediate Similarity	NPD3095	Discontinued
0.7451	Intermediate Similarity	NPD9611	Approved
0.7451	Intermediate Similarity	NPD9609	Approved
0.7451	Intermediate Similarity	NPD9612	Approved
0.7451	Intermediate Similarity	NPD9495	Approved
0.7434	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD1548	Phase 1
0.7407	Intermediate Similarity	NPD4750	Phase 3
0.7407	Intermediate Similarity	NPD1792	Phase 2
0.7383	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1133	Approved
0.7373	Intermediate Similarity	NPD1135	Approved
0.7373	Intermediate Similarity	NPD4103	Phase 2
0.7373	Intermediate Similarity	NPD1131	Approved
0.7373	Intermediate Similarity	NPD1129	Approved
0.7373	Intermediate Similarity	NPD3094	Phase 2
0.7373	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1134	Approved
0.7368	Intermediate Similarity	NPD1357	Approved
0.7347	Intermediate Similarity	NPD9295	Approved
0.734	Intermediate Similarity	NPD9089	Approved
0.7333	Intermediate Similarity	NPD9500	Approved
0.7328	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD9621	Approved
0.7311	Intermediate Similarity	NPD9620	Approved
0.7311	Intermediate Similarity	NPD9619	Approved
0.729	Intermediate Similarity	NPD3134	Approved
0.7257	Intermediate Similarity	NPD9568	Approved
0.7248	Intermediate Similarity	NPD5451	Approved
0.7241	Intermediate Similarity	NPD3421	Phase 3
0.7238	Intermediate Similarity	NPD855	Approved
0.7238	Intermediate Similarity	NPD854	Approved
0.7234	Intermediate Similarity	NPD9093	Approved
0.7232	Intermediate Similarity	NPD475	Phase 2
0.7222	Intermediate Similarity	NPD2342	Discontinued
0.7222	Intermediate Similarity	NPD1358	Approved
0.7207	Intermediate Similarity	NPD7635	Approved
0.7203	Intermediate Similarity	NPD6582	Phase 2
0.7203	Intermediate Similarity	NPD6583	Phase 3
0.7203	Intermediate Similarity	NPD3685	Discontinued
0.7182	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6671	Approved
0.7155	Intermediate Similarity	NPD3019	Approved
0.7155	Intermediate Similarity	NPD4059	Approved
0.7155	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7131	Intermediate Similarity	NPD3027	Phase 3
0.713	Intermediate Similarity	NPD5304	Approved
0.713	Intermediate Similarity	NPD5303	Approved
0.7107	Intermediate Similarity	NPD5736	Approved
0.7105	Intermediate Similarity	NPD9493	Approved
0.7103	Intermediate Similarity	NPD1237	Approved
0.7103	Intermediate Similarity	NPD10	Approved
0.7103	Intermediate Similarity	NPD310	Approved
0.7103	Intermediate Similarity	NPD315	Approved
0.7103	Intermediate Similarity	NPD314	Approved
0.7103	Intermediate Similarity	NPD309	Approved
0.7103	Intermediate Similarity	NPD311	Approved
0.708	Intermediate Similarity	NPD1791	Approved
0.708	Intermediate Similarity	NPD1793	Approved
0.708	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD598	Approved
0.7073	Intermediate Similarity	NPD597	Approved
0.7073	Intermediate Similarity	NPD601	Approved
0.7069	Intermediate Similarity	NPD4093	Discontinued
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD9250	Approved
0.7034	Intermediate Similarity	NPD422	Phase 1
0.703	Intermediate Similarity	NPD9365	Approved
0.7025	Intermediate Similarity	NPD6584	Phase 3
0.7016	Intermediate Similarity	NPD1136	Approved
0.7016	Intermediate Similarity	NPD829	Discontinued
0.7016	Intermediate Similarity	NPD1132	Approved
0.7016	Intermediate Similarity	NPD1130	Approved
0.7009	Intermediate Similarity	NPD4626	Approved
0.7009	Intermediate Similarity	NPD5846	Approved
0.7009	Intermediate Similarity	NPD4589	Approved
0.7009	Intermediate Similarity	NPD6516	Phase 2
0.7009	Intermediate Similarity	NPD2286	Discontinued
0.7009	Intermediate Similarity	NPD2667	Approved
0.7009	Intermediate Similarity	NPD1751	Approved
0.7009	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD74	Approved
0.7	Intermediate Similarity	NPD9266	Approved
0.6992	Remote Similarity	NPD3136	Phase 2
0.6991	Remote Similarity	NPD5283	Phase 1
0.699	Remote Similarity	NPD9296	Approved
0.6983	Remote Similarity	NPD1894	Discontinued
0.6975	Remote Similarity	NPD2231	Phase 2
0.6975	Remote Similarity	NPD2235	Phase 2
0.6967	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD3847	Discontinued
0.6942	Remote Similarity	NPD1818	Approved
0.6942	Remote Similarity	NPD1820	Approved
0.6942	Remote Similarity	NPD1819	Approved
0.6942	Remote Similarity	NPD1817	Approved
0.6939	Remote Similarity	NPD9073	Approved
0.6923	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD291	Approved
0.6911	Remote Similarity	NPD4908	Phase 1
0.6909	Remote Similarity	NPD9264	Approved
0.6909	Remote Similarity	NPD9267	Approved
0.6909	Remote Similarity	NPD9263	Approved
0.6909	Remote Similarity	NPD9532	Phase 3
0.6903	Remote Similarity	NPD5535	Approved
0.69	Remote Similarity	NPD9094	Approved
0.6891	Remote Similarity	NPD1535	Discovery
0.6891	Remote Similarity	NPD1091	Approved
0.6885	Remote Similarity	NPD859	Approved
0.6885	Remote Similarity	NPD3690	Phase 2
0.6885	Remote Similarity	NPD599	Approved
0.6885	Remote Similarity	NPD602	Approved
0.6885	Remote Similarity	NPD3691	Phase 2
0.6885	Remote Similarity	NPD858	Approved
0.688	Remote Similarity	NPD6663	Approved
0.688	Remote Similarity	NPD6405	Approved
0.688	Remote Similarity	NPD6407	Approved
0.686	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3052	Approved
0.685	Remote Similarity	NPD2568	Approved
0.685	Remote Similarity	NPD3054	Approved
0.6838	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1759	Phase 1
0.6833	Remote Similarity	NPD1481	Phase 2
0.6825	Remote Similarity	NPD3061	Approved
0.6825	Remote Similarity	NPD3059	Approved
0.6825	Remote Similarity	NPD3062	Approved
0.6825	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1613	Approved
0.6825	Remote Similarity	NPD3620	Phase 2
0.6825	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.681	Remote Similarity	NPD405	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3596	Phase 2
0.6807	Remote Similarity	NPD3496	Discontinued

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