NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.16
Volume:	281.134
LogP:	4.465
LogD:	4.036
LogS:	-3.308
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	2.556
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701
MDCK Permeability:	2.545466850278899e-05
Pgp-inhibitor:	0.161
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	99.39879608154297%
Volume Distribution (VD):	2.123
Pgp-substrate:	0.9557106494903564%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.889
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.671
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	13.495
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.578
Skin Sensitization:	0.94
Carcinogencity:	0.071
Eye Corrosion:	0.413
Eye Irritation:	0.962
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC152097

Natural Product ID:	NPC152097
*Common Name:**	Geroquinol
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]benzene-1,4-diol
Synonyms:	Geroquinol
Standard InCHIKey:	ZSCRTFONTNMQBL-NTUHNPAUSA-N
Standard InCHI:	InChI=1S/C16H22O2/c1-12(2)5-4-6-13(3)7-8-14-11-15(17)9-10-16(14)18/h5,7,9-11,17-18H,4,6,8H2,1-3H3/b13-7+
SMILES:	C/C(=CCc1cc(O)ccc1O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459815
PubChem CID:	5281857
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	DOI[10.1016/S0960-894X(97)00071-1]
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[11170674]
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	formosan	n.a.	PMID[20718475]
NPO40780	Amaroucium multiplicatum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2607356]
NPO40784	Aplidium antillense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[3404153]
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[7586067]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26142	Carex fedia	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29107	Vellozia patens	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28465	Paraschistochila pinnatifolia	Species	Schistochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO926	Adiantum raddianum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28180	Ornithogalum saundersiae	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29179	Usnea cavernosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29351	Streptomyces gangtokensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29138	Tetracera rutenbergii	Species	Dilleniaceae	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	4
MIC	12
Others	6

Activity Type	# Activity
Cell Line	2
Organism	18
Others	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.3	ug.mL-1	PMID[518735]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.034	ug.mL-1	PMID[518735]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[518735]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	64.0	ug.mL-1	PMID[518735]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[518735]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[518735]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	256.0	ug.mL-1	PMID[518735]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	256.0	ug.mL-1	PMID[518735]
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	256.0	ug.mL-1	PMID[518735]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	=	128.0	ug.mL-1	PMID[518735]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	2.0	ug ml-1	PMID[518735]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	1.0	ug ml-1	PMID[518735]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MBC	>	4.0	ug ml-1	PMID[518735]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug.mL-1	PMID[518736]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[518736]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[518736]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.01	ppm	PMID[518736]
NPT1221	Organism	Gambusia affinis	Gambusia affinis	LC50	=	4.6	ppm	PMID[518736]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	0.1	ug.mL-1	PMID[518737]
NPT2	Others	Unspecified		IC50	=	0.2	ug.mL-1	PMID[518737]

☑ 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 NPC152097 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	225
0.1-0.2	1750
0.2-0.3	5801
0.3-0.4	13542
0.4-0.5	5819
0.5-0.6	10046
0.6-0.7	4146
0.7-0.8	1037
0.8-0.85	179
0.85-0.9	104
0.9-0.95	34
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC260775
0.9785	High Similarity	NPC129373
0.9785	High Similarity	NPC48730
0.9785	High Similarity	NPC248396
0.9785	High Similarity	NPC130756
0.9785	High Similarity	NPC12931
0.9785	High Similarity	NPC70677
0.9783	High Similarity	NPC475078
0.9579	High Similarity	NPC108497
0.956	High Similarity	NPC29373
0.9474	High Similarity	NPC80800
0.9474	High Similarity	NPC477685
0.9381	High Similarity	NPC47284
0.9286	High Similarity	NPC155072
0.9286	High Similarity	NPC53740
0.9192	High Similarity	NPC320439
0.9175	High Similarity	NPC269212
0.9167	High Similarity	NPC130103
0.914	High Similarity	NPC3358
0.914	High Similarity	NPC162314
0.914	High Similarity	NPC306884
0.914	High Similarity	NPC147284
0.914	High Similarity	NPC94139
0.914	High Similarity	NPC210497
0.913	High Similarity	NPC192
0.9121	High Similarity	NPC27974
0.9091	High Similarity	NPC469913
0.9082	High Similarity	NPC475580
0.9072	High Similarity	NPC12221
0.9043	High Similarity	NPC245187
0.9032	High Similarity	NPC231150
0.9011	High Similarity	NPC407
0.9011	High Similarity	NPC307235
0.901	High Similarity	NPC98392
0.9	High Similarity	NPC474352
0.9	High Similarity	NPC233320
0.898	High Similarity	NPC233827
0.898	High Similarity	NPC471228
0.898	High Similarity	NPC235762
0.8969	High Similarity	NPC72729
0.8969	High Similarity	NPC174911
0.8958	High Similarity	NPC79241
0.8958	High Similarity	NPC6597
0.8958	High Similarity	NPC474073
0.8958	High Similarity	NPC88420
0.8911	High Similarity	NPC279887
0.8911	High Similarity	NPC68260
0.8901	High Similarity	NPC155393
0.8889	High Similarity	NPC130817
0.8889	High Similarity	NPC475225
0.8889	High Similarity	NPC272029
0.8878	High Similarity	NPC252105
0.8866	High Similarity	NPC33675
0.8866	High Similarity	NPC299762
0.8854	High Similarity	NPC312132
0.8854	High Similarity	NPC259512
0.8842	High Similarity	NPC76938
0.8842	High Similarity	NPC152415
0.8835	High Similarity	NPC470770
0.8835	High Similarity	NPC228609
0.8835	High Similarity	NPC77772
0.8835	High Similarity	NPC54373
0.8835	High Similarity	NPC266937
0.8824	High Similarity	NPC26013
0.8824	High Similarity	NPC473524
0.8824	High Similarity	NPC282855
0.8817	High Similarity	NPC177420
0.8817	High Similarity	NPC280347
0.8791	High Similarity	NPC150837
0.8791	High Similarity	NPC286904
0.8776	High Similarity	NPC166761
0.875	High Similarity	NPC177962
0.875	High Similarity	NPC302371
0.875	High Similarity	NPC32714
0.875	High Similarity	NPC62867
0.8738	High Similarity	NPC471535
0.8738	High Similarity	NPC208229
0.8737	High Similarity	NPC55903
0.8723	High Similarity	NPC312304
0.8723	High Similarity	NPC55561
0.8713	High Similarity	NPC54765
0.8713	High Similarity	NPC67250
0.871	High Similarity	NPC25493
0.871	High Similarity	NPC113460
0.87	High Similarity	NPC93831
0.8654	High Similarity	NPC275627
0.8654	High Similarity	NPC469912
0.8632	High Similarity	NPC306074
0.8627	High Similarity	NPC232523
0.8627	High Similarity	NPC66834
0.8627	High Similarity	NPC204901
0.8627	High Similarity	NPC158253
0.8617	High Similarity	NPC123273
0.8617	High Similarity	NPC242240
0.8617	High Similarity	NPC318325
0.8614	High Similarity	NPC138942
0.8614	High Similarity	NPC37802
0.8602	High Similarity	NPC23167
0.86	High Similarity	NPC302219
0.86	High Similarity	NPC94351
0.86	High Similarity	NPC249828
0.86	High Similarity	NPC196479
0.86	High Similarity	NPC71002
0.86	High Similarity	NPC168303
0.86	High Similarity	NPC24404
0.86	High Similarity	NPC313030
0.86	High Similarity	NPC53051
0.86	High Similarity	NPC242342
0.86	High Similarity	NPC222522
0.86	High Similarity	NPC85479
0.86	High Similarity	NPC106396
0.86	High Similarity	NPC146798
0.8586	High Similarity	NPC294741
0.8586	High Similarity	NPC225506
0.8586	High Similarity	NPC10588
0.8585	High Similarity	NPC197513
0.8571	High Similarity	NPC77492
0.8571	High Similarity	NPC474920
0.8571	High Similarity	NPC156313
0.8557	High Similarity	NPC274678
0.8557	High Similarity	NPC26244
0.8557	High Similarity	NPC222146
0.8544	High Similarity	NPC95344
0.8529	High Similarity	NPC12640
0.8529	High Similarity	NPC310456
0.8529	High Similarity	NPC99836
0.8529	High Similarity	NPC201662
0.8515	High Similarity	NPC218879
0.8515	High Similarity	NPC244513
0.8515	High Similarity	NPC288411
0.8515	High Similarity	NPC323810
0.8515	High Similarity	NPC227458
0.8511	High Similarity	NPC19680
0.85	High Similarity	NPC137415
0.85	High Similarity	NPC147310
0.85	High Similarity	NPC11280
0.85	High Similarity	NPC166313
0.85	High Similarity	NPC294186
0.85	High Similarity	NPC24407
0.85	High Similarity	NPC284011
0.85	High Similarity	NPC72947
0.85	High Similarity	NPC192032
0.8495	Intermediate Similarity	NPC197783
0.8491	Intermediate Similarity	NPC296144
0.8491	Intermediate Similarity	NPC28784
0.8491	Intermediate Similarity	NPC76400
0.8485	Intermediate Similarity	NPC252821
0.8485	Intermediate Similarity	NPC122005
0.8485	Intermediate Similarity	NPC128723
0.8469	Intermediate Similarity	NPC473388
0.8462	Intermediate Similarity	NPC19808
0.8462	Intermediate Similarity	NPC33728
0.8454	Intermediate Similarity	NPC316301
0.8454	Intermediate Similarity	NPC289769
0.8454	Intermediate Similarity	NPC151715
0.8454	Intermediate Similarity	NPC128062
0.8454	Intermediate Similarity	NPC27323
0.8438	Intermediate Similarity	NPC270547
0.8438	Intermediate Similarity	NPC204210
0.8438	Intermediate Similarity	NPC304541
0.8431	Intermediate Similarity	NPC471350
0.8431	Intermediate Similarity	NPC117115
0.8426	Intermediate Similarity	NPC141001
0.8421	Intermediate Similarity	NPC258219
0.8421	Intermediate Similarity	NPC98772
0.8416	Intermediate Similarity	NPC168829
0.8416	Intermediate Similarity	NPC168393
0.8411	Intermediate Similarity	NPC473931
0.8411	Intermediate Similarity	NPC474114
0.8411	Intermediate Similarity	NPC114918
0.8411	Intermediate Similarity	NPC474050
0.8411	Intermediate Similarity	NPC471534
0.8404	Intermediate Similarity	NPC184169
0.8396	Intermediate Similarity	NPC228452
0.8396	Intermediate Similarity	NPC98372
0.8387	Intermediate Similarity	NPC248817
0.8387	Intermediate Similarity	NPC175313
0.8384	Intermediate Similarity	NPC109955
0.8381	Intermediate Similarity	NPC132720
0.8367	Intermediate Similarity	NPC8392
0.8365	Intermediate Similarity	NPC241549
0.8365	Intermediate Similarity	NPC306295
0.8365	Intermediate Similarity	NPC169450
0.8365	Intermediate Similarity	NPC174981
0.8351	Intermediate Similarity	NPC138117
0.8351	Intermediate Similarity	NPC325292
0.8351	Intermediate Similarity	NPC271440
0.835	Intermediate Similarity	NPC477814
0.8349	Intermediate Similarity	NPC320864
0.8349	Intermediate Similarity	NPC269414
0.8333	Intermediate Similarity	NPC241891
0.8333	Intermediate Similarity	NPC300017
0.8333	Intermediate Similarity	NPC232165
0.8333	Intermediate Similarity	NPC47950
0.8333	Intermediate Similarity	NPC102216
0.8333	Intermediate Similarity	NPC473718
0.8302	Intermediate Similarity	NPC4493
0.8302	Intermediate Similarity	NPC476632
0.8302	Intermediate Similarity	NPC225679
0.8302	Intermediate Similarity	NPC95716

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 NPC152097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	1070
0.2-0.3	1433
0.3-0.4	2950
0.4-0.5	1882
0.5-0.6	1100
0.6-0.7	398
0.7-0.8	67
0.8-0.85	12
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9368	High Similarity	NPD289	Clinical (unspecified phase)
0.9149	High Similarity	NPD844	Approved
0.8854	High Similarity	NPD288	Approved
0.8646	High Similarity	NPD2933	Approved
0.8646	High Similarity	NPD2934	Approved
0.8571	High Similarity	NPD7635	Approved
0.8557	High Similarity	NPD2859	Approved
0.8557	High Similarity	NPD2860	Approved
0.8542	High Similarity	NPD845	Approved
0.8505	High Similarity	NPD6671	Approved
0.8485	Intermediate Similarity	NPD3020	Approved
0.8454	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD940	Approved
0.8317	Intermediate Similarity	NPD846	Approved
0.8286	Intermediate Similarity	NPD4750	Phase 3
0.828	Intermediate Similarity	NPD111	Approved
0.8182	Intermediate Similarity	NPD1809	Phase 2
0.8113	Intermediate Similarity	NPD3021	Approved
0.8113	Intermediate Similarity	NPD3022	Approved
0.8	Intermediate Similarity	NPD1445	Approved
0.8	Intermediate Similarity	NPD1444	Approved
0.7925	Intermediate Similarity	NPD2342	Discontinued
0.7912	Intermediate Similarity	NPD9088	Approved
0.7864	Intermediate Similarity	NPD1242	Phase 1
0.7778	Intermediate Similarity	NPD1792	Phase 2
0.7739	Intermediate Similarity	NPD3496	Discontinued
0.767	Intermediate Similarity	NPD9273	Approved
0.7664	Intermediate Similarity	NPD968	Approved
0.7636	Intermediate Similarity	NPD228	Approved
0.7632	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9618	Approved
0.7589	Intermediate Similarity	NPD497	Approved
0.7589	Intermediate Similarity	NPD9614	Approved
0.7547	Intermediate Similarity	NPD9500	Approved
0.7524	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD495	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.75	Intermediate Similarity	NPD498	Approved
0.75	Intermediate Similarity	NPD496	Approved
0.7479	Intermediate Similarity	NPD6696	Suspended
0.7478	Intermediate Similarity	NPD3091	Approved
0.7477	Intermediate Similarity	NPD9608	Approved
0.7477	Intermediate Similarity	NPD9610	Approved
0.7477	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD9087	Approved
0.7438	Intermediate Similarity	NPD2861	Phase 2
0.7434	Intermediate Similarity	NPD1791	Approved
0.7434	Intermediate Similarity	NPD1793	Approved
0.7411	Intermediate Similarity	NPD9377	Approved
0.7411	Intermediate Similarity	NPD9379	Approved
0.74	Intermediate Similarity	NPD9295	Approved
0.7395	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9616	Approved
0.7391	Intermediate Similarity	NPD9613	Approved
0.7391	Intermediate Similarity	NPD9615	Approved
0.735	Intermediate Similarity	NPD2932	Approved
0.735	Intermediate Similarity	NPD3019	Approved
0.735	Intermediate Similarity	NPD4059	Approved
0.735	Intermediate Similarity	NPD4626	Approved
0.7345	Intermediate Similarity	NPD1398	Phase 1
0.7345	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD316	Approved
0.7311	Intermediate Similarity	NPD2233	Approved
0.7311	Intermediate Similarity	NPD2230	Approved
0.7311	Intermediate Similarity	NPD2232	Approved
0.7304	Intermediate Similarity	NPD7340	Approved
0.7304	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD290	Approved
0.7265	Intermediate Similarity	NPD4093	Discontinued
0.725	Intermediate Similarity	NPD4749	Approved
0.7236	Intermediate Similarity	NPD600	Approved
0.7236	Intermediate Similarity	NPD596	Approved
0.7234	Intermediate Similarity	NPD9294	Approved
0.7232	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3092	Approved
0.7227	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD709	Approved
0.7207	Intermediate Similarity	NPD2684	Approved
0.7203	Intermediate Similarity	NPD4589	Approved
0.7179	Intermediate Similarity	NPD5303	Approved
0.7179	Intermediate Similarity	NPD5304	Approved
0.7155	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1983	Approved
0.7143	Intermediate Similarity	NPD1981	Approved
0.7143	Intermediate Similarity	NPD1980	Approved
0.7143	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3094	Phase 2
0.713	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1201	Approved
0.7063	Intermediate Similarity	NPD839	Approved
0.7063	Intermediate Similarity	NPD840	Approved
0.7059	Intermediate Similarity	NPD9384	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD9381	Approved
0.7059	Intermediate Similarity	NPD2286	Discontinued
0.7059	Intermediate Similarity	NPD3095	Discontinued
0.7059	Intermediate Similarity	NPD1751	Approved
0.7054	Intermediate Similarity	NPD9266	Approved
0.7054	Intermediate Similarity	NPD74	Approved
0.7043	Intermediate Similarity	NPD5283	Phase 1
0.7041	Intermediate Similarity	NPD9089	Approved
0.704	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD1759	Phase 1
0.7034	Intermediate Similarity	NPD7330	Discontinued
0.7025	Intermediate Similarity	NPD2231	Phase 2
0.7025	Intermediate Similarity	NPD2235	Phase 2
0.7009	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD2935	Discontinued
0.6992	Remote Similarity	NPD3055	Approved
0.6992	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3053	Approved
0.6975	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5691	Approved
0.6975	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD9622	Approved
0.6967	Remote Similarity	NPD1755	Approved
0.6964	Remote Similarity	NPD9264	Approved
0.6964	Remote Similarity	NPD9267	Approved
0.6964	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD821	Approved
0.6957	Remote Similarity	NPD7843	Approved
0.6949	Remote Similarity	NPD1758	Phase 1
0.6949	Remote Similarity	NPD856	Approved
0.6949	Remote Similarity	NPD16	Approved
0.6942	Remote Similarity	NPD1611	Approved
0.6939	Remote Similarity	NPD9093	Approved
0.6935	Remote Similarity	NPD6584	Phase 3
0.6935	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD256	Approved
0.6923	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5311	Approved
0.6911	Remote Similarity	NPD5310	Approved
0.6905	Remote Similarity	NPD3027	Phase 3
0.6891	Remote Similarity	NPD1548	Phase 1
0.688	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD4060	Phase 1
0.6864	Remote Similarity	NPD7636	Approved
0.686	Remote Similarity	NPD3143	Discontinued
0.6855	Remote Similarity	NPD1470	Approved
0.685	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9244	Approved
0.6842	Remote Similarity	NPD5451	Approved
0.6838	Remote Similarity	NPD475	Phase 2
0.6833	Remote Similarity	NPD1357	Approved
0.6829	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4908	Phase 1
0.6814	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1138	Approved
0.6807	Remote Similarity	NPD318	Approved
0.6807	Remote Similarity	NPD317	Approved
0.6803	Remote Similarity	NPD1535	Discovery
0.6803	Remote Similarity	NPD1610	Phase 2
0.6803	Remote Similarity	NPD422	Phase 1
0.68	Remote Similarity	NPD602	Approved
0.68	Remote Similarity	NPD2195	Approved
0.68	Remote Similarity	NPD9619	Approved
0.68	Remote Similarity	NPD599	Approved
0.68	Remote Similarity	NPD9621	Approved
0.68	Remote Similarity	NPD2194	Approved
0.68	Remote Similarity	NPD9620	Approved
0.68	Remote Similarity	NPD858	Approved
0.68	Remote Similarity	NPD859	Approved
0.6777	Remote Similarity	NPD2667	Approved
0.6777	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2561	Approved
0.6748	Remote Similarity	NPD1481	Phase 2
0.6748	Remote Similarity	NPD3070	Discontinued
0.6748	Remote Similarity	NPD2562	Approved
0.6746	Remote Similarity	NPD3637	Approved
0.6746	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2237	Approved
0.6746	Remote Similarity	NPD1712	Approved
0.6746	Remote Similarity	NPD3636	Approved
0.6746	Remote Similarity	NPD3635	Approved
0.6744	Remote Similarity	NPD2238	Phase 2
0.6726	Remote Similarity	NPD3134	Approved
0.6724	Remote Similarity	NPD1137	Approved
0.6724	Remote Similarity	NPD1139	Approved
0.6723	Remote Similarity	NPD9568	Approved
0.6721	Remote Similarity	NPD3023	Approved
0.6721	Remote Similarity	NPD3026	Approved
0.6721	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3421	Phase 3
0.672	Remote Similarity	NPD1133	Approved
0.672	Remote Similarity	NPD1134	Approved
0.672	Remote Similarity	NPD1131	Approved
0.672	Remote Similarity	NPD2797	Approved
0.672	Remote Similarity	NPD1129	Approved
0.672	Remote Similarity	NPD1135	Approved
0.6719	Remote Similarity	NPD597	Approved
0.6719	Remote Similarity	NPD601	Approved
0.6719	Remote Similarity	NPD4907	Clinical (unspecified phase)

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