NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	140.05
Volume:	139.533
LogP:	-0.114
LogD:	0.355
LogS:	0.173
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	2.007
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.559
MDCK Permeability:	9.144956493400969e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	29.28843116760254%
Volume Distribution (VD):	0.966
Pgp-substrate:	67.86076354980469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.715
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	14.215
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.625
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.917
Carcinogencity:	0.359
Eye Corrosion:	0.255
Eye Irritation:	0.979
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC88420

Natural Product ID:	NPC88420
*Common Name:**	Gentisyl Alcohol
IUPAC Name:	2-(hydroxymethyl)benzene-1,4-diol
Synonyms:	Gentisyl Alcohol
Standard InCHIKey:	PUZSUVGRVHEUQO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8O3/c8-4-5-3-6(9)1-2-7(5)10/h1-3,8-10H,4H2
SMILES:	c1cc(c(cc1O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448800
PubChem CID:	188287
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000136] 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
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678666]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027772]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15184162]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22103394]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25084548]
NPO40268	Penicillium concentricum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28409637]
NPO33084	Geosmithia langdonii	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30298736]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	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	7
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17100.0	nM	PMID[450155]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6400.0	nM	PMID[450155]
NPT1	Others	Radical scavenging activity		IC50	=	1400.0	nM	PMID[450153]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2200.0	nM	PMID[450153]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<	50000.0	nM	PMID[450153]
NPT35	Others	n.a.		IC50	=	400.0	nM	PMID[450153]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	8500.0	nM	PMID[450154]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	10400.0	nM	PMID[450154]

☑ 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 NPC88420 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	397
0.1-0.2	2120
0.2-0.3	7724
0.3-0.4	12336
0.4-0.5	5611
0.5-0.6	9785
0.6-0.7	3718
0.7-0.8	832
0.8-0.85	125
0.85-0.9	42
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9368	High Similarity	NPC130103
0.9348	High Similarity	NPC29373
0.9341	High Similarity	NPC47950
0.9341	High Similarity	NPC312304
0.9278	High Similarity	NPC130817
0.8969	High Similarity	NPC174911
0.8958	High Similarity	NPC152097
0.8958	High Similarity	NPC475078
0.8911	High Similarity	NPC241549
0.8911	High Similarity	NPC169450
0.8866	High Similarity	NPC260775
0.8812	High Similarity	NPC474352
0.8812	High Similarity	NPC66834
0.88	High Similarity	NPC471350
0.8788	High Similarity	NPC471228
0.8788	High Similarity	NPC235762
0.8776	High Similarity	NPC48730
0.8776	High Similarity	NPC70677
0.8776	High Similarity	NPC130756
0.8776	High Similarity	NPC129373
0.8776	High Similarity	NPC12931
0.8776	High Similarity	NPC248396
0.8763	High Similarity	NPC474073
0.875	High Similarity	NPC302371
0.8713	High Similarity	NPC67250
0.87	High Similarity	NPC475225
0.8687	High Similarity	NPC80800
0.8687	High Similarity	NPC12221
0.8641	High Similarity	NPC473524
0.8632	High Similarity	NPC231150
0.86	High Similarity	NPC233827
0.86	High Similarity	NPC108497
0.8587	High Similarity	NPC286904
0.8587	High Similarity	NPC150837
0.8526	High Similarity	NPC300478
0.8526	High Similarity	NPC300017
0.8515	High Similarity	NPC475580
0.8515	High Similarity	NPC93831
0.8511	High Similarity	NPC104216
0.8511	High Similarity	NPC27974
0.8505	High Similarity	NPC301321
0.85	High Similarity	NPC477685
0.8495	Intermediate Similarity	NPC155393
0.8462	Intermediate Similarity	NPC316052
0.8462	Intermediate Similarity	NPC98392
0.8454	Intermediate Similarity	NPC245187
0.8447	Intermediate Similarity	NPC233320
0.8431	Intermediate Similarity	NPC47284
0.8416	Intermediate Similarity	NPC269212
0.8416	Intermediate Similarity	NPC168393
0.8404	Intermediate Similarity	NPC307235
0.8404	Intermediate Similarity	NPC407
0.84	Intermediate Similarity	NPC294741
0.8396	Intermediate Similarity	NPC228452
0.8381	Intermediate Similarity	NPC471535
0.8351	Intermediate Similarity	NPC138117
0.8351	Intermediate Similarity	NPC325292
0.8351	Intermediate Similarity	NPC295295
0.835	Intermediate Similarity	NPC155072
0.835	Intermediate Similarity	NPC54765
0.835	Intermediate Similarity	NPC53740
0.8349	Intermediate Similarity	NPC320864
0.8333	Intermediate Similarity	NPC323810
0.8333	Intermediate Similarity	NPC232165
0.8333	Intermediate Similarity	NPC272029
0.8333	Intermediate Similarity	NPC192
0.8333	Intermediate Similarity	NPC102216
0.8318	Intermediate Similarity	NPC261343
0.8317	Intermediate Similarity	NPC110764
0.83	Intermediate Similarity	NPC128723
0.83	Intermediate Similarity	NPC131587
0.8283	Intermediate Similarity	NPC283711
0.8283	Intermediate Similarity	NPC259512
0.8283	Intermediate Similarity	NPC312132
0.8269	Intermediate Similarity	NPC61033
0.8269	Intermediate Similarity	NPC320439
0.8269	Intermediate Similarity	NPC305603
0.8252	Intermediate Similarity	NPC292452
0.8241	Intermediate Similarity	NPC470837
0.8241	Intermediate Similarity	NPC197513
0.8218	Intermediate Similarity	NPC10588
0.8218	Intermediate Similarity	NPC166761
0.8218	Intermediate Similarity	NPC72729
0.82	Intermediate Similarity	NPC156313
0.82	Intermediate Similarity	NPC6597
0.82	Intermediate Similarity	NPC79241
0.82	Intermediate Similarity	NPC291789
0.819	Intermediate Similarity	NPC95344
0.8182	Intermediate Similarity	NPC313650
0.8182	Intermediate Similarity	NPC274678
0.8173	Intermediate Similarity	NPC469913
0.8163	Intermediate Similarity	NPC94139
0.8163	Intermediate Similarity	NPC147284
0.8163	Intermediate Similarity	NPC55903
0.8163	Intermediate Similarity	NPC306884
0.8163	Intermediate Similarity	NPC210497
0.8163	Intermediate Similarity	NPC162314
0.8163	Intermediate Similarity	NPC3358
0.8155	Intermediate Similarity	NPC227458
0.8155	Intermediate Similarity	NPC12278
0.8155	Intermediate Similarity	NPC244513
0.8155	Intermediate Similarity	NPC218879
0.8148	Intermediate Similarity	NPC28784
0.8148	Intermediate Similarity	NPC296144
0.8137	Intermediate Similarity	NPC143659
0.8137	Intermediate Similarity	NPC100340
0.8137	Intermediate Similarity	NPC72947
0.8137	Intermediate Similarity	NPC284011
0.8131	Intermediate Similarity	NPC275627
0.8131	Intermediate Similarity	NPC54373
0.8125	Intermediate Similarity	NPC19680
0.8119	Intermediate Similarity	NPC33675
0.8119	Intermediate Similarity	NPC299762
0.8119	Intermediate Similarity	NPC80027
0.8108	Intermediate Similarity	NPC283616
0.8095	Intermediate Similarity	NPC204901
0.8095	Intermediate Similarity	NPC232523
0.8095	Intermediate Similarity	NPC158253
0.8091	Intermediate Similarity	NPC290470
0.8091	Intermediate Similarity	NPC154256
0.8085	Intermediate Similarity	NPC265146
0.8085	Intermediate Similarity	NPC124436
0.8081	Intermediate Similarity	NPC76938
0.8081	Intermediate Similarity	NPC152415
0.8081	Intermediate Similarity	NPC128062
0.8077	Intermediate Similarity	NPC37802
0.8073	Intermediate Similarity	NPC474114
0.8073	Intermediate Similarity	NPC474050
0.8073	Intermediate Similarity	NPC473931
0.8061	Intermediate Similarity	NPC306074
0.8061	Intermediate Similarity	NPC204210
0.8058	Intermediate Similarity	NPC53051
0.8058	Intermediate Similarity	NPC302219
0.8058	Intermediate Similarity	NPC106396
0.8058	Intermediate Similarity	NPC85479
0.8058	Intermediate Similarity	NPC94351
0.8058	Intermediate Similarity	NPC24404
0.8058	Intermediate Similarity	NPC146798
0.8058	Intermediate Similarity	NPC168303
0.8058	Intermediate Similarity	NPC222522
0.8058	Intermediate Similarity	NPC71002
0.8058	Intermediate Similarity	NPC249828
0.8058	Intermediate Similarity	NPC313030
0.8058	Intermediate Similarity	NPC242342
0.8056	Intermediate Similarity	NPC473521
0.8039	Intermediate Similarity	NPC161571
0.8039	Intermediate Similarity	NPC275053
0.8039	Intermediate Similarity	NPC213730
0.8039	Intermediate Similarity	NPC248573
0.8037	Intermediate Similarity	NPC132720
0.8036	Intermediate Similarity	NPC121866
0.8021	Intermediate Similarity	NPC23167
0.802	Intermediate Similarity	NPC315921
0.802	Intermediate Similarity	NPC109955
0.8019	Intermediate Similarity	NPC174981
0.8019	Intermediate Similarity	NPC68260
0.8019	Intermediate Similarity	NPC279887
0.8019	Intermediate Similarity	NPC262365
0.8	Intermediate Similarity	NPC248817
0.8	Intermediate Similarity	NPC175313
0.8	Intermediate Similarity	NPC201662
0.8	Intermediate Similarity	NPC257182
0.8	Intermediate Similarity	NPC474486
0.8	Intermediate Similarity	NPC107522
0.8	Intermediate Similarity	NPC246679
0.8	Intermediate Similarity	NPC12640
0.8	Intermediate Similarity	NPC32714
0.8	Intermediate Similarity	NPC99836
0.7982	Intermediate Similarity	NPC319803
0.7981	Intermediate Similarity	NPC241891
0.7981	Intermediate Similarity	NPC30506
0.798	Intermediate Similarity	NPC271440
0.7963	Intermediate Similarity	NPC77772
0.7963	Intermediate Similarity	NPC228609
0.7963	Intermediate Similarity	NPC470770
0.7963	Intermediate Similarity	NPC266937
0.7961	Intermediate Similarity	NPC166313
0.7961	Intermediate Similarity	NPC40258
0.7961	Intermediate Similarity	NPC137415
0.7961	Intermediate Similarity	NPC252105
0.7961	Intermediate Similarity	NPC147310
0.7961	Intermediate Similarity	NPC91461
0.7961	Intermediate Similarity	NPC11280
0.7961	Intermediate Similarity	NPC294186
0.7961	Intermediate Similarity	NPC24407
0.7961	Intermediate Similarity	NPC192032
0.7961	Intermediate Similarity	NPC7686
0.7944	Intermediate Similarity	NPC282855
0.7944	Intermediate Similarity	NPC202647
0.7944	Intermediate Similarity	NPC19808
0.7944	Intermediate Similarity	NPC26013
0.7944	Intermediate Similarity	NPC33728
0.7941	Intermediate Similarity	NPC78119
0.7941	Intermediate Similarity	NPC51333
0.7941	Intermediate Similarity	NPC216468
0.7941	Intermediate Similarity	NPC132078
0.7938	Intermediate Similarity	NPC113460
0.7938	Intermediate Similarity	NPC25493
0.7921	Intermediate Similarity	NPC202986
0.7917	Intermediate Similarity	NPC197783

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 NPC88420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	1030
0.2-0.3	1907
0.3-0.4	2950
0.4-0.5	1611
0.5-0.6	947
0.6-0.7	271
0.7-0.8	51
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8776	High Similarity	NPD289	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD844	Approved
0.8283	Intermediate Similarity	NPD288	Approved
0.8085	Intermediate Similarity	NPD111	Approved
0.8039	Intermediate Similarity	NPD1242	Phase 1
0.802	Intermediate Similarity	NPD9273	Approved
0.7961	Intermediate Similarity	NPD846	Approved
0.7961	Intermediate Similarity	NPD940	Approved
0.7912	Intermediate Similarity	NPD9088	Approved
0.783	Intermediate Similarity	NPD968	Approved
0.7802	Intermediate Similarity	NPD9294	Approved
0.78	Intermediate Similarity	NPD845	Approved
0.7778	Intermediate Similarity	NPD4750	Phase 3
0.7727	Intermediate Similarity	NPD7635	Approved
0.7723	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD2934	Approved
0.7723	Intermediate Similarity	NPD2933	Approved
0.7679	Intermediate Similarity	NPD6671	Approved
0.7647	Intermediate Similarity	NPD2859	Approved
0.7647	Intermediate Similarity	NPD2860	Approved
0.7596	Intermediate Similarity	NPD3020	Approved
0.7593	Intermediate Similarity	NPD290	Approved
0.7589	Intermediate Similarity	NPD9618	Approved
0.7589	Intermediate Similarity	NPD9614	Approved
0.7476	Intermediate Similarity	NPD1809	Phase 2
0.7473	Intermediate Similarity	NPD9087	Approved
0.7431	Intermediate Similarity	NPD2342	Discontinued
0.74	Intermediate Similarity	NPD9295	Approved
0.7396	Intermediate Similarity	NPD9089	Approved
0.7391	Intermediate Similarity	NPD9613	Approved
0.7391	Intermediate Similarity	NPD9616	Approved
0.7391	Intermediate Similarity	NPD9615	Approved
0.7377	Intermediate Similarity	NPD600	Approved
0.7377	Intermediate Similarity	NPD596	Approved
0.7364	Intermediate Similarity	NPD9266	Approved
0.7364	Intermediate Similarity	NPD74	Approved
0.7339	Intermediate Similarity	NPD1445	Approved
0.7339	Intermediate Similarity	NPD1444	Approved
0.7328	Intermediate Similarity	NPD316	Approved
0.7321	Intermediate Similarity	NPD228	Approved
0.7297	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3021	Approved
0.7297	Intermediate Similarity	NPD3022	Approved
0.7292	Intermediate Similarity	NPD9093	Approved
0.7288	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9264	Approved
0.7273	Intermediate Similarity	NPD9263	Approved
0.7232	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9500	Approved
0.7203	Intermediate Similarity	NPD9384	Approved
0.7203	Intermediate Similarity	NPD9381	Approved
0.72	Intermediate Similarity	NPD840	Approved
0.72	Intermediate Similarity	NPD839	Approved
0.7179	Intermediate Similarity	NPD1548	Phase 1
0.7179	Intermediate Similarity	NPD3091	Approved
0.7155	Intermediate Similarity	NPD9493	Approved
0.7154	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.713	Intermediate Similarity	NPD497	Approved
0.7105	Intermediate Similarity	NPD9379	Approved
0.7105	Intermediate Similarity	NPD9377	Approved
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7083	Intermediate Similarity	NPD1091	Approved
0.7043	Intermediate Similarity	NPD498	Approved
0.7043	Intermediate Similarity	NPD496	Approved
0.7043	Intermediate Similarity	NPD495	Approved
0.7018	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD9610	Approved
0.7	Intermediate Similarity	NPD9608	Approved
0.6992	Remote Similarity	NPD3094	Phase 2
0.6967	Remote Similarity	NPD9622	Approved
0.6961	Remote Similarity	NPD9094	Approved
0.6942	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3092	Approved
0.6935	Remote Similarity	NPD602	Approved
0.6935	Remote Similarity	NPD859	Approved
0.6935	Remote Similarity	NPD858	Approved
0.6935	Remote Similarity	NPD599	Approved
0.6935	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1778	Approved
0.6909	Remote Similarity	NPD9261	Approved
0.6905	Remote Similarity	NPD3027	Phase 3
0.6903	Remote Similarity	NPD2684	Approved
0.6897	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1759	Phase 1
0.6891	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2235	Phase 2
0.6885	Remote Similarity	NPD2231	Phase 2
0.6855	Remote Similarity	NPD1135	Approved
0.6855	Remote Similarity	NPD1134	Approved
0.6855	Remote Similarity	NPD1131	Approved
0.6855	Remote Similarity	NPD1133	Approved
0.6855	Remote Similarity	NPD1129	Approved
0.685	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9281	Approved
0.6838	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1793	Approved
0.6838	Remote Similarity	NPD1791	Approved
0.6833	Remote Similarity	NPD1357	Approved
0.6829	Remote Similarity	NPD4749	Approved
0.6829	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD317	Approved
0.6807	Remote Similarity	NPD16	Approved
0.6807	Remote Similarity	NPD1758	Phase 1
0.6807	Remote Similarity	NPD856	Approved
0.6807	Remote Similarity	NPD318	Approved
0.6803	Remote Similarity	NPD1201	Approved
0.68	Remote Similarity	NPD9619	Approved
0.68	Remote Similarity	NPD9620	Approved
0.68	Remote Similarity	NPD9621	Approved
0.678	Remote Similarity	NPD709	Approved
0.6777	Remote Similarity	NPD3095	Discontinued
0.6777	Remote Similarity	NPD4626	Approved
0.6774	Remote Similarity	NPD6696	Suspended
0.6768	Remote Similarity	NPD9250	Approved
0.6752	Remote Similarity	NPD2229	Approved
0.6752	Remote Similarity	NPD1398	Phase 1
0.6752	Remote Similarity	NPD2234	Approved
0.6752	Remote Similarity	NPD2228	Approved
0.6748	Remote Similarity	NPD2233	Approved
0.6748	Remote Similarity	NPD2232	Approved
0.6748	Remote Similarity	NPD2230	Approved
0.6746	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2935	Discontinued
0.6727	Remote Similarity	NPD3028	Approved
0.6721	Remote Similarity	NPD1980	Approved
0.6721	Remote Similarity	NPD1981	Approved
0.6721	Remote Similarity	NPD1983	Approved
0.6697	Remote Similarity	NPD9495	Approved
0.6696	Remote Similarity	NPD9244	Approved
0.6693	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD9073	Approved
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD558	Phase 2
0.6667	Remote Similarity	NPD821	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD7843	Approved
0.6641	Remote Similarity	NPD2568	Approved
0.6641	Remote Similarity	NPD4625	Phase 3
0.6639	Remote Similarity	NPD2932	Approved
0.6639	Remote Similarity	NPD2286	Discontinued
0.6639	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7157	Approved
0.6639	Remote Similarity	NPD4059	Approved
0.6639	Remote Similarity	NPD3019	Approved
0.6615	Remote Similarity	NPD2238	Phase 2
0.6613	Remote Similarity	NPD9269	Phase 2
0.6612	Remote Similarity	NPD9545	Approved
0.6612	Remote Similarity	NPD1182	Approved
0.6604	Remote Similarity	NPD9365	Approved
0.6589	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD601	Approved
0.6589	Remote Similarity	NPD598	Approved
0.6589	Remote Similarity	NPD597	Approved
0.6587	Remote Similarity	NPD1470	Approved
0.6587	Remote Similarity	NPD1164	Approved
0.6583	Remote Similarity	NPD7340	Approved
0.6574	Remote Similarity	NPD9296	Approved
0.6557	Remote Similarity	NPD5691	Approved
0.6557	Remote Similarity	NPD4093	Discontinued
0.6557	Remote Similarity	NPD9268	Approved
0.6545	Remote Similarity	NPD9611	Approved
0.6545	Remote Similarity	NPD9096	Approved
0.6545	Remote Similarity	NPD68	Approved
0.6545	Remote Similarity	NPD9609	Approved
0.6545	Remote Similarity	NPD9095	Approved
0.6545	Remote Similarity	NPD9612	Approved
0.6545	Remote Similarity	NPD9097	Approved
0.6542	Remote Similarity	NPD9251	Approved
0.6538	Remote Similarity	NPD1130	Approved
0.6538	Remote Similarity	NPD1132	Approved
0.6538	Remote Similarity	NPD1136	Approved
0.6535	Remote Similarity	NPD3690	Phase 2
0.6535	Remote Similarity	NPD6584	Phase 3
0.6535	Remote Similarity	NPD3691	Phase 2
0.6532	Remote Similarity	NPD1535	Discovery
0.6532	Remote Similarity	NPD1611	Approved
0.6504	Remote Similarity	NPD1751	Approved
0.6504	Remote Similarity	NPD4589	Approved
0.65	Remote Similarity	NPD255	Approved
0.65	Remote Similarity	NPD256	Approved
0.6491	Remote Similarity	NPD9697	Approved
0.6489	Remote Similarity	NPD943	Approved
0.6489	Remote Similarity	NPD4060	Phase 1
0.6489	Remote Similarity	NPD3062	Approved
0.6489	Remote Similarity	NPD3061	Approved
0.6489	Remote Similarity	NPD3059	Approved
0.6484	Remote Similarity	NPD1712	Approved
0.6484	Remote Similarity	NPD5736	Approved
0.648	Remote Similarity	NPD2562	Approved
0.648	Remote Similarity	NPD1481	Phase 2
0.648	Remote Similarity	NPD9717	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