NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	137.05
Volume:	139.103
LogP:	0.132
LogD:	0.282
LogS:	-1.31
# Rotatable Bonds:	1
TPSA:	63.32
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	1.477
Fsp3:	0.0
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:	-4.618
MDCK Permeability:	9.894606591842603e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.901
Plasma Protein Binding (PPB):	53.91624450683594%
Volume Distribution (VD):	0.99
Pgp-substrate:	64.84800720214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.366
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.638
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.47
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	13.435
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.168
Carcinogencity:	0.295
Eye Corrosion:	0.011
Eye Irritation:	0.981
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC160179

Natural Product ID:	NPC160179
*Common Name:**	4-Hydroxybenzamide
IUPAC Name:	4-hydroxybenzamide
Synonyms:	4-Hydroxy-Benzamide; 4-Hydroxybenzamide
Standard InCHIKey:	QXSAKPUBHTZHKW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H7NO2/c8-7(10)5-1-3-6(9)4-2-5/h1-4,9H,(H2,8,10)
SMILES:	NC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL123617
PubChem CID:	65052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0000178] Benzamides

*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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	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	1
Others	5

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2562	Individual Protein	Poly [ADP-ribose] polymerase-1	Homo sapiens	IC50	=	280000.0	nM	PMID[485000]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	2.48	n.a.	PMID[485001]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	log(1/ID50)	=	2.23	n.a.	PMID[485001]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[485001]
NPT5723	Individual Protein	Poly [ADP-ribose] polymerase 10	Homo sapiens	Inhibition	=	27.0	%	PMID[485004]
NPT27	Others	Unspecified		log(1/ID50)	=	2.38	n.a.	PMID[485001]

☑ 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 NPC160179 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	301
0.1-0.2	2844
0.2-0.3	8475
0.3-0.4	9014
0.4-0.5	8318
0.5-0.6	10945
0.6-0.7	2604
0.7-0.8	185
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8378	Intermediate Similarity	NPC219913
0.8304	Intermediate Similarity	NPC6984
0.8295	Intermediate Similarity	NPC238412
0.823	Intermediate Similarity	NPC29883
0.823	Intermediate Similarity	NPC226699
0.8158	Intermediate Similarity	NPC17525
0.8142	Intermediate Similarity	NPC184658
0.8087	Intermediate Similarity	NPC95172
0.8018	Intermediate Similarity	NPC29601
0.8017	Intermediate Similarity	NPC116842
0.7949	Intermediate Similarity	NPC212718
0.7949	Intermediate Similarity	NPC268388
0.7949	Intermediate Similarity	NPC114682
0.7881	Intermediate Similarity	NPC231717
0.7823	Intermediate Similarity	NPC268348
0.782	Intermediate Similarity	NPC314252
0.7815	Intermediate Similarity	NPC11824
0.7815	Intermediate Similarity	NPC242136
0.7739	Intermediate Similarity	NPC163734
0.7686	Intermediate Similarity	NPC278102
0.7686	Intermediate Similarity	NPC322197
0.7672	Intermediate Similarity	NPC187913
0.7656	Intermediate Similarity	NPC305717
0.7623	Intermediate Similarity	NPC281686
0.7623	Intermediate Similarity	NPC131192
0.7623	Intermediate Similarity	NPC188867
0.7623	Intermediate Similarity	NPC106551
0.7611	Intermediate Similarity	NPC280869
0.7607	Intermediate Similarity	NPC141523
0.7607	Intermediate Similarity	NPC303264
0.7607	Intermediate Similarity	NPC34715
0.7574	Intermediate Similarity	NPC13696
0.7561	Intermediate Similarity	NPC150919
0.7556	Intermediate Similarity	NPC160747
0.7544	Intermediate Similarity	NPC52472
0.7542	Intermediate Similarity	NPC100551
0.7542	Intermediate Similarity	NPC224584
0.7522	Intermediate Similarity	NPC260000
0.7521	Intermediate Similarity	NPC69332
0.7521	Intermediate Similarity	NPC95178
0.7521	Intermediate Similarity	NPC29989
0.75	Intermediate Similarity	NPC27633
0.75	Intermediate Similarity	NPC283844
0.75	Intermediate Similarity	NPC249435
0.75	Intermediate Similarity	NPC273282
0.75	Intermediate Similarity	NPC94298
0.75	Intermediate Similarity	NPC161943
0.75	Intermediate Similarity	NPC474890
0.75	Intermediate Similarity	NPC241089
0.7477	Intermediate Similarity	NPC181709
0.7456	Intermediate Similarity	NPC125732
0.7456	Intermediate Similarity	NPC245561
0.744	Intermediate Similarity	NPC473767
0.744	Intermediate Similarity	NPC239697
0.744	Intermediate Similarity	NPC156654
0.744	Intermediate Similarity	NPC161617
0.744	Intermediate Similarity	NPC158222
0.7411	Intermediate Similarity	NPC81010
0.7411	Intermediate Similarity	NPC32977
0.7407	Intermediate Similarity	NPC43218
0.7407	Intermediate Similarity	NPC316574
0.7381	Intermediate Similarity	NPC159525
0.7373	Intermediate Similarity	NPC70843
0.7348	Intermediate Similarity	NPC120251
0.7345	Intermediate Similarity	NPC286006
0.7339	Intermediate Similarity	NPC83718
0.7333	Intermediate Similarity	NPC88141
0.7328	Intermediate Similarity	NPC472585
0.7323	Intermediate Similarity	NPC216216
0.7323	Intermediate Similarity	NPC297186
0.7323	Intermediate Similarity	NPC248363
0.7319	Intermediate Similarity	NPC301702
0.7302	Intermediate Similarity	NPC61779
0.7288	Intermediate Similarity	NPC13495
0.728	Intermediate Similarity	NPC174087
0.728	Intermediate Similarity	NPC230349
0.7273	Intermediate Similarity	NPC183648
0.7273	Intermediate Similarity	NPC21162
0.7266	Intermediate Similarity	NPC45438
0.7266	Intermediate Similarity	NPC267552
0.7266	Intermediate Similarity	NPC73532
0.7266	Intermediate Similarity	NPC120545
0.7266	Intermediate Similarity	NPC295034
0.7266	Intermediate Similarity	NPC19174
0.7266	Intermediate Similarity	NPC224273
0.7266	Intermediate Similarity	NPC27581
0.7266	Intermediate Similarity	NPC115159
0.7266	Intermediate Similarity	NPC156139
0.7266	Intermediate Similarity	NPC143427
0.7265	Intermediate Similarity	NPC68269
0.7246	Intermediate Similarity	NPC33011
0.7244	Intermediate Similarity	NPC150323
0.7227	Intermediate Similarity	NPC317592
0.7222	Intermediate Similarity	NPC142638
0.7222	Intermediate Similarity	NPC229353
0.7222	Intermediate Similarity	NPC40649
0.7222	Intermediate Similarity	NPC184527
0.7222	Intermediate Similarity	NPC209486
0.7222	Intermediate Similarity	NPC317784
0.7217	Intermediate Similarity	NPC201967
0.7217	Intermediate Similarity	NPC107619
0.7213	Intermediate Similarity	NPC57879
0.7213	Intermediate Similarity	NPC23332
0.7209	Intermediate Similarity	NPC67300
0.7209	Intermediate Similarity	NPC309765
0.7209	Intermediate Similarity	NPC133909
0.7209	Intermediate Similarity	NPC32032
0.7209	Intermediate Similarity	NPC139171
0.7209	Intermediate Similarity	NPC68167
0.7209	Intermediate Similarity	NPC91478
0.7207	Intermediate Similarity	NPC62765
0.7203	Intermediate Similarity	NPC8931
0.7203	Intermediate Similarity	NPC120693
0.7203	Intermediate Similarity	NPC261573
0.7188	Intermediate Similarity	NPC190971
0.7185	Intermediate Similarity	NPC266425
0.7177	Intermediate Similarity	NPC81808
0.7177	Intermediate Similarity	NPC163154
0.7174	Intermediate Similarity	NPC181526
0.7165	Intermediate Similarity	NPC100395
0.7165	Intermediate Similarity	NPC319950
0.7155	Intermediate Similarity	NPC130193
0.7154	Intermediate Similarity	NPC174991
0.7154	Intermediate Similarity	NPC17693
0.7153	Intermediate Similarity	NPC236795
0.7143	Intermediate Similarity	NPC151764
0.7132	Intermediate Similarity	NPC473360
0.7132	Intermediate Similarity	NPC242895
0.7132	Intermediate Similarity	NPC303737
0.7131	Intermediate Similarity	NPC222905
0.7121	Intermediate Similarity	NPC321561
0.712	Intermediate Similarity	NPC161304
0.712	Intermediate Similarity	NPC240163
0.7119	Intermediate Similarity	NPC68055
0.7119	Intermediate Similarity	NPC13426
0.7119	Intermediate Similarity	NPC178902
0.7113	Intermediate Similarity	NPC17760
0.7109	Intermediate Similarity	NPC130931
0.7109	Intermediate Similarity	NPC294037
0.7099	Intermediate Similarity	NPC13238
0.7099	Intermediate Similarity	NPC184219
0.7097	Intermediate Similarity	NPC211421
0.7097	Intermediate Similarity	NPC309808
0.7097	Intermediate Similarity	NPC98543
0.7097	Intermediate Similarity	NPC223004
0.7094	Intermediate Similarity	NPC289381
0.7094	Intermediate Similarity	NPC155847
0.7094	Intermediate Similarity	NPC253746
0.7083	Intermediate Similarity	NPC188677
0.7077	Intermediate Similarity	NPC225710
0.7077	Intermediate Similarity	NPC291189
0.7077	Intermediate Similarity	NPC69403
0.7077	Intermediate Similarity	NPC282577
0.7068	Intermediate Similarity	NPC145888
0.7068	Intermediate Similarity	NPC161593
0.7068	Intermediate Similarity	NPC16031
0.7064	Intermediate Similarity	NPC124436
0.7064	Intermediate Similarity	NPC265146
0.7063	Intermediate Similarity	NPC108288
0.7063	Intermediate Similarity	NPC312800
0.7063	Intermediate Similarity	NPC128825
0.7059	Intermediate Similarity	NPC169766
0.7054	Intermediate Similarity	NPC146642
0.7054	Intermediate Similarity	NPC326079
0.7054	Intermediate Similarity	NPC149246
0.7049	Intermediate Similarity	NPC172046
0.7049	Intermediate Similarity	NPC290566
0.7049	Intermediate Similarity	NPC145638
0.7045	Intermediate Similarity	NPC49938
0.7043	Intermediate Similarity	NPC246679
0.7043	Intermediate Similarity	NPC257182
0.704	Intermediate Similarity	NPC252004
0.704	Intermediate Similarity	NPC276111
0.704	Intermediate Similarity	NPC285350
0.704	Intermediate Similarity	NPC118288
0.7039	Intermediate Similarity	NPC66490
0.7025	Intermediate Similarity	NPC228737
0.7016	Intermediate Similarity	NPC146422
0.7008	Intermediate Similarity	NPC269414
0.7008	Intermediate Similarity	NPC28169
0.7008	Intermediate Similarity	NPC160199
0.7	Intermediate Similarity	NPC248817
0.7	Intermediate Similarity	NPC215392
0.7	Intermediate Similarity	NPC142577
0.7	Intermediate Similarity	NPC175313
0.6993	Remote Similarity	NPC473196
0.6993	Remote Similarity	NPC146370
0.6992	Remote Similarity	NPC8745
0.6992	Remote Similarity	NPC473751
0.6992	Remote Similarity	NPC110211
0.6992	Remote Similarity	NPC95309
0.6992	Remote Similarity	NPC204579
0.6992	Remote Similarity	NPC62952
0.6984	Remote Similarity	NPC4665
0.6984	Remote Similarity	NPC220540
0.6984	Remote Similarity	NPC23402
0.6983	Remote Similarity	NPC283711
0.6975	Remote Similarity	NPC304638
0.6975	Remote Similarity	NPC470202
0.6975	Remote Similarity	NPC135784

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 NPC160179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	954
0.2-0.3	993
0.3-0.4	2377
0.4-0.5	2781
0.5-0.6	1498
0.6-0.7	274
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.823	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD256	Approved
0.7686	Intermediate Similarity	NPD255	Approved
0.7647	Intermediate Similarity	NPD9508	Approved
0.7623	Intermediate Similarity	NPD9568	Approved
0.7542	Intermediate Similarity	NPD74	Approved
0.7542	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.7458	Intermediate Similarity	NPD9263	Approved
0.7458	Intermediate Similarity	NPD9267	Approved
0.7458	Intermediate Similarity	NPD9264	Approved
0.7407	Intermediate Similarity	NPD9279	Approved
0.7407	Intermediate Similarity	NPD743	Approved
0.7324	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD75	Approved
0.7319	Intermediate Similarity	NPD9277	Approved
0.7292	Intermediate Similarity	NPD824	Approved
0.7292	Intermediate Similarity	NPD3229	Phase 2
0.7246	Intermediate Similarity	NPD9278	Suspended
0.7246	Intermediate Similarity	NPD9274	Approved
0.7246	Intermediate Similarity	NPD9275	Approved
0.7246	Intermediate Similarity	NPD9276	Approved
0.7244	Intermediate Similarity	NPD9272	Approved
0.7207	Intermediate Similarity	NPD9258	Approved
0.7207	Intermediate Similarity	NPD9256	Approved
0.7203	Intermediate Similarity	NPD9608	Approved
0.7203	Intermediate Similarity	NPD9610	Approved
0.7165	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1670	Discontinued
0.7121	Intermediate Similarity	NPD258	Approved
0.7121	Intermediate Similarity	NPD257	Approved
0.7119	Intermediate Similarity	NPD9261	Approved
0.7077	Intermediate Similarity	NPD9269	Phase 2
0.7068	Intermediate Similarity	NPD9569	Approved
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9493	Approved
0.7049	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD9281	Approved
0.7031	Intermediate Similarity	NPD9268	Approved
0.7016	Intermediate Similarity	NPD9377	Approved
0.7016	Intermediate Similarity	NPD9379	Approved
0.6993	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9494	Approved
0.6923	Remote Similarity	NPD9273	Approved
0.6894	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1755	Approved
0.6861	Remote Similarity	NPD259	Phase 1
0.6853	Remote Similarity	NPD1196	Approved
0.6847	Remote Similarity	NPD9259	Approved
0.6847	Remote Similarity	NPD9257	Approved
0.6842	Remote Similarity	NPD196	Phase 1
0.6838	Remote Similarity	NPD9537	Phase 1
0.6838	Remote Similarity	NPD9536	Phase 1
0.6822	Remote Similarity	NPD1759	Phase 1
0.6812	Remote Similarity	NPD826	Approved
0.6812	Remote Similarity	NPD825	Approved
0.6791	Remote Similarity	NPD1164	Approved
0.6783	Remote Similarity	NPD1195	Approved
0.6779	Remote Similarity	NPD3684	Discontinued
0.6763	Remote Similarity	NPD275	Approved
0.6763	Remote Similarity	NPD274	Approved
0.6763	Remote Similarity	NPD555	Phase 2
0.6744	Remote Similarity	NPD1758	Phase 1
0.6714	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1543	Discontinued
0.6711	Remote Similarity	NPD3455	Phase 2
0.6691	Remote Similarity	NPD943	Approved
0.6691	Remote Similarity	NPD3140	Approved
0.6691	Remote Similarity	NPD1240	Approved
0.6691	Remote Similarity	NPD3142	Approved
0.669	Remote Similarity	NPD7450	Phase 2
0.6688	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD2592	Discontinued
0.6641	Remote Similarity	NPD9618	Approved
0.6641	Remote Similarity	NPD9614	Approved
0.6639	Remote Similarity	NPD1237	Approved
0.6623	Remote Similarity	NPD1309	Phase 2
0.6623	Remote Similarity	NPD2672	Discontinued
0.6623	Remote Similarity	NPD1307	Phase 2
0.6619	Remote Similarity	NPD520	Approved
0.6617	Remote Similarity	NPD1201	Approved
0.6615	Remote Similarity	NPD317	Approved
0.6615	Remote Similarity	NPD856	Approved
0.6615	Remote Similarity	NPD318	Approved
0.6615	Remote Similarity	NPD16	Approved
0.661	Remote Similarity	NPD2859	Approved
0.661	Remote Similarity	NPD2860	Approved
0.6596	Remote Similarity	NPD1607	Approved
0.6594	Remote Similarity	NPD3136	Phase 2
0.6594	Remote Similarity	NPD9718	Approved
0.6591	Remote Similarity	NPD9384	Approved
0.6591	Remote Similarity	NPD9381	Approved
0.6581	Remote Similarity	NPD1168	Approved
0.6573	Remote Similarity	NPD9570	Approved
0.6569	Remote Similarity	NPD4208	Discontinued
0.6567	Remote Similarity	NPD3972	Approved
0.6567	Remote Similarity	NPD9717	Approved
0.6562	Remote Similarity	NPD2228	Approved
0.6562	Remote Similarity	NPD2229	Approved
0.6562	Remote Similarity	NPD6020	Phase 2
0.6562	Remote Similarity	NPD1241	Discontinued
0.6562	Remote Similarity	NPD2234	Approved
0.6547	Remote Similarity	NPD3764	Approved
0.6544	Remote Similarity	NPD1470	Approved
0.6544	Remote Similarity	NPD1203	Approved
0.6543	Remote Similarity	NPD5637	Discontinued
0.6541	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD230	Phase 1
0.6525	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD927	Approved
0.6522	Remote Similarity	NPD4207	Discontinued
0.6522	Remote Similarity	NPD2614	Approved
0.6516	Remote Similarity	NPD955	Approved
0.6503	Remote Similarity	NPD1510	Phase 2
0.6503	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD9613	Approved
0.6489	Remote Similarity	NPD9615	Approved
0.6489	Remote Similarity	NPD9616	Approved
0.6481	Remote Similarity	NPD5445	Approved
0.6478	Remote Similarity	NPD1220	Phase 1
0.6458	Remote Similarity	NPD1538	Phase 1
0.6458	Remote Similarity	NPD1537	Approved
0.6458	Remote Similarity	NPD1519	Approved
0.6456	Remote Similarity	NPD5183	Approved
0.6456	Remote Similarity	NPD5186	Approved
0.6446	Remote Similarity	NPD3020	Approved
0.6444	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1202	Approved
0.6439	Remote Similarity	NPD316	Approved
0.6434	Remote Similarity	NPD6636	Phase 3
0.6423	Remote Similarity	NPD552	Approved
0.6423	Remote Similarity	NPD553	Approved
0.6423	Remote Similarity	NPD9567	Approved
0.6419	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD1981	Approved
0.6418	Remote Similarity	NPD1983	Approved
0.6418	Remote Similarity	NPD9692	Approved
0.6418	Remote Similarity	NPD9693	Approved
0.6418	Remote Similarity	NPD1980	Approved
0.6414	Remote Similarity	NPD9477	Approved
0.6414	Remote Similarity	NPD2344	Approved
0.64	Remote Similarity	NPD1445	Approved
0.64	Remote Similarity	NPD1444	Approved
0.6397	Remote Similarity	NPD9622	Approved
0.6393	Remote Similarity	NPD1242	Phase 1
0.6389	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD9260	Approved
0.637	Remote Similarity	NPD1549	Phase 2
0.637	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1221	Approved
0.6355	Remote Similarity	NPD9087	Approved
0.6352	Remote Similarity	NPD1161	Approved
0.635	Remote Similarity	NPD1574	Approved
0.635	Remote Similarity	NPD5310	Approved
0.635	Remote Similarity	NPD5311	Approved
0.635	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1523	Approved
0.6345	Remote Similarity	NPD1522	Approved
0.6343	Remote Similarity	NPD2932	Approved
0.6343	Remote Similarity	NPD3019	Approved
0.6341	Remote Similarity	NPD846	Approved
0.6341	Remote Similarity	NPD940	Approved
0.6335	Remote Similarity	NPD3366	Approved
0.6328	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2562	Approved
0.6324	Remote Similarity	NPD2561	Approved
0.6324	Remote Similarity	NPD1481	Phase 2
0.6319	Remote Similarity	NPD1536	Approved
0.6309	Remote Similarity	NPD3300	Phase 2
0.6304	Remote Similarity	NPD3055	Approved
0.6304	Remote Similarity	NPD1593	Approved
0.6304	Remote Similarity	NPD3053	Approved
0.6301	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2361	Approved
0.6296	Remote Similarity	NPD1544	Phase 1
0.6291	Remote Similarity	NPD2186	Approved
0.6277	Remote Similarity	NPD5157	Phase 1
0.6277	Remote Similarity	NPD5159	Phase 2
0.6277	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD9088	Approved
0.626	Remote Similarity	NPD1793	Approved
0.626	Remote Similarity	NPD1791	Approved
0.6259	Remote Similarity	NPD9619	Approved
0.6259	Remote Similarity	NPD9620	Approved
0.6259	Remote Similarity	NPD9621	Approved
0.6258	Remote Similarity	NPD1170	Approved
0.6258	Remote Similarity	NPD7577	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