NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.08
Volume:	179.994
LogP:	3.285
LogD:	2.359
LogS:	-3.24
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	1.372
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.591
MDCK Permeability:	2.2109734345576726e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	88.21065521240234%
Volume Distribution (VD):	0.222
Pgp-substrate:	12.413317680358887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.146
CYP1A2-substrate:	0.456
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	1.034
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.081
Carcinogencity:	0.038
Eye Corrosion:	0.041
Eye Irritation:	0.989
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC304873

Natural Product ID:	NPC304873
*Common Name:**	4-Isopropylbenzoic Acid
IUPAC Name:	4-propan-2-ylbenzoic acid
Synonyms:	4-Isopropyl-Benzoic Acid; 4-Isopropylbenzoic Acid
Standard InCHIKey:	CKMXAIVXVKGGFM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h3-7H,1-2H3,(H,11,12)
SMILES:	CC(c1ccc(cc1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL116158
PubChem CID:	10820
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	stem	n.a.	PMID[12560039]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[23507295]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650.3	Perilla frutescens (l.) britt. var. crispa (thunb.) hand.-mazz.	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24109	Armillaria edodes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22653	Ecionemia geodides	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24395	Diospyros melanoxylon	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24256	Athrotaxis selaginoides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14621	Cuminum cyminum	Species	Apiaceae	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
NPO14621	NPC304873	Other	Seed	0.1	0.1	0.1	mg/100g	Database [DUKE]

☑ 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	2
MIC	1
Others	1

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	LogD	=	3.28	n.a.	PMID[544323]
NPT2	Others	Unspecified	IC50	=	1920000.0	nM	PMID[544324]
NPT2	Others	Unspecified	IC50	=	524807460249.77	nM	PMID[544324]
NPT2	Others	Unspecified	MIC	=	200000.0	nM	PMID[544325]

☑ 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 NPC304873 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	211
0.1-0.2	1242
0.2-0.3	3030
0.3-0.4	9169
0.4-0.5	12607
0.5-0.6	11478
0.6-0.7	4166
0.7-0.8	715
0.8-0.85	52
0.85-0.9	16
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC217621
0.9583	High Similarity	NPC25458
0.9574	High Similarity	NPC253423
0.949	High Similarity	NPC105899
0.93	High Similarity	NPC249811
0.9271	High Similarity	NPC229242
0.9263	High Similarity	NPC61944
0.9126	High Similarity	NPC66208
0.9091	High Similarity	NPC255676
0.902	High Similarity	NPC318327
0.8936	High Similarity	NPC62765
0.8868	High Similarity	NPC186933
0.88	High Similarity	NPC284477
0.8737	High Similarity	NPC70940
0.8737	High Similarity	NPC274455
0.8737	High Similarity	NPC86670
0.87	High Similarity	NPC282895
0.8692	High Similarity	NPC476357
0.8667	High Similarity	NPC474057
0.8617	High Similarity	NPC322387
0.86	High Similarity	NPC203925
0.86	High Similarity	NPC228435
0.8529	High Similarity	NPC329556
0.8515	High Similarity	NPC70624
0.8511	High Similarity	NPC318107
0.8476	Intermediate Similarity	NPC85493
0.8455	Intermediate Similarity	NPC160199
0.8431	Intermediate Similarity	NPC188895
0.8384	Intermediate Similarity	NPC130398
0.8364	Intermediate Similarity	NPC158157
0.8333	Intermediate Similarity	NPC329064
0.8318	Intermediate Similarity	NPC260818
0.8317	Intermediate Similarity	NPC225060
0.8304	Intermediate Similarity	NPC472708
0.8286	Intermediate Similarity	NPC37914
0.8283	Intermediate Similarity	NPC261181
0.8265	Intermediate Similarity	NPC110704
0.8257	Intermediate Similarity	NPC153053
0.8246	Intermediate Similarity	NPC167323
0.8246	Intermediate Similarity	NPC269923
0.8246	Intermediate Similarity	NPC25168
0.8241	Intermediate Similarity	NPC321852
0.8235	Intermediate Similarity	NPC146351
0.8218	Intermediate Similarity	NPC276775
0.8218	Intermediate Similarity	NPC92754
0.8218	Intermediate Similarity	NPC249912
0.8191	Intermediate Similarity	NPC285773
0.8182	Intermediate Similarity	NPC274839
0.8165	Intermediate Similarity	NPC128368
0.8158	Intermediate Similarity	NPC165197
0.8155	Intermediate Similarity	NPC473325
0.8148	Intermediate Similarity	NPC95126
0.8148	Intermediate Similarity	NPC475002
0.8137	Intermediate Similarity	NPC78701
0.8137	Intermediate Similarity	NPC35448
0.8103	Intermediate Similarity	NPC85511
0.8095	Intermediate Similarity	NPC31786
0.8095	Intermediate Similarity	NPC249067
0.8095	Intermediate Similarity	NPC329282
0.8091	Intermediate Similarity	NPC196673
0.8058	Intermediate Similarity	NPC325497
0.8037	Intermediate Similarity	NPC211439
0.8037	Intermediate Similarity	NPC34715
0.8034	Intermediate Similarity	NPC117794
0.8019	Intermediate Similarity	NPC209632
0.8018	Intermediate Similarity	NPC306740
0.8017	Intermediate Similarity	NPC297193
0.8	Intermediate Similarity	NPC272524
0.8	Intermediate Similarity	NPC291426
0.8	Intermediate Similarity	NPC247976
0.7982	Intermediate Similarity	NPC476003
0.7981	Intermediate Similarity	NPC42211
0.7966	Intermediate Similarity	NPC472592
0.7963	Intermediate Similarity	NPC83628
0.7963	Intermediate Similarity	NPC265407
0.7961	Intermediate Similarity	NPC210529
0.7961	Intermediate Similarity	NPC160548
0.7961	Intermediate Similarity	NPC175852
0.7949	Intermediate Similarity	NPC275145
0.7946	Intermediate Similarity	NPC161304
0.7944	Intermediate Similarity	NPC37622
0.7944	Intermediate Similarity	NPC187913
0.7944	Intermediate Similarity	NPC30594
0.7944	Intermediate Similarity	NPC119271
0.7938	Intermediate Similarity	NPC474211
0.7938	Intermediate Similarity	NPC93843
0.7928	Intermediate Similarity	NPC211421
0.7928	Intermediate Similarity	NPC471721
0.7925	Intermediate Similarity	NPC472221
0.7925	Intermediate Similarity	NPC324786
0.7925	Intermediate Similarity	NPC114594
0.7925	Intermediate Similarity	NPC472222
0.7917	Intermediate Similarity	NPC168855
0.7909	Intermediate Similarity	NPC82899
0.7909	Intermediate Similarity	NPC270699
0.7909	Intermediate Similarity	NPC158282
0.7905	Intermediate Similarity	NPC45613
0.789	Intermediate Similarity	NPC196246
0.789	Intermediate Similarity	NPC95172
0.789	Intermediate Similarity	NPC214067
0.7885	Intermediate Similarity	NPC118343
0.7872	Intermediate Similarity	NPC127343
0.787	Intermediate Similarity	NPC226699
0.787	Intermediate Similarity	NPC56493
0.7863	Intermediate Similarity	NPC472703
0.7857	Intermediate Similarity	NPC93181
0.7857	Intermediate Similarity	NPC81808
0.785	Intermediate Similarity	NPC172483
0.7843	Intermediate Similarity	NPC172925
0.7838	Intermediate Similarity	NPC93287
0.7835	Intermediate Similarity	NPC474354
0.7833	Intermediate Similarity	NPC115797
0.7833	Intermediate Similarity	NPC51448
0.783	Intermediate Similarity	NPC301943
0.783	Intermediate Similarity	NPC89886
0.783	Intermediate Similarity	NPC160382
0.783	Intermediate Similarity	NPC474365
0.783	Intermediate Similarity	NPC274443
0.783	Intermediate Similarity	NPC60679
0.7818	Intermediate Similarity	NPC305912
0.7818	Intermediate Similarity	NPC1082
0.7818	Intermediate Similarity	NPC210089
0.7818	Intermediate Similarity	NPC133308
0.7812	Intermediate Similarity	NPC288903
0.7812	Intermediate Similarity	NPC44830
0.781	Intermediate Similarity	NPC52472
0.781	Intermediate Similarity	NPC469481
0.7807	Intermediate Similarity	NPC125252
0.7798	Intermediate Similarity	NPC17417
0.7798	Intermediate Similarity	NPC269023
0.7798	Intermediate Similarity	NPC224584
0.7798	Intermediate Similarity	NPC10251
0.7798	Intermediate Similarity	NPC469636
0.7798	Intermediate Similarity	NPC99846
0.7797	Intermediate Similarity	NPC472704
0.7788	Intermediate Similarity	NPC317280
0.7788	Intermediate Similarity	NPC329387
0.7788	Intermediate Similarity	NPC322197
0.7778	Intermediate Similarity	NPC185763
0.7778	Intermediate Similarity	NPC100767
0.7778	Intermediate Similarity	NPC184658
0.7778	Intermediate Similarity	NPC6984
0.7778	Intermediate Similarity	NPC83409
0.7768	Intermediate Similarity	NPC237366
0.7768	Intermediate Similarity	NPC307651
0.7767	Intermediate Similarity	NPC261947
0.7748	Intermediate Similarity	NPC292834
0.7739	Intermediate Similarity	NPC474890
0.7739	Intermediate Similarity	NPC41567
0.7739	Intermediate Similarity	NPC328694
0.7739	Intermediate Similarity	NPC273282
0.7739	Intermediate Similarity	NPC161943
0.7736	Intermediate Similarity	NPC244427
0.7736	Intermediate Similarity	NPC222390
0.7731	Intermediate Similarity	NPC236189
0.7727	Intermediate Similarity	NPC174099
0.7727	Intermediate Similarity	NPC251854
0.7727	Intermediate Similarity	NPC93084
0.7719	Intermediate Similarity	NPC212891
0.7719	Intermediate Similarity	NPC83718
0.7714	Intermediate Similarity	NPC245561
0.7706	Intermediate Similarity	NPC29883
0.7706	Intermediate Similarity	NPC141523
0.77	Intermediate Similarity	NPC1793
0.7699	Intermediate Similarity	NPC221275
0.7699	Intermediate Similarity	NPC474685
0.7692	Intermediate Similarity	NPC179092
0.7692	Intermediate Similarity	NPC178395
0.7692	Intermediate Similarity	NPC292665
0.7692	Intermediate Similarity	NPC222876
0.7692	Intermediate Similarity	NPC272454
0.7692	Intermediate Similarity	NPC115188
0.7692	Intermediate Similarity	NPC26433
0.7692	Intermediate Similarity	NPC301987
0.7692	Intermediate Similarity	NPC35856
0.7692	Intermediate Similarity	NPC472981
0.7692	Intermediate Similarity	NPC159760
0.7692	Intermediate Similarity	NPC244994
0.7679	Intermediate Similarity	NPC231717
0.7679	Intermediate Similarity	NPC17693
0.7672	Intermediate Similarity	NPC233165
0.7672	Intermediate Similarity	NPC184579
0.7667	Intermediate Similarity	NPC287473
0.7667	Intermediate Similarity	NPC470765
0.7667	Intermediate Similarity	NPC275576
0.7664	Intermediate Similarity	NPC13426
0.766	Intermediate Similarity	NPC50192
0.7658	Intermediate Similarity	NPC474157
0.7658	Intermediate Similarity	NPC167504
0.7653	Intermediate Similarity	NPC294134
0.7653	Intermediate Similarity	NPC95965
0.7653	Intermediate Similarity	NPC252067
0.7652	Intermediate Similarity	NPC228318
0.7652	Intermediate Similarity	NPC240664
0.7647	Intermediate Similarity	NPC477153
0.7647	Intermediate Similarity	NPC228739
0.7642	Intermediate Similarity	NPC133809
0.7642	Intermediate Similarity	NPC128248
0.7642	Intermediate Similarity	NPC136810
0.7642	Intermediate Similarity	NPC225079

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 NPC304873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	889
0.2-0.3	1281
0.3-0.4	2644
0.4-0.5	2492
0.5-0.6	1146
0.6-0.7	378
0.7-0.8	71
0.8-0.85	16
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD9258	Approved
0.8936	High Similarity	NPD9256	Approved
0.8737	High Similarity	NPD1086	Approved
0.8737	High Similarity	NPD1090	Approved
0.8737	High Similarity	NPD1089	Approved
0.8692	High Similarity	NPD5951	Approved
0.8632	High Similarity	NPD800	Approved
0.86	High Similarity	NPD2066	Phase 3
0.8557	High Similarity	NPD1088	Approved
0.8529	High Similarity	NPD1929	Approved
0.8529	High Similarity	NPD1930	Approved
0.8529	High Similarity	NPD1931	Clinical (unspecified phase)
0.8511	High Similarity	NPD9259	Approved
0.8511	High Similarity	NPD9257	Approved
0.8476	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1087	Approved
0.8384	Intermediate Similarity	NPD1693	Approved
0.8283	Intermediate Similarity	NPD1202	Approved
0.8265	Intermediate Similarity	NPD1239	Approved
0.8252	Intermediate Similarity	NPD1932	Approved
0.8241	Intermediate Similarity	NPD9508	Approved
0.823	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD1565	Approved
0.8218	Intermediate Similarity	NPD1564	Approved
0.8218	Intermediate Similarity	NPD1566	Phase 3
0.8191	Intermediate Similarity	NPD9491	Approved
0.8131	Intermediate Similarity	NPD2329	Discontinued
0.8095	Intermediate Similarity	NPD1237	Approved
0.8095	Intermediate Similarity	NPD164	Approved
0.7979	Intermediate Similarity	NPD226	Approved
0.7961	Intermediate Similarity	NPD9495	Approved
0.7949	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD1563	Approved
0.789	Intermediate Similarity	NPD1317	Discontinued
0.7885	Intermediate Similarity	NPD1238	Approved
0.7843	Intermediate Similarity	NPD9260	Approved
0.7843	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5277	Phase 2
0.7818	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2182	Approved
0.7766	Intermediate Similarity	NPD9490	Approved
0.7759	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD9267	Approved
0.7706	Intermediate Similarity	NPD9264	Approved
0.7706	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD9263	Approved
0.77	Intermediate Similarity	NPD5347	Phase 2
0.77	Intermediate Similarity	NPD5346	Phase 2
0.7699	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD227	Approved
0.766	Intermediate Similarity	NPD225	Approved
0.7636	Intermediate Similarity	NPD9266	Approved
0.7636	Intermediate Similarity	NPD74	Approved
0.7596	Intermediate Similarity	NPD1989	Approved
0.7593	Intermediate Similarity	NPD5909	Discontinued
0.7565	Intermediate Similarity	NPD9493	Approved
0.7561	Intermediate Similarity	NPD7008	Discontinued
0.7561	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2629	Approved
0.7521	Intermediate Similarity	NPD1245	Approved
0.75	Intermediate Similarity	NPD6647	Phase 2
0.75	Intermediate Similarity	NPD4793	Discontinued
0.75	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6966	Discovery
0.7391	Intermediate Similarity	NPD1246	Approved
0.7377	Intermediate Similarity	NPD1164	Approved
0.734	Intermediate Similarity	NPD9716	Approved
0.7339	Intermediate Similarity	NPD9261	Approved
0.7333	Intermediate Similarity	NPD6287	Discontinued
0.7317	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1104	Approved
0.7311	Intermediate Similarity	NPD2345	Approved
0.7295	Intermediate Similarity	NPD1888	Phase 1
0.7282	Intermediate Similarity	NPD3672	Approved
0.7282	Intermediate Similarity	NPD3673	Approved
0.7273	Intermediate Similarity	NPD4878	Approved
0.7265	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9281	Approved
0.7227	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD288	Approved
0.719	Intermediate Similarity	NPD1201	Approved
0.7167	Intermediate Similarity	NPD5306	Approved
0.7167	Intermediate Similarity	NPD5305	Approved
0.7157	Intermediate Similarity	NPD650	Approved
0.7155	Intermediate Similarity	NPD1280	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD7631	Approved
0.7132	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9717	Approved
0.713	Intermediate Similarity	NPD253	Approved
0.7129	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3971	Phase 1
0.7097	Intermediate Similarity	NPD1470	Approved
0.7087	Intermediate Similarity	NPD3764	Approved
0.7083	Intermediate Similarity	NPD4102	Approved
0.7083	Intermediate Similarity	NPD4105	Approved
0.7071	Intermediate Similarity	NPD942	Approved
0.7059	Intermediate Similarity	NPD7610	Discontinued
0.7049	Intermediate Similarity	NPD4806	Approved
0.7049	Intermediate Similarity	NPD4807	Approved
0.7048	Intermediate Similarity	NPD7609	Phase 3
0.704	Intermediate Similarity	NPD2798	Approved
0.7037	Intermediate Similarity	NPD3495	Discontinued
0.7034	Intermediate Similarity	NPD256	Approved
0.7034	Intermediate Similarity	NPD255	Approved
0.7027	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4308	Phase 3
0.7015	Intermediate Similarity	NPD7003	Approved
0.701	Intermediate Similarity	NPD9294	Approved
0.7009	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6049	Phase 2
0.7	Intermediate Similarity	NPD7009	Phase 2
0.6992	Remote Similarity	NPD1608	Approved
0.697	Remote Similarity	NPD5404	Approved
0.697	Remote Similarity	NPD5408	Approved
0.697	Remote Similarity	NPD5405	Approved
0.697	Remote Similarity	NPD5406	Approved
0.6967	Remote Similarity	NPD4136	Approved
0.6967	Remote Similarity	NPD4135	Approved
0.6967	Remote Similarity	NPD4106	Approved
0.6967	Remote Similarity	NPD1889	Phase 1
0.696	Remote Similarity	NPD2797	Approved
0.6953	Remote Similarity	NPD411	Approved
0.6944	Remote Similarity	NPD844	Approved
0.6935	Remote Similarity	NPD5157	Phase 1
0.6935	Remote Similarity	NPD5159	Phase 2
0.6935	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1101	Approved
0.6917	Remote Similarity	NPD2346	Discontinued
0.6916	Remote Similarity	NPD845	Approved
0.6911	Remote Similarity	NPD1281	Approved
0.6911	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3020	Approved
0.6899	Remote Similarity	NPD7714	Approved
0.6899	Remote Similarity	NPD7715	Approved
0.6897	Remote Similarity	NPD3643	Approved
0.6897	Remote Similarity	NPD3642	Approved
0.6897	Remote Similarity	NPD3644	Approved
0.6894	Remote Similarity	NPD2799	Discontinued
0.6891	Remote Similarity	NPD4198	Discontinued
0.6889	Remote Similarity	NPD4628	Phase 3
0.6885	Remote Similarity	NPD9272	Approved
0.6885	Remote Similarity	NPD3019	Approved
0.6885	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2650	Approved
0.6864	Remote Similarity	NPD2652	Approved
0.6855	Remote Similarity	NPD3972	Approved
0.6852	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1616	Discontinued
0.6825	Remote Similarity	NPD1203	Approved
0.6822	Remote Similarity	NPD1508	Approved
0.6822	Remote Similarity	NPD2313	Discontinued
0.681	Remote Similarity	NPD2067	Discontinued
0.6803	Remote Similarity	NPD9268	Approved
0.6791	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4980	Approved
0.6772	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6085	Phase 2
0.6757	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD9712	Approved
0.6754	Remote Similarity	NPD5048	Discontinued
0.6748	Remote Similarity	NPD4626	Approved
0.6748	Remote Similarity	NPD17	Approved
0.6746	Remote Similarity	NPD1876	Approved
0.6727	Remote Similarity	NPD9566	Approved
0.6726	Remote Similarity	NPD5765	Approved
0.672	Remote Similarity	NPD9269	Phase 2
0.6719	Remote Similarity	NPD3664	Approved
0.6719	Remote Similarity	NPD3661	Approved
0.6719	Remote Similarity	NPD3662	Phase 3
0.6719	Remote Similarity	NPD3663	Approved
0.6718	Remote Similarity	NPD4307	Phase 2
0.6716	Remote Similarity	NPD2935	Discontinued
0.6696	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6685	Approved
0.6694	Remote Similarity	NPD9568	Approved
0.6694	Remote Similarity	NPD4879	Approved
0.6694	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9693	Approved
0.6694	Remote Similarity	NPD9692	Approved
0.6692	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD9710	Approved
0.6667	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9711	Approved
0.6642	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7961	Discontinued
0.6641	Remote Similarity	NPD6663	Approved
0.6639	Remote Similarity	NPD6858	Approved
0.6639	Remote Similarity	NPD7094	Approved
0.6639	Remote Similarity	NPD1758	Phase 1

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