NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	2.02
LogD:	2.115
LogS:	-1.725
# 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:	0.695
Synthetic Accessibility Score:	1.445
Fsp3:	0.222
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:	-4.697
MDCK Permeability:	6.338600360322744e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	78.20467376708984%
Volume Distribution (VD):	0.186
Pgp-substrate:	12.884016036987305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.321
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.357
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	8.575
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.356
Carcinogencity:	0.116
Eye Corrosion:	0.942
Eye Irritation:	0.985
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC329064

Natural Product ID:	NPC329064
*Common Name:**	M-Tolyl-Acetic Acid
IUPAC Name:	2-(3-methylphenyl)acetic acid
Synonyms:	m-Tolyl-acetic acid
Standard InCHIKey:	GJMPSRSMBJLKKB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O2/c1-7-3-2-4-8(5-7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
SMILES:	OC(=O)Cc1cccc(c1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL136369
PubChem CID:	12121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001091] Toluenes

*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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Others	6

Activity Type	# Activity
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		LogP	=	1.89	n.a.	PMID[533707]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	0.0	%	PMID[533707]
NPT35	Others	n.a.		LogP	=	1.98	n.a.	PMID[533708]
NPT35	Others	n.a.		LogD	=	1.35	n.a.	PMID[533708]
NPT35	Others	n.a.		LogD	=	-0.7	n.a.	PMID[533708]
NPT35	Others	n.a.		pKa	=	4.13	n.a.	PMID[533708]

☑ 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 NPC329064 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	200
0.1-0.2	1138
0.2-0.3	3434
0.3-0.4	12127
0.4-0.5	15332
0.5-0.6	8414
0.6-0.7	1741
0.7-0.8	270
0.8-0.85	25
0.85-0.9	9
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9405	High Similarity	NPC322387
0.939	High Similarity	NPC285773
0.9101	High Similarity	NPC172925
0.908	High Similarity	NPC86670
0.908	High Similarity	NPC274455
0.908	High Similarity	NPC70940
0.9024	High Similarity	NPC127343
0.8929	High Similarity	NPC44830
0.8929	High Similarity	NPC288903
0.8721	High Similarity	NPC294134
0.8721	High Similarity	NPC95965
0.8632	High Similarity	NPC329556
0.8556	High Similarity	NPC86987
0.8511	High Similarity	NPC217621
0.8387	Intermediate Similarity	NPC261947
0.8352	Intermediate Similarity	NPC110704
0.8352	Intermediate Similarity	NPC317645
0.8333	Intermediate Similarity	NPC25458
0.8333	Intermediate Similarity	NPC304873
0.8298	Intermediate Similarity	NPC253423
0.8229	Intermediate Similarity	NPC128248
0.8229	Intermediate Similarity	NPC136810
0.8229	Intermediate Similarity	NPC225079
0.8229	Intermediate Similarity	NPC133809
0.8211	Intermediate Similarity	NPC229242
0.8182	Intermediate Similarity	NPC37914
0.8182	Intermediate Similarity	NPC94751
0.8182	Intermediate Similarity	NPC142326
0.8161	Intermediate Similarity	NPC323103
0.814	Intermediate Similarity	NPC121800
0.8132	Intermediate Similarity	NPC9822
0.8125	Intermediate Similarity	NPC228435
0.8081	Intermediate Similarity	NPC105899
0.8068	Intermediate Similarity	NPC270507
0.8061	Intermediate Similarity	NPC255676
0.8049	Intermediate Similarity	NPC155429
0.8043	Intermediate Similarity	NPC62765
0.8041	Intermediate Similarity	NPC264728
0.8023	Intermediate Similarity	NPC170484
0.8021	Intermediate Similarity	NPC160548
0.8021	Intermediate Similarity	NPC210529
0.8021	Intermediate Similarity	NPC271475
0.8021	Intermediate Similarity	NPC175852
0.802	Intermediate Similarity	NPC318327
0.8	Intermediate Similarity	NPC61944
0.7978	Intermediate Similarity	NPC267704
0.7976	Intermediate Similarity	NPC189371
0.7961	Intermediate Similarity	NPC66208
0.7955	Intermediate Similarity	NPC103387
0.7921	Intermediate Similarity	NPC249811
0.7917	Intermediate Similarity	NPC226041
0.7917	Intermediate Similarity	NPC477767
0.7879	Intermediate Similarity	NPC160382
0.7872	Intermediate Similarity	NPC323164
0.7864	Intermediate Similarity	NPC95126
0.7864	Intermediate Similarity	NPC475002
0.7857	Intermediate Similarity	NPC94487
0.7857	Intermediate Similarity	NPC52472
0.7849	Intermediate Similarity	NPC84288
0.7835	Intermediate Similarity	NPC120393
0.7812	Intermediate Similarity	NPC469893
0.7802	Intermediate Similarity	NPC318107
0.78	Intermediate Similarity	NPC329282
0.7778	Intermediate Similarity	NPC474820
0.7778	Intermediate Similarity	NPC284477
0.7778	Intermediate Similarity	NPC475978
0.7755	Intermediate Similarity	NPC221825
0.7755	Intermediate Similarity	NPC245561
0.7738	Intermediate Similarity	NPC285679
0.7736	Intermediate Similarity	NPC186933
0.7732	Intermediate Similarity	NPC324569
0.7732	Intermediate Similarity	NPC469892
0.7732	Intermediate Similarity	NPC469890
0.7732	Intermediate Similarity	NPC469891
0.7723	Intermediate Similarity	NPC134120
0.7723	Intermediate Similarity	NPC471186
0.7723	Intermediate Similarity	NPC172483
0.7708	Intermediate Similarity	NPC130398
0.7701	Intermediate Similarity	NPC224544
0.77	Intermediate Similarity	NPC13426
0.77	Intermediate Similarity	NPC247976
0.77	Intermediate Similarity	NPC274443
0.7677	Intermediate Similarity	NPC282895
0.7677	Intermediate Similarity	NPC469481
0.7647	Intermediate Similarity	NPC85560
0.7647	Intermediate Similarity	NPC108218
0.7647	Intermediate Similarity	NPC83409
0.7647	Intermediate Similarity	NPC185763
0.7647	Intermediate Similarity	NPC244933
0.7647	Intermediate Similarity	NPC317592
0.7642	Intermediate Similarity	NPC471721
0.7634	Intermediate Similarity	NPC477693
0.7634	Intermediate Similarity	NPC477704
0.7619	Intermediate Similarity	NPC74458
0.7604	Intermediate Similarity	NPC261181
0.7604	Intermediate Similarity	NPC34243
0.76	Intermediate Similarity	NPC244427
0.76	Intermediate Similarity	NPC222390
0.7579	Intermediate Similarity	NPC141607
0.7579	Intermediate Similarity	NPC187725
0.7576	Intermediate Similarity	NPC7435
0.7576	Intermediate Similarity	NPC12730
0.7576	Intermediate Similarity	NPC280869
0.7576	Intermediate Similarity	NPC203925
0.7573	Intermediate Similarity	NPC112903
0.757	Intermediate Similarity	NPC476357
0.757	Intermediate Similarity	NPC221275
0.7551	Intermediate Similarity	NPC276775
0.7551	Intermediate Similarity	NPC293628
0.7551	Intermediate Similarity	NPC249912
0.7551	Intermediate Similarity	NPC270654
0.7551	Intermediate Similarity	NPC122493
0.7551	Intermediate Similarity	NPC10781
0.7551	Intermediate Similarity	NPC92754
0.7549	Intermediate Similarity	NPC13495
0.7547	Intermediate Similarity	NPC93287
0.7527	Intermediate Similarity	NPC89377
0.7524	Intermediate Similarity	NPC474057
0.75	Intermediate Similarity	NPC85493
0.75	Intermediate Similarity	NPC473325
0.75	Intermediate Similarity	NPC70624
0.7477	Intermediate Similarity	NPC109241
0.7477	Intermediate Similarity	NPC211421
0.7476	Intermediate Similarity	NPC100767
0.7475	Intermediate Similarity	NPC78701
0.7475	Intermediate Similarity	NPC35448
0.7475	Intermediate Similarity	NPC225060
0.7475	Intermediate Similarity	NPC260000
0.7474	Intermediate Similarity	NPC258627
0.7455	Intermediate Similarity	NPC328694
0.7453	Intermediate Similarity	NPC292834
0.7451	Intermediate Similarity	NPC19136
0.7451	Intermediate Similarity	NPC472222
0.7451	Intermediate Similarity	NPC472221
0.7444	Intermediate Similarity	NPC133050
0.7442	Intermediate Similarity	NPC208075
0.7431	Intermediate Similarity	NPC158157
0.7431	Intermediate Similarity	NPC212891
0.7429	Intermediate Similarity	NPC234639
0.7426	Intermediate Similarity	NPC188895
0.7419	Intermediate Similarity	NPC474211
0.7416	Intermediate Similarity	NPC300205
0.7412	Intermediate Similarity	NPC208302
0.7407	Intermediate Similarity	NPC306740
0.7404	Intermediate Similarity	NPC228737
0.7404	Intermediate Similarity	NPC156648
0.74	Intermediate Similarity	NPC54647
0.74	Intermediate Similarity	NPC325497
0.74	Intermediate Similarity	NPC476042
0.74	Intermediate Similarity	NPC146351
0.7396	Intermediate Similarity	NPC476484
0.7391	Intermediate Similarity	NPC44546
0.7391	Intermediate Similarity	NPC168855
0.7386	Intermediate Similarity	NPC298023
0.7374	Intermediate Similarity	NPC289201
0.7374	Intermediate Similarity	NPC156021
0.7368	Intermediate Similarity	NPC220893
0.7368	Intermediate Similarity	NPC231591
0.7364	Intermediate Similarity	NPC45794
0.7358	Intermediate Similarity	NPC210089
0.7358	Intermediate Similarity	NPC260818
0.7347	Intermediate Similarity	NPC206764
0.7333	Intermediate Similarity	NPC281604
0.7333	Intermediate Similarity	NPC31274
0.7333	Intermediate Similarity	NPC164086
0.7333	Intermediate Similarity	NPC190567
0.7333	Intermediate Similarity	NPC328178
0.7327	Intermediate Similarity	NPC42211
0.7326	Intermediate Similarity	NPC271437
0.7312	Intermediate Similarity	NPC474354
0.7312	Intermediate Similarity	NPC58616
0.7312	Intermediate Similarity	NPC475710
0.7303	Intermediate Similarity	NPC2785
0.7303	Intermediate Similarity	NPC103488
0.7303	Intermediate Similarity	NPC36342
0.7303	Intermediate Similarity	NPC285470
0.73	Intermediate Similarity	NPC317280
0.73	Intermediate Similarity	NPC329387
0.7297	Intermediate Similarity	NPC474890
0.7297	Intermediate Similarity	NPC161943
0.7297	Intermediate Similarity	NPC273282
0.729	Intermediate Similarity	NPC471189
0.729	Intermediate Similarity	NPC186128
0.729	Intermediate Similarity	NPC321852
0.729	Intermediate Similarity	NPC471188
0.7283	Intermediate Similarity	NPC477770
0.7282	Intermediate Similarity	NPC31786
0.7282	Intermediate Similarity	NPC249067
0.7273	Intermediate Similarity	NPC83718
0.7263	Intermediate Similarity	NPC325441
0.7263	Intermediate Similarity	NPC304760
0.7255	Intermediate Similarity	NPC320891
0.7255	Intermediate Similarity	NPC474112
0.7253	Intermediate Similarity	NPC145053
0.7238	Intermediate Similarity	NPC21929
0.7238	Intermediate Similarity	NPC34715
0.7238	Intermediate Similarity	NPC203732
0.7234	Intermediate Similarity	NPC93843
0.7234	Intermediate Similarity	NPC160339
0.7234	Intermediate Similarity	NPC307

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 NPC329064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	870
0.2-0.3	1449
0.3-0.4	3043
0.4-0.5	2218
0.5-0.6	1008
0.6-0.7	286
0.7-0.8	37
0.8-0.85	9
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.939	High Similarity	NPD9491	Approved
0.9186	High Similarity	NPD800	Approved
0.9146	High Similarity	NPD226	Approved
0.9101	High Similarity	NPD688	Clinical (unspecified phase)
0.908	High Similarity	NPD1089	Approved
0.908	High Similarity	NPD1090	Approved
0.908	High Similarity	NPD1086	Approved
0.8902	High Similarity	NPD9490	Approved
0.8876	High Similarity	NPD1088	Approved
0.878	High Similarity	NPD227	Approved
0.878	High Similarity	NPD225	Approved
0.8764	High Similarity	NPD1239	Approved
0.8736	High Similarity	NPD1087	Approved
0.8681	High Similarity	NPD1693	Approved
0.8632	High Similarity	NPD1930	Approved
0.8632	High Similarity	NPD1929	Approved
0.8632	High Similarity	NPD1931	Clinical (unspecified phase)
0.8539	High Similarity	NPD5346	Phase 2
0.8539	High Similarity	NPD5347	Phase 2
0.8523	High Similarity	NPD4793	Discontinued
0.8495	Intermediate Similarity	NPD1566	Phase 3
0.8495	Intermediate Similarity	NPD1565	Approved
0.8495	Intermediate Similarity	NPD1564	Approved
0.8316	Intermediate Similarity	NPD2066	Phase 3
0.8172	Intermediate Similarity	NPD1563	Approved
0.8172	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD9256	Approved
0.8043	Intermediate Similarity	NPD9258	Approved
0.8021	Intermediate Similarity	NPD9495	Approved
0.802	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1989	Approved
0.7849	Intermediate Similarity	NPD3672	Approved
0.7849	Intermediate Similarity	NPD3673	Approved
0.7802	Intermediate Similarity	NPD9257	Approved
0.7802	Intermediate Similarity	NPD9259	Approved
0.7778	Intermediate Similarity	NPD1932	Approved
0.7736	Intermediate Similarity	NPD5951	Approved
0.7653	Intermediate Similarity	NPD253	Approved
0.7629	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD1202	Approved
0.7576	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD2629	Approved
0.7551	Intermediate Similarity	NPD9566	Approved
0.75	Intermediate Similarity	NPD2329	Discontinued
0.7429	Intermediate Similarity	NPD1317	Discontinued
0.7423	Intermediate Similarity	NPD1066	Discontinued
0.7321	Intermediate Similarity	NPD2345	Approved
0.7321	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2650	Approved
0.7315	Intermediate Similarity	NPD2652	Approved
0.7315	Intermediate Similarity	NPD1280	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5909	Discontinued
0.7282	Intermediate Similarity	NPD1237	Approved
0.7282	Intermediate Similarity	NPD164	Approved
0.7248	Intermediate Similarity	NPD1246	Approved
0.7228	Intermediate Similarity	NPD1238	Approved
0.7222	Intermediate Similarity	NPD181	Approved
0.7212	Intermediate Similarity	NPD1018	Approved
0.7196	Intermediate Similarity	NPD3642	Approved
0.7196	Intermediate Similarity	NPD3643	Approved
0.7196	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3644	Approved
0.7184	Intermediate Similarity	NPD5765	Approved
0.7172	Intermediate Similarity	NPD9260	Approved
0.7159	Intermediate Similarity	NPD9716	Approved
0.7143	Intermediate Similarity	NPD467	Phase 1
0.7143	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6685	Approved
0.713	Intermediate Similarity	NPD9508	Approved
0.7103	Intermediate Similarity	NPD4234	Approved
0.7103	Intermediate Similarity	NPD4233	Approved
0.7103	Intermediate Similarity	NPD1752	Approved
0.7103	Intermediate Similarity	NPD1756	Approved
0.7103	Intermediate Similarity	NPD5278	Discontinued
0.7091	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4766	Approved
0.7083	Intermediate Similarity	NPD1101	Approved
0.7069	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD942	Approved
0.7064	Intermediate Similarity	NPD5277	Phase 2
0.7059	Intermediate Similarity	NPD7798	Approved
0.7048	Intermediate Similarity	NPD1040	Phase 2
0.7048	Intermediate Similarity	NPD5048	Discontinued
0.7037	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD255	Approved
0.7027	Intermediate Similarity	NPD256	Approved
0.7019	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6647	Phase 2
0.7009	Intermediate Similarity	NPD2182	Approved
0.7009	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD9294	Approved
0.6979	Remote Similarity	NPD650	Approved
0.6944	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2067	Discontinued
0.693	Remote Similarity	NPD4105	Approved
0.693	Remote Similarity	NPD1245	Approved
0.693	Remote Similarity	NPD4102	Approved
0.6916	Remote Similarity	NPD9264	Approved
0.6916	Remote Similarity	NPD9263	Approved
0.6916	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD9267	Approved
0.6915	Remote Similarity	NPD3971	Phase 1
0.6909	Remote Similarity	NPD2607	Approved
0.6909	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD531	Approved
0.69	Remote Similarity	NPD720	Approved
0.69	Remote Similarity	NPD719	Approved
0.69	Remote Similarity	NPD845	Approved
0.6893	Remote Similarity	NPD1067	Discontinued
0.6881	Remote Similarity	NPD188	Approved
0.6881	Remote Similarity	NPD189	Phase 3
0.687	Remote Similarity	NPD5306	Approved
0.687	Remote Similarity	NPD5305	Approved
0.6869	Remote Similarity	NPD530	Approved
0.6869	Remote Similarity	NPD7609	Phase 3
0.6864	Remote Similarity	NPD1574	Approved
0.6852	Remote Similarity	NPD9266	Approved
0.6852	Remote Similarity	NPD476	Approved
0.6852	Remote Similarity	NPD74	Approved
0.6847	Remote Similarity	NPD6010	Discontinued
0.6847	Remote Similarity	NPD1370	Approved
0.6847	Remote Similarity	NPD1373	Approved
0.6847	Remote Similarity	NPD1371	Approved
0.6847	Remote Similarity	NPD1374	Approved
0.6838	Remote Similarity	NPD1608	Approved
0.6814	Remote Similarity	NPD3797	Approved
0.6814	Remote Similarity	NPD9493	Approved
0.681	Remote Similarity	NPD4136	Approved
0.681	Remote Similarity	NPD4135	Approved
0.681	Remote Similarity	NPD4106	Approved
0.6807	Remote Similarity	NPD1164	Approved
0.6804	Remote Similarity	NPD9538	Approved
0.68	Remote Similarity	NPD752	Approved
0.68	Remote Similarity	NPD159	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7631	Approved
0.6783	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6993	Approved
0.6783	Remote Similarity	NPD6994	Approved
0.6757	Remote Similarity	NPD6858	Approved
0.6757	Remote Similarity	NPD7094	Approved
0.6752	Remote Similarity	NPD3131	Approved
0.6752	Remote Similarity	NPD4807	Approved
0.6752	Remote Similarity	NPD4215	Approved
0.6752	Remote Similarity	NPD4218	Approved
0.6752	Remote Similarity	NPD4216	Approved
0.6752	Remote Similarity	NPD2608	Approved
0.6752	Remote Similarity	NPD2611	Approved
0.6752	Remote Similarity	NPD4806	Approved
0.6752	Remote Similarity	NPD3132	Approved
0.6752	Remote Similarity	NPD5618	Discontinued
0.6752	Remote Similarity	NPD2610	Approved
0.6752	Remote Similarity	NPD2609	Approved
0.6752	Remote Similarity	NPD4217	Approved
0.6752	Remote Similarity	NPD2612	Approved
0.6752	Remote Similarity	NPD1281	Approved
0.675	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6085	Phase 2
0.6733	Remote Similarity	NPD1409	Phase 3
0.6731	Remote Similarity	NPD9712	Approved
0.6724	Remote Similarity	NPD4199	Phase 3
0.6724	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6966	Discovery
0.6721	Remote Similarity	NPD7008	Discontinued
0.6721	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3495	Discontinued
0.6698	Remote Similarity	NPD9261	Approved
0.6696	Remote Similarity	NPD3798	Phase 3
0.6696	Remote Similarity	NPD4479	Discontinued
0.6696	Remote Similarity	NPD3598	Phase 3
0.6696	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6049	Phase 2
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD4574	Approved
0.6667	Remote Similarity	NPD4576	Approved
0.6667	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD747	Discontinued
0.6635	Remote Similarity	NPD9710	Approved
0.6635	Remote Similarity	NPD9711	Approved
0.6633	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7610	Discontinued
0.6609	Remote Similarity	NPD1758	Phase 1
0.6609	Remote Similarity	NPD6065	Approved
0.6602	Remote Similarity	NPD844	Approved
0.6602	Remote Similarity	NPD2860	Approved
0.6602	Remote Similarity	NPD1809	Phase 2
0.6602	Remote Similarity	NPD2859	Approved
0.6581	Remote Similarity	NPD2932	Approved
0.6581	Remote Similarity	NPD1104	Approved
0.6581	Remote Similarity	NPD17	Approved
0.6581	Remote Similarity	NPD3019	Approved
0.6579	Remote Similarity	NPD4198	Discontinued
0.6579	Remote Similarity	NPD1348	Approved
0.6574	Remote Similarity	NPD999	Phase 2
0.6571	Remote Similarity	NPD3020	Approved
0.6569	Remote Similarity	NPD3719	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