NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.1
Volume:	246.826
LogP:	3.308
LogD:	3.048
LogS:	-3.063
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	1.616
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893
MDCK Permeability:	3.095394276897423e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.636
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	89.49298858642578%
Volume Distribution (VD):	0.2
Pgp-substrate:	5.732117652893066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.385
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.122
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	4.757
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.259
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.79
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.18
Carcinogencity:	0.025
Eye Corrosion:	0.028
Eye Irritation:	0.99
Respiratory Toxicity:	0.262

Download Data

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

Natural Product: NPC321852

Natural Product ID:	NPC321852
*Common Name:**	2-Pentoxycarbonylbenzoic Acid
IUPAC Name:	2-pentoxycarbonylbenzoic acid
Synonyms:
Standard InCHIKey:	FPGPRAKRYDSZAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16O4/c1-2-3-6-9-17-13(16)11-8-5-4-7-10(11)12(14)15/h4-5,7-8H,2-3,6,9H2,1H3,(H,14,15)
SMILES:	CCCCCOC(=O)c1ccccc1C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1871247
PubChem CID:	90531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10388717]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820136]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11695850]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1282214]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15102880]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15123652]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[15239850]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15466478]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16538977]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17499416]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18039809]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1814736]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1928373]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572262]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19662622]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951405]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2188748]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23384552]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23723388]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24085302]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24096206]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24343604]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24503197]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24814225]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070706]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25727742]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26041992]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26485038]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26608498]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654758]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26676627]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466123]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3025936]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4002232]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[518564]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6273168]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6572072]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6806263]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6825837]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6833497]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7311739]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7645303]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8069858]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8452569]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9179722]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9435160]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9606952]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9629662]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9660093]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9694933]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17164	Rattus norvegicus	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
Potency	5

Activity Type	# Activity
Cell Line	1
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	1299.0	nM	PMID[497674]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[497674]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[497674]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[497674]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[497674]

☑ 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 NPC321852 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	209
0.1-0.2	1100
0.2-0.3	3042
0.3-0.4	8241
0.4-0.5	11335
0.5-0.6	11061
0.6-0.7	6798
0.7-0.8	804
0.8-0.85	59
0.85-0.9	27
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC260818
0.981	High Similarity	NPC153053
0.9709	High Similarity	NPC85493
0.9612	High Similarity	NPC56493
0.9519	High Similarity	NPC10251
0.9519	High Similarity	NPC17417
0.9515	High Similarity	NPC119271
0.9429	High Similarity	NPC196246
0.9429	High Similarity	NPC174099
0.9429	High Similarity	NPC93084
0.9429	High Similarity	NPC251854
0.9429	High Similarity	NPC214067
0.934	High Similarity	NPC1082
0.934	High Similarity	NPC305912
0.932	High Similarity	NPC31786
0.9252	High Similarity	NPC82899
0.9252	High Similarity	NPC270699
0.9029	High Similarity	NPC282895
0.8909	High Similarity	NPC237366
0.8909	High Similarity	NPC307651
0.8857	High Similarity	NPC89886
0.8835	High Similarity	NPC35448
0.8835	High Similarity	NPC229242
0.8835	High Similarity	NPC78701
0.8818	High Similarity	NPC272524
0.8796	High Similarity	NPC83628
0.8796	High Similarity	NPC265407
0.8762	High Similarity	NPC45613
0.875	High Similarity	NPC146351
0.8738	High Similarity	NPC249912
0.8738	High Similarity	NPC92754
0.8738	High Similarity	NPC276775
0.8679	High Similarity	NPC474365
0.8679	High Similarity	NPC301943
0.8661	High Similarity	NPC306740
0.8654	High Similarity	NPC225060
0.8636	High Similarity	NPC474157
0.8636	High Similarity	NPC476003
0.8611	High Similarity	NPC37622
0.8611	High Similarity	NPC30594
0.8585	High Similarity	NPC284477
0.8571	High Similarity	NPC474363
0.8544	High Similarity	NPC130398
0.8519	High Similarity	NPC209632
0.8505	High Similarity	NPC60679
0.8496	Intermediate Similarity	NPC210092
0.8496	Intermediate Similarity	NPC474685
0.8491	Intermediate Similarity	NPC42211
0.8491	Intermediate Similarity	NPC70624
0.8487	Intermediate Similarity	NPC246166
0.8468	Intermediate Similarity	NPC210089
0.8455	Intermediate Similarity	NPC469636
0.8426	Intermediate Similarity	NPC114594
0.8421	Intermediate Similarity	NPC149691
0.8396	Intermediate Similarity	NPC203925
0.8396	Intermediate Similarity	NPC325497
0.8396	Intermediate Similarity	NPC118343
0.8393	Intermediate Similarity	NPC158282
0.8349	Intermediate Similarity	NPC269457
0.8347	Intermediate Similarity	NPC169913
0.8333	Intermediate Similarity	NPC295664
0.8333	Intermediate Similarity	NPC255676
0.8319	Intermediate Similarity	NPC223351
0.8304	Intermediate Similarity	NPC167504
0.8291	Intermediate Similarity	NPC204784
0.8288	Intermediate Similarity	NPC269023
0.8288	Intermediate Similarity	NPC99846
0.8264	Intermediate Similarity	NPC275576
0.8246	Intermediate Similarity	NPC308744
0.8241	Intermediate Similarity	NPC188895
0.8241	Intermediate Similarity	NPC304873
0.823	Intermediate Similarity	NPC79496
0.823	Intermediate Similarity	NPC474314
0.8224	Intermediate Similarity	NPC217621
0.8208	Intermediate Similarity	NPC253423
0.8174	Intermediate Similarity	NPC81808
0.8167	Intermediate Similarity	NPC46634
0.8158	Intermediate Similarity	NPC128368
0.8155	Intermediate Similarity	NPC62765
0.813	Intermediate Similarity	NPC51448
0.813	Intermediate Similarity	NPC115797
0.8125	Intermediate Similarity	NPC474364
0.8113	Intermediate Similarity	NPC61944
0.8099	Intermediate Similarity	NPC471466
0.8099	Intermediate Similarity	NPC228739
0.8073	Intermediate Similarity	NPC25458
0.807	Intermediate Similarity	NPC66208
0.8058	Intermediate Similarity	NPC173443
0.8036	Intermediate Similarity	NPC211439
0.8036	Intermediate Similarity	NPC249811
0.8018	Intermediate Similarity	NPC105899
0.8017	Intermediate Similarity	NPC472703
0.8	Intermediate Similarity	NPC161611
0.7983	Intermediate Similarity	NPC90522
0.7983	Intermediate Similarity	NPC328459
0.7966	Intermediate Similarity	NPC240664
0.7965	Intermediate Similarity	NPC318327
0.7951	Intermediate Similarity	NPC472704
0.7949	Intermediate Similarity	NPC100353
0.7931	Intermediate Similarity	NPC477411
0.7931	Intermediate Similarity	NPC196075
0.7917	Intermediate Similarity	NPC473243
0.7917	Intermediate Similarity	NPC72977
0.7899	Intermediate Similarity	NPC94637
0.7899	Intermediate Similarity	NPC94298
0.7899	Intermediate Similarity	NPC27633
0.789	Intermediate Similarity	NPC228435
0.7885	Intermediate Similarity	NPC220893
0.7876	Intermediate Similarity	NPC470391
0.7874	Intermediate Similarity	NPC7012
0.7864	Intermediate Similarity	NPC89377
0.7863	Intermediate Similarity	NPC186933
0.7857	Intermediate Similarity	NPC272946
0.7851	Intermediate Similarity	NPC50872
0.7845	Intermediate Similarity	NPC474176
0.7838	Intermediate Similarity	NPC160382
0.7829	Intermediate Similarity	NPC477896
0.7829	Intermediate Similarity	NPC477893
0.7826	Intermediate Similarity	NPC474057
0.7826	Intermediate Similarity	NPC243355
0.7823	Intermediate Similarity	NPC470765
0.7797	Intermediate Similarity	NPC226093
0.7788	Intermediate Similarity	NPC472316
0.7788	Intermediate Similarity	NPC136962
0.7788	Intermediate Similarity	NPC472315
0.7788	Intermediate Similarity	NPC475203
0.7788	Intermediate Similarity	NPC474376
0.7768	Intermediate Similarity	NPC329282
0.7767	Intermediate Similarity	NPC318107
0.776	Intermediate Similarity	NPC470753
0.776	Intermediate Similarity	NPC473220
0.776	Intermediate Similarity	NPC472706
0.776	Intermediate Similarity	NPC475236
0.776	Intermediate Similarity	NPC110211
0.776	Intermediate Similarity	NPC204579
0.7759	Intermediate Similarity	NPC212415
0.7757	Intermediate Similarity	NPC261181
0.7752	Intermediate Similarity	NPC472591
0.7752	Intermediate Similarity	NPC329913
0.7752	Intermediate Similarity	NPC43627
0.775	Intermediate Similarity	NPC254233
0.7742	Intermediate Similarity	NPC184219
0.7734	Intermediate Similarity	NPC233692
0.7731	Intermediate Similarity	NPC158157
0.7731	Intermediate Similarity	NPC128825
0.7731	Intermediate Similarity	NPC131192
0.7724	Intermediate Similarity	NPC217756
0.7717	Intermediate Similarity	NPC27712
0.7712	Intermediate Similarity	NPC474095
0.7712	Intermediate Similarity	NPC228936
0.7706	Intermediate Similarity	NPC270654
0.7698	Intermediate Similarity	NPC472707
0.7692	Intermediate Similarity	NPC17693
0.7692	Intermediate Similarity	NPC232888
0.7692	Intermediate Similarity	NPC474097
0.7692	Intermediate Similarity	NPC13784
0.7692	Intermediate Similarity	NPC477367
0.7686	Intermediate Similarity	NPC202015
0.7686	Intermediate Similarity	NPC472708
0.768	Intermediate Similarity	NPC121272
0.768	Intermediate Similarity	NPC476599
0.768	Intermediate Similarity	NPC49938
0.7679	Intermediate Similarity	NPC91820
0.7679	Intermediate Similarity	NPC82426
0.7674	Intermediate Similarity	NPC477364
0.767	Intermediate Similarity	NPC294134
0.767	Intermediate Similarity	NPC58616
0.7669	Intermediate Similarity	NPC471602
0.7669	Intermediate Similarity	NPC29771
0.7669	Intermediate Similarity	NPC256463
0.7669	Intermediate Similarity	NPC306835
0.7669	Intermediate Similarity	NPC216312
0.7669	Intermediate Similarity	NPC111422
0.7669	Intermediate Similarity	NPC476477
0.7669	Intermediate Similarity	NPC299405
0.7667	Intermediate Similarity	NPC469574
0.7667	Intermediate Similarity	NPC45794
0.7661	Intermediate Similarity	NPC12881
0.7661	Intermediate Similarity	NPC140118
0.7661	Intermediate Similarity	NPC85511
0.7658	Intermediate Similarity	NPC473325
0.7652	Intermediate Similarity	NPC469511
0.7652	Intermediate Similarity	NPC281604
0.7647	Intermediate Similarity	NPC135730
0.7638	Intermediate Similarity	NPC2596
0.7638	Intermediate Similarity	NPC473744
0.7636	Intermediate Similarity	NPC175852
0.7636	Intermediate Similarity	NPC210529
0.7636	Intermediate Similarity	NPC160548
0.7634	Intermediate Similarity	NPC472374
0.7634	Intermediate Similarity	NPC472372
0.7632	Intermediate Similarity	NPC37115
0.7627	Intermediate Similarity	NPC196673
0.7627	Intermediate Similarity	NPC87069
0.7623	Intermediate Similarity	NPC233282
0.7619	Intermediate Similarity	NPC304760
0.7619	Intermediate Similarity	NPC51292
0.7615	Intermediate Similarity	NPC203486
0.7615	Intermediate Similarity	NPC38420
0.7615	Intermediate Similarity	NPC311492

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 NPC321852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	805
0.2-0.3	1379
0.3-0.4	2647
0.4-0.5	2401
0.5-0.6	1238
0.6-0.7	415
0.7-0.8	65
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9519	High Similarity	NPD2182	Approved
0.932	High Similarity	NPD164	Approved
0.8807	High Similarity	NPD2181	Clinical (unspecified phase)
0.8396	Intermediate Similarity	NPD1238	Approved
0.8155	Intermediate Similarity	NPD9256	Approved
0.8155	Intermediate Similarity	NPD9258	Approved
0.8125	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD9545	Approved
0.7863	Intermediate Similarity	NPD5951	Approved
0.7863	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD9259	Approved
0.7767	Intermediate Similarity	NPD9257	Approved
0.7759	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD1202	Approved
0.7731	Intermediate Similarity	NPD9493	Approved
0.7717	Intermediate Similarity	NPD7008	Discontinued
0.7679	Intermediate Similarity	NPD6647	Phase 2
0.7642	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD9495	Approved
0.7611	Intermediate Similarity	NPD1237	Approved
0.7586	Intermediate Similarity	NPD2067	Discontinued
0.7519	Intermediate Similarity	NPD3764	Approved
0.748	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1090	Approved
0.7477	Intermediate Similarity	NPD1089	Approved
0.7477	Intermediate Similarity	NPD1086	Approved
0.7476	Intermediate Similarity	NPD9491	Approved
0.7456	Intermediate Similarity	NPD5909	Discontinued
0.744	Intermediate Similarity	NPD9717	Approved
0.7411	Intermediate Similarity	NPD2066	Phase 3
0.7395	Intermediate Similarity	NPD5277	Phase 2
0.7383	Intermediate Similarity	NPD800	Approved
0.7368	Intermediate Similarity	NPD1929	Approved
0.7368	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1930	Approved
0.736	Intermediate Similarity	NPD6287	Discontinued
0.7339	Intermediate Similarity	NPD1088	Approved
0.7339	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1989	Approved
0.7281	Intermediate Similarity	NPD1932	Approved
0.7273	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2629	Approved
0.7244	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD230	Phase 1
0.7207	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9260	Approved
0.7207	Intermediate Similarity	NPD1693	Approved
0.7206	Intermediate Similarity	NPD2346	Discontinued
0.7206	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1087	Approved
0.7167	Intermediate Similarity	NPD9508	Approved
0.7156	Intermediate Similarity	NPD3673	Approved
0.7156	Intermediate Similarity	NPD3672	Approved
0.7154	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1317	Discontinued
0.7132	Intermediate Similarity	NPD1203	Approved
0.7121	Intermediate Similarity	NPD2313	Discontinued
0.7119	Intermediate Similarity	NPD9267	Approved
0.7119	Intermediate Similarity	NPD9264	Approved
0.7119	Intermediate Similarity	NPD9263	Approved
0.7119	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD226	Approved
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7091	Intermediate Similarity	NPD1239	Approved
0.709	Intermediate Similarity	NPD447	Suspended
0.7087	Intermediate Similarity	NPD9490	Approved
0.7083	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1019	Discontinued
0.7077	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6085	Phase 2
0.7073	Intermediate Similarity	NPD4198	Discontinued
0.7071	Intermediate Similarity	NPD7236	Approved
0.7069	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1104	Approved
0.7063	Intermediate Similarity	NPD5305	Approved
0.7063	Intermediate Similarity	NPD5306	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD2329	Discontinued
0.7059	Intermediate Similarity	NPD9266	Approved
0.7054	Intermediate Similarity	NPD2198	Approved
0.7054	Intermediate Similarity	NPD2199	Approved
0.705	Intermediate Similarity	NPD4628	Phase 3
0.7049	Intermediate Similarity	NPD1241	Discontinued
0.7037	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD969	Suspended
0.7014	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4135	Approved
0.7008	Intermediate Similarity	NPD4106	Approved
0.7008	Intermediate Similarity	NPD4136	Approved
0.7007	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD2797	Approved
0.6981	Remote Similarity	NPD3971	Phase 1
0.6978	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1358	Approved
0.6953	Remote Similarity	NPD4807	Approved
0.6953	Remote Similarity	NPD4806	Approved
0.693	Remote Similarity	NPD1565	Approved
0.693	Remote Similarity	NPD1564	Approved
0.693	Remote Similarity	NPD1566	Phase 3
0.6929	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6909	Remote Similarity	NPD689	Discontinued
0.6909	Remote Similarity	NPD5347	Phase 2
0.6909	Remote Similarity	NPD5346	Phase 2
0.6906	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1894	Discontinued
0.6899	Remote Similarity	NPD1481	Phase 2
0.6899	Remote Similarity	NPD4878	Approved
0.6897	Remote Similarity	NPD3226	Approved
0.6891	Remote Similarity	NPD3134	Approved
0.6881	Remote Similarity	NPD650	Approved
0.6881	Remote Similarity	NPD4793	Discontinued
0.688	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3496	Discontinued
0.687	Remote Similarity	NPD1470	Approved
0.687	Remote Similarity	NPD553	Approved
0.687	Remote Similarity	NPD552	Approved
0.687	Remote Similarity	NPD9567	Approved
0.6866	Remote Similarity	NPD411	Approved
0.6866	Remote Similarity	NPD3268	Approved
0.6855	Remote Similarity	NPD9281	Approved
0.6853	Remote Similarity	NPD2533	Approved
0.6853	Remote Similarity	NPD2532	Approved
0.6853	Remote Similarity	NPD2534	Approved
0.685	Remote Similarity	NPD4102	Approved
0.685	Remote Similarity	NPD4105	Approved
0.6831	Remote Similarity	NPD7440	Discontinued
0.6828	Remote Similarity	NPD7239	Suspended
0.6827	Remote Similarity	NPD225	Approved
0.6827	Remote Similarity	NPD227	Approved
0.6825	Remote Similarity	NPD2347	Approved
0.6822	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD5647	Approved
0.6818	Remote Similarity	NPD2798	Approved
0.6815	Remote Similarity	NPD7961	Discontinued
0.6812	Remote Similarity	NPD4308	Phase 3
0.6809	Remote Similarity	NPD3750	Approved
0.6807	Remote Similarity	NPD5048	Discontinued
0.6806	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD4626	Approved
0.6786	Remote Similarity	NPD7609	Phase 3
0.6781	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9261	Approved
0.6774	Remote Similarity	NPD2652	Approved
0.6774	Remote Similarity	NPD2650	Approved
0.6769	Remote Similarity	NPD1608	Approved
0.6769	Remote Similarity	NPD3972	Approved
0.6769	Remote Similarity	NPD6637	Approved
0.6767	Remote Similarity	NPD9494	Approved
0.6765	Remote Similarity	NPD3373	Approved
0.6765	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2979	Phase 3
0.6763	Remote Similarity	NPD1551	Phase 2
0.675	Remote Similarity	NPD6685	Approved
0.6739	Remote Similarity	NPD2567	Approved
0.6739	Remote Similarity	NPD2569	Approved
0.6731	Remote Similarity	NPD9294	Approved
0.6727	Remote Similarity	NPD1282	Approved
0.6726	Remote Similarity	NPD7631	Approved
0.6724	Remote Similarity	NPD5926	Approved
0.6719	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5691	Approved
0.6718	Remote Similarity	NPD5157	Phase 1
0.6718	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5159	Phase 2
0.6715	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9716	Approved
0.6692	Remote Similarity	NPD1281	Approved
0.6692	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD520	Approved
0.6691	Remote Similarity	NPD6233	Phase 2
0.669	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD1563	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD5667	Approved
0.6643	Remote Similarity	NPD4476	Approved
0.6643	Remote Similarity	NPD4477	Approved
0.6642	Remote Similarity	NPD3662	Phase 3
0.6642	Remote Similarity	NPD3663	Approved
0.6642	Remote Similarity	NPD3664	Approved
0.6642	Remote Similarity	NPD5204	Approved
0.6642	Remote Similarity	NPD3661	Approved
0.6641	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6010	Discontinued
0.6618	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6798	Discontinued
0.6617	Remote Similarity	NPD2159	Approved
0.6617	Remote Similarity	NPD6362	Approved
0.6617	Remote Similarity	NPD2625	Approved
0.6617	Remote Similarity	NPD2626	Approved
0.6617	Remote Similarity	NPD1164	Approved
0.6617	Remote Similarity	NPD2627	Approved
0.6617	Remote Similarity	NPD2160	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