NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	1.771
LogD:	1.702
LogS:	-1.419
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	1.808
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:	-4.488
MDCK Permeability:	2.127723564626649e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.649
Plasma Protein Binding (PPB):	74.20914459228516%
Volume Distribution (VD):	0.933
Pgp-substrate:	25.898048400878906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.701
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	11.676
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.386
Skin Sensitization:	0.347
Carcinogencity:	0.556
Eye Corrosion:	0.932
Eye Irritation:	0.994
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC231717

Natural Product ID:	NPC231717
*Common Name:**	1-(4-Hydroxy-2-Methylphenyl)Ethanone
IUPAC Name:	1-(4-hydroxy-2-methylphenyl)ethanone
Synonyms:
Standard InCHIKey:	IAMNVCJECQWBLZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O2/c1-6-5-8(11)3-4-9(6)7(2)10/h3-5,11H,1-2H3
SMILES:	Oc1ccc(c(c1)C)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL47807
PubChem CID:	70133
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21348469]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3735324]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	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

Activity Type	# Activity
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5340	Protein Family	Inosine-5'-monophosphate dehydrogenase (IMPDH)	Homo sapiens	IC50	=	620000.0	nM	PMID[567554]

☑ 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 NPC231717 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	311
0.1-0.2	1931
0.2-0.3	4629
0.3-0.4	12102
0.4-0.5	6372
0.5-0.6	7568
0.6-0.7	7670
0.7-0.8	1882
0.8-0.85	194
0.85-0.9	28
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC6984
0.9333	High Similarity	NPC226699
0.9159	High Similarity	NPC95172
0.9151	High Similarity	NPC34715
0.9065	High Similarity	NPC17525
0.9035	High Similarity	NPC190971
0.9018	High Similarity	NPC150919
0.8957	High Similarity	NPC120545
0.8899	High Similarity	NPC116842
0.8879	High Similarity	NPC282577
0.8879	High Similarity	NPC91478
0.8839	High Similarity	NPC322197
0.8829	High Similarity	NPC11824
0.8829	High Similarity	NPC242136
0.8818	High Similarity	NPC212718
0.8818	High Similarity	NPC114682
0.8818	High Similarity	NPC268388
0.8761	High Similarity	NPC477453
0.8667	High Similarity	NPC280869
0.8655	High Similarity	NPC123506
0.8621	High Similarity	NPC285829
0.8621	High Similarity	NPC206778
0.8611	High Similarity	NPC219913
0.8596	High Similarity	NPC108288
0.8595	High Similarity	NPC96024
0.8583	High Similarity	NPC15837
0.8583	High Similarity	NPC254492
0.8571	High Similarity	NPC199273
0.8571	High Similarity	NPC260000
0.8547	High Similarity	NPC248363
0.8545	High Similarity	NPC224584
0.8534	High Similarity	NPC473767
0.8522	High Similarity	NPC125252
0.8512	High Similarity	NPC69424
0.8512	High Similarity	NPC84672
0.8512	High Similarity	NPC72667
0.8512	High Similarity	NPC176130
0.8512	High Similarity	NPC78364
0.8509	High Similarity	NPC161304
0.8509	High Similarity	NPC240163
0.85	High Similarity	NPC477454
0.8455	Intermediate Similarity	NPC141523
0.8455	Intermediate Similarity	NPC117609
0.8455	Intermediate Similarity	NPC29883
0.8443	Intermediate Similarity	NPC234175
0.8443	Intermediate Similarity	NPC95537
0.844	Intermediate Similarity	NPC163734
0.843	Intermediate Similarity	NPC473691
0.8417	Intermediate Similarity	NPC310540
0.8403	Intermediate Similarity	NPC307174
0.8403	Intermediate Similarity	NPC217756
0.8403	Intermediate Similarity	NPC164947
0.8376	Intermediate Similarity	NPC161617
0.8374	Intermediate Similarity	NPC171460
0.8374	Intermediate Similarity	NPC276238
0.8374	Intermediate Similarity	NPC92624
0.8365	Intermediate Similarity	NPC181709
0.8364	Intermediate Similarity	NPC69332
0.8364	Intermediate Similarity	NPC317592
0.8364	Intermediate Similarity	NPC95178
0.8364	Intermediate Similarity	NPC184658
0.8364	Intermediate Similarity	NPC187913
0.8364	Intermediate Similarity	NPC29989
0.8362	Intermediate Similarity	NPC269414
0.8361	Intermediate Similarity	NPC324209
0.8348	Intermediate Similarity	NPC278102
0.8347	Intermediate Similarity	NPC262671
0.8347	Intermediate Similarity	NPC201728
0.8333	Intermediate Similarity	NPC273683
0.832	Intermediate Similarity	NPC477407
0.8319	Intermediate Similarity	NPC198336
0.8306	Intermediate Similarity	NPC27659
0.8306	Intermediate Similarity	NPC259942
0.8306	Intermediate Similarity	NPC108129
0.8305	Intermediate Similarity	NPC216297
0.8305	Intermediate Similarity	NPC473662
0.8305	Intermediate Similarity	NPC7151
0.8293	Intermediate Similarity	NPC3009
0.8293	Intermediate Similarity	NPC41263
0.8291	Intermediate Similarity	NPC41567
0.8291	Intermediate Similarity	NPC249435
0.8291	Intermediate Similarity	NPC474890
0.8291	Intermediate Similarity	NPC161943
0.8291	Intermediate Similarity	NPC273282
0.8279	Intermediate Similarity	NPC231774
0.8279	Intermediate Similarity	NPC51037
0.8279	Intermediate Similarity	NPC160499
0.8276	Intermediate Similarity	NPC131192
0.8264	Intermediate Similarity	NPC13238
0.8261	Intermediate Similarity	NPC81808
0.825	Intermediate Similarity	NPC283514
0.825	Intermediate Similarity	NPC139171
0.825	Intermediate Similarity	NPC300274
0.825	Intermediate Similarity	NPC46634
0.8241	Intermediate Similarity	NPC52472
0.824	Intermediate Similarity	NPC471851
0.824	Intermediate Similarity	NPC93015
0.8235	Intermediate Similarity	NPC216216
0.8235	Intermediate Similarity	NPC272454
0.8235	Intermediate Similarity	NPC301987
0.8235	Intermediate Similarity	NPC292665
0.8235	Intermediate Similarity	NPC35856
0.8235	Intermediate Similarity	NPC115188
0.8235	Intermediate Similarity	NPC26433
0.8235	Intermediate Similarity	NPC159760
0.8235	Intermediate Similarity	NPC244994
0.8235	Intermediate Similarity	NPC222876
0.8235	Intermediate Similarity	NPC179092
0.8235	Intermediate Similarity	NPC178395
0.823	Intermediate Similarity	NPC183648
0.8226	Intermediate Similarity	NPC303910
0.8226	Intermediate Similarity	NPC99731
0.822	Intermediate Similarity	NPC184579
0.822	Intermediate Similarity	NPC232178
0.822	Intermediate Similarity	NPC158222
0.822	Intermediate Similarity	NPC233165
0.8211	Intermediate Similarity	NPC473787
0.8211	Intermediate Similarity	NPC32163
0.8211	Intermediate Similarity	NPC16651
0.8205	Intermediate Similarity	NPC174087
0.8205	Intermediate Similarity	NPC160199
0.8198	Intermediate Similarity	NPC70843
0.8189	Intermediate Similarity	NPC282780
0.8189	Intermediate Similarity	NPC166480
0.8189	Intermediate Similarity	NPC50924
0.8182	Intermediate Similarity	NPC79672
0.8182	Intermediate Similarity	NPC375356
0.8167	Intermediate Similarity	NPC295034
0.8165	Intermediate Similarity	NPC472585
0.816	Intermediate Similarity	NPC247477
0.816	Intermediate Similarity	NPC17840
0.8158	Intermediate Similarity	NPC23332
0.8151	Intermediate Similarity	NPC159525
0.8148	Intermediate Similarity	NPC245561
0.8145	Intermediate Similarity	NPC237225
0.8145	Intermediate Similarity	NPC165257
0.8145	Intermediate Similarity	NPC179898
0.8145	Intermediate Similarity	NPC247250
0.8145	Intermediate Similarity	NPC767
0.8142	Intermediate Similarity	NPC88141
0.8136	Intermediate Similarity	NPC94298
0.8136	Intermediate Similarity	NPC209486
0.8136	Intermediate Similarity	NPC328694
0.8136	Intermediate Similarity	NPC40649
0.8136	Intermediate Similarity	NPC27633
0.813	Intermediate Similarity	NPC8745
0.813	Intermediate Similarity	NPC306765
0.813	Intermediate Similarity	NPC3224
0.8125	Intermediate Similarity	NPC228737
0.812	Intermediate Similarity	NPC28951
0.812	Intermediate Similarity	NPC83718
0.812	Intermediate Similarity	NPC325646
0.812	Intermediate Similarity	NPC61062
0.812	Intermediate Similarity	NPC277394
0.812	Intermediate Similarity	NPC299252
0.8115	Intermediate Similarity	NPC474766
0.8115	Intermediate Similarity	NPC142956
0.8115	Intermediate Similarity	NPC74507
0.8115	Intermediate Similarity	NPC234890
0.8115	Intermediate Similarity	NPC164014
0.8115	Intermediate Similarity	NPC173978
0.811	Intermediate Similarity	NPC294226
0.811	Intermediate Similarity	NPC477139
0.811	Intermediate Similarity	NPC78307
0.811	Intermediate Similarity	NPC52407
0.8108	Intermediate Similarity	NPC13495
0.8099	Intermediate Similarity	NPC68167
0.8099	Intermediate Similarity	NPC309765
0.8095	Intermediate Similarity	NPC244699
0.8083	Intermediate Similarity	NPC236520
0.8083	Intermediate Similarity	NPC165197
0.8083	Intermediate Similarity	NPC297186
0.8083	Intermediate Similarity	NPC294361
0.8083	Intermediate Similarity	NPC146642
0.807	Intermediate Similarity	NPC222905
0.807	Intermediate Similarity	NPC21162
0.8067	Intermediate Similarity	NPC79933
0.8067	Intermediate Similarity	NPC31296
0.8067	Intermediate Similarity	NPC156654
0.8067	Intermediate Similarity	NPC473974
0.8067	Intermediate Similarity	NPC258366
0.8065	Intermediate Similarity	NPC107672
0.8065	Intermediate Similarity	NPC209959
0.8062	Intermediate Similarity	NPC38158
0.8056	Intermediate Similarity	NPC229242
0.8049	Intermediate Similarity	NPC10926
0.8049	Intermediate Similarity	NPC103540
0.8047	Intermediate Similarity	NPC202225
0.8047	Intermediate Similarity	NPC44437
0.8037	Intermediate Similarity	NPC257182
0.8034	Intermediate Similarity	NPC4665
0.8033	Intermediate Similarity	NPC275145
0.8033	Intermediate Similarity	NPC174991
0.8033	Intermediate Similarity	NPC135062
0.8018	Intermediate Similarity	NPC52087
0.8018	Intermediate Similarity	NPC120693
0.8018	Intermediate Similarity	NPC261573
0.8018	Intermediate Similarity	NPC8931
0.8017	Intermediate Similarity	NPC73532
0.8017	Intermediate Similarity	NPC156139

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 NPC231717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1003
0.2-0.3	1358
0.3-0.4	2829
0.4-0.5	2015
0.5-0.6	1163
0.6-0.7	377
0.7-0.8	66
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD405	Clinical (unspecified phase)
0.8455	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD1201	Approved
0.8136	Intermediate Similarity	NPD9545	Approved
0.8049	Intermediate Similarity	NPD1470	Approved
0.8	Intermediate Similarity	NPD2932	Approved
0.8	Intermediate Similarity	NPD3019	Approved
0.7923	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD9494	Approved
0.7752	Intermediate Similarity	NPD943	Approved
0.7739	Intermediate Similarity	NPD9266	Approved
0.7739	Intermediate Similarity	NPD74	Approved
0.7667	Intermediate Similarity	NPD9493	Approved
0.7661	Intermediate Similarity	NPD9269	Phase 2
0.7652	Intermediate Similarity	NPD9264	Approved
0.7652	Intermediate Similarity	NPD9267	Approved
0.7652	Intermediate Similarity	NPD9263	Approved
0.7623	Intermediate Similarity	NPD9268	Approved
0.7619	Intermediate Similarity	NPD1164	Approved
0.7615	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1755	Approved
0.7597	Intermediate Similarity	NPD3764	Approved
0.7596	Intermediate Similarity	NPD111	Approved
0.754	Intermediate Similarity	NPD1876	Approved
0.752	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD3020	Approved
0.7481	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1240	Approved
0.7477	Intermediate Similarity	NPD288	Approved
0.7455	Intermediate Similarity	NPD2934	Approved
0.7455	Intermediate Similarity	NPD2933	Approved
0.7434	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7407	Intermediate Similarity	NPD9256	Approved
0.7407	Intermediate Similarity	NPD9258	Approved
0.7402	Intermediate Similarity	NPD1283	Approved
0.7395	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1237	Approved
0.7387	Intermediate Similarity	NPD2859	Approved
0.7387	Intermediate Similarity	NPD2860	Approved
0.7387	Intermediate Similarity	NPD844	Approved
0.7368	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD3023	Approved
0.736	Intermediate Similarity	NPD3026	Approved
0.7339	Intermediate Similarity	NPD3024	Approved
0.7339	Intermediate Similarity	NPD3025	Approved
0.7339	Intermediate Similarity	NPD1651	Approved
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.7304	Intermediate Similarity	NPD9261	Approved
0.7295	Intermediate Similarity	NPD256	Approved
0.7295	Intermediate Similarity	NPD255	Approved
0.7281	Intermediate Similarity	NPD1242	Phase 1
0.7259	Intermediate Similarity	NPD1510	Phase 2
0.7244	Intermediate Similarity	NPD1608	Approved
0.7227	Intermediate Similarity	NPD3021	Approved
0.7227	Intermediate Similarity	NPD3022	Approved
0.7213	Intermediate Similarity	NPD5951	Approved
0.7213	Intermediate Similarity	NPD9281	Approved
0.7206	Intermediate Similarity	NPD2935	Discontinued
0.7194	Intermediate Similarity	NPD2309	Approved
0.7188	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1281	Approved
0.7155	Intermediate Similarity	NPD1929	Approved
0.7155	Intermediate Similarity	NPD1930	Approved
0.7155	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4626	Approved
0.7122	Intermediate Similarity	NPD3750	Approved
0.7109	Intermediate Similarity	NPD9717	Approved
0.7099	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD9568	Approved
0.7094	Intermediate Similarity	NPD164	Approved
0.708	Intermediate Similarity	NPD1809	Phase 2
0.7069	Intermediate Similarity	NPD940	Approved
0.7069	Intermediate Similarity	NPD846	Approved
0.7054	Intermediate Similarity	NPD845	Approved
0.7037	Intermediate Similarity	NPD9257	Approved
0.7037	Intermediate Similarity	NPD9259	Approved
0.7029	Intermediate Similarity	NPD2346	Discontinued
0.7023	Intermediate Similarity	NPD257	Approved
0.7023	Intermediate Similarity	NPD258	Approved
0.7021	Intermediate Similarity	NPD3300	Phase 2
0.7008	Intermediate Similarity	NPD17	Approved
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD4628	Phase 3
0.6984	Remote Similarity	NPD3091	Approved
0.6978	Remote Similarity	NPD1549	Phase 2
0.6977	Remote Similarity	NPD4878	Approved
0.6975	Remote Similarity	NPD1445	Approved
0.6975	Remote Similarity	NPD1444	Approved
0.6972	Remote Similarity	NPD650	Approved
0.6972	Remote Similarity	NPD1511	Approved
0.6967	Remote Similarity	NPD228	Approved
0.6947	Remote Similarity	NPD1203	Approved
0.6942	Remote Similarity	NPD1792	Phase 2
0.694	Remote Similarity	NPD411	Approved
0.6929	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2342	Discontinued
0.6912	Remote Similarity	NPD447	Suspended
0.6911	Remote Similarity	NPD7635	Approved
0.6906	Remote Similarity	NPD1471	Phase 3
0.6906	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5536	Phase 2
0.6903	Remote Similarity	NPD1202	Approved
0.6897	Remote Similarity	NPD2066	Phase 3
0.6892	Remote Similarity	NPD7819	Suspended
0.6885	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4059	Approved
0.6875	Remote Similarity	NPD1512	Approved
0.686	Remote Similarity	NPD2182	Approved
0.6849	Remote Similarity	NPD3226	Approved
0.6846	Remote Similarity	NPD1481	Phase 2
0.6842	Remote Similarity	NPD9569	Approved
0.6838	Remote Similarity	NPD3140	Approved
0.6838	Remote Similarity	NPD3142	Approved
0.681	Remote Similarity	NPD9495	Approved
0.6807	Remote Similarity	NPD9610	Approved
0.6807	Remote Similarity	NPD9608	Approved
0.6806	Remote Similarity	NPD2532	Approved
0.6806	Remote Similarity	NPD2534	Approved
0.6806	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2533	Approved
0.6803	Remote Similarity	NPD4750	Phase 3
0.68	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4093	Discontinued
0.6797	Remote Similarity	NPD5691	Approved
0.678	Remote Similarity	NPD1932	Approved
0.6774	Remote Similarity	NPD9379	Approved
0.6774	Remote Similarity	NPD9377	Approved
0.6769	Remote Similarity	NPD3092	Approved
0.6769	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1535	Discovery
0.6765	Remote Similarity	NPD259	Phase 1
0.6763	Remote Similarity	NPD3748	Approved
0.6759	Remote Similarity	NPD9491	Approved
0.6748	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2286	Discontinued
0.6744	Remote Similarity	NPD1751	Approved
0.6735	Remote Similarity	NPD7458	Discontinued
0.6735	Remote Similarity	NPD824	Approved
0.6726	Remote Similarity	NPD7609	Phase 3
0.6723	Remote Similarity	NPD9500	Approved
0.672	Remote Similarity	NPD2229	Approved
0.672	Remote Similarity	NPD2228	Approved
0.672	Remote Similarity	NPD2234	Approved
0.6719	Remote Similarity	NPD1759	Phase 1
0.6715	Remote Similarity	NPD826	Approved
0.6715	Remote Similarity	NPD825	Approved
0.6714	Remote Similarity	NPD6099	Approved
0.6714	Remote Similarity	NPD2796	Approved
0.6714	Remote Similarity	NPD6100	Approved
0.6713	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD1934	Approved
0.6696	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1693	Approved
0.6694	Remote Similarity	NPD3134	Approved
0.6694	Remote Similarity	NPD9508	Approved
0.6692	Remote Similarity	NPD2797	Approved
0.6691	Remote Similarity	NPD2313	Discontinued
0.6691	Remote Similarity	NPD3268	Approved
0.669	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD275	Approved
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD555	Phase 2
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD274	Approved
0.6645	Remote Similarity	NPD3749	Approved
0.6643	Remote Similarity	NPD4308	Phase 3
0.6643	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD8032	Phase 2
0.6642	Remote Similarity	NPD520	Approved
0.6641	Remote Similarity	NPD1758	Phase 1
0.664	Remote Similarity	NPD5277	Phase 2
0.6639	Remote Similarity	NPD1358	Approved
0.6637	Remote Similarity	NPD1090	Approved
0.6637	Remote Similarity	NPD1089	Approved
0.6637	Remote Similarity	NPD1086	Approved
0.6623	Remote Similarity	NPD2296	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