NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.08
Volume:	179.994
LogP:	2.41
LogD:	2.284
LogS:	-2.738
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	1.391
Fsp3:	0.3
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:	-4.462
MDCK Permeability:	2.3012371457298286e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.563

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	82.3936538696289%
Volume Distribution (VD):	0.533
Pgp-substrate:	11.72799015045166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.848
CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.368
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.257
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	8.662
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.503
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.181
Carcinogencity:	0.567
Eye Corrosion:	0.08
Eye Irritation:	0.952
Respiratory Toxicity:	0.299

Download Data

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

Natural Product: NPC23332

Natural Product ID:	NPC23332
*Common Name:**	1-(4-Methoxyphenyl)Propan-1-One
IUPAC Name:	1-(4-methoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	ZJVAWPKTWVFKHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O2/c1-3-10(11)8-4-6-9(12-2)7-5-8/h4-7H,3H2,1-2H3
SMILES:	CCC(=O)c1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444556
PubChem CID:	67144
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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	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

☑ 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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	>	50.0	ug.mL-1	PMID[465779]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[465779]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	50.0	ug.mL-1	PMID[465779]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	50.0	ug.mL-1	PMID[465779]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	>	50.0	ug.mL-1	PMID[465779]

☑ 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 NPC23332 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	315
0.1-0.2	2210
0.2-0.3	5173
0.3-0.4	11424
0.4-0.5	5744
0.5-0.6	6201
0.6-0.7	8714
0.7-0.8	2674
0.8-0.85	195
0.85-0.9	37
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC183648
0.945	High Similarity	NPC469954
0.9434	High Similarity	NPC57879
0.932	High Similarity	NPC38209
0.9266	High Similarity	NPC220540
0.9223	High Similarity	NPC298224
0.9182	High Similarity	NPC470860
0.9174	High Similarity	NPC252004
0.9115	High Similarity	NPC225245
0.8962	High Similarity	NPC1065
0.8938	High Similarity	NPC61779
0.8879	High Similarity	NPC141252
0.8879	High Similarity	NPC11799
0.8879	High Similarity	NPC474691
0.8835	High Similarity	NPC175298
0.8739	High Similarity	NPC279916
0.8739	High Similarity	NPC53953
0.8729	High Similarity	NPC65041
0.8729	High Similarity	NPC470858
0.8727	High Similarity	NPC54626
0.8716	High Similarity	NPC234639
0.8704	High Similarity	NPC226699
0.8684	High Similarity	NPC171023
0.8673	High Similarity	NPC19290
0.8655	High Similarity	NPC177925
0.8644	High Similarity	NPC30216
0.8632	High Similarity	NPC69403
0.8632	High Similarity	NPC291189
0.8621	High Similarity	NPC295317
0.8611	High Similarity	NPC6984
0.8584	High Similarity	NPC188907
0.8583	High Similarity	NPC293387
0.8583	High Similarity	NPC16651
0.8583	High Similarity	NPC32163
0.8583	High Similarity	NPC286683
0.8571	High Similarity	NPC11824
0.8545	High Similarity	NPC95172
0.8545	High Similarity	NPC259554
0.8522	High Similarity	NPC166591
0.8512	High Similarity	NPC186098
0.8512	High Similarity	NPC80694
0.8509	High Similarity	NPC131192
0.85	High Similarity	NPC237868
0.85	High Similarity	NPC474737
0.8491	Intermediate Similarity	NPC13755
0.8487	Intermediate Similarity	NPC255073
0.8487	Intermediate Similarity	NPC221798
0.8448	Intermediate Similarity	NPC201284
0.8443	Intermediate Similarity	NPC66246
0.8443	Intermediate Similarity	NPC211120
0.8443	Intermediate Similarity	NPC939
0.8443	Intermediate Similarity	NPC170546
0.8435	Intermediate Similarity	NPC240664
0.8435	Intermediate Similarity	NPC45104
0.8435	Intermediate Similarity	NPC217423
0.8417	Intermediate Similarity	NPC165556
0.8417	Intermediate Similarity	NPC2771
0.8407	Intermediate Similarity	NPC109241
0.8393	Intermediate Similarity	NPC212718
0.8393	Intermediate Similarity	NPC114682
0.8376	Intermediate Similarity	NPC470092
0.8374	Intermediate Similarity	NPC282230
0.8374	Intermediate Similarity	NPC247779
0.8374	Intermediate Similarity	NPC183348
0.8362	Intermediate Similarity	NPC293424
0.8362	Intermediate Similarity	NPC94298
0.8362	Intermediate Similarity	NPC32298
0.8362	Intermediate Similarity	NPC27633
0.8361	Intermediate Similarity	NPC2596
0.835	Intermediate Similarity	NPC321956
0.8347	Intermediate Similarity	NPC474264
0.8347	Intermediate Similarity	NPC154275
0.8347	Intermediate Similarity	NPC475236
0.8333	Intermediate Similarity	NPC179686
0.8306	Intermediate Similarity	NPC470977
0.8306	Intermediate Similarity	NPC125153
0.8306	Intermediate Similarity	NPC196979
0.8306	Intermediate Similarity	NPC15083
0.8306	Intermediate Similarity	NPC470976
0.8291	Intermediate Similarity	NPC35744
0.8291	Intermediate Similarity	NPC54243
0.8288	Intermediate Similarity	NPC17525
0.8279	Intermediate Similarity	NPC49852
0.8279	Intermediate Similarity	NPC37512
0.8279	Intermediate Similarity	NPC475496
0.8279	Intermediate Similarity	NPC121104
0.8279	Intermediate Similarity	NPC305518
0.8279	Intermediate Similarity	NPC128428
0.8279	Intermediate Similarity	NPC428300
0.8264	Intermediate Similarity	NPC473626
0.8261	Intermediate Similarity	NPC322358
0.8257	Intermediate Similarity	NPC2518
0.8252	Intermediate Similarity	NPC71853
0.825	Intermediate Similarity	NPC182646
0.8246	Intermediate Similarity	NPC242136
0.8241	Intermediate Similarity	NPC84325
0.824	Intermediate Similarity	NPC112192
0.824	Intermediate Similarity	NPC128348
0.824	Intermediate Similarity	NPC309717
0.824	Intermediate Similarity	NPC189106
0.824	Intermediate Similarity	NPC50763
0.824	Intermediate Similarity	NPC64359
0.824	Intermediate Similarity	NPC164236
0.824	Intermediate Similarity	NPC313618
0.824	Intermediate Similarity	NPC284424
0.824	Intermediate Similarity	NPC66384
0.824	Intermediate Similarity	NPC470859
0.824	Intermediate Similarity	NPC308037
0.824	Intermediate Similarity	NPC183103
0.824	Intermediate Similarity	NPC262359
0.824	Intermediate Similarity	NPC153453
0.8235	Intermediate Similarity	NPC314329
0.8226	Intermediate Similarity	NPC66905
0.8226	Intermediate Similarity	NPC245395
0.822	Intermediate Similarity	NPC230951
0.8211	Intermediate Similarity	NPC50583
0.8211	Intermediate Similarity	NPC473907
0.8211	Intermediate Similarity	NPC125887
0.8205	Intermediate Similarity	NPC206007
0.8205	Intermediate Similarity	NPC152159
0.819	Intermediate Similarity	NPC316062
0.8182	Intermediate Similarity	NPC56332
0.8182	Intermediate Similarity	NPC128730
0.8175	Intermediate Similarity	NPC87231
0.8175	Intermediate Similarity	NPC129132
0.8175	Intermediate Similarity	NPC182428
0.8175	Intermediate Similarity	NPC212631
0.8175	Intermediate Similarity	NPC205468
0.8175	Intermediate Similarity	NPC257756
0.8175	Intermediate Similarity	NPC229646
0.8174	Intermediate Similarity	NPC114144
0.8167	Intermediate Similarity	NPC114298
0.8167	Intermediate Similarity	NPC67300
0.816	Intermediate Similarity	NPC239134
0.816	Intermediate Similarity	NPC279596
0.816	Intermediate Similarity	NPC164295
0.8158	Intermediate Similarity	NPC231717
0.8155	Intermediate Similarity	NPC99886
0.8155	Intermediate Similarity	NPC8002
0.8155	Intermediate Similarity	NPC177844
0.8155	Intermediate Similarity	NPC259134
0.8145	Intermediate Similarity	NPC69235
0.8145	Intermediate Similarity	NPC78662
0.8145	Intermediate Similarity	NPC8005
0.8145	Intermediate Similarity	NPC60558
0.8145	Intermediate Similarity	NPC212379
0.8145	Intermediate Similarity	NPC473894
0.8142	Intermediate Similarity	NPC116842
0.8142	Intermediate Similarity	NPC473809
0.813	Intermediate Similarity	NPC203719
0.813	Intermediate Similarity	NPC117237
0.8115	Intermediate Similarity	NPC224657
0.811	Intermediate Similarity	NPC292998
0.811	Intermediate Similarity	NPC337373
0.811	Intermediate Similarity	NPC472365
0.811	Intermediate Similarity	NPC56031
0.811	Intermediate Similarity	NPC263670
0.811	Intermediate Similarity	NPC223354
0.811	Intermediate Similarity	NPC312318
0.811	Intermediate Similarity	NPC139813
0.811	Intermediate Similarity	NPC192304
0.811	Intermediate Similarity	NPC27643
0.811	Intermediate Similarity	NPC242294
0.811	Intermediate Similarity	NPC175098
0.811	Intermediate Similarity	NPC188646
0.8108	Intermediate Similarity	NPC176971
0.8108	Intermediate Similarity	NPC326447
0.8099	Intermediate Similarity	NPC257976
0.8099	Intermediate Similarity	NPC242372
0.8099	Intermediate Similarity	NPC164778
0.8099	Intermediate Similarity	NPC473942
0.8099	Intermediate Similarity	NPC4181
0.8099	Intermediate Similarity	NPC472888
0.8095	Intermediate Similarity	NPC278556
0.8091	Intermediate Similarity	NPC109637
0.808	Intermediate Similarity	NPC109778
0.808	Intermediate Similarity	NPC185497
0.808	Intermediate Similarity	NPC285776
0.808	Intermediate Similarity	NPC307732
0.808	Intermediate Similarity	NPC42292
0.807	Intermediate Similarity	NPC268388
0.807	Intermediate Similarity	NPC233238
0.8067	Intermediate Similarity	NPC246214
0.8065	Intermediate Similarity	NPC2401
0.8065	Intermediate Similarity	NPC475017
0.8056	Intermediate Similarity	NPC100870
0.8056	Intermediate Similarity	NPC280869
0.8047	Intermediate Similarity	NPC164136
0.8047	Intermediate Similarity	NPC89504
0.8047	Intermediate Similarity	NPC88065
0.8047	Intermediate Similarity	NPC286336
0.8047	Intermediate Similarity	NPC125269
0.8047	Intermediate Similarity	NPC139519
0.8047	Intermediate Similarity	NPC95485
0.8036	Intermediate Similarity	NPC34715
0.8036	Intermediate Similarity	NPC157473
0.8036	Intermediate Similarity	NPC151530
0.8033	Intermediate Similarity	NPC312404
0.8033	Intermediate Similarity	NPC107846
0.8033	Intermediate Similarity	NPC273686

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 NPC23332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	1051
0.2-0.3	1342
0.3-0.4	2614
0.4-0.5	1979
0.5-0.6	1215
0.6-0.7	503
0.7-0.8	111
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD1241	Discontinued
0.8957	High Similarity	NPD3972	Approved
0.8487	Intermediate Similarity	NPD1876	Approved
0.8362	Intermediate Similarity	NPD9545	Approved
0.824	Intermediate Similarity	NPD3142	Approved
0.824	Intermediate Similarity	NPD1240	Approved
0.824	Intermediate Similarity	NPD3140	Approved
0.8235	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD9494	Approved
0.811	Intermediate Similarity	NPD1607	Approved
0.8108	Intermediate Similarity	NPD3134	Approved
0.8036	Intermediate Similarity	NPD1358	Approved
0.7983	Intermediate Similarity	NPD1651	Approved
0.7923	Intermediate Similarity	NPD2796	Approved
0.7913	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD2798	Approved
0.7881	Intermediate Similarity	NPD9493	Approved
0.7876	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD9717	Approved
0.7846	Intermediate Similarity	NPD1510	Phase 2
0.7815	Intermediate Similarity	NPD5536	Phase 2
0.7787	Intermediate Similarity	NPD1281	Approved
0.7778	Intermediate Similarity	NPD6832	Phase 2
0.7769	Intermediate Similarity	NPD17	Approved
0.776	Intermediate Similarity	NPD1019	Discontinued
0.7744	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2344	Approved
0.7727	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2353	Approved
0.7669	Intermediate Similarity	NPD1549	Phase 2
0.7634	Intermediate Similarity	NPD743	Approved
0.763	Intermediate Similarity	NPD3887	Approved
0.7611	Intermediate Similarity	NPD164	Approved
0.7603	Intermediate Similarity	NPD1894	Discontinued
0.76	Intermediate Similarity	NPD1283	Approved
0.7594	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1608	Approved
0.7576	Intermediate Similarity	NPD2799	Discontinued
0.7568	Intermediate Similarity	NPD1238	Approved
0.7556	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD9697	Approved
0.7541	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1203	Approved
0.754	Intermediate Similarity	NPD3266	Approved
0.754	Intermediate Similarity	NPD3267	Approved
0.7522	Intermediate Similarity	NPD9261	Approved
0.7519	Intermediate Similarity	NPD2935	Discontinued
0.7518	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.7481	Intermediate Similarity	NPD1243	Approved
0.7481	Intermediate Similarity	NPD2654	Approved
0.7463	Intermediate Similarity	NPD1471	Phase 3
0.7444	Intermediate Similarity	NPD3748	Approved
0.744	Intermediate Similarity	NPD1481	Phase 2
0.7436	Intermediate Similarity	NPD5451	Approved
0.7419	Intermediate Similarity	NPD3847	Discontinued
0.7407	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4307	Phase 2
0.7398	Intermediate Similarity	NPD5691	Approved
0.7395	Intermediate Similarity	NPD5535	Approved
0.7385	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2313	Discontinued
0.7381	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1535	Discovery
0.7357	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2182	Approved
0.7348	Intermediate Similarity	NPD1933	Approved
0.7348	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4626	Approved
0.7338	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD196	Phase 1
0.7319	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD228	Approved
0.7305	Intermediate Similarity	NPD957	Approved
0.7299	Intermediate Similarity	NPD7003	Approved
0.7287	Intermediate Similarity	NPD454	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7265	Intermediate Similarity	NPD9267	Approved
0.7265	Intermediate Similarity	NPD9264	Approved
0.7265	Intermediate Similarity	NPD9263	Approved
0.7264	Intermediate Similarity	NPD9259	Approved
0.7264	Intermediate Similarity	NPD9257	Approved
0.7254	Intermediate Similarity	NPD7458	Discontinued
0.7252	Intermediate Similarity	NPD3268	Approved
0.7252	Intermediate Similarity	NPD411	Approved
0.725	Intermediate Similarity	NPD821	Approved
0.725	Intermediate Similarity	NPD7843	Approved
0.7234	Intermediate Similarity	NPD920	Approved
0.7218	Intermediate Similarity	NPD230	Phase 1
0.7218	Intermediate Similarity	NPD447	Suspended
0.7214	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6599	Discontinued
0.7203	Intermediate Similarity	NPD9266	Approved
0.7203	Intermediate Similarity	NPD74	Approved
0.72	Intermediate Similarity	NPD1778	Approved
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7185	Intermediate Similarity	NPD4308	Phase 3
0.7174	Intermediate Similarity	NPD3750	Approved
0.7174	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2186	Approved
0.7155	Intermediate Similarity	NPD1237	Approved
0.7154	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7411	Suspended
0.7153	Intermediate Similarity	NPD958	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD1511	Approved
0.7131	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3764	Approved
0.7121	Intermediate Similarity	NPD6798	Discontinued
0.7121	Intermediate Similarity	NPD1296	Phase 2
0.712	Intermediate Similarity	NPD5585	Approved
0.7119	Intermediate Similarity	NPD290	Approved
0.7117	Intermediate Similarity	NPD1202	Approved
0.7113	Intermediate Similarity	NPD1670	Discontinued
0.7103	Intermediate Similarity	NPD6280	Approved
0.7103	Intermediate Similarity	NPD7577	Discontinued
0.7103	Intermediate Similarity	NPD6279	Approved
0.7087	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD4380	Phase 2
0.708	Intermediate Similarity	NPD2346	Discontinued
0.7073	Intermediate Similarity	NPD7157	Approved
0.7071	Intermediate Similarity	NPD7440	Discontinued
0.7068	Intermediate Similarity	NPD6233	Phase 2
0.7068	Intermediate Similarity	NPD8032	Phase 2
0.7068	Intermediate Similarity	NPD4062	Phase 3
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1512	Approved
0.7042	Intermediate Similarity	NPD6273	Approved
0.7037	Intermediate Similarity	NPD6651	Approved
0.7034	Intermediate Similarity	NPD6386	Approved
0.7034	Intermediate Similarity	NPD6385	Approved
0.7034	Intermediate Similarity	NPD968	Approved
0.7021	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3496	Discontinued
0.7007	Intermediate Similarity	NPD5978	Approved
0.7007	Intermediate Similarity	NPD1551	Phase 2
0.7007	Intermediate Similarity	NPD5977	Approved
0.7	Intermediate Similarity	NPD9258	Approved
0.7	Intermediate Similarity	NPD9256	Approved
0.6986	Remote Similarity	NPD1934	Approved
0.6986	Remote Similarity	NPD6801	Discontinued
0.6972	Remote Similarity	NPD4662	Approved
0.6972	Remote Similarity	NPD4661	Approved
0.697	Remote Similarity	NPD2614	Approved
0.6963	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD3882	Suspended
0.6939	Remote Similarity	NPD2801	Approved
0.6939	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3225	Approved
0.6923	Remote Similarity	NPD5049	Phase 3
0.6913	Remote Similarity	NPD7075	Discontinued
0.6903	Remote Similarity	NPD2934	Approved
0.6903	Remote Similarity	NPD2933	Approved
0.6897	Remote Similarity	NPD824	Approved
0.6892	Remote Similarity	NPD2296	Approved
0.6892	Remote Similarity	NPD3817	Phase 2
0.6892	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD943	Approved
0.6885	Remote Similarity	NPD1139	Approved
0.6885	Remote Similarity	NPD1137	Approved
0.6884	Remote Similarity	NPD2438	Suspended
0.6884	Remote Similarity	NPD4476	Approved
0.6884	Remote Similarity	NPD2531	Phase 2
0.6884	Remote Similarity	NPD4477	Approved
0.688	Remote Similarity	NPD3596	Phase 2
0.6879	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3869	Phase 3
0.6875	Remote Similarity	NPD3873	Phase 3
0.687	Remote Similarity	NPD1164	Approved
0.6867	Remote Similarity	NPD919	Approved
0.6867	Remote Similarity	NPD6862	Phase 2
0.6857	Remote Similarity	NPD2800	Approved
0.6855	Remote Similarity	NPD9281	Approved
0.6853	Remote Similarity	NPD5401	Approved
0.6852	Remote Similarity	NPD111	Approved
0.685	Remote Similarity	NPD9268	Approved
0.6849	Remote Similarity	NPD2592	Discontinued
0.6846	Remote Similarity	NPD4359	Approved
0.6842	Remote Similarity	NPD2860	Approved
0.6842	Remote Similarity	NPD2859	Approved
0.6842	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4622	Approved
0.6838	Remote Similarity	NPD4618	Approved
0.6829	Remote Similarity	NPD1138	Approved
0.6822	Remote Similarity	NPD6287	Discontinued
0.6822	Remote Similarity	NPD1201	Approved
0.6821	Remote Similarity	NPD5494	Approved
0.6818	Remote Similarity	NPD5647	Approved
0.6803	Remote Similarity	NPD6873	Phase 2
0.68	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.68	Remote Similarity	NPD255	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