NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	206.081
LogP:	2.156
LogD:	2.053
LogS:	-2.809
# Rotatable Bonds:	4
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	1.545
Fsp3:	0.364
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:	-4.524
MDCK Permeability:	2.5658382583060302e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	72.94422149658203%
Volume Distribution (VD):	0.648
Pgp-substrate:	16.67034149169922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.583
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.459

ADMET: Excretion

Clearance (CL):	9.316
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.335
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.155
Carcinogencity:	0.193
Eye Corrosion:	0.036
Eye Irritation:	0.635
Respiratory Toxicity:	0.421

Download Data

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

Natural Product: NPC225245

Natural Product ID:	NPC225245
*Common Name:**	1-(3,4-Dimethoxyphenyl)Propan-1-One
IUPAC Name:	1-(3,4-dimethoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	SBMSBQOMJGZBRY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-4-9(12)8-5-6-10(13-2)11(7-8)14-3/h5-7H,4H2,1-3H3
SMILES:	CCC(=O)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479685
PubChem CID:	15781
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
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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
Potency	6

Activity Type	# Activity
Individual Protein	3
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	707.9	nM	PMID[514240]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[514240]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[514240]
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	>	50.0	ug.mL-1	PMID[514239]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[514239]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	50.0	ug.mL-1	PMID[514239]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	50.0	ug.mL-1	PMID[514239]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	50.0	ug.mL-1	PMID[514239]
NPT2	Others	Unspecified		Potency	=	730.8	nM	PMID[514240]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[514240]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[514240]

☑ 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 NPC225245 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	380
0.1-0.2	2083
0.2-0.3	5304
0.3-0.4	11993
0.4-0.5	4894
0.5-0.6	5017
0.6-0.7	9250
0.7-0.8	3500
0.8-0.85	195
0.85-0.9	60
0.9-0.95	18
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC474691
0.9492	High Similarity	NPC30216
0.9483	High Similarity	NPC295317
0.9417	High Similarity	NPC16651
0.9417	High Similarity	NPC286683
0.9417	High Similarity	NPC32163
0.9174	High Similarity	NPC154275
0.9115	High Similarity	NPC23332
0.9091	High Similarity	NPC473626
0.904	High Similarity	NPC153453
0.904	High Similarity	NPC50763
0.9027	High Similarity	NPC183648
0.8943	High Similarity	NPC203719
0.8943	High Similarity	NPC117237
0.888	High Similarity	NPC66905
0.888	High Similarity	NPC285776
0.8843	High Similarity	NPC114298
0.8828	High Similarity	NPC95485
0.8828	High Similarity	NPC89504
0.8828	High Similarity	NPC88065
0.8828	High Similarity	NPC139519
0.878	High Similarity	NPC120066
0.877	High Similarity	NPC242372
0.877	High Similarity	NPC257976
0.877	High Similarity	NPC4181
0.877	High Similarity	NPC164778
0.874	High Similarity	NPC111888
0.873	High Similarity	NPC299010
0.873	High Similarity	NPC298268
0.872	High Similarity	NPC304747
0.8699	High Similarity	NPC312404
0.8699	High Similarity	NPC273686
0.8682	High Similarity	NPC208760
0.8672	High Similarity	NPC283823
0.8672	High Similarity	NPC159418
0.8667	High Similarity	NPC299406
0.8655	High Similarity	NPC469954
0.8626	High Similarity	NPC325625
0.8626	High Similarity	NPC470962
0.8621	High Similarity	NPC54626
0.8621	High Similarity	NPC57879
0.8583	High Similarity	NPC205502
0.8571	High Similarity	NPC268317
0.8561	High Similarity	NPC223336
0.856	High Similarity	NPC179777
0.856	High Similarity	NPC177925
0.8538	High Similarity	NPC143649
0.8534	High Similarity	NPC179309
0.8527	High Similarity	NPC288743
0.85	High Similarity	NPC185738
0.85	High Similarity	NPC150919
0.8496	Intermediate Similarity	NPC908
0.8496	Intermediate Similarity	NPC138438
0.8496	Intermediate Similarity	NPC292792
0.8496	Intermediate Similarity	NPC38209
0.8492	Intermediate Similarity	NPC276466
0.8492	Intermediate Similarity	NPC5018
0.8492	Intermediate Similarity	NPC123722
0.8492	Intermediate Similarity	NPC151167
0.8492	Intermediate Similarity	NPC123228
0.8487	Intermediate Similarity	NPC220540
0.8485	Intermediate Similarity	NPC44573
0.8462	Intermediate Similarity	NPC155098
0.8462	Intermediate Similarity	NPC144662
0.8455	Intermediate Similarity	NPC201777
0.8433	Intermediate Similarity	NPC84273
0.843	Intermediate Similarity	NPC166591
0.843	Intermediate Similarity	NPC171023
0.8421	Intermediate Similarity	NPC4796
0.8417	Intermediate Similarity	NPC470860
0.8413	Intermediate Similarity	NPC90128
0.8413	Intermediate Similarity	NPC84076
0.8413	Intermediate Similarity	NPC303680
0.8407	Intermediate Similarity	NPC298224
0.8403	Intermediate Similarity	NPC252004
0.8397	Intermediate Similarity	NPC204592
0.8374	Intermediate Similarity	NPC158949
0.837	Intermediate Similarity	NPC192597
0.837	Intermediate Similarity	NPC125134
0.837	Intermediate Similarity	NPC86455
0.837	Intermediate Similarity	NPC176030
0.837	Intermediate Similarity	NPC137920
0.837	Intermediate Similarity	NPC169214
0.837	Intermediate Similarity	NPC28326
0.837	Intermediate Similarity	NPC312256
0.837	Intermediate Similarity	NPC141817
0.837	Intermediate Similarity	NPC229218
0.8359	Intermediate Similarity	NPC150809
0.8359	Intermediate Similarity	NPC304622
0.8359	Intermediate Similarity	NPC261759
0.8358	Intermediate Similarity	NPC28398
0.8358	Intermediate Similarity	NPC50823
0.8347	Intermediate Similarity	NPC240664
0.8346	Intermediate Similarity	NPC281020
0.8346	Intermediate Similarity	NPC46947
0.8333	Intermediate Similarity	NPC77955
0.8321	Intermediate Similarity	NPC237330
0.8321	Intermediate Similarity	NPC45404
0.832	Intermediate Similarity	NPC163083
0.832	Intermediate Similarity	NPC141252
0.832	Intermediate Similarity	NPC244876
0.832	Intermediate Similarity	NPC11799
0.8319	Intermediate Similarity	NPC12714
0.8319	Intermediate Similarity	NPC310905
0.8309	Intermediate Similarity	NPC46161
0.8309	Intermediate Similarity	NPC239608
0.8309	Intermediate Similarity	NPC46880
0.8306	Intermediate Similarity	NPC177291
0.8306	Intermediate Similarity	NPC194416
0.8296	Intermediate Similarity	NPC58229
0.8296	Intermediate Similarity	NPC110419
0.8295	Intermediate Similarity	NPC172673
0.8271	Intermediate Similarity	NPC95679
0.8271	Intermediate Similarity	NPC25305
0.8271	Intermediate Similarity	NPC157944
0.8271	Intermediate Similarity	NPC474274
0.8271	Intermediate Similarity	NPC110899
0.8271	Intermediate Similarity	NPC125417
0.8271	Intermediate Similarity	NPC112068
0.8268	Intermediate Similarity	NPC474737
0.8258	Intermediate Similarity	NPC274613
0.8258	Intermediate Similarity	NPC38101
0.825	Intermediate Similarity	NPC294941
0.8248	Intermediate Similarity	NPC207732
0.8248	Intermediate Similarity	NPC142165
0.8244	Intermediate Similarity	NPC327410
0.8235	Intermediate Similarity	NPC27220
0.8235	Intermediate Similarity	NPC185607
0.8226	Intermediate Similarity	NPC471877
0.8222	Intermediate Similarity	NPC326065
0.8211	Intermediate Similarity	NPC61779
0.8209	Intermediate Similarity	NPC284409
0.8203	Intermediate Similarity	NPC158654
0.8197	Intermediate Similarity	NPC280001
0.8195	Intermediate Similarity	NPC324929
0.819	Intermediate Similarity	NPC1065
0.8189	Intermediate Similarity	NPC257589
0.8189	Intermediate Similarity	NPC53305
0.8189	Intermediate Similarity	NPC470858
0.8188	Intermediate Similarity	NPC160777
0.8188	Intermediate Similarity	NPC224687
0.8188	Intermediate Similarity	NPC73416
0.8188	Intermediate Similarity	NPC136278
0.8188	Intermediate Similarity	NPC30890
0.8182	Intermediate Similarity	NPC311339
0.8175	Intermediate Similarity	NPC182646
0.8175	Intermediate Similarity	NPC469978
0.8175	Intermediate Similarity	NPC469615
0.8175	Intermediate Similarity	NPC119663
0.8175	Intermediate Similarity	NPC50954
0.8175	Intermediate Similarity	NPC254659
0.8175	Intermediate Similarity	NPC473090
0.8168	Intermediate Similarity	NPC239302
0.8167	Intermediate Similarity	NPC303522
0.8154	Intermediate Similarity	NPC477694
0.8154	Intermediate Similarity	NPC477705
0.8129	Intermediate Similarity	NPC24257
0.8129	Intermediate Similarity	NPC165389
0.8129	Intermediate Similarity	NPC231013
0.8129	Intermediate Similarity	NPC216314
0.8129	Intermediate Similarity	NPC120924
0.8129	Intermediate Similarity	NPC153620
0.8129	Intermediate Similarity	NPC195919
0.8125	Intermediate Similarity	NPC92207
0.8125	Intermediate Similarity	NPC127937
0.8125	Intermediate Similarity	NPC474264
0.8125	Intermediate Similarity	NPC276014
0.8116	Intermediate Similarity	NPC469683
0.8116	Intermediate Similarity	NPC327052
0.8116	Intermediate Similarity	NPC229787
0.8116	Intermediate Similarity	NPC308006
0.8116	Intermediate Similarity	NPC113089
0.8116	Intermediate Similarity	NPC472836
0.8116	Intermediate Similarity	NPC293201
0.8115	Intermediate Similarity	NPC316062
0.8102	Intermediate Similarity	NPC299154
0.8095	Intermediate Similarity	NPC256167
0.8095	Intermediate Similarity	NPC286573
0.8092	Intermediate Similarity	NPC477706
0.8077	Intermediate Similarity	NPC226855
0.8074	Intermediate Similarity	NPC233780
0.8074	Intermediate Similarity	NPC207516
0.8071	Intermediate Similarity	NPC205522
0.8071	Intermediate Similarity	NPC93034
0.8071	Intermediate Similarity	NPC472885
0.8071	Intermediate Similarity	NPC119660
0.8071	Intermediate Similarity	NPC294972
0.8071	Intermediate Similarity	NPC469539
0.8071	Intermediate Similarity	NPC469540
0.8067	Intermediate Similarity	NPC137685
0.8062	Intermediate Similarity	NPC12022
0.8062	Intermediate Similarity	NPC293641
0.8062	Intermediate Similarity	NPC20287
0.8062	Intermediate Similarity	NPC223807
0.8062	Intermediate Similarity	NPC64948
0.8062	Intermediate Similarity	NPC20404
0.806	Intermediate Similarity	NPC160425
0.8058	Intermediate Similarity	NPC287495
0.8058	Intermediate Similarity	NPC296575
0.8058	Intermediate Similarity	NPC213482

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 NPC225245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	1038
0.2-0.3	1571
0.3-0.4	2681
0.4-0.5	1793
0.5-0.6	1112
0.6-0.7	484
0.7-0.8	93
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8943	High Similarity	NPD9494	Approved
0.85	High Similarity	NPD5536	Phase 2
0.8319	Intermediate Similarity	NPD1241	Discontinued
0.824	Intermediate Similarity	NPD3972	Approved
0.8031	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD228	Approved
0.797	Intermediate Similarity	NPD447	Suspended
0.7969	Intermediate Similarity	NPD1876	Approved
0.7943	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD1651	Approved
0.7724	Intermediate Similarity	NPD6385	Approved
0.7724	Intermediate Similarity	NPD6386	Approved
0.7704	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD9545	Approved
0.7687	Intermediate Similarity	NPD5977	Approved
0.7687	Intermediate Similarity	NPD5978	Approved
0.7667	Intermediate Similarity	NPD1358	Approved
0.7635	Intermediate Similarity	NPD3882	Suspended
0.763	Intermediate Similarity	NPD3142	Approved
0.763	Intermediate Similarity	NPD3140	Approved
0.763	Intermediate Similarity	NPD1240	Approved
0.7619	Intermediate Similarity	NPD2801	Approved
0.7606	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1281	Approved
0.7597	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD824	Approved
0.7578	Intermediate Similarity	NPD17	Approved
0.7574	Intermediate Similarity	NPD1933	Approved
0.7551	Intermediate Similarity	NPD1934	Approved
0.7518	Intermediate Similarity	NPD1607	Approved
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD5494	Approved
0.7482	Intermediate Similarity	NPD2796	Approved
0.745	Intermediate Similarity	NPD3817	Phase 2
0.7444	Intermediate Similarity	NPD2798	Approved
0.7438	Intermediate Similarity	NPD3134	Approved
0.7434	Intermediate Similarity	NPD1247	Approved
0.7429	Intermediate Similarity	NPD2344	Approved
0.7429	Intermediate Similarity	NPD2353	Approved
0.7429	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1283	Approved
0.7419	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD919	Approved
0.7415	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1510	Phase 2
0.7405	Intermediate Similarity	NPD1608	Approved
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7379	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD943	Approved
0.7365	Intermediate Similarity	NPD6873	Phase 2
0.7364	Intermediate Similarity	NPD9268	Approved
0.7357	Intermediate Similarity	NPD2935	Discontinued
0.7343	Intermediate Similarity	NPD3887	Approved
0.7338	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD5353	Approved
0.731	Intermediate Similarity	NPD3146	Approved
0.731	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7286	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9493	Approved
0.7254	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6799	Approved
0.7236	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5691	Approved
0.7231	Intermediate Similarity	NPD1357	Approved
0.7226	Intermediate Similarity	NPD5242	Approved
0.7222	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD2354	Approved
0.7211	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6832	Phase 2
0.7203	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3705	Approved
0.7194	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1019	Discontinued
0.7177	Intermediate Similarity	NPD2684	Approved
0.7176	Intermediate Similarity	NPD4626	Approved
0.7171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6232	Discontinued
0.7153	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4110	Phase 3
0.7152	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7473	Discontinued
0.7133	Intermediate Similarity	NPD1549	Phase 2
0.7132	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD164	Approved
0.7114	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD411	Approved
0.7092	Intermediate Similarity	NPD743	Approved
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.7083	Intermediate Similarity	NPD1243	Approved
0.707	Intermediate Similarity	NPD6166	Phase 2
0.707	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2346	Discontinued
0.7047	Intermediate Similarity	NPD957	Approved
0.7045	Intermediate Similarity	NPD1778	Approved
0.7042	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD1465	Phase 2
0.7023	Intermediate Similarity	NPD1894	Discontinued
0.702	Intermediate Similarity	NPD7110	Phase 1
0.702	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2981	Phase 2
0.7	Intermediate Similarity	NPD2649	Approved
0.7	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD2651	Approved
0.6993	Remote Similarity	NPD2438	Suspended
0.6985	Remote Similarity	NPD3267	Approved
0.6985	Remote Similarity	NPD3266	Approved
0.6985	Remote Similarity	NPD1203	Approved
0.698	Remote Similarity	NPD920	Approved
0.697	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5585	Approved
0.6966	Remote Similarity	NPD2654	Approved
0.6963	Remote Similarity	NPD2983	Phase 2
0.6963	Remote Similarity	NPD2982	Phase 2
0.6959	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6876	Approved
0.6954	Remote Similarity	NPD6599	Discontinued
0.6954	Remote Similarity	NPD6875	Approved
0.6954	Remote Similarity	NPD4380	Phase 2
0.6953	Remote Similarity	NPD7843	Approved
0.6944	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1238	Approved
0.6939	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5844	Phase 1
0.6937	Remote Similarity	NPD7054	Approved
0.6935	Remote Similarity	NPD9697	Approved
0.6929	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8032	Phase 2
0.6928	Remote Similarity	NPD7819	Suspended
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD7003	Approved
0.6918	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6273	Approved
0.6911	Remote Similarity	NPD9261	Approved
0.6908	Remote Similarity	NPD958	Approved
0.6906	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD2182	Approved
0.6901	Remote Similarity	NPD2492	Phase 1
0.6901	Remote Similarity	NPD2653	Approved
0.6894	Remote Similarity	NPD7472	Approved
0.6894	Remote Similarity	NPD7074	Phase 3
0.6892	Remote Similarity	NPD4357	Discontinued
0.6889	Remote Similarity	NPD1481	Phase 2
0.6887	Remote Similarity	NPD3455	Phase 2
0.6884	Remote Similarity	NPD3018	Phase 2
0.6879	Remote Similarity	NPD2821	Approved
0.6875	Remote Similarity	NPD2163	Approved
0.6875	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6190	Approved
0.6867	Remote Similarity	NPD3639	Approved
0.6867	Remote Similarity	NPD3641	Approved
0.6867	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3640	Phase 3
0.6866	Remote Similarity	NPD3847	Discontinued
0.6866	Remote Similarity	NPD3496	Discontinued
0.6863	Remote Similarity	NPD6280	Approved
0.6863	Remote Similarity	NPD6279	Approved
0.6857	Remote Similarity	NPD5718	Phase 2
0.6857	Remote Similarity	NPD6798	Discontinued
0.6857	Remote Similarity	NPD5111	Phase 2
0.6857	Remote Similarity	NPD5109	Approved
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5110	Phase 2
0.6857	Remote Similarity	NPD3764	Approved
0.685	Remote Similarity	NPD5451	Approved
0.6846	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6355	Discontinued
0.6825	Remote Similarity	NPD290	Approved
0.6822	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD1535	Discovery
0.681	Remote Similarity	NPD7685	Pre-registration
0.6809	Remote Similarity	NPD6233	Phase 2
0.6809	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2674	Phase 3
0.6809	Remote Similarity	NPD4062	Phase 3
0.6806	Remote Similarity	NPD4308	Phase 3
0.6803	Remote Similarity	NPD3750	Approved
0.6803	Remote Similarity	NPD8166	Discontinued
0.6795	Remote Similarity	NPD7075	Discontinued
0.6791	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2922	Phase 1
0.6788	Remote Similarity	NPD196	Phase 1
0.6786	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7095	Approved
0.6776	Remote Similarity	NPD3226	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