NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	180.228
LogP:	2.277
LogD:	2.233
LogS:	-3.095
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	1.866
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:	-4.527
MDCK Permeability:	2.9433345844154246e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.846
Plasma Protein Binding (PPB):	89.50078582763672%
Volume Distribution (VD):	0.874
Pgp-substrate:	13.40639877319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.392
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.728
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	13.059
Half-life (T1/2):	0.654

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.364
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.154
Carcinogencity:	0.929
Eye Corrosion:	0.032
Eye Irritation:	0.68
Respiratory Toxicity:	0.218

Download Data

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

Natural Product: NPC286683

Natural Product ID:	NPC286683
*Common Name:**	1-(1,3-Benzodioxol-5-Yl)Propan-1-One
IUPAC Name:	1-(1,3-benzodioxol-5-yl)propan-1-one
Synonyms:
Standard InCHIKey:	RVBJGSPBFIUTTR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O3/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h3-5H,2,6H2,1H3
SMILES:	CCC(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453952
PubChem CID:	95682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	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[530754]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[530754]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	50.0	ug.mL-1	PMID[530754]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	50.0	ug.mL-1	PMID[530754]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	40.0	ug.mL-1	PMID[530754]

☑ 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 NPC286683 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	382
0.1-0.2	1895
0.2-0.3	5161
0.3-0.4	12248
0.4-0.5	5110
0.5-0.6	5249
0.6-0.7	10181
0.7-0.8	2310
0.8-0.85	112
0.85-0.9	42
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC225245
0.935	High Similarity	NPC120066
0.9187	High Similarity	NPC474691
0.896	High Similarity	NPC30216
0.8943	High Similarity	NPC295317
0.8898	High Similarity	NPC16651
0.8898	High Similarity	NPC32163
0.8889	High Similarity	NPC86455
0.8889	High Similarity	NPC125134
0.8889	High Similarity	NPC137920
0.8881	High Similarity	NPC28398
0.8855	High Similarity	NPC45404
0.8824	High Similarity	NPC46880
0.8819	High Similarity	NPC154275
0.8788	High Similarity	NPC38101
0.8696	High Similarity	NPC224687
0.8692	High Similarity	NPC477705
0.8692	High Similarity	NPC477694
0.8686	High Similarity	NPC469978
0.8651	High Similarity	NPC256167
0.8633	High Similarity	NPC153620
0.8633	High Similarity	NPC24257
0.8626	High Similarity	NPC477706
0.8623	High Similarity	NPC229787
0.8623	High Similarity	NPC327052
0.8618	High Similarity	NPC212643
0.8618	High Similarity	NPC199209
0.8605	High Similarity	NPC64948
0.8594	High Similarity	NPC473626
0.8583	High Similarity	NPC23332
0.8561	High Similarity	NPC50763
0.8561	High Similarity	NPC153453
0.8561	High Similarity	NPC296575
0.855	High Similarity	NPC285776
0.8537	High Similarity	NPC111225
0.85	High Similarity	NPC31279
0.85	High Similarity	NPC183648
0.848	Intermediate Similarity	NPC69670
0.8462	Intermediate Similarity	NPC203719
0.8462	Intermediate Similarity	NPC117237
0.844	Intermediate Similarity	NPC470088
0.8421	Intermediate Similarity	NPC111888
0.8417	Intermediate Similarity	NPC127326
0.8409	Intermediate Similarity	NPC299010
0.8409	Intermediate Similarity	NPC66905
0.837	Intermediate Similarity	NPC89504
0.837	Intermediate Similarity	NPC95485
0.837	Intermediate Similarity	NPC139519
0.837	Intermediate Similarity	NPC88065
0.8359	Intermediate Similarity	NPC114298
0.8358	Intermediate Similarity	NPC283823
0.8358	Intermediate Similarity	NPC159418
0.8345	Intermediate Similarity	NPC472564
0.8333	Intermediate Similarity	NPC57501
0.8322	Intermediate Similarity	NPC37220
0.8309	Intermediate Similarity	NPC102260
0.8309	Intermediate Similarity	NPC230968
0.8295	Intermediate Similarity	NPC257976
0.8295	Intermediate Similarity	NPC242372
0.8295	Intermediate Similarity	NPC164778
0.8295	Intermediate Similarity	NPC4181
0.8281	Intermediate Similarity	NPC114845
0.8276	Intermediate Similarity	NPC148497
0.8276	Intermediate Similarity	NPC153008
0.8276	Intermediate Similarity	NPC308555
0.8271	Intermediate Similarity	NPC298268
0.8261	Intermediate Similarity	NPC470855
0.8258	Intermediate Similarity	NPC304747
0.8254	Intermediate Similarity	NPC205502
0.8235	Intermediate Similarity	NPC208760
0.8235	Intermediate Similarity	NPC204592
0.8231	Intermediate Similarity	NPC312404
0.8231	Intermediate Similarity	NPC273686
0.8222	Intermediate Similarity	NPC205915
0.8222	Intermediate Similarity	NPC288743
0.8219	Intermediate Similarity	NPC244371
0.8219	Intermediate Similarity	NPC478213
0.8207	Intermediate Similarity	NPC220577
0.8207	Intermediate Similarity	NPC118332
0.8201	Intermediate Similarity	NPC51681
0.8194	Intermediate Similarity	NPC205054
0.8189	Intermediate Similarity	NPC299406
0.8188	Intermediate Similarity	NPC470962
0.8188	Intermediate Similarity	NPC325625
0.8175	Intermediate Similarity	NPC469954
0.8168	Intermediate Similarity	NPC85830
0.8163	Intermediate Similarity	NPC3273
0.8163	Intermediate Similarity	NPC254163
0.8162	Intermediate Similarity	NPC155098
0.816	Intermediate Similarity	NPC220540
0.8156	Intermediate Similarity	NPC15743
0.8154	Intermediate Similarity	NPC141252
0.8154	Intermediate Similarity	NPC11799
0.8151	Intermediate Similarity	NPC68882
0.8151	Intermediate Similarity	NPC292460
0.8143	Intermediate Similarity	NPC104956
0.814	Intermediate Similarity	NPC193484
0.8138	Intermediate Similarity	NPC234152
0.813	Intermediate Similarity	NPC54626
0.813	Intermediate Similarity	NPC57879
0.8129	Intermediate Similarity	NPC223336
0.8125	Intermediate Similarity	NPC127827
0.8108	Intermediate Similarity	NPC261484
0.8106	Intermediate Similarity	NPC179777
0.8106	Intermediate Similarity	NPC177925
0.8102	Intermediate Similarity	NPC143649
0.8095	Intermediate Similarity	NPC268317
0.8095	Intermediate Similarity	NPC279930
0.8095	Intermediate Similarity	NPC57211
0.8095	Intermediate Similarity	NPC470860
0.8085	Intermediate Similarity	NPC27220
0.8082	Intermediate Similarity	NPC279061
0.8071	Intermediate Similarity	NPC908
0.8071	Intermediate Similarity	NPC138438
0.8069	Intermediate Similarity	NPC227980
0.8058	Intermediate Similarity	NPC44573
0.8058	Intermediate Similarity	NPC233780
0.8058	Intermediate Similarity	NPC46947
0.8054	Intermediate Similarity	NPC474990
0.8054	Intermediate Similarity	NPC310206
0.8054	Intermediate Similarity	NPC82733
0.8054	Intermediate Similarity	NPC76458
0.8049	Intermediate Similarity	NPC179309
0.8047	Intermediate Similarity	NPC119949
0.8045	Intermediate Similarity	NPC5018
0.8045	Intermediate Similarity	NPC223807
0.8045	Intermediate Similarity	NPC276466
0.8045	Intermediate Similarity	NPC123722
0.8045	Intermediate Similarity	NPC151167
0.8045	Intermediate Similarity	NPC281020
0.8045	Intermediate Similarity	NPC123228
0.8043	Intermediate Similarity	NPC160425
0.8042	Intermediate Similarity	NPC30890
0.8041	Intermediate Similarity	NPC284353
0.8041	Intermediate Similarity	NPC478238
0.8031	Intermediate Similarity	NPC240664
0.8031	Intermediate Similarity	NPC185738
0.8031	Intermediate Similarity	NPC150919
0.803	Intermediate Similarity	NPC470858
0.8029	Intermediate Similarity	NPC144662
0.8029	Intermediate Similarity	NPC110958
0.8029	Intermediate Similarity	NPC19890
0.8027	Intermediate Similarity	NPC137813
0.8027	Intermediate Similarity	NPC104728
0.8027	Intermediate Similarity	NPC52623
0.8027	Intermediate Similarity	NPC35544
0.8014	Intermediate Similarity	NPC84273
0.8	Intermediate Similarity	NPC62518
0.8	Intermediate Similarity	NPC177291
0.8	Intermediate Similarity	NPC292792
0.8	Intermediate Similarity	NPC68619
0.8	Intermediate Similarity	NPC215375
0.8	Intermediate Similarity	NPC15764
0.8	Intermediate Similarity	NPC472567
0.8	Intermediate Similarity	NPC194416
0.8	Intermediate Similarity	NPC201777
0.8	Intermediate Similarity	NPC4796
0.8	Intermediate Similarity	NPC24193
0.8	Intermediate Similarity	NPC38209
0.7987	Intermediate Similarity	NPC109765
0.7987	Intermediate Similarity	NPC261090
0.7986	Intermediate Similarity	NPC88345
0.7986	Intermediate Similarity	NPC110899
0.7986	Intermediate Similarity	NPC125417
0.7986	Intermediate Similarity	NPC95679
0.7986	Intermediate Similarity	NPC166184
0.7986	Intermediate Similarity	NPC112068
0.7986	Intermediate Similarity	NPC25305
0.7984	Intermediate Similarity	NPC344161
0.7972	Intermediate Similarity	NPC474158
0.7972	Intermediate Similarity	NPC213900
0.797	Intermediate Similarity	NPC303680
0.797	Intermediate Similarity	NPC84076
0.797	Intermediate Similarity	NPC90128
0.7969	Intermediate Similarity	NPC166591
0.7969	Intermediate Similarity	NPC171023
0.7959	Intermediate Similarity	NPC288316
0.7959	Intermediate Similarity	NPC104353
0.7958	Intermediate Similarity	NPC312256
0.7958	Intermediate Similarity	NPC176030
0.7958	Intermediate Similarity	NPC192597
0.7958	Intermediate Similarity	NPC229218
0.7958	Intermediate Similarity	NPC28326
0.7958	Intermediate Similarity	NPC141817
0.7958	Intermediate Similarity	NPC169214
0.7947	Intermediate Similarity	NPC139876
0.7945	Intermediate Similarity	NPC475722
0.7943	Intermediate Similarity	NPC50823
0.7943	Intermediate Similarity	NPC326065
0.7937	Intermediate Similarity	NPC252004
0.7937	Intermediate Similarity	NPC294941
0.7933	Intermediate Similarity	NPC167595
0.7933	Intermediate Similarity	NPC258644
0.7933	Intermediate Similarity	NPC202495
0.7933	Intermediate Similarity	NPC226759
0.7931	Intermediate Similarity	NPC181464
0.7931	Intermediate Similarity	NPC469539
0.7931	Intermediate Similarity	NPC469540
0.7929	Intermediate Similarity	NPC284409
0.7926	Intermediate Similarity	NPC150809

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 NPC286683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	1032
0.2-0.3	1626
0.3-0.4	2796
0.4-0.5	1781
0.5-0.6	1069
0.6-0.7	428
0.7-0.8	62
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD9494	Approved
0.844	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD5536	Phase 2
0.7857	Intermediate Similarity	NPD1241	Discontinued
0.7803	Intermediate Similarity	NPD3972	Approved
0.7769	Intermediate Similarity	NPD1357	Approved
0.7727	Intermediate Similarity	NPD3705	Approved
0.7698	Intermediate Similarity	NPD1933	Approved
0.7698	Intermediate Similarity	NPD447	Suspended
0.7687	Intermediate Similarity	NPD1876	Approved
0.7612	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD228	Approved
0.7533	Intermediate Similarity	NPD7028	Phase 2
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD6386	Approved
0.7483	Intermediate Similarity	NPD6385	Approved
0.7451	Intermediate Similarity	NPD5978	Approved
0.7451	Intermediate Similarity	NPD5977	Approved
0.7447	Intermediate Similarity	NPD230	Phase 1
0.7445	Intermediate Similarity	NPD2798	Approved
0.7442	Intermediate Similarity	NPD5283	Phase 1
0.7424	Intermediate Similarity	NPD9545	Approved
0.7419	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD2492	Phase 1
0.7381	Intermediate Similarity	NPD1358	Approved
0.7372	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD1651	Approved
0.7351	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD1281	Approved
0.7325	Intermediate Similarity	NPD1247	Approved
0.7313	Intermediate Similarity	NPD17	Approved
0.731	Intermediate Similarity	NPD2344	Approved
0.7305	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2801	Approved
0.7254	Intermediate Similarity	NPD3142	Approved
0.7254	Intermediate Similarity	NPD3140	Approved
0.7254	Intermediate Similarity	NPD1240	Approved
0.7237	Intermediate Similarity	NPD824	Approved
0.7233	Intermediate Similarity	NPD3926	Phase 2
0.7226	Intermediate Similarity	NPD3817	Phase 2
0.7208	Intermediate Similarity	NPD1934	Approved
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2353	Approved
0.7192	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1471	Phase 3
0.7174	Intermediate Similarity	NPD1283	Approved
0.7165	Intermediate Similarity	NPD3134	Approved
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.7161	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7054	Approved
0.7153	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD6873	Phase 2
0.7134	Intermediate Similarity	NPD7685	Pre-registration
0.7133	Intermediate Similarity	NPD1511	Approved
0.7123	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD2935	Discontinued
0.7117	Intermediate Similarity	NPD7074	Phase 3
0.7117	Intermediate Similarity	NPD7472	Approved
0.7115	Intermediate Similarity	NPD5353	Approved
0.7114	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD3887	Approved
0.7111	Intermediate Similarity	NPD9268	Approved
0.7097	Intermediate Similarity	NPD37	Approved
0.7095	Intermediate Similarity	NPD1243	Approved
0.7086	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3146	Approved
0.7078	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD1510	Phase 2
0.7047	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4110	Phase 3
0.7039	Intermediate Similarity	NPD1512	Approved
0.7029	Intermediate Similarity	NPD9269	Phase 2
0.7029	Intermediate Similarity	NPD9717	Approved
0.7027	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6799	Approved
0.7019	Intermediate Similarity	NPD5242	Approved
0.7015	Intermediate Similarity	NPD9493	Approved
0.7014	Intermediate Similarity	NPD943	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD7199	Phase 2
0.6993	Remote Similarity	NPD920	Approved
0.6988	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7808	Phase 3
0.6986	Remote Similarity	NPD743	Approved
0.6985	Remote Similarity	NPD5691	Approved
0.698	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6832	Phase 2
0.697	Remote Similarity	NPD6797	Phase 2
0.6966	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4967	Phase 2
0.6962	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4965	Approved
0.6962	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6232	Discontinued
0.6954	Remote Similarity	NPD643	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1019	Discontinued
0.6947	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4626	Approved
0.6933	Remote Similarity	NPD7473	Discontinued
0.6928	Remote Similarity	NPD7251	Discontinued
0.6918	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD411	Approved
0.6875	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD164	Approved
0.6875	Remote Similarity	NPD2313	Discontinued
0.6875	Remote Similarity	NPD6234	Discontinued
0.6867	Remote Similarity	NPD2654	Approved
0.6846	Remote Similarity	NPD2346	Discontinued
0.6839	Remote Similarity	NPD957	Approved
0.6835	Remote Similarity	NPD1465	Phase 2
0.6828	Remote Similarity	NPD8032	Phase 2
0.6824	Remote Similarity	NPD3748	Approved
0.6824	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6273	Approved
0.6812	Remote Similarity	NPD1778	Approved
0.68	Remote Similarity	NPD1549	Phase 2
0.6794	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD1894	Discontinued
0.6788	Remote Similarity	NPD2163	Approved
0.6782	Remote Similarity	NPD2746	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2745	Approved
0.6781	Remote Similarity	NPD4307	Phase 2
0.6781	Remote Similarity	NPD2979	Phase 3
0.6779	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD6279	Approved
0.6772	Remote Similarity	NPD6280	Approved
0.6768	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6166	Phase 2
0.6765	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3267	Approved
0.6761	Remote Similarity	NPD3266	Approved
0.6761	Remote Similarity	NPD1203	Approved
0.6753	Remote Similarity	NPD2532	Approved
0.6753	Remote Similarity	NPD2533	Approved
0.6753	Remote Similarity	NPD2534	Approved
0.6752	Remote Similarity	NPD6599	Discontinued
0.6747	Remote Similarity	NPD5844	Phase 1
0.6744	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5585	Approved
0.6735	Remote Similarity	NPD6355	Discontinued
0.6733	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7819	Suspended
0.6726	Remote Similarity	NPD6559	Discontinued
0.6712	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7003	Approved
0.6709	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD958	Approved
0.6709	Remote Similarity	NPD7110	Phase 1
0.6693	Remote Similarity	NPD1238	Approved
0.6692	Remote Similarity	NPD9697	Approved
0.6689	Remote Similarity	NPD2653	Approved
0.6688	Remote Similarity	NPD2651	Approved
0.6688	Remote Similarity	NPD2649	Approved
0.6688	Remote Similarity	NPD4357	Discontinued
0.6688	Remote Similarity	NPD3455	Phase 2
0.6687	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2821	Approved
0.6667	Remote Similarity	NPD2981	Phase 2
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD1670	Discontinued
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4380	Phase 2
0.6646	Remote Similarity	NPD6876	Approved
0.6646	Remote Similarity	NPD6875	Approved
0.6645	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6798	Discontinued
0.6644	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3496	Discontinued
0.6643	Remote Similarity	NPD3847	Discontinued
0.6625	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1653	Approved
0.6623	Remote Similarity	NPD7266	Discontinued
0.6623	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1375	Discontinued
0.6621	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2983	Phase 2
0.662	Remote Similarity	NPD2982	Phase 2
0.6619	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7075	Discontinued

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