NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	2.938
LogD:	2.966
LogS:	-3.8
# Rotatable Bonds:	3
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.017
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.568
MDCK Permeability:	2.4258868506876752e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	98.03424072265625%
Volume Distribution (VD):	0.582
Pgp-substrate:	2.5118815898895264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.203
CYP2C9-inhibitor:	0.822
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.536
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	10.603
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.829
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.222
Carcinogencity:	0.926
Eye Corrosion:	0.004
Eye Irritation:	0.656
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC224687

Natural Product ID:	NPC224687
*Common Name:**	2-Methoxy-3,4-Methylenedioxybenzophenone
IUPAC Name:	(4-methoxy-1,3-benzodioxol-5-yl)-phenylmethanone
Synonyms:
Standard InCHIKey:	SUKAEERDMQPLMM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-17-14-11(7-8-12-15(14)19-9-18-12)13(16)10-5-3-2-4-6-10/h2-8H,9H2,1H3
SMILES:	COc1c(ccc2c1OCO2)C(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497717
PubChem CID:	11999967
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	roots	n.a.	n.a.	PMID[16724860]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24216090]
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	54.0	%	PMID[463410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	524000.0	nM	PMID[463410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	PC50	>	100.0	uM	PMID[463411]

☑ 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 NPC224687 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	498
0.1-0.2	2013
0.2-0.3	5082
0.3-0.4	11385
0.4-0.5	5897
0.5-0.6	3930
0.6-0.7	5762
0.7-0.8	6447
0.8-0.85	1487
0.85-0.9	180
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC296575
0.9517	High Similarity	NPC148497
0.9517	High Similarity	NPC153008
0.9452	High Similarity	NPC244371
0.9452	High Similarity	NPC478213
0.9384	High Similarity	NPC68882
0.9379	High Similarity	NPC234152
0.932	High Similarity	NPC57211
0.9315	High Similarity	NPC279061
0.9262	High Similarity	NPC310206
0.9257	High Similarity	NPC478238
0.9252	High Similarity	NPC104728
0.9252	High Similarity	NPC292460
0.9252	High Similarity	NPC35544
0.9252	High Similarity	NPC52623
0.9214	High Similarity	NPC44573
0.92	High Similarity	NPC62518
0.92	High Similarity	NPC215375
0.9189	High Similarity	NPC279930
0.9133	High Similarity	NPC258644
0.9133	High Similarity	NPC167595
0.9128	High Similarity	NPC284353
0.9103	High Similarity	NPC88345
0.9091	High Similarity	NPC185607
0.9079	High Similarity	NPC260640
0.9079	High Similarity	NPC295009
0.9073	High Similarity	NPC113055
0.9067	High Similarity	NPC301897
0.9067	High Similarity	NPC155063
0.9054	High Similarity	NPC220577
0.9021	High Similarity	NPC58229
0.902	High Similarity	NPC478199
0.9013	High Similarity	NPC285973
0.9013	High Similarity	NPC225624
0.8973	High Similarity	NPC195919
0.8973	High Similarity	NPC231013
0.8973	High Similarity	NPC216314
0.8973	High Similarity	NPC120924
0.8954	High Similarity	NPC34376
0.8954	High Similarity	NPC162668
0.8954	High Similarity	NPC94155
0.8947	High Similarity	NPC238405
0.8947	High Similarity	NPC257914
0.8947	High Similarity	NPC104459
0.8912	High Similarity	NPC117463
0.8904	High Similarity	NPC471590
0.8904	High Similarity	NPC136278
0.8903	High Similarity	NPC187923
0.8897	High Similarity	NPC287722
0.8897	High Similarity	NPC119663
0.8897	High Similarity	NPC476054
0.8896	High Similarity	NPC18284
0.8896	High Similarity	NPC302741
0.8896	High Similarity	NPC273021
0.8889	High Similarity	NPC269906
0.8889	High Similarity	NPC131557
0.8882	High Similarity	NPC474990
0.8865	High Similarity	NPC38101
0.8865	High Similarity	NPC143649
0.8851	High Similarity	NPC63256
0.8851	High Similarity	NPC10304
0.8851	High Similarity	NPC287395
0.8851	High Similarity	NPC183655
0.8844	High Similarity	NPC24257
0.8844	High Similarity	NPC12377
0.8844	High Similarity	NPC153620
0.8839	High Similarity	NPC110257
0.8836	High Similarity	NPC113089
0.8836	High Similarity	NPC142165
0.8836	High Similarity	NPC229787
0.8836	High Similarity	NPC293201
0.8836	High Similarity	NPC182842
0.8811	High Similarity	NPC470962
0.8811	High Similarity	NPC46947
0.88	High Similarity	NPC288316
0.88	High Similarity	NPC104353
0.8792	High Similarity	NPC139293
0.8792	High Similarity	NPC69430
0.8792	High Similarity	NPC200060
0.8792	High Similarity	NPC40290
0.8792	High Similarity	NPC474648
0.8792	High Similarity	NPC142876
0.8792	High Similarity	NPC264289
0.8792	High Similarity	NPC333691
0.8792	High Similarity	NPC195763
0.8792	High Similarity	NPC264550
0.8784	High Similarity	NPC205522
0.8784	High Similarity	NPC474999
0.8784	High Similarity	NPC93034
0.8784	High Similarity	NPC188074
0.8784	High Similarity	NPC470511
0.8784	High Similarity	NPC119660
0.8784	High Similarity	NPC125449
0.8774	High Similarity	NPC469575
0.8774	High Similarity	NPC125991
0.8774	High Similarity	NPC61141
0.8767	High Similarity	NPC9966
0.8767	High Similarity	NPC254659
0.8767	High Similarity	NPC70853
0.875	High Similarity	NPC18954
0.8734	High Similarity	NPC41853
0.8733	High Similarity	NPC472279
0.8733	High Similarity	NPC156953
0.8733	High Similarity	NPC29231
0.8726	High Similarity	NPC113093
0.8725	High Similarity	NPC183236
0.8725	High Similarity	NPC203747
0.8725	High Similarity	NPC194653
0.8725	High Similarity	NPC139364
0.8725	High Similarity	NPC80710
0.8725	High Similarity	NPC254702
0.8718	High Similarity	NPC470178
0.8716	High Similarity	NPC215932
0.8716	High Similarity	NPC106461
0.8716	High Similarity	NPC40818
0.8716	High Similarity	NPC14958
0.8716	High Similarity	NPC110639
0.871	High Similarity	NPC470756
0.8707	High Similarity	NPC207732
0.8701	High Similarity	NPC325122
0.8701	High Similarity	NPC125713
0.8699	High Similarity	NPC301178
0.8699	High Similarity	NPC312256
0.8699	High Similarity	NPC284556
0.8699	High Similarity	NPC29536
0.8696	High Similarity	NPC286683
0.869	High Similarity	NPC50823
0.8684	High Similarity	NPC186507
0.8679	High Similarity	NPC212748
0.8675	High Similarity	NPC149614
0.8675	High Similarity	NPC262623
0.8671	High Similarity	NPC167479
0.8667	High Similarity	NPC102003
0.8667	High Similarity	NPC92722
0.8667	High Similarity	NPC238366
0.8658	High Similarity	NPC85233
0.8658	High Similarity	NPC299923
0.8649	High Similarity	NPC87295
0.8649	High Similarity	NPC213482
0.8639	High Similarity	NPC471417
0.8636	High Similarity	NPC19097
0.863	High Similarity	NPC110419
0.8627	High Similarity	NPC38898
0.8625	High Similarity	NPC475964
0.8625	High Similarity	NPC157522
0.8618	High Similarity	NPC100971
0.8618	High Similarity	NPC216769
0.8618	High Similarity	NPC181209
0.8618	High Similarity	NPC308555
0.8618	High Similarity	NPC269451
0.8618	High Similarity	NPC121522
0.8618	High Similarity	NPC209487
0.8618	High Similarity	NPC131266
0.8618	High Similarity	NPC100263
0.8618	High Similarity	NPC304954
0.8618	High Similarity	NPC291802
0.8618	High Similarity	NPC245382
0.8618	High Similarity	NPC35763
0.8616	High Similarity	NPC211309
0.8611	High Similarity	NPC474274
0.8611	High Similarity	NPC157944
0.8609	High Similarity	NPC179183
0.8609	High Similarity	NPC239363
0.8609	High Similarity	NPC62354
0.8609	High Similarity	NPC189270
0.8609	High Similarity	NPC5840
0.8609	High Similarity	NPC260582
0.86	High Similarity	NPC272721
0.86	High Similarity	NPC131451
0.86	High Similarity	NPC15329
0.86	High Similarity	NPC43669
0.86	High Similarity	NPC476342
0.86	High Similarity	NPC196277
0.86	High Similarity	NPC476058
0.8592	High Similarity	NPC182428
0.8591	High Similarity	NPC310259
0.8591	High Similarity	NPC283002
0.8591	High Similarity	NPC302408
0.859	High Similarity	NPC209411
0.859	High Similarity	NPC471290
0.859	High Similarity	NPC239890
0.8581	High Similarity	NPC242893
0.8581	High Similarity	NPC23955
0.8581	High Similarity	NPC38065
0.8581	High Similarity	NPC27106
0.8581	High Similarity	NPC16935
0.8581	High Similarity	NPC474158
0.8571	High Similarity	NPC62640
0.8571	High Similarity	NPC45131
0.8571	High Similarity	NPC72455
0.8571	High Similarity	NPC211120
0.8562	High Similarity	NPC271779
0.8562	High Similarity	NPC167091
0.8562	High Similarity	NPC124714
0.8562	High Similarity	NPC292214
0.8562	High Similarity	NPC472408
0.8562	High Similarity	NPC206238
0.8562	High Similarity	NPC88645
0.8553	High Similarity	NPC135345
0.8553	High Similarity	NPC256406

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 NPC224687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	433
0.1-0.2	995
0.2-0.3	1800
0.3-0.4	2793
0.4-0.5	1716
0.5-0.6	928
0.6-0.7	338
0.7-0.8	119
0.8-0.85	25
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD6980	Clinical (unspecified phase)
0.8671	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD3882	Suspended
0.8526	High Similarity	NPD5494	Approved
0.8462	Intermediate Similarity	NPD919	Approved
0.8392	Intermediate Similarity	NPD1240	Approved
0.8377	Intermediate Similarity	NPD1934	Approved
0.8365	Intermediate Similarity	NPD3926	Phase 2
0.8354	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8288	Intermediate Similarity	NPD1510	Phase 2
0.8276	Intermediate Similarity	NPD1607	Approved
0.8269	Intermediate Similarity	NPD3817	Phase 2
0.8231	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.8212	Intermediate Similarity	NPD1511	Approved
0.816	Intermediate Similarity	NPD7054	Approved
0.8138	Intermediate Similarity	NPD943	Approved
0.811	Intermediate Similarity	NPD7472	Approved
0.8105	Intermediate Similarity	NPD1512	Approved
0.8092	Intermediate Similarity	NPD6799	Approved
0.8092	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1933	Approved
0.8075	Intermediate Similarity	NPD6232	Discontinued
0.8067	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD920	Approved
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7964	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7808	Phase 3
0.7952	Intermediate Similarity	NPD6797	Phase 2
0.7933	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7251	Discontinued
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6166	Phase 2
0.7862	Intermediate Similarity	NPD7819	Suspended
0.7862	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD37	Approved
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7785	Intermediate Similarity	NPD4380	Phase 2
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD447	Suspended
0.7716	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7682	Intermediate Similarity	NPD3748	Approved
0.7654	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD4967	Phase 2
0.7654	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7632	Intermediate Similarity	NPD2935	Discontinued
0.7625	Intermediate Similarity	NPD7411	Suspended
0.7619	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3749	Approved
0.7603	Intermediate Similarity	NPD2798	Approved
0.76	Intermediate Similarity	NPD230	Phase 1
0.7597	Intermediate Similarity	NPD2654	Approved
0.759	Intermediate Similarity	NPD5242	Approved
0.758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD2532	Approved
0.758	Intermediate Similarity	NPD2534	Approved
0.7561	Intermediate Similarity	NPD6234	Discontinued
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.7485	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD2800	Approved
0.7468	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD2344	Approved
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD9494	Approved
0.7407	Intermediate Similarity	NPD6385	Approved
0.7407	Intermediate Similarity	NPD6386	Approved
0.74	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6832	Phase 2
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5353	Approved
0.7378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD3972	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5005	Approved
0.7322	Intermediate Similarity	NPD5006	Approved
0.7315	Intermediate Similarity	NPD3018	Phase 2
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3705	Approved
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7251	Intermediate Similarity	NPD7228	Approved
0.7241	Intermediate Similarity	NPD17	Approved
0.7235	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2403	Approved
0.723	Intermediate Similarity	NPD1876	Approved
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7215	Intermediate Similarity	NPD4628	Phase 3
0.7211	Intermediate Similarity	NPD2981	Phase 2
0.7208	Intermediate Similarity	NPD6651	Approved
0.7207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4420	Approved
0.7188	Intermediate Similarity	NPD4357	Discontinued
0.7184	Intermediate Similarity	NPD7685	Pre-registration
0.7181	Intermediate Similarity	NPD1203	Approved
0.7178	Intermediate Similarity	NPD3226	Approved
0.7172	Intermediate Similarity	NPD9268	Approved
0.7171	Intermediate Similarity	NPD2313	Discontinued
0.7162	Intermediate Similarity	NPD2983	Phase 2
0.7162	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2982	Phase 2
0.716	Intermediate Similarity	NPD6959	Discontinued
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD7028	Phase 2
0.7126	Intermediate Similarity	NPD5953	Discontinued
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7117	Intermediate Similarity	NPD1653	Approved
0.7113	Intermediate Similarity	NPD5283	Phase 1
0.7095	Intermediate Similarity	NPD1608	Approved
0.7095	Intermediate Similarity	NPD9717	Approved
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7240	Approved
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5977	Approved
0.7066	Intermediate Similarity	NPD5978	Approved
0.7059	Intermediate Similarity	NPD1296	Phase 2
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1019	Discontinued
0.7018	Intermediate Similarity	NPD5710	Approved
0.7018	Intermediate Similarity	NPD5711	Approved
0.7011	Intermediate Similarity	NPD7286	Phase 2
0.6993	Remote Similarity	NPD1241	Discontinued
0.6968	Remote Similarity	NPD4307	Phase 2
0.6966	Remote Similarity	NPD9493	Approved
0.6954	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD3267	Approved
0.6954	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1470	Approved
0.6949	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD411	Approved
0.6948	Remote Similarity	NPD3764	Approved
0.6946	Remote Similarity	NPD6279	Approved
0.6946	Remote Similarity	NPD6280	Approved
0.6939	Remote Similarity	NPD1651	Approved
0.6935	Remote Similarity	NPD6776	Approved
0.6935	Remote Similarity	NPD6781	Approved
0.6935	Remote Similarity	NPD6782	Approved
0.6935	Remote Similarity	NPD6780	Approved
0.6935	Remote Similarity	NPD6777	Approved
0.6935	Remote Similarity	NPD6779	Approved
0.6935	Remote Similarity	NPD6778	Approved
0.6919	Remote Similarity	NPD6808	Phase 2
0.6918	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2353	Approved
0.6913	Remote Similarity	NPD1281	Approved
0.6911	Remote Similarity	NPD8151	Discontinued
0.691	Remote Similarity	NPD8313	Approved
0.691	Remote Similarity	NPD8312	Approved
0.6886	Remote Similarity	NPD6873	Phase 2
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7390	Discontinued
0.6871	Remote Similarity	NPD9545	Approved
0.6855	Remote Similarity	NPD3539	Phase 1
0.6855	Remote Similarity	NPD6099	Approved
0.6855	Remote Similarity	NPD6100	Approved
0.6852	Remote Similarity	NPD3887	Approved
0.6852	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7435	Discontinued
0.6825	Remote Similarity	NPD7697	Approved
0.6825	Remote Similarity	NPD7698	Approved
0.6825	Remote Similarity	NPD7696	Phase 3
0.6824	Remote Similarity	NPD1357	Approved
0.6821	Remote Similarity	NPD7229	Phase 3
0.6813	Remote Similarity	NPD3540	Phase 1
0.6813	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.68	Remote Similarity	NPD422	Phase 1
0.68	Remote Similarity	NPD1201	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