NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	2.568
LogD:	2.815
LogS:	-3.94
# Rotatable Bonds:	2
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	2.754
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:	-4.699
MDCK Permeability:	2.7719066565623507e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.224
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.78

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	94.06974029541016%
Volume Distribution (VD):	1.079
Pgp-substrate:	5.180579662322998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.714
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	12.404
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.066
Carcinogencity:	0.931
Eye Corrosion:	0.004
Eye Irritation:	0.07
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC208584

Natural Product ID:	NPC208584
*Common Name:**	7-Methoxy-8-(4-Methylfuran-3-Yl)Chromen-2-One
IUPAC Name:	7-methoxy-8-(4-methylfuran-3-yl)chromen-2-one
Synonyms:
Standard InCHIKey:	INZNSTVWSRDWLF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-9-7-18-8-11(9)14-12(17-2)5-3-10-4-6-13(16)19-15(10)14/h3-8H,1-2H3
SMILES:	Cc1cocc1c1c(ccc2ccc(=O)oc12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098140
PubChem CID:	46831977
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO5744	Galipea panamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20423106]
NPO5744	Galipea panamensis	Species	Rutaceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	CC50	=	33.0	ug.mL-1	PMID[524158]
NPT3632	Organism	Leishmania panamensis	Leishmania panamensis	EC50	=	10.0	ug.mL-1	PMID[524158]
NPT2	Others	Unspecified		Selectivity Index	=	3.0	n.a.	PMID[524158]

☑ 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 NPC208584 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	467
0.1-0.2	1967
0.2-0.3	4789
0.3-0.4	10773
0.4-0.5	7541
0.5-0.6	4714
0.6-0.7	5729
0.7-0.8	5258
0.8-0.85	948
0.85-0.9	437
0.9-0.95	65
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.958	High Similarity	NPC88445
0.9577	High Similarity	NPC74539
0.9577	High Similarity	NPC304443
0.9514	High Similarity	NPC191104
0.9437	High Similarity	NPC246903
0.9296	High Similarity	NPC313036
0.9296	High Similarity	NPC166858
0.9296	High Similarity	NPC51146
0.9241	High Similarity	NPC266743
0.9236	High Similarity	NPC190572
0.9133	High Similarity	NPC269495
0.9133	High Similarity	NPC270044
0.9128	High Similarity	NPC295608
0.9128	High Similarity	NPC278010
0.9128	High Similarity	NPC250769
0.9116	High Similarity	NPC155882
0.9091	High Similarity	NPC254010
0.9085	High Similarity	NPC262635
0.906	High Similarity	NPC131725
0.9058	High Similarity	NPC175159
0.9013	High Similarity	NPC49009
0.9013	High Similarity	NPC169
0.8986	High Similarity	NPC472517
0.8986	High Similarity	NPC135303
0.8986	High Similarity	NPC148423
0.8954	High Similarity	NPC14822
0.8912	High Similarity	NPC198427
0.8889	High Similarity	NPC303210
0.8889	High Similarity	NPC95472
0.8889	High Similarity	NPC239270
0.8889	High Similarity	NPC470856
0.8867	High Similarity	NPC130015
0.8867	High Similarity	NPC38361
0.8859	High Similarity	NPC472406
0.8851	High Similarity	NPC306788
0.8839	High Similarity	NPC179464
0.8824	High Similarity	NPC33320
0.8808	High Similarity	NPC41719
0.88	High Similarity	NPC98028
0.88	High Similarity	NPC472407
0.8774	High Similarity	NPC78612
0.8774	High Similarity	NPC234536
0.8766	High Similarity	NPC243509
0.875	High Similarity	NPC233776
0.875	High Similarity	NPC36414
0.8742	High Similarity	NPC263676
0.8741	High Similarity	NPC472516
0.8732	High Similarity	NPC229128
0.8726	High Similarity	NPC67450
0.8726	High Similarity	NPC210460
0.8726	High Similarity	NPC155264
0.8726	High Similarity	NPC193881
0.8723	High Similarity	NPC55147
0.871	High Similarity	NPC216092
0.8693	High Similarity	NPC247677
0.8693	High Similarity	NPC160015
0.869	High Similarity	NPC136095
0.869	High Similarity	NPC472515
0.8681	High Similarity	NPC253616
0.8645	High Similarity	NPC260296
0.8645	High Similarity	NPC115432
0.8636	High Similarity	NPC260902
0.8636	High Similarity	NPC296957
0.8618	High Similarity	NPC67654
0.8611	High Similarity	NPC268081
0.8611	High Similarity	NPC29638
0.8592	High Similarity	NPC54503
0.8581	High Similarity	NPC184702
0.8581	High Similarity	NPC476350
0.8581	High Similarity	NPC476349
0.8581	High Similarity	NPC17262
0.8581	High Similarity	NPC244750
0.8571	High Similarity	NPC470625
0.8571	High Similarity	NPC297985
0.8562	High Similarity	NPC1477
0.8562	High Similarity	NPC213608
0.8553	High Similarity	NPC156244
0.8553	High Similarity	NPC116604
0.8552	High Similarity	NPC103001
0.8544	High Similarity	NPC179015
0.8544	High Similarity	NPC173149
0.8543	High Similarity	NPC37226
0.8543	High Similarity	NPC226644
0.8516	High Similarity	NPC65504
0.8506	High Similarity	NPC474542
0.85	High Similarity	NPC472519
0.8497	Intermediate Similarity	NPC5871
0.8497	Intermediate Similarity	NPC41326
0.8497	Intermediate Similarity	NPC271681
0.8497	Intermediate Similarity	NPC253872
0.8489	Intermediate Similarity	NPC188327
0.8489	Intermediate Similarity	NPC234109
0.8481	Intermediate Similarity	NPC155640
0.8477	Intermediate Similarity	NPC135325
0.8471	Intermediate Similarity	NPC264293
0.8462	Intermediate Similarity	NPC250076
0.8457	Intermediate Similarity	NPC233956
0.8457	Intermediate Similarity	NPC72455
0.8456	Intermediate Similarity	NPC71739
0.8456	Intermediate Similarity	NPC76657
0.8456	Intermediate Similarity	NPC470932
0.8447	Intermediate Similarity	NPC144288
0.8447	Intermediate Similarity	NPC281835
0.8442	Intermediate Similarity	NPC122365
0.844	Intermediate Similarity	NPC170546
0.844	Intermediate Similarity	NPC66246
0.8438	Intermediate Similarity	NPC320789
0.8435	Intermediate Similarity	NPC310370
0.8435	Intermediate Similarity	NPC183642
0.8435	Intermediate Similarity	NPC473209
0.8431	Intermediate Similarity	NPC170169
0.8431	Intermediate Similarity	NPC189773
0.8431	Intermediate Similarity	NPC290671
0.8421	Intermediate Similarity	NPC317492
0.8421	Intermediate Similarity	NPC296030
0.8421	Intermediate Similarity	NPC39929
0.8418	Intermediate Similarity	NPC193998
0.8417	Intermediate Similarity	NPC165556
0.8414	Intermediate Similarity	NPC104796
0.8414	Intermediate Similarity	NPC223616
0.8411	Intermediate Similarity	NPC130581
0.8411	Intermediate Similarity	NPC12148
0.8403	Intermediate Similarity	NPC307412
0.8403	Intermediate Similarity	NPC55149
0.8403	Intermediate Similarity	NPC247743
0.84	Intermediate Similarity	NPC171656
0.84	Intermediate Similarity	NPC131766
0.84	Intermediate Similarity	NPC230943
0.8392	Intermediate Similarity	NPC19157
0.8389	Intermediate Similarity	NPC53192
0.8387	Intermediate Similarity	NPC148938
0.8387	Intermediate Similarity	NPC198490
0.838	Intermediate Similarity	NPC183348
0.838	Intermediate Similarity	NPC282230
0.8375	Intermediate Similarity	NPC323137
0.8369	Intermediate Similarity	NPC199204
0.8369	Intermediate Similarity	NPC50583
0.8366	Intermediate Similarity	NPC230713
0.8366	Intermediate Similarity	NPC78335
0.8366	Intermediate Similarity	NPC119929
0.8365	Intermediate Similarity	NPC65846
0.8365	Intermediate Similarity	NPC15819
0.8356	Intermediate Similarity	NPC254741
0.8355	Intermediate Similarity	NPC168085
0.8354	Intermediate Similarity	NPC325176
0.8354	Intermediate Similarity	NPC107244
0.8345	Intermediate Similarity	NPC66705
0.8345	Intermediate Similarity	NPC61499
0.8344	Intermediate Similarity	NPC473927
0.8344	Intermediate Similarity	NPC51641
0.8344	Intermediate Similarity	NPC300267
0.8344	Intermediate Similarity	NPC40583
0.8344	Intermediate Similarity	NPC210826
0.8333	Intermediate Similarity	NPC120220
0.8333	Intermediate Similarity	NPC19860
0.8333	Intermediate Similarity	NPC225884
0.8333	Intermediate Similarity	NPC302181
0.8333	Intermediate Similarity	NPC163557
0.8333	Intermediate Similarity	NPC222036
0.8333	Intermediate Similarity	NPC295696
0.8333	Intermediate Similarity	NPC7526
0.8333	Intermediate Similarity	NPC13879
0.8333	Intermediate Similarity	NPC229646
0.8333	Intermediate Similarity	NPC51404
0.8323	Intermediate Similarity	NPC235333
0.8323	Intermediate Similarity	NPC472462
0.8323	Intermediate Similarity	NPC183874
0.8322	Intermediate Similarity	NPC470977
0.8322	Intermediate Similarity	NPC196979
0.8322	Intermediate Similarity	NPC229916
0.8322	Intermediate Similarity	NPC15083
0.8322	Intermediate Similarity	NPC470976
0.8313	Intermediate Similarity	NPC329215
0.8313	Intermediate Similarity	NPC136641
0.8313	Intermediate Similarity	NPC259007
0.8313	Intermediate Similarity	NPC204088
0.8312	Intermediate Similarity	NPC115324
0.8311	Intermediate Similarity	NPC254994
0.8311	Intermediate Similarity	NPC137009
0.831	Intermediate Similarity	NPC168710
0.8301	Intermediate Similarity	NPC164299
0.8301	Intermediate Similarity	NPC178202
0.8301	Intermediate Similarity	NPC221868
0.8301	Intermediate Similarity	NPC37208
0.8299	Intermediate Similarity	NPC332594
0.8299	Intermediate Similarity	NPC221046
0.8299	Intermediate Similarity	NPC38153
0.8299	Intermediate Similarity	NPC307883
0.8298	Intermediate Similarity	NPC37512
0.8293	Intermediate Similarity	NPC224165
0.8293	Intermediate Similarity	NPC53917
0.8291	Intermediate Similarity	NPC43971
0.8291	Intermediate Similarity	NPC74749
0.8291	Intermediate Similarity	NPC19554
0.8289	Intermediate Similarity	NPC17816
0.8289	Intermediate Similarity	NPC14875
0.8288	Intermediate Similarity	NPC283331
0.8282	Intermediate Similarity	NPC472584
0.8282	Intermediate Similarity	NPC475964
0.828	Intermediate Similarity	NPC212967

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 NPC208584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	998
0.2-0.3	1747
0.3-0.4	2755
0.4-0.5	1845
0.5-0.6	961
0.6-0.7	299
0.7-0.8	96
0.8-0.85	25
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9577	High Similarity	NPD920	Approved
0.9437	High Similarity	NPD642	Clinical (unspecified phase)
0.9296	High Similarity	NPD643	Clinical (unspecified phase)
0.9085	High Similarity	NPD1243	Approved
0.8824	High Similarity	NPD919	Approved
0.8471	Intermediate Similarity	NPD1247	Approved
0.8299	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3748	Approved
0.8231	Intermediate Similarity	NPD2796	Approved
0.8165	Intermediate Similarity	NPD3749	Approved
0.8089	Intermediate Similarity	NPD7819	Suspended
0.8039	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6799	Approved
0.7962	Intermediate Similarity	NPD7411	Suspended
0.795	Intermediate Similarity	NPD5494	Approved
0.7947	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2533	Approved
0.7922	Intermediate Similarity	NPD2532	Approved
0.7922	Intermediate Similarity	NPD2534	Approved
0.7919	Intermediate Similarity	NPD1510	Phase 2
0.7911	Intermediate Similarity	NPD6801	Discontinued
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7881	Intermediate Similarity	NPD1549	Phase 2
0.7881	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1296	Phase 2
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7829	Intermediate Similarity	NPD2800	Approved
0.7826	Intermediate Similarity	NPD7075	Discontinued
0.7815	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.777	Intermediate Similarity	NPD1240	Approved
0.7758	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7702	Intermediate Similarity	NPD3817	Phase 2
0.7697	Intermediate Similarity	NPD2344	Approved
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7692	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7673	Intermediate Similarity	NPD4380	Phase 2
0.7667	Intermediate Similarity	NPD1607	Approved
0.7665	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7654	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4307	Phase 2
0.764	Intermediate Similarity	NPD1465	Phase 2
0.764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7229	Phase 3
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7606	Intermediate Similarity	NPD17	Approved
0.7603	Intermediate Similarity	NPD1019	Discontinued
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3882	Suspended
0.753	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD1511	Approved
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7469	Intermediate Similarity	NPD1934	Approved
0.7468	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7448	Intermediate Similarity	NPD1608	Approved
0.7448	Intermediate Similarity	NPD9717	Approved
0.7427	Intermediate Similarity	NPD5953	Discontinued
0.7425	Intermediate Similarity	NPD6808	Phase 2
0.7423	Intermediate Similarity	NPD2801	Approved
0.7421	Intermediate Similarity	NPD1512	Approved
0.7415	Intermediate Similarity	NPD1203	Approved
0.7415	Intermediate Similarity	NPD2797	Approved
0.7412	Intermediate Similarity	NPD7286	Phase 2
0.74	Intermediate Similarity	NPD3268	Approved
0.7396	Intermediate Similarity	NPD7473	Discontinued
0.7378	Intermediate Similarity	NPD5402	Approved
0.7378	Intermediate Similarity	NPD4288	Approved
0.7375	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD6959	Discontinued
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7355	Intermediate Similarity	NPD2346	Discontinued
0.7343	Intermediate Similarity	NPD9545	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5711	Approved
0.7321	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3764	Approved
0.7278	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.726	Intermediate Similarity	NPD1281	Approved
0.726	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6279	Approved
0.7256	Intermediate Similarity	NPD6280	Approved
0.7255	Intermediate Similarity	NPD447	Suspended
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3225	Approved
0.7226	Intermediate Similarity	NPD7033	Discontinued
0.7211	Intermediate Similarity	NPD3972	Approved
0.7191	Intermediate Similarity	NPD4287	Approved
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1876	Approved
0.7114	Intermediate Similarity	NPD1283	Approved
0.7108	Intermediate Similarity	NPD5760	Phase 2
0.7108	Intermediate Similarity	NPD5761	Phase 2
0.7107	Intermediate Similarity	NPD7003	Approved
0.7103	Intermediate Similarity	NPD1548	Phase 1
0.7099	Intermediate Similarity	NPD6273	Approved
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD4477	Approved
0.707	Intermediate Similarity	NPD4476	Approved
0.7066	Intermediate Similarity	NPD5353	Approved
0.7063	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD411	Approved
0.7055	Intermediate Similarity	NPD5691	Approved
0.7048	Intermediate Similarity	NPD37	Approved
0.7045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4908	Phase 1
0.7035	Intermediate Similarity	NPD2403	Approved
0.7035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD9697	Approved
0.7025	Intermediate Similarity	NPD2353	Approved
0.7025	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4966	Approved
0.7024	Intermediate Similarity	NPD4967	Phase 2
0.7024	Intermediate Similarity	NPD4965	Approved
0.702	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD7054	Approved
0.7006	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.6988	Remote Similarity	NPD6385	Approved
0.6988	Remote Similarity	NPD5890	Approved
0.6988	Remote Similarity	NPD5889	Approved
0.6988	Remote Similarity	NPD6386	Approved
0.6987	Remote Similarity	NPD6651	Approved
0.6975	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1729	Discontinued
0.6971	Remote Similarity	NPD7074	Phase 3
0.6971	Remote Similarity	NPD7472	Approved
0.6964	Remote Similarity	NPD2296	Approved
0.6964	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2438	Suspended
0.6954	Remote Similarity	NPD7177	Discontinued
0.6954	Remote Similarity	NPD1164	Approved
0.6948	Remote Similarity	NPD6798	Discontinued
0.6941	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD1651	Approved
0.6932	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD4622	Approved
0.6923	Remote Similarity	NPD5535	Approved
0.6923	Remote Similarity	NPD4618	Approved
0.6893	Remote Similarity	NPD7251	Discontinued
0.6892	Remote Similarity	NPD1778	Approved
0.689	Remote Similarity	NPD2186	Approved
0.6882	Remote Similarity	NPD6971	Discontinued
0.6875	Remote Similarity	NPD2424	Discontinued
0.6871	Remote Similarity	NPD1894	Discontinued
0.6867	Remote Similarity	NPD1481	Phase 2
0.6863	Remote Similarity	NPD9494	Approved
0.6859	Remote Similarity	NPD3140	Approved
0.6859	Remote Similarity	NPD3142	Approved
0.6859	Remote Similarity	NPD943	Approved
0.6855	Remote Similarity	NPD2531	Phase 2
0.6855	Remote Similarity	NPD6100	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