NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.07
Volume:	259.083
LogP:	2.033
LogD:	1.514
LogS:	-2.861
# Rotatable Bonds:	6
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	2.429
Fsp3:	0.143
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:	-4.62
MDCK Permeability:	2.9911401725257747e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.344
Plasma Protein Binding (PPB):	93.51618957519531%
Volume Distribution (VD):	0.794
Pgp-substrate:	4.055361747741699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.534
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	13.504
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.33
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.295
Carcinogencity:	0.573
Eye Corrosion:	0.029
Eye Irritation:	0.779
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC474314

Natural Product ID:	NPC474314
*Common Name:**	Melodorinol
IUPAC Name:	[(3Z)-2-hydroxy-3-(5-oxofuran-2-ylidene)propyl] benzoate
Synonyms:	Melodorinol
Standard InCHIKey:	WQHRXHYOKDRIRR-WQLSENKSSA-N
Standard InCHI:	InChI=1S/C14H12O5/c15-11(8-12-6-7-13(16)19-12)9-18-14(17)10-4-2-1-3-5-10/h1-8,11,15H,9H2/b12-8-
SMILES:	OC(/C=C1/C=CC(=O)O1)COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465071
PubChem CID:	5388649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919592]
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.89	ug ml-1	PMID[551980]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.99	ug ml-1	PMID[551980]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.87	ug ml-1	PMID[551980]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	3.75	ug ml-1	PMID[551980]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	=	3.32	ug ml-1	PMID[551980]

☑ 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 NPC474314 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	235
0.1-0.2	986
0.2-0.3	3305
0.3-0.4	8366
0.4-0.5	10674
0.5-0.6	10992
0.6-0.7	7291
0.7-0.8	746
0.8-0.85	73
0.85-0.9	20
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC474364
0.9074	High Similarity	NPC158282
0.8909	High Similarity	NPC474363
0.8857	High Similarity	NPC91820
0.8857	High Similarity	NPC82426
0.8818	High Similarity	NPC272524
0.8636	High Similarity	NPC476003
0.8624	High Similarity	NPC281604
0.8558	High Similarity	NPC276775
0.8558	High Similarity	NPC92754
0.8558	High Similarity	NPC249912
0.8532	High Similarity	NPC156648
0.8519	High Similarity	NPC269457
0.8505	High Similarity	NPC474365
0.8505	High Similarity	NPC301943
0.8496	Intermediate Similarity	NPC474685
0.8482	Intermediate Similarity	NPC474176
0.8476	Intermediate Similarity	NPC78701
0.8476	Intermediate Similarity	NPC225060
0.8476	Intermediate Similarity	NPC35448
0.8407	Intermediate Similarity	NPC308744
0.8407	Intermediate Similarity	NPC87069
0.8396	Intermediate Similarity	NPC118343
0.8396	Intermediate Similarity	NPC146351
0.8365	Intermediate Similarity	NPC130398
0.8333	Intermediate Similarity	NPC160382
0.8333	Intermediate Similarity	NPC246166
0.8319	Intermediate Similarity	NPC161611
0.8318	Intermediate Similarity	NPC70624
0.8318	Intermediate Similarity	NPC42211
0.8304	Intermediate Similarity	NPC260818
0.8304	Intermediate Similarity	NPC474157
0.8288	Intermediate Similarity	NPC83628
0.8288	Intermediate Similarity	NPC265407
0.8288	Intermediate Similarity	NPC469636
0.8273	Intermediate Similarity	NPC30594
0.8273	Intermediate Similarity	NPC37622
0.8257	Intermediate Similarity	NPC242913
0.8257	Intermediate Similarity	NPC114594
0.8257	Intermediate Similarity	NPC280616
0.8257	Intermediate Similarity	NPC171831
0.823	Intermediate Similarity	NPC321852
0.8224	Intermediate Similarity	NPC325497
0.8224	Intermediate Similarity	NPC203925
0.8214	Intermediate Similarity	NPC174099
0.8198	Intermediate Similarity	NPC277788
0.8182	Intermediate Similarity	NPC209632
0.8165	Intermediate Similarity	NPC60679
0.8165	Intermediate Similarity	NPC89886
0.8131	Intermediate Similarity	NPC175852
0.8131	Intermediate Similarity	NPC160548
0.8131	Intermediate Similarity	NPC210529
0.8125	Intermediate Similarity	NPC85493
0.8108	Intermediate Similarity	NPC474376
0.8108	Intermediate Similarity	NPC37115
0.8108	Intermediate Similarity	NPC472316
0.8108	Intermediate Similarity	NPC136962
0.8108	Intermediate Similarity	NPC119271
0.8108	Intermediate Similarity	NPC472315
0.8108	Intermediate Similarity	NPC475203
0.8091	Intermediate Similarity	NPC269644
0.8087	Intermediate Similarity	NPC307651
0.8087	Intermediate Similarity	NPC237366
0.8087	Intermediate Similarity	NPC153053
0.8073	Intermediate Similarity	NPC188895
0.807	Intermediate Similarity	NPC185840
0.8051	Intermediate Similarity	NPC471033
0.8051	Intermediate Similarity	NPC311091
0.8036	Intermediate Similarity	NPC56493
0.8017	Intermediate Similarity	NPC210092
0.8017	Intermediate Similarity	NPC306740
0.8016	Intermediate Similarity	NPC104854
0.7984	Intermediate Similarity	NPC472707
0.7981	Intermediate Similarity	NPC62765
0.7966	Intermediate Similarity	NPC469574
0.7965	Intermediate Similarity	NPC10251
0.7965	Intermediate Similarity	NPC99846
0.7965	Intermediate Similarity	NPC17417
0.7965	Intermediate Similarity	NPC269023
0.7951	Intermediate Similarity	NPC471466
0.7949	Intermediate Similarity	NPC149691
0.7944	Intermediate Similarity	NPC61944
0.7931	Intermediate Similarity	NPC172525
0.7931	Intermediate Similarity	NPC477411
0.7928	Intermediate Similarity	NPC31786
0.7909	Intermediate Similarity	NPC45613
0.7903	Intermediate Similarity	NPC114096
0.7899	Intermediate Similarity	NPC94298
0.7899	Intermediate Similarity	NPC94637
0.7899	Intermediate Similarity	NPC27633
0.7895	Intermediate Similarity	NPC214067
0.7895	Intermediate Similarity	NPC93084
0.7895	Intermediate Similarity	NPC251854
0.7895	Intermediate Similarity	NPC196246
0.7891	Intermediate Similarity	NPC38420
0.7891	Intermediate Similarity	NPC136608
0.7885	Intermediate Similarity	NPC173443
0.7881	Intermediate Similarity	NPC128249
0.7874	Intermediate Similarity	NPC233692
0.787	Intermediate Similarity	NPC270654
0.787	Intermediate Similarity	NPC253423
0.7869	Intermediate Similarity	NPC223351
0.7863	Intermediate Similarity	NPC81808
0.7857	Intermediate Similarity	NPC472919
0.7846	Intermediate Similarity	NPC27721
0.7845	Intermediate Similarity	NPC17693
0.7845	Intermediate Similarity	NPC265002
0.7845	Intermediate Similarity	NPC128368
0.784	Intermediate Similarity	NPC148026
0.7838	Intermediate Similarity	NPC234305
0.7833	Intermediate Similarity	NPC90522
0.7833	Intermediate Similarity	NPC328459
0.7826	Intermediate Similarity	NPC305912
0.7826	Intermediate Similarity	NPC210089
0.7826	Intermediate Similarity	NPC1082
0.7823	Intermediate Similarity	NPC236405
0.7815	Intermediate Similarity	NPC240664
0.7798	Intermediate Similarity	NPC229242
0.7797	Intermediate Similarity	NPC226093
0.7788	Intermediate Similarity	NPC51174
0.7778	Intermediate Similarity	NPC301857
0.7769	Intermediate Similarity	NPC243059
0.7769	Intermediate Similarity	NPC202729
0.7769	Intermediate Similarity	NPC72977
0.7769	Intermediate Similarity	NPC233282
0.7769	Intermediate Similarity	NPC280827
0.7768	Intermediate Similarity	NPC249067
0.7767	Intermediate Similarity	NPC318107
0.776	Intermediate Similarity	NPC110211
0.7759	Intermediate Similarity	NPC82899
0.7759	Intermediate Similarity	NPC234376
0.7759	Intermediate Similarity	NPC270699
0.7757	Intermediate Similarity	NPC261181
0.7752	Intermediate Similarity	NPC311492
0.7752	Intermediate Similarity	NPC28836
0.7752	Intermediate Similarity	NPC114116
0.7748	Intermediate Similarity	NPC284477
0.7748	Intermediate Similarity	NPC25458
0.7736	Intermediate Similarity	NPC472319
0.7734	Intermediate Similarity	NPC239358
0.7731	Intermediate Similarity	NPC131192
0.7731	Intermediate Similarity	NPC128825
0.7727	Intermediate Similarity	NPC98911
0.7727	Intermediate Similarity	NPC217621
0.7727	Intermediate Similarity	NPC472318
0.7727	Intermediate Similarity	NPC228435
0.7724	Intermediate Similarity	NPC475692
0.7724	Intermediate Similarity	NPC291189
0.7724	Intermediate Similarity	NPC474283
0.7724	Intermediate Similarity	NPC69403
0.7705	Intermediate Similarity	NPC50872
0.7692	Intermediate Similarity	NPC89377
0.7686	Intermediate Similarity	NPC61779
0.768	Intermediate Similarity	NPC275576
0.768	Intermediate Similarity	NPC88403
0.768	Intermediate Similarity	NPC79608
0.768	Intermediate Similarity	NPC476033
0.768	Intermediate Similarity	NPC4164
0.7674	Intermediate Similarity	NPC302844
0.7674	Intermediate Similarity	NPC472248
0.7672	Intermediate Similarity	NPC243355
0.7672	Intermediate Similarity	NPC167504
0.7667	Intermediate Similarity	NPC217423
0.7667	Intermediate Similarity	NPC45104
0.7661	Intermediate Similarity	NPC228739
0.7661	Intermediate Similarity	NPC475691
0.7658	Intermediate Similarity	NPC282895
0.7652	Intermediate Similarity	NPC475195
0.7647	Intermediate Similarity	NPC210531
0.7647	Intermediate Similarity	NPC100353
0.7634	Intermediate Similarity	NPC52523
0.7634	Intermediate Similarity	NPC217673
0.7619	Intermediate Similarity	NPC304760
0.7619	Intermediate Similarity	NPC474476
0.7619	Intermediate Similarity	NPC472706
0.7619	Intermediate Similarity	NPC204579
0.7619	Intermediate Similarity	NPC169913
0.7619	Intermediate Similarity	NPC475236
0.7611	Intermediate Similarity	NPC85977
0.7607	Intermediate Similarity	NPC79496
0.7603	Intermediate Similarity	NPC293424
0.76	Intermediate Similarity	NPC221798
0.76	Intermediate Similarity	NPC288945
0.7597	Intermediate Similarity	NPC473777
0.7597	Intermediate Similarity	NPC233860
0.7589	Intermediate Similarity	NPC304873
0.7586	Intermediate Similarity	NPC326187
0.7583	Intermediate Similarity	NPC190298
0.7581	Intermediate Similarity	NPC476351
0.7581	Intermediate Similarity	NPC311219
0.7581	Intermediate Similarity	NPC472703
0.7578	Intermediate Similarity	NPC226855
0.7576	Intermediate Similarity	NPC39549
0.7576	Intermediate Similarity	NPC215109
0.7576	Intermediate Similarity	NPC471345
0.7576	Intermediate Similarity	NPC170604
0.757	Intermediate Similarity	NPC317645
0.757	Intermediate Similarity	NPC119631
0.7565	Intermediate Similarity	NPC211439
0.7565	Intermediate Similarity	NPC20485

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 NPC474314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	714
0.2-0.3	1510
0.3-0.4	2781
0.4-0.5	2229
0.5-0.6	1291
0.6-0.7	392
0.7-0.8	40
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD690	Clinical (unspecified phase)
0.8396	Intermediate Similarity	NPD1238	Approved
0.8142	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD9495	Approved
0.8053	Intermediate Similarity	NPD2067	Discontinued
0.7981	Intermediate Similarity	NPD9258	Approved
0.7981	Intermediate Similarity	NPD9256	Approved
0.7965	Intermediate Similarity	NPD2182	Approved
0.7928	Intermediate Similarity	NPD164	Approved
0.7913	Intermediate Similarity	NPD969	Suspended
0.7899	Intermediate Similarity	NPD9545	Approved
0.7881	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD1237	Approved
0.7767	Intermediate Similarity	NPD9257	Approved
0.7767	Intermediate Similarity	NPD9259	Approved
0.7757	Intermediate Similarity	NPD1202	Approved
0.7731	Intermediate Similarity	NPD9493	Approved
0.7619	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD9717	Approved
0.7578	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2629	Approved
0.7522	Intermediate Similarity	NPD6647	Phase 2
0.7426	Intermediate Similarity	NPD4628	Phase 3
0.7414	Intermediate Similarity	NPD1358	Approved
0.7402	Intermediate Similarity	NPD1203	Approved
0.735	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5909	Discontinued
0.7265	Intermediate Similarity	NPD9267	Approved
0.7265	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9264	Approved
0.7265	Intermediate Similarity	NPD9263	Approved
0.7222	Intermediate Similarity	NPD689	Discontinued
0.7218	Intermediate Similarity	NPD447	Suspended
0.7218	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD1019	Discontinued
0.7209	Intermediate Similarity	NPD5647	Approved
0.7207	Intermediate Similarity	NPD9260	Approved
0.7203	Intermediate Similarity	NPD9266	Approved
0.7203	Intermediate Similarity	NPD74	Approved
0.7196	Intermediate Similarity	NPD1282	Approved
0.719	Intermediate Similarity	NPD1241	Discontinued
0.7154	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD9491	Approved
0.7121	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD5403	Approved
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7092	Intermediate Similarity	NPD5401	Approved
0.7087	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6287	Discontinued
0.7069	Intermediate Similarity	NPD9261	Approved
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2198	Approved
0.7054	Intermediate Similarity	NPD2199	Approved
0.7045	Intermediate Similarity	NPD7008	Discontinued
0.704	Intermediate Similarity	NPD1894	Discontinued
0.7034	Intermediate Similarity	NPD3134	Approved
0.7025	Intermediate Similarity	NPD9508	Approved
0.7007	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD2159	Approved
0.7	Intermediate Similarity	NPD2160	Approved
0.7	Intermediate Similarity	NPD2626	Approved
0.7	Intermediate Similarity	NPD2627	Approved
0.7	Intermediate Similarity	NPD2625	Approved
0.7	Intermediate Similarity	NPD2628	Approved
0.6992	Remote Similarity	NPD6798	Discontinued
0.6992	Remote Similarity	NPD2313	Discontinued
0.6992	Remote Similarity	NPD9281	Approved
0.6992	Remote Similarity	NPD411	Approved
0.6975	Remote Similarity	NPD290	Approved
0.6967	Remote Similarity	NPD5277	Phase 2
0.6963	Remote Similarity	NPD6355	Discontinued
0.6963	Remote Similarity	NPD1933	Approved
0.694	Remote Similarity	NPD6233	Phase 2
0.694	Remote Similarity	NPD4062	Phase 3
0.6935	Remote Similarity	NPD4198	Discontinued
0.6929	Remote Similarity	NPD5305	Approved
0.6929	Remote Similarity	NPD5306	Approved
0.6923	Remote Similarity	NPD1930	Approved
0.6923	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9490	Approved
0.6923	Remote Similarity	NPD1929	Approved
0.6923	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6653	Approved
0.6912	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6799	Approved
0.6899	Remote Similarity	NPD1481	Phase 2
0.6875	Remote Similarity	NPD4136	Approved
0.6875	Remote Similarity	NPD4135	Approved
0.6875	Remote Similarity	NPD4106	Approved
0.6857	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5951	Approved
0.6838	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2347	Approved
0.6822	Remote Similarity	NPD4807	Approved
0.6822	Remote Similarity	NPD4806	Approved
0.6822	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6085	Phase 2
0.6815	Remote Similarity	NPD520	Approved
0.6812	Remote Similarity	NPD4308	Phase 3
0.681	Remote Similarity	NPD7798	Approved
0.681	Remote Similarity	NPD2066	Phase 3
0.6809	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9697	Approved
0.6803	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD226	Approved
0.6781	Remote Similarity	NPD3455	Phase 2
0.6779	Remote Similarity	NPD5402	Approved
0.6777	Remote Similarity	NPD2684	Approved
0.6767	Remote Similarity	NPD3662	Phase 3
0.6767	Remote Similarity	NPD3663	Approved
0.6767	Remote Similarity	NPD3661	Approved
0.6767	Remote Similarity	NPD5204	Approved
0.6767	Remote Similarity	NPD3664	Approved
0.6763	Remote Similarity	NPD2240	Approved
0.6763	Remote Similarity	NPD2239	Approved
0.6763	Remote Similarity	NPD2935	Discontinued
0.6761	Remote Similarity	NPD3887	Approved
0.6761	Remote Similarity	NPD2354	Approved
0.6761	Remote Similarity	NPD6190	Approved
0.6757	Remote Similarity	NPD800	Approved
0.6757	Remote Similarity	NPD6801	Discontinued
0.6754	Remote Similarity	NPD1693	Approved
0.6744	Remote Similarity	NPD3496	Discontinued
0.6742	Remote Similarity	NPD553	Approved
0.6742	Remote Similarity	NPD9567	Approved
0.6742	Remote Similarity	NPD2797	Approved
0.6742	Remote Similarity	NPD552	Approved
0.6739	Remote Similarity	NPD2567	Approved
0.6739	Remote Similarity	NPD2569	Approved
0.6731	Remote Similarity	NPD9294	Approved
0.6719	Remote Similarity	NPD4105	Approved
0.6719	Remote Similarity	NPD4102	Approved
0.6714	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7440	Discontinued
0.6713	Remote Similarity	NPD7236	Approved
0.6699	Remote Similarity	NPD9716	Approved
0.6696	Remote Similarity	NPD1086	Approved
0.6696	Remote Similarity	NPD1090	Approved
0.6696	Remote Similarity	NPD1989	Approved
0.6696	Remote Similarity	NPD1089	Approved
0.6695	Remote Similarity	NPD1932	Approved
0.6694	Remote Similarity	NPD7843	Approved
0.6692	Remote Similarity	NPD2798	Approved
0.6692	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2799	Discontinued
0.669	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD1104	Approved
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5667	Approved
0.6643	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4307	Phase 2
0.6642	Remote Similarity	NPD454	Approved
0.6642	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD9269	Phase 2
0.6641	Remote Similarity	NPD1608	Approved
0.6641	Remote Similarity	NPD3972	Approved
0.6637	Remote Similarity	NPD1239	Approved
0.6622	Remote Similarity	NPD4380	Phase 2
0.6622	Remote Similarity	NPD6599	Discontinued
0.6621	Remote Similarity	NPD4662	Approved
0.6621	Remote Similarity	NPD4661	Approved
0.6618	Remote Similarity	NPD3268	Approved
0.6617	Remote Similarity	NPD6362	Approved
0.66	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2353	Approved
0.6596	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2346	Discontinued
0.6596	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6005	Phase 3
0.6596	Remote Similarity	NPD6002	Phase 3
0.6596	Remote Similarity	NPD6004	Phase 3
0.6593	Remote Similarity	NPD4617	Approved
0.6593	Remote Similarity	NPD5201	Approved
0.6593	Remote Similarity	NPD5203	Approved
0.6593	Remote Similarity	NPD4620	Approved
0.6591	Remote Similarity	NPD5157	Phase 1
0.6591	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5159	Phase 2
0.6589	Remote Similarity	NPD9268	Approved
0.6585	Remote Similarity	NPD9713	Approved
0.6579	Remote Similarity	NPD7075	Discontinued
0.6579	Remote Similarity	NPD1088	Approved
0.6577	Remote Similarity	NPD1087	Approved
0.6577	Remote Similarity	NPD958	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