NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.06
Volume:	265.136
LogP:	4.16
LogD:	2.934
LogS:	-3.9
# Rotatable Bonds:	1
TPSA:	66.74
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	2.582
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	1.353375228063669e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	97.86699676513672%
Volume Distribution (VD):	0.974
Pgp-substrate:	3.016247034072876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	9.815
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.938
Carcinogencity:	0.222
Eye Corrosion:	0.007
Eye Irritation:	0.938
Respiratory Toxicity:	0.667

Download Data

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

Natural Product: NPC304387

Natural Product ID:	NPC304387
*Common Name:**	Moracin X
IUPAC Name:	5-furo[3,2-f][1]benzofuran-2-ylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	WWGOYNYKPSPHDA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O4/c17-12-4-11(5-13(18)7-12)15-6-10-3-9-1-2-19-14(9)8-16(10)20-15/h1-8,17-18H
SMILES:	Oc1cc(O)cc(c1)c1oc2c(c1)cc1c(c2)occ1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397404
PubChem CID:	46177529
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	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	6
MIC	3
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	2
NON-MOLECULAR	3
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7.3	ug.mL-1	PMID[513157]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5.9	ug.mL-1	PMID[513157]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	31.7	%	PMID[513158]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	>	70000.0	nM	PMID[513158]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[513157]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[513157]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[513157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.9	ug.mL-1	PMID[513157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.8	ug.mL-1	PMID[513157]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.4	ug.mL-1	PMID[513157]

☑ 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 NPC304387 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	551
0.1-0.2	2114
0.2-0.3	5297
0.3-0.4	12164
0.4-0.5	5356
0.5-0.6	4689
0.6-0.7	5609
0.7-0.8	4472
0.8-0.85	2024
0.85-0.9	386
0.9-0.95	32
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC253872
0.9474	High Similarity	NPC116604
0.9412	High Similarity	NPC263676
0.9304	High Similarity	NPC193998
0.9231	High Similarity	NPC247677
0.9231	High Similarity	NPC160015
0.9221	High Similarity	NPC170169
0.9187	High Similarity	NPC38914
0.9172	High Similarity	NPC296957
0.9172	High Similarity	NPC260902
0.9167	High Similarity	NPC198490
0.9161	High Similarity	NPC130015
0.9161	High Similarity	NPC38361
0.9161	High Similarity	NPC67654
0.9156	High Similarity	NPC230713
0.9156	High Similarity	NPC78335
0.9114	High Similarity	NPC472877
0.9114	High Similarity	NPC476350
0.9114	High Similarity	NPC476349
0.9103	High Similarity	NPC183874
0.9097	High Similarity	NPC156244
0.9091	High Similarity	NPC226644
0.9091	High Similarity	NPC37226
0.9091	High Similarity	NPC178202
0.9085	High Similarity	NPC198427
0.9085	High Similarity	NPC17816
0.9079	High Similarity	NPC155144
0.9074	High Similarity	NPC241820
0.9057	High Similarity	NPC220582
0.9057	High Similarity	NPC304839
0.9045	High Similarity	NPC233776
0.9045	High Similarity	NPC148938
0.9032	High Similarity	NPC135303
0.9032	High Similarity	NPC148423
0.9026	High Similarity	NPC306788
0.9024	High Similarity	NPC157522
0.9006	High Similarity	NPC109180
0.8994	High Similarity	NPC40583
0.8981	High Similarity	NPC235333
0.8981	High Similarity	NPC213608
0.8981	High Similarity	NPC1477
0.8981	High Similarity	NPC122365
0.8981	High Similarity	NPC472462
0.8974	High Similarity	NPC115324
0.8974	High Similarity	NPC472407
0.8968	High Similarity	NPC39929
0.8968	High Similarity	NPC296030
0.8961	High Similarity	NPC130581
0.8961	High Similarity	NPC12148
0.8954	High Similarity	NPC98926
0.8931	High Similarity	NPC246647
0.8931	High Similarity	NPC212967
0.8931	High Similarity	NPC164110
0.8931	High Similarity	NPC96342
0.8924	High Similarity	NPC297531
0.8924	High Similarity	NPC213936
0.8917	High Similarity	NPC5871
0.8917	High Similarity	NPC207624
0.891	High Similarity	NPC472406
0.891	High Similarity	NPC167576
0.8903	High Similarity	NPC135325
0.8896	High Similarity	NPC51641
0.8896	High Similarity	NPC210826
0.8896	High Similarity	NPC190572
0.8896	High Similarity	NPC300267
0.8896	High Similarity	NPC53640
0.8889	High Similarity	NPC302181
0.8889	High Similarity	NPC225884
0.8868	High Similarity	NPC180924
0.8861	High Similarity	NPC41719
0.8854	High Similarity	NPC58668
0.8854	High Similarity	NPC23668
0.8854	High Similarity	NPC193976
0.8854	High Similarity	NPC106372
0.8831	High Similarity	NPC230943
0.8827	High Similarity	NPC219861
0.8824	High Similarity	NPC53192
0.8812	High Similarity	NPC65504
0.8812	High Similarity	NPC268360
0.8797	High Similarity	NPC142308
0.8795	High Similarity	NPC28589
0.8795	High Similarity	NPC248593
0.879	High Similarity	NPC155882
0.8773	High Similarity	NPC38591
0.8773	High Similarity	NPC472581
0.8765	High Similarity	NPC45124
0.8765	High Similarity	NPC74854
0.8765	High Similarity	NPC30655
0.875	High Similarity	NPC137100
0.8742	High Similarity	NPC72370
0.8735	High Similarity	NPC131866
0.8727	High Similarity	NPC50394
0.8727	High Similarity	NPC320789
0.8727	High Similarity	NPC167479
0.8726	High Similarity	NPC37208
0.8726	High Similarity	NPC317492
0.8726	High Similarity	NPC221868
0.872	High Similarity	NPC136641
0.872	High Similarity	NPC291110
0.8704	High Similarity	NPC260296
0.8704	High Similarity	NPC115432
0.8696	High Similarity	NPC270044
0.8696	High Similarity	NPC269495
0.8693	High Similarity	NPC28337
0.869	High Similarity	NPC236327
0.869	High Similarity	NPC300657
0.869	High Similarity	NPC290304
0.8688	High Similarity	NPC474542
0.8688	High Similarity	NPC99199
0.8678	High Similarity	NPC60848
0.8675	High Similarity	NPC41853
0.8667	High Similarity	NPC277480
0.8662	High Similarity	NPC168085
0.8662	High Similarity	NPC272194
0.8659	High Similarity	NPC65846
0.8642	High Similarity	NPC244750
0.8634	High Similarity	NPC45131
0.8634	High Similarity	NPC474386
0.8631	High Similarity	NPC277510
0.8625	High Similarity	NPC158261
0.8625	High Similarity	NPC42458
0.8623	High Similarity	NPC120220
0.8614	High Similarity	NPC247973
0.8614	High Similarity	NPC476459
0.8608	High Similarity	NPC214493
0.8608	High Similarity	NPC266499
0.8608	High Similarity	NPC88445
0.8606	High Similarity	NPC474591
0.8606	High Similarity	NPC37183
0.8598	High Similarity	NPC3448
0.8598	High Similarity	NPC477239
0.859	High Similarity	NPC271590
0.859	High Similarity	NPC110776
0.8589	High Similarity	NPC169
0.8571	High Similarity	NPC472584
0.8563	High Similarity	NPC53252
0.8563	High Similarity	NPC211309
0.8562	High Similarity	NPC125300
0.8562	High Similarity	NPC41326
0.8553	High Similarity	NPC472421
0.8553	High Similarity	NPC13282
0.8553	High Similarity	NPC191104
0.8545	High Similarity	NPC159508
0.8545	High Similarity	NPC110257
0.8545	High Similarity	NPC155640
0.8544	High Similarity	NPC186397
0.8544	High Similarity	NPC37135
0.8544	High Similarity	NPC39195
0.8537	High Similarity	NPC188486
0.8537	High Similarity	NPC472346
0.8537	High Similarity	NPC24761
0.8535	High Similarity	NPC476153
0.8535	High Similarity	NPC215885
0.8535	High Similarity	NPC187282
0.8535	High Similarity	NPC24136
0.8535	High Similarity	NPC73320
0.8535	High Similarity	NPC2416
0.8535	High Similarity	NPC290133
0.8528	High Similarity	NPC196879
0.8528	High Similarity	NPC16935
0.8526	High Similarity	NPC172182
0.8526	High Similarity	NPC262935
0.8526	High Similarity	NPC251182
0.8521	High Similarity	NPC117450
0.8521	High Similarity	NPC62640
0.8519	High Similarity	NPC472461
0.8516	High Similarity	NPC3188
0.8509	High Similarity	NPC208806
0.8506	High Similarity	NPC137009
0.8503	High Similarity	NPC286230
0.8503	High Similarity	NPC253730
0.85	High Similarity	NPC472423
0.85	High Similarity	NPC474744
0.85	High Similarity	NPC318424
0.85	High Similarity	NPC474772
0.8494	Intermediate Similarity	NPC300053
0.8494	Intermediate Similarity	NPC169471
0.8491	Intermediate Similarity	NPC223988
0.8485	Intermediate Similarity	NPC84515
0.8485	Intermediate Similarity	NPC312056
0.8485	Intermediate Similarity	NPC272722
0.8481	Intermediate Similarity	NPC308200
0.8481	Intermediate Similarity	NPC74539
0.8481	Intermediate Similarity	NPC304443
0.8476	Intermediate Similarity	NPC49009
0.8471	Intermediate Similarity	NPC303185
0.8471	Intermediate Similarity	NPC234629
0.8471	Intermediate Similarity	NPC184649
0.8471	Intermediate Similarity	NPC311741
0.8471	Intermediate Similarity	NPC66804
0.8471	Intermediate Similarity	NPC246903
0.8466	Intermediate Similarity	NPC196448
0.8462	Intermediate Similarity	NPC226942
0.8462	Intermediate Similarity	NPC307286
0.8462	Intermediate Similarity	NPC96791
0.8462	Intermediate Similarity	NPC470636
0.8462	Intermediate Similarity	NPC169479
0.8462	Intermediate Similarity	NPC159855
0.8462	Intermediate Similarity	NPC73028
0.8452	Intermediate Similarity	NPC101366

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 NPC304387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	1056
0.2-0.3	1788
0.3-0.4	2775
0.4-0.5	1765
0.5-0.6	893
0.6-0.7	255
0.7-0.8	95
0.8-0.85	30
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8481	Intermediate Similarity	NPD920	Approved
0.8471	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD1247	Approved
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8282	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2344	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8232	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2800	Approved
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1934	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.8084	Intermediate Similarity	NPD919	Approved
0.8063	Intermediate Similarity	NPD1511	Approved
0.8061	Intermediate Similarity	NPD7819	Suspended
0.805	Intermediate Similarity	NPD2309	Approved
0.8038	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7965	Intermediate Similarity	NPD3818	Discontinued
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7963	Intermediate Similarity	NPD1512	Approved
0.7962	Intermediate Similarity	NPD1551	Phase 2
0.7962	Intermediate Similarity	NPD2796	Approved
0.7952	Intermediate Similarity	NPD2801	Approved
0.7929	Intermediate Similarity	NPD5494	Approved
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7844	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6166	Phase 2
0.7746	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7733	Intermediate Similarity	NPD6232	Discontinued
0.773	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD7473	Discontinued
0.7679	Intermediate Similarity	NPD6801	Discontinued
0.7654	Intermediate Similarity	NPD3750	Approved
0.764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3817	Phase 2
0.7578	Intermediate Similarity	NPD1471	Phase 3
0.756	Intermediate Similarity	NPD6599	Discontinued
0.7557	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD943	Approved
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.7485	Intermediate Similarity	NPD5402	Approved
0.7485	Intermediate Similarity	NPD2296	Approved
0.7472	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6651	Approved
0.743	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD7390	Discontinued
0.7405	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4287	Approved
0.7374	Intermediate Similarity	NPD7472	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7348	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD6797	Phase 2
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD7229	Phase 3
0.733	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD6808	Phase 2
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7326	Intermediate Similarity	NPD5761	Phase 2
0.7326	Intermediate Similarity	NPD5760	Phase 2
0.7308	Intermediate Similarity	NPD1203	Approved
0.7293	Intermediate Similarity	NPD7251	Discontinued
0.7283	Intermediate Similarity	NPD8434	Phase 2
0.7278	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD6279	Approved
0.7267	Intermediate Similarity	NPD6280	Approved
0.7262	Intermediate Similarity	NPD5401	Approved
0.7253	Intermediate Similarity	NPD7808	Phase 3
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1729	Discontinued
0.7176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD230	Phase 1
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4628	Phase 3
0.712	Intermediate Similarity	NPD8312	Approved
0.712	Intermediate Similarity	NPD8313	Approved
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD3764	Approved
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7062	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD447	Suspended
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.703	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4361	Phase 2
0.7013	Intermediate Similarity	NPD1548	Phase 1
0.7006	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7199	Phase 2
0.6981	Remote Similarity	NPD1470	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6966	Remote Similarity	NPD6234	Discontinued
0.6964	Remote Similarity	NPD2654	Approved
0.6963	Remote Similarity	NPD4360	Phase 2
0.6963	Remote Similarity	NPD4363	Phase 3
0.6961	Remote Similarity	NPD2403	Approved
0.6959	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4965	Approved
0.6949	Remote Similarity	NPD4967	Phase 2
0.6949	Remote Similarity	NPD4966	Approved
0.6947	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7033	Discontinued
0.6919	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4625	Phase 3
0.6914	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1608	Approved
0.6894	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9494	Approved
0.6891	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD1164	Approved
0.6871	Remote Similarity	NPD411	Approved
0.6851	Remote Similarity	NPD3787	Discontinued
0.6835	Remote Similarity	NPD422	Phase 1
0.6835	Remote Similarity	NPD1201	Approved
0.6832	Remote Similarity	NPD2798	Approved
0.6826	Remote Similarity	NPD4308	Phase 3
0.6813	Remote Similarity	NPD3225	Approved
0.6798	Remote Similarity	NPD4288	Approved
0.6798	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD9545	Approved
0.6792	Remote Similarity	NPD3972	Approved
0.679	Remote Similarity	NPD2861	Phase 2
0.678	Remote Similarity	NPD37	Approved
0.678	Remote Similarity	NPD6844	Discontinued
0.6776	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3266	Approved
0.677	Remote Similarity	NPD3267	Approved
0.6766	Remote Similarity	NPD8151	Discontinued
0.6746	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6004	Phase 3
0.6746	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6005	Phase 3
0.6746	Remote Similarity	NPD6002	Phase 3
0.6742	Remote Similarity	NPD8455	Phase 2
0.6728	Remote Similarity	NPD1019	Discontinued
0.6725	Remote Similarity	NPD7003	Approved
0.6723	Remote Similarity	NPD5889	Approved
0.6723	Remote Similarity	NPD5890	Approved
0.6722	Remote Similarity	NPD6971	Discontinued
0.6709	Remote Similarity	NPD17	Approved
0.6708	Remote Similarity	NPD1876	Approved
0.6707	Remote Similarity	NPD3027	Phase 3
0.6706	Remote Similarity	NPD2424	Discontinued
0.6705	Remote Similarity	NPD7458	Discontinued
0.6703	Remote Similarity	NPD7228	Approved
0.6703	Remote Similarity	NPD2163	Approved
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	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