NPASS Compound

Structure

CID183874 OpenBabel06191715562D 25 28 0 0 0 0 0 0 0 0999 V2000 3.8454 -2.7042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3482 -1.9129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6680 -1.1798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9087 -1.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3454 -1.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6140 -0.0563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 23 1 0 0 0 0 3 4 1 0 0 0 0 3 11 2 0 0 0 0 4 15 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 14 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	343.11
LogP:	4.791
LogD:	3.595
LogS:	-3.804
# Rotatable Bonds:	2
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	3.055
Fsp3:	0.2
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:	-4.851
MDCK Permeability:	1.431609780411236e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.723
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.86567687988281%
Volume Distribution (VD):	1.069
Pgp-substrate:	5.085237503051758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.792
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	11.453
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.702
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.809
Carcinogencity:	0.361
Eye Corrosion:	0.003
Eye Irritation:	0.11
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC183874

Natural Product ID:	NPC183874
*Common Name:**	5-(4-Methoxy-8-Methyl-7,10-Dihydrofuro[2,3-G][1]Benzoxepin-2-Yl)Benzene-1,3-Diol
IUPAC Name:	5-(4-methoxy-8-methyl-7,10-dihydrofuro[2,3-g][1]benzoxepin-2-yl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	QRLJHLHVDMQXPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-11-3-4-15-19(24-10-11)9-18(23-2)16-8-17(25-20(15)16)12-5-13(21)7-14(22)6-12/h3,5-9,21-22H,4,10H2,1-2H3
SMILES:	CC1=CCc2c(cc(c3cc(c4cc(cc(c4)O)O)oc23)OC)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397395
PubChem CID:	5319891
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.	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.	root	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
MIC	10

Activity Type	# Activity
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[480209]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[480209]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[480209]
NPT610	Others	Molecular identity unknown		MIC	=	15.0	ug.mL-1	PMID[480209]
NPT610	Others	Molecular identity unknown		MIC	=	100.0	ug.mL-1	PMID[480209]
NPT610	Others	Molecular identity unknown		MIC	=	1000.0	ug.mL-1	PMID[480209]
NPT610	Others	Molecular identity unknown		MIC	=	50.0	ug.mL-1	PMID[480209]
NPT2955	Organism	Rosellinia necatrix	Rosellinia necatrix	MIC	=	15.0	ug.mL-1	PMID[480209]

☑ 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 NPC183874 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	388
0.1-0.2	1730
0.2-0.3	4012
0.3-0.4	10201
0.4-0.5	8177
0.5-0.6	3740
0.6-0.7	5361
0.7-0.8	4873
0.8-0.85	2267
0.85-0.9	1766
0.9-0.95	164
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC198490
0.9728	High Similarity	NPC170169
0.9726	High Similarity	NPC178202
0.966	High Similarity	NPC78335
0.966	High Similarity	NPC230713
0.9592	High Similarity	NPC226644
0.9592	High Similarity	NPC37226
0.9589	High Similarity	NPC17816
0.9533	High Similarity	NPC148938
0.953	High Similarity	NPC5871
0.947	High Similarity	NPC180924
0.9467	High Similarity	NPC235333
0.9467	High Similarity	NPC472462
0.9467	High Similarity	NPC213608
0.9467	High Similarity	NPC1477
0.9463	High Similarity	NPC106372
0.9463	High Similarity	NPC58668
0.9459	High Similarity	NPC296030
0.9459	High Similarity	NPC39929
0.9456	High Similarity	NPC12148
0.9456	High Similarity	NPC130581
0.9412	High Similarity	NPC220582
0.9412	High Similarity	NPC304839
0.9408	High Similarity	NPC96342
0.9408	High Similarity	NPC246647
0.9408	High Similarity	NPC164110
0.9408	High Similarity	NPC212967
0.9404	High Similarity	NPC297531
0.9404	High Similarity	NPC213936
0.94	High Similarity	NPC253872
0.94	High Similarity	NPC207624
0.9396	High Similarity	NPC167576
0.9392	High Similarity	NPC135325
0.9388	High Similarity	NPC51641
0.9388	High Similarity	NPC300267
0.9388	High Similarity	NPC210826
0.9351	High Similarity	NPC45124
0.9351	High Similarity	NPC30655
0.9351	High Similarity	NPC74854
0.9342	High Similarity	NPC247677
0.9342	High Similarity	NPC160015
0.9333	High Similarity	NPC115324
0.9333	High Similarity	NPC193976
0.9333	High Similarity	NPC23668
0.932	High Similarity	NPC98926
0.932	High Similarity	NPC155144
0.9281	High Similarity	NPC260902
0.9281	High Similarity	NPC268360
0.9281	High Similarity	NPC65504
0.9281	High Similarity	NPC296957
0.9272	High Similarity	NPC142308
0.9272	High Similarity	NPC263676
0.9252	High Similarity	NPC302181
0.9252	High Similarity	NPC225884
0.9221	High Similarity	NPC40583
0.9221	High Similarity	NPC476349
0.9221	High Similarity	NPC476350
0.9211	High Similarity	NPC72370
0.9211	High Similarity	NPC122365
0.9205	High Similarity	NPC116604
0.92	High Similarity	NPC37208
0.92	High Similarity	NPC221868
0.92	High Similarity	NPC317492
0.9189	High Similarity	NPC230943
0.9184	High Similarity	NPC53192
0.9172	High Similarity	NPC37183
0.9167	High Similarity	NPC193998
0.915	High Similarity	NPC99199
0.9145	High Similarity	NPC67654
0.9133	High Similarity	NPC272194
0.9133	High Similarity	NPC168085
0.9128	High Similarity	NPC24136
0.9128	High Similarity	NPC290133
0.9128	High Similarity	NPC187282
0.9128	High Similarity	NPC130176
0.9128	High Similarity	NPC99454
0.9114	High Similarity	NPC53640
0.9114	High Similarity	NPC277480
0.9103	High Similarity	NPC304387
0.9091	High Similarity	NPC45131
0.9079	High Similarity	NPC156244
0.9073	High Similarity	NPC266499
0.9057	High Similarity	NPC247973
0.9045	High Similarity	NPC219861
0.9038	High Similarity	NPC115432
0.9038	High Similarity	NPC260296
0.9032	High Similarity	NPC196448
0.902	High Similarity	NPC130015
0.902	High Similarity	NPC38361
0.9013	High Similarity	NPC13282
0.9013	High Similarity	NPC472421
0.9007	High Similarity	NPC186397
0.9007	High Similarity	NPC37135
0.9007	High Similarity	NPC39195
0.8987	High Similarity	NPC472581
0.8974	High Similarity	NPC244750
0.8974	High Similarity	NPC472877
0.8974	High Similarity	NPC196879
0.8968	High Similarity	NPC137100
0.8954	High Similarity	NPC474772
0.8954	High Similarity	NPC474744
0.8954	High Similarity	NPC472423
0.8954	High Similarity	NPC318424
0.8947	High Similarity	NPC223988
0.8944	High Similarity	NPC131866
0.894	High Similarity	NPC308200
0.894	High Similarity	NPC198427
0.8938	High Similarity	NPC50394
0.8933	High Similarity	NPC470890
0.8933	High Similarity	NPC224714
0.8933	High Similarity	NPC234629
0.8933	High Similarity	NPC311741
0.8931	High Similarity	NPC474591
0.8931	High Similarity	NPC38914
0.8931	High Similarity	NPC291110
0.8926	High Similarity	NPC73028
0.8926	High Similarity	NPC96791
0.8926	High Similarity	NPC470636
0.8926	High Similarity	NPC226942
0.8924	High Similarity	NPC272722
0.8924	High Similarity	NPC312056
0.8924	High Similarity	NPC84515
0.8919	High Similarity	NPC253822
0.8919	High Similarity	NPC28337
0.8912	High Similarity	NPC124269
0.891	High Similarity	NPC269495
0.8903	High Similarity	NPC233776
0.8896	High Similarity	NPC40356
0.8896	High Similarity	NPC125300
0.8896	High Similarity	NPC476238
0.8896	High Similarity	NPC31627
0.8896	High Similarity	NPC154683
0.8896	High Similarity	NPC327269
0.8896	High Similarity	NPC473996
0.8889	High Similarity	NPC37348
0.8889	High Similarity	NPC148423
0.8889	High Similarity	NPC472633
0.8889	High Similarity	NPC321896
0.8889	High Similarity	NPC135303
0.8889	High Similarity	NPC476185
0.8889	High Similarity	NPC472406
0.8882	High Similarity	NPC266572
0.8882	High Similarity	NPC211309
0.8882	High Similarity	NPC145467
0.8874	High Similarity	NPC472629
0.8874	High Similarity	NPC299011
0.8868	High Similarity	NPC159508
0.8868	High Similarity	NPC155640
0.8868	High Similarity	NPC109180
0.8868	High Similarity	NPC38591
0.8868	High Similarity	NPC133065
0.8867	High Similarity	NPC251182
0.8867	High Similarity	NPC106985
0.8867	High Similarity	NPC164980
0.8867	High Similarity	NPC143896
0.8867	High Similarity	NPC175504
0.8867	High Similarity	NPC91560
0.8867	High Similarity	NPC17262
0.8867	High Similarity	NPC166138
0.8867	High Similarity	NPC149026
0.8867	High Similarity	NPC169591
0.8867	High Similarity	NPC310130
0.8867	High Similarity	NPC150408
0.8867	High Similarity	NPC68104
0.8867	High Similarity	NPC257097
0.8867	High Similarity	NPC172182
0.8867	High Similarity	NPC262935
0.8867	High Similarity	NPC75049
0.8867	High Similarity	NPC18585
0.8867	High Similarity	NPC221432
0.8867	High Similarity	NPC39329
0.8861	High Similarity	NPC188486
0.8859	High Similarity	NPC279650
0.8859	High Similarity	NPC166689
0.8859	High Similarity	NPC258630
0.8859	High Similarity	NPC321980
0.8859	High Similarity	NPC55832
0.8859	High Similarity	NPC96408
0.8859	High Similarity	NPC470089
0.8859	High Similarity	NPC470087
0.8859	High Similarity	NPC171870
0.8859	High Similarity	NPC26051
0.8859	High Similarity	NPC469404
0.8859	High Similarity	NPC110969
0.8859	High Similarity	NPC52789
0.8859	High Similarity	NPC17170
0.8859	High Similarity	NPC156190
0.8859	High Similarity	NPC3188
0.8859	High Similarity	NPC268204
0.8854	High Similarity	NPC16935
0.8851	High Similarity	NPC477956
0.8851	High Similarity	NPC137009
0.8851	High Similarity	NPC37206
0.8846	High Similarity	NPC208152
0.8846	High Similarity	NPC78492
0.8846	High Similarity	NPC474386
0.8844	High Similarity	NPC188879
0.8844	High Similarity	NPC472419
0.8834	High Similarity	NPC310794
0.8831	High Similarity	NPC474417

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 NPC183874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	988
0.2-0.3	1619
0.3-0.4	2651
0.4-0.5	1862
0.5-0.6	1121
0.6-0.7	382
0.7-0.8	118
0.8-0.85	48
0.85-0.9	18
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8608	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD920	Approved
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8533	High Similarity	NPD1549	Phase 2
0.8509	High Similarity	NPD6959	Discontinued
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8477	Intermediate Similarity	NPD2800	Approved
0.8477	Intermediate Similarity	NPD1243	Approved
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8467	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2344	Approved
0.8467	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8442	Intermediate Similarity	NPD2532	Approved
0.8442	Intermediate Similarity	NPD2534	Approved
0.8442	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2533	Approved
0.8438	Intermediate Similarity	NPD3749	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD1934	Approved
0.8408	Intermediate Similarity	NPD4380	Phase 2
0.84	Intermediate Similarity	NPD2796	Approved
0.8365	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD1607	Approved
0.8312	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD1247	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8258	Intermediate Similarity	NPD1511	Approved
0.8253	Intermediate Similarity	NPD3818	Discontinued
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2309	Approved
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.816	Intermediate Similarity	NPD919	Approved
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8153	Intermediate Similarity	NPD1512	Approved
0.8148	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7974	Intermediate Similarity	NPD2799	Discontinued
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7895	Intermediate Similarity	NPD5953	Discontinued
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD7286	Phase 2
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6651	Approved
0.7836	Intermediate Similarity	NPD7074	Phase 3
0.7834	Intermediate Similarity	NPD3750	Approved
0.7815	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7390	Discontinued
0.7798	Intermediate Similarity	NPD5711	Approved
0.7798	Intermediate Similarity	NPD5710	Approved
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD5402	Approved
0.7733	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD7229	Phase 3
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD2296	Approved
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7616	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7808	Phase 3
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1465	Phase 2
0.7582	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7548	Intermediate Similarity	NPD230	Phase 1
0.7546	Intermediate Similarity	NPD5403	Approved
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1471	Phase 3
0.753	Intermediate Similarity	NPD6279	Approved
0.753	Intermediate Similarity	NPD6280	Approved
0.7529	Intermediate Similarity	NPD1729	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD1203	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD4287	Approved
0.7438	Intermediate Similarity	NPD2654	Approved
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD6808	Phase 2
0.7381	Intermediate Similarity	NPD5761	Phase 2
0.7381	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4361	Phase 2
0.7337	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7325	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD9717	Approved
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5406	Approved
0.725	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5405	Approved
0.725	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD3764	Approved
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7208	Intermediate Similarity	NPD2798	Approved
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7171	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1470	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD411	Approved
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD422	Phase 1
0.7102	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7073	Intermediate Similarity	NPD7003	Approved
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7067	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7052	Intermediate Similarity	NPD6971	Discontinued
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD1164	Approved
0.7032	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4749	Approved
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD6781	Approved
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6776	Approved
0.6994	Remote Similarity	NPD6005	Phase 3
0.6994	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6002	Phase 3
0.6994	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6004	Phase 3
0.6993	Remote Similarity	NPD1201	Approved
0.6987	Remote Similarity	NPD1019	Discontinued
0.6974	Remote Similarity	NPD17	Approved
0.6964	Remote Similarity	NPD6273	Approved
0.6961	Remote Similarity	NPD6104	Discontinued
0.6959	Remote Similarity	NPD7584	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