NPASS Compound

Structure

CID198490 OpenBabel06191715582D 23 26 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 2.3482 -1.9129 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 1.6680 -1.1798 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 -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 -0.0000 1.6180 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 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 0.9511 1.3090 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 2.6831 0.3090 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 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 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 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 18 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 12 19 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	317.024
LogP:	4.777
LogD:	3.588
LogS:	-3.709
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.654
Synthetic Accessibility Score:	2.951
Fsp3:	0.158
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:	-4.818
MDCK Permeability:	1.5179908587015234e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.398
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.97284698486328%
Volume Distribution (VD):	1.153
Pgp-substrate:	1.7820546627044678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	11.915
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.672
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.891
Carcinogencity:	0.705
Eye Corrosion:	0.003
Eye Irritation:	0.118
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC198490

Natural Product ID:	NPC198490
*Common Name:**	5-(8-Methyl-7,10-Dihydrofuro[2,3-G][1]Benzoxepin-2-Yl)Benzene-1,3-Diol
IUPAC Name:	5-(8-methyl-7,10-dihydrofuro[2,3-g][1]benzoxepin-2-yl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	PRQYZCKJWCQXNM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-11-2-4-16-17(22-10-11)5-3-12-8-18(23-19(12)16)13-6-14(20)9-15(21)7-13/h2-3,5-9,20-21H,4,10H2,1H3
SMILES:	CC1=CCc2c(ccc3cc(c4cc(cc(c4)O)O)oc23)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397394
PubChem CID:	5319890
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	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
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	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[568544]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[568544]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[568544]
NPT610	Others	Molecular identity unknown		MIC	=	15.0	ug.mL-1	PMID[568544]
NPT610	Others	Molecular identity unknown		MIC	=	500.0	ug.mL-1	PMID[568544]
NPT610	Others	Molecular identity unknown		MIC	=	50.0	ug.mL-1	PMID[568544]
NPT2955	Organism	Rosellinia necatrix	Rosellinia necatrix	MIC	=	15.0	ug.mL-1	PMID[568544]

☑ 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 NPC198490 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	391
0.1-0.2	1727
0.2-0.3	4100
0.3-0.4	10562
0.4-0.5	7656
0.5-0.6	3741
0.6-0.7	5488
0.7-0.8	4953
0.8-0.85	2276
0.85-0.9	1613
0.9-0.95	161
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC183874
0.9796	High Similarity	NPC170169
0.9728	High Similarity	NPC78335
0.9728	High Similarity	NPC230713
0.966	High Similarity	NPC178202
0.966	High Similarity	NPC226644
0.966	High Similarity	NPC37226
0.96	High Similarity	NPC148938
0.9533	High Similarity	NPC213608
0.9533	High Similarity	NPC1477
0.9533	High Similarity	NPC472462
0.9533	High Similarity	NPC235333
0.9527	High Similarity	NPC39929
0.9527	High Similarity	NPC296030
0.9524	High Similarity	NPC17816
0.9524	High Similarity	NPC130581
0.9524	High Similarity	NPC12148
0.9474	High Similarity	NPC164110
0.9474	High Similarity	NPC212967
0.9474	High Similarity	NPC96342
0.9474	High Similarity	NPC246647
0.947	High Similarity	NPC213936
0.947	High Similarity	NPC297531
0.9467	High Similarity	NPC207624
0.9467	High Similarity	NPC5871
0.9463	High Similarity	NPC167576
0.9459	High Similarity	NPC135325
0.9456	High Similarity	NPC51641
0.9456	High Similarity	NPC210826
0.9456	High Similarity	NPC300267
0.9408	High Similarity	NPC247677
0.9408	High Similarity	NPC160015
0.9408	High Similarity	NPC180924
0.94	High Similarity	NPC115324
0.94	High Similarity	NPC106372
0.94	High Similarity	NPC193976
0.94	High Similarity	NPC58668
0.94	High Similarity	NPC23668
0.9388	High Similarity	NPC155144
0.9388	High Similarity	NPC98926
0.9351	High Similarity	NPC220582
0.9351	High Similarity	NPC304839
0.9346	High Similarity	NPC65504
0.9346	High Similarity	NPC296957
0.9346	High Similarity	NPC268360
0.9346	High Similarity	NPC260902
0.9338	High Similarity	NPC142308
0.9338	High Similarity	NPC253872
0.9338	High Similarity	NPC263676
0.932	High Similarity	NPC225884
0.932	High Similarity	NPC302181
0.929	High Similarity	NPC30655
0.929	High Similarity	NPC74854
0.929	High Similarity	NPC45124
0.9286	High Similarity	NPC40583
0.9286	High Similarity	NPC476349
0.9286	High Similarity	NPC476350
0.9276	High Similarity	NPC72370
0.9276	High Similarity	NPC122365
0.9272	High Similarity	NPC116604
0.9267	High Similarity	NPC37208
0.9267	High Similarity	NPC317492
0.9267	High Similarity	NPC221868
0.9257	High Similarity	NPC230943
0.9252	High Similarity	NPC53192
0.9231	High Similarity	NPC193998
0.9216	High Similarity	NPC99199
0.9211	High Similarity	NPC67654
0.92	High Similarity	NPC168085
0.92	High Similarity	NPC272194
0.9195	High Similarity	NPC99454
0.9195	High Similarity	NPC130176
0.9177	High Similarity	NPC53640
0.9177	High Similarity	NPC277480
0.9167	High Similarity	NPC304387
0.9145	High Similarity	NPC156244
0.9139	High Similarity	NPC266499
0.9119	High Similarity	NPC247973
0.9114	High Similarity	NPC37183
0.9108	High Similarity	NPC219861
0.9103	High Similarity	NPC115432
0.9103	High Similarity	NPC260296
0.9085	High Similarity	NPC38361
0.9085	High Similarity	NPC130015
0.9079	High Similarity	NPC13282
0.9079	High Similarity	NPC472421
0.9073	High Similarity	NPC37135
0.9073	High Similarity	NPC39195
0.9073	High Similarity	NPC186397
0.9067	High Similarity	NPC290133
0.9067	High Similarity	NPC187282
0.9067	High Similarity	NPC24136
0.9051	High Similarity	NPC472581
0.9038	High Similarity	NPC244750
0.9038	High Similarity	NPC472877
0.9032	High Similarity	NPC137100
0.9032	High Similarity	NPC45131
0.902	High Similarity	NPC474772
0.902	High Similarity	NPC318424
0.902	High Similarity	NPC472423
0.902	High Similarity	NPC474744
0.9013	High Similarity	NPC223988
0.9007	High Similarity	NPC198427
0.9007	High Similarity	NPC308200
0.9006	High Similarity	NPC131866
0.9	High Similarity	NPC311741
0.9	High Similarity	NPC234629
0.9	High Similarity	NPC50394
0.8994	High Similarity	NPC38914
0.8994	High Similarity	NPC474591
0.8987	High Similarity	NPC312056
0.8987	High Similarity	NPC84515
0.8987	High Similarity	NPC272722
0.898	High Similarity	NPC124269
0.8974	High Similarity	NPC269495
0.8974	High Similarity	NPC196448
0.8968	High Similarity	NPC233776
0.8961	High Similarity	NPC31627
0.8961	High Similarity	NPC476238
0.8961	High Similarity	NPC473996
0.8961	High Similarity	NPC327269
0.8954	High Similarity	NPC148423
0.8954	High Similarity	NPC321896
0.8954	High Similarity	NPC476185
0.8954	High Similarity	NPC472633
0.8954	High Similarity	NPC135303
0.8954	High Similarity	NPC472406
0.8954	High Similarity	NPC37348
0.8947	High Similarity	NPC145467
0.8947	High Similarity	NPC266572
0.894	High Similarity	NPC472629
0.894	High Similarity	NPC299011
0.8933	High Similarity	NPC75049
0.8933	High Similarity	NPC257097
0.8933	High Similarity	NPC166138
0.8933	High Similarity	NPC68104
0.8933	High Similarity	NPC221432
0.8933	High Similarity	NPC169591
0.8933	High Similarity	NPC39329
0.8933	High Similarity	NPC106985
0.8933	High Similarity	NPC164980
0.8933	High Similarity	NPC149026
0.8933	High Similarity	NPC17262
0.8933	High Similarity	NPC18585
0.8933	High Similarity	NPC143896
0.8933	High Similarity	NPC175504
0.8933	High Similarity	NPC310130
0.8933	High Similarity	NPC91560
0.8933	High Similarity	NPC150408
0.8931	High Similarity	NPC155640
0.8931	High Similarity	NPC159508
0.8931	High Similarity	NPC38591
0.8931	High Similarity	NPC109180
0.8926	High Similarity	NPC469404
0.8926	High Similarity	NPC3188
0.8926	High Similarity	NPC26051
0.8926	High Similarity	NPC52789
0.8926	High Similarity	NPC268204
0.8926	High Similarity	NPC470087
0.8926	High Similarity	NPC321980
0.8926	High Similarity	NPC110969
0.8926	High Similarity	NPC470089
0.8926	High Similarity	NPC55832
0.8924	High Similarity	NPC188486
0.8919	High Similarity	NPC137009
0.8919	High Similarity	NPC477956
0.8917	High Similarity	NPC196879
0.8917	High Similarity	NPC16935
0.8912	High Similarity	NPC188879
0.8912	High Similarity	NPC472419
0.891	High Similarity	NPC208152
0.891	High Similarity	NPC78492
0.8896	High Similarity	NPC471675
0.8896	High Similarity	NPC310794
0.8896	High Similarity	NPC472636
0.8896	High Similarity	NPC472580
0.8889	High Similarity	NPC10027
0.8889	High Similarity	NPC65775
0.8889	High Similarity	NPC471114
0.8882	High Similarity	NPC237635
0.8882	High Similarity	NPC476459
0.8882	High Similarity	NPC79469
0.8882	High Similarity	NPC286230
0.8882	High Similarity	NPC14875
0.8882	High Similarity	NPC241820
0.8882	High Similarity	NPC24673
0.8882	High Similarity	NPC201731
0.8882	High Similarity	NPC104406
0.8882	High Similarity	NPC97716
0.8882	High Similarity	NPC253730
0.8875	High Similarity	NPC291110
0.8875	High Similarity	NPC169471
0.8875	High Similarity	NPC36320
0.8875	High Similarity	NPC136641
0.8874	High Similarity	NPC124780
0.8874	High Similarity	NPC236766
0.8874	High Similarity	NPC470890
0.8874	High Similarity	NPC273538
0.8874	High Similarity	NPC209040
0.8874	High Similarity	NPC473015

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 NPC198490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	988
0.2-0.3	1531
0.3-0.4	2671
0.4-0.5	1846
0.5-0.6	1167
0.6-0.7	403
0.7-0.8	119
0.8-0.85	47
0.85-0.9	20
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.8671	High Similarity	NPD3882	Suspended
0.8636	High Similarity	NPD920	Approved
0.8627	High Similarity	NPD7410	Clinical (unspecified phase)
0.86	High Similarity	NPD1549	Phase 2
0.8554	High Similarity	NPD6559	Discontinued
0.8544	High Similarity	NPD7819	Suspended
0.8535	High Similarity	NPD7411	Suspended
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8533	High Similarity	NPD2344	Approved
0.8523	High Similarity	NPD1510	Phase 2
0.8506	High Similarity	NPD642	Clinical (unspecified phase)
0.8503	High Similarity	NPD1240	Approved
0.85	High Similarity	NPD3749	Approved
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD1934	Approved
0.8471	Intermediate Similarity	NPD4380	Phase 2
0.8467	Intermediate Similarity	NPD2796	Approved
0.8457	Intermediate Similarity	NPD6959	Discontinued
0.8428	Intermediate Similarity	NPD2801	Approved
0.8421	Intermediate Similarity	NPD1243	Approved
0.8421	Intermediate Similarity	NPD2800	Approved
0.8395	Intermediate Similarity	NPD5494	Approved
0.8389	Intermediate Similarity	NPD1607	Approved
0.8387	Intermediate Similarity	NPD2532	Approved
0.8387	Intermediate Similarity	NPD2534	Approved
0.8387	Intermediate Similarity	NPD2533	Approved
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8377	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8312	Intermediate Similarity	NPD2309	Approved
0.8303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD3926	Phase 2
0.8224	Intermediate Similarity	NPD2935	Discontinued
0.8221	Intermediate Similarity	NPD919	Approved
0.8217	Intermediate Similarity	NPD1512	Approved
0.8205	Intermediate Similarity	NPD6799	Approved
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8137	Intermediate Similarity	NPD6801	Discontinued
0.8098	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2799	Discontinued
0.8037	Intermediate Similarity	NPD3817	Phase 2
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7953	Intermediate Similarity	NPD5953	Discontinued
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7941	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7286	Phase 2
0.7935	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3226	Approved
0.7836	Intermediate Similarity	NPD7054	Approved
0.7818	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD943	Approved
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7751	Intermediate Similarity	NPD7229	Phase 3
0.7751	Intermediate Similarity	NPD5710	Approved
0.7751	Intermediate Similarity	NPD5711	Approved
0.775	Intermediate Similarity	NPD7390	Discontinued
0.7746	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6797	Phase 2
0.7711	Intermediate Similarity	NPD2296	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7701	Intermediate Similarity	NPD7251	Discontinued
0.7674	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7808	Phase 3
0.7657	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5403	Approved
0.7595	Intermediate Similarity	NPD1471	Phase 3
0.759	Intermediate Similarity	NPD6280	Approved
0.759	Intermediate Similarity	NPD6279	Approved
0.7586	Intermediate Similarity	NPD1729	Discontinued
0.758	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.755	Intermediate Similarity	NPD1203	Approved
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5401	Approved
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6808	Phase 2
0.744	Intermediate Similarity	NPD5761	Phase 2
0.744	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2654	Approved
0.7391	Intermediate Similarity	NPD4361	Phase 2
0.7391	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD447	Suspended
0.7358	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7351	Intermediate Similarity	NPD9717	Approved
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8313	Approved
0.7318	Intermediate Similarity	NPD8312	Approved
0.7317	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7312	Intermediate Similarity	NPD5408	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD3751	Discontinued
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7237	Intermediate Similarity	NPD1608	Approved
0.7215	Intermediate Similarity	NPD1613	Approved
0.7215	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD411	Approved
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7176	Intermediate Similarity	NPD37	Approved
0.7175	Intermediate Similarity	NPD7177	Discontinued
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7168	Intermediate Similarity	NPD6234	Discontinued
0.7159	Intermediate Similarity	NPD2403	Approved
0.7159	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7134	Intermediate Similarity	NPD7003	Approved
0.7133	Intermediate Similarity	NPD9545	Approved
0.7124	Intermediate Similarity	NPD3972	Approved
0.7117	Intermediate Similarity	NPD2424	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2861	Phase 2
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.711	Intermediate Similarity	NPD6971	Discontinued
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD1164	Approved
0.7066	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1201	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7053	Intermediate Similarity	NPD6778	Approved
0.7053	Intermediate Similarity	NPD6781	Approved
0.7053	Intermediate Similarity	NPD6777	Approved
0.7053	Intermediate Similarity	NPD6780	Approved
0.7053	Intermediate Similarity	NPD6782	Approved
0.7053	Intermediate Similarity	NPD6776	Approved
0.7053	Intermediate Similarity	NPD6779	Approved
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7039	Intermediate Similarity	NPD17	Approved
0.7027	Intermediate Similarity	NPD1241	Discontinued
0.7024	Intermediate Similarity	NPD6273	Approved
0.7017	Intermediate Similarity	NPD6104	Discontinued
0.701	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD9494	Approved
0.7006	Intermediate Similarity	NPD5242	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