NPASS Compound

Structure

CID14662 OpenBabel06191715342D 32 36 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 25 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 28 1 0 0 0 0 18 23 2 0 0 0 0 18 29 1 0 0 0 0 19 11 1 1 0 0 0 19 21 1 0 0 0 0 19 31 1 0 0 0 0 20 27 2 0 0 0 0 21 12 1 6 0 0 0 21 32 1 0 0 0 0 22 24 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.12
Volume:	424.835
LogP:	3.399
LogD:	2.779
LogS:	-5.372
# Rotatable Bonds:	4
TPSA:	107.59
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	3.407
Fsp3:	0.208
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.861
MDCK Permeability:	5.5395437811966985e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	78.96533966064453%
Volume Distribution (VD):	0.763
Pgp-substrate:	20.273977279663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.635
CYP3A4-inhibitor:	0.64
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	5.03
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.195
Skin Sensitization:	0.708
Carcinogencity:	0.73
Eye Corrosion:	0.003
Eye Irritation:	0.204
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC14662

Natural Product ID:	NPC14662
*Common Name:**	Kielcorin
IUPAC Name:	(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-[1,4]dioxino[2,3-c]xanthen-7-one
Synonyms:
Standard InCHIKey:	LRBDQYXCSFVISO-FPOVZHCZSA-N
Standard InCHI:	InChI=1S/C24H20O8/c1-28-17-9-12(7-8-15(17)26)21-19(11-25)31-24-22-14(10-18(29-2)23(24)32-21)20(27)13-5-3-4-6-16(13)30-22/h3-10,19,21,25-26H,11H2,1-2H3/t19-,21-/m0/s1
SMILES:	COc1cc(ccc1O)[C@H]1[C@H](CO)Oc2c3c(cc(c2O1)OC)c(=O)c1ccccc1o3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3813904
PubChem CID:	23242592
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11914965]
NPO40174	Kielmeyera variabilis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26900954]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27116034]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667821]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21963	Hypericum japonicum	Species	Hypericaceae	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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	PMID[507578]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	>	512.0	ug.mL-1	PMID[507578]

☑ 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 NPC14662 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	452
0.1-0.2	1841
0.2-0.3	4757
0.3-0.4	10758
0.4-0.5	7045
0.5-0.6	3908
0.6-0.7	5260
0.7-0.8	4772
0.8-0.85	1911
0.85-0.9	1260
0.9-0.95	701
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC243877
0.9625	High Similarity	NPC295082
0.9623	High Similarity	NPC125039
0.9623	High Similarity	NPC7154
0.9623	High Similarity	NPC7688
0.9623	High Similarity	NPC58223
0.9623	High Similarity	NPC36916
0.9623	High Similarity	NPC72787
0.9623	High Similarity	NPC36
0.9568	High Similarity	NPC81332
0.9568	High Similarity	NPC262580
0.9568	High Similarity	NPC289396
0.9568	High Similarity	NPC271848
0.9568	High Similarity	NPC212038
0.9557	High Similarity	NPC113163
0.9557	High Similarity	NPC66618
0.9557	High Similarity	NPC165970
0.9557	High Similarity	NPC288131
0.9557	High Similarity	NPC84324
0.9557	High Similarity	NPC305987
0.9557	High Similarity	NPC158188
0.95	High Similarity	NPC477840
0.9497	High Similarity	NPC477841
0.9497	High Similarity	NPC220912
0.9497	High Similarity	NPC476247
0.9494	High Similarity	NPC101731
0.949	High Similarity	NPC99597
0.949	High Similarity	NPC475267
0.949	High Similarity	NPC210084
0.949	High Similarity	NPC156057
0.949	High Similarity	NPC474208
0.949	High Similarity	NPC474836
0.949	High Similarity	NPC162869
0.949	High Similarity	NPC48208
0.9455	High Similarity	NPC476618
0.9455	High Similarity	NPC476620
0.9455	High Similarity	NPC472387
0.9455	High Similarity	NPC476619
0.9455	High Similarity	NPC476622
0.9455	High Similarity	NPC476621
0.9455	High Similarity	NPC476623
0.9434	High Similarity	NPC308992
0.9434	High Similarity	NPC142252
0.9434	High Similarity	NPC228383
0.943	High Similarity	NPC284127
0.943	High Similarity	NPC476410
0.943	High Similarity	NPC172202
0.9427	High Similarity	NPC255106
0.9427	High Similarity	NPC235165
0.9427	High Similarity	NPC472916
0.9398	High Similarity	NPC185275
0.9398	High Similarity	NPC324742
0.939	High Similarity	NPC51774
0.939	High Similarity	NPC236191
0.939	High Similarity	NPC239549
0.9387	High Similarity	NPC471416
0.9387	High Similarity	NPC34287
0.9387	High Similarity	NPC183357
0.9387	High Similarity	NPC103307
0.9387	High Similarity	NPC44558
0.9387	High Similarity	NPC22195
0.9387	High Similarity	NPC21190
0.9387	High Similarity	NPC474434
0.9383	High Similarity	NPC260266
0.9379	High Similarity	NPC224280
0.9379	High Similarity	NPC234052
0.9375	High Similarity	NPC474034
0.9375	High Similarity	NPC474033
0.9375	High Similarity	NPC219927
0.9371	High Similarity	NPC263449
0.9367	High Similarity	NPC245758
0.9367	High Similarity	NPC96167
0.9367	High Similarity	NPC472914
0.9367	High Similarity	NPC183851
0.9367	High Similarity	NPC63454
0.9367	High Similarity	NPC472911
0.9367	High Similarity	NPC472913
0.9367	High Similarity	NPC470402
0.9367	High Similarity	NPC472910
0.9367	High Similarity	NPC222814
0.9363	High Similarity	NPC37392
0.9363	High Similarity	NPC2928
0.9337	High Similarity	NPC265380
0.9329	High Similarity	NPC267254
0.9329	High Similarity	NPC205076
0.9329	High Similarity	NPC307518
0.9329	High Similarity	NPC48773
0.9329	High Similarity	NPC301683
0.9325	High Similarity	NPC471457
0.9325	High Similarity	NPC229687
0.9325	High Similarity	NPC95855
0.9325	High Similarity	NPC475212
0.9325	High Similarity	NPC210042
0.9325	High Similarity	NPC183036
0.9325	High Similarity	NPC472383
0.9325	High Similarity	NPC472381
0.9325	High Similarity	NPC112755
0.9325	High Similarity	NPC170675
0.9317	High Similarity	NPC272064
0.9313	High Similarity	NPC134783
0.9313	High Similarity	NPC266314
0.9313	High Similarity	NPC472632
0.9313	High Similarity	NPC26326
0.9308	High Similarity	NPC190487
0.9308	High Similarity	NPC250214
0.9308	High Similarity	NPC95936
0.9308	High Similarity	NPC154304
0.9299	High Similarity	NPC472915
0.9299	High Similarity	NPC18727
0.9299	High Similarity	NPC292214
0.9299	High Similarity	NPC88645
0.9299	High Similarity	NPC167091
0.9299	High Similarity	NPC206238
0.9299	High Similarity	NPC271779
0.9277	High Similarity	NPC472992
0.9277	High Similarity	NPC472991
0.9273	High Similarity	NPC204693
0.9268	High Similarity	NPC231194
0.9268	High Similarity	NPC224462
0.9268	High Similarity	NPC51326
0.9268	High Similarity	NPC74559
0.9268	High Similarity	NPC105511
0.9268	High Similarity	NPC476365
0.9264	High Similarity	NPC45400
0.9264	High Similarity	NPC93099
0.9264	High Similarity	NPC117854
0.9264	High Similarity	NPC6588
0.9264	High Similarity	NPC477154
0.9259	High Similarity	NPC142614
0.9259	High Similarity	NPC50960
0.9259	High Similarity	NPC471788
0.9255	High Similarity	NPC83922
0.9255	High Similarity	NPC472448
0.925	High Similarity	NPC471976
0.925	High Similarity	NPC188967
0.925	High Similarity	NPC174953
0.925	High Similarity	NPC53889
0.9245	High Similarity	NPC129684
0.9245	High Similarity	NPC299520
0.9245	High Similarity	NPC474055
0.9245	High Similarity	NPC185526
0.9245	High Similarity	NPC78225
0.9245	High Similarity	NPC472598
0.9245	High Similarity	NPC262286
0.9245	High Similarity	NPC223787
0.9245	High Similarity	NPC36852
0.9245	High Similarity	NPC291508
0.9245	High Similarity	NPC469584
0.9245	High Similarity	NPC181960
0.9245	High Similarity	NPC52530
0.9241	High Similarity	NPC4455
0.9241	High Similarity	NPC138360
0.9241	High Similarity	NPC280339
0.9241	High Similarity	NPC213622
0.9241	High Similarity	NPC201136
0.9241	High Similarity	NPC256612
0.9241	High Similarity	NPC208197
0.9241	High Similarity	NPC146165
0.9241	High Similarity	NPC50715
0.9241	High Similarity	NPC92659
0.9241	High Similarity	NPC128863
0.9241	High Similarity	NPC20830
0.9241	High Similarity	NPC183597
0.9241	High Similarity	NPC227325
0.9241	High Similarity	NPC167815
0.9241	High Similarity	NPC196439
0.9241	High Similarity	NPC163780
0.9241	High Similarity	NPC472909
0.9241	High Similarity	NPC2476
0.9236	High Similarity	NPC101996
0.9236	High Similarity	NPC236637
0.9236	High Similarity	NPC180234
0.9236	High Similarity	NPC120537
0.9236	High Similarity	NPC477231
0.9236	High Similarity	NPC161277
0.9236	High Similarity	NPC39007
0.9236	High Similarity	NPC302950
0.9236	High Similarity	NPC257648
0.9236	High Similarity	NPC219582
0.9236	High Similarity	NPC199100
0.9217	High Similarity	NPC102028
0.9217	High Similarity	NPC142996
0.9212	High Similarity	NPC475155
0.9212	High Similarity	NPC156977
0.9212	High Similarity	NPC257667
0.9212	High Similarity	NPC67134
0.9212	High Similarity	NPC186847
0.9212	High Similarity	NPC3583
0.9212	High Similarity	NPC47140
0.9212	High Similarity	NPC121333
0.9212	High Similarity	NPC259152
0.9212	High Similarity	NPC472386
0.9212	High Similarity	NPC472454
0.9207	High Similarity	NPC58053
0.9207	High Similarity	NPC326877
0.9207	High Similarity	NPC186807
0.9207	High Similarity	NPC226294
0.9207	High Similarity	NPC201292
0.9207	High Similarity	NPC177480
0.9207	High Similarity	NPC475942

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 NPC14662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	965
0.2-0.3	1918
0.3-0.4	2669
0.4-0.5	1736
0.5-0.6	935
0.6-0.7	344
0.7-0.8	113
0.8-0.85	24
0.85-0.9	19
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9623	High Similarity	NPD6168	Clinical (unspecified phase)
0.9623	High Similarity	NPD6166	Phase 2
0.9623	High Similarity	NPD6167	Clinical (unspecified phase)
0.9236	High Similarity	NPD1934	Approved
0.9177	High Similarity	NPD2801	Approved
0.9152	High Similarity	NPD7074	Phase 3
0.9091	High Similarity	NPD7054	Approved
0.9062	High Similarity	NPD4868	Clinical (unspecified phase)
0.9057	High Similarity	NPD2393	Clinical (unspecified phase)
0.9036	High Similarity	NPD7472	Approved
0.8916	High Similarity	NPD3818	Discontinued
0.8896	High Similarity	NPD5494	Approved
0.8876	High Similarity	NPD4338	Clinical (unspecified phase)
0.8869	High Similarity	NPD6797	Phase 2
0.8869	High Similarity	NPD7993	Clinical (unspecified phase)
0.8827	High Similarity	NPD3882	Suspended
0.8817	High Similarity	NPD7251	Discontinued
0.8765	High Similarity	NPD7808	Phase 3
0.875	High Similarity	NPD4380	Phase 2
0.8659	High Similarity	NPD4381	Clinical (unspecified phase)
0.8639	High Similarity	NPD5844	Phase 1
0.8608	High Similarity	NPD1511	Approved
0.8537	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD6959	Discontinued
0.85	High Similarity	NPD1512	Approved
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD5402	Approved
0.8424	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8364	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7473	Discontinued
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD6559	Discontinued
0.8165	Intermediate Similarity	NPD2796	Approved
0.8156	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7819	Suspended
0.814	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.7977	Intermediate Similarity	NPD3926	Phase 2
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD1247	Approved
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1240	Approved
0.7943	Intermediate Similarity	NPD3751	Discontinued
0.7895	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5401	Approved
0.7877	Intermediate Similarity	NPD8313	Approved
0.7877	Intermediate Similarity	NPD8312	Approved
0.7862	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7844	Intermediate Similarity	NPD1653	Approved
0.7841	Intermediate Similarity	NPD7228	Approved
0.7836	Intermediate Similarity	NPD7768	Phase 2
0.7816	Intermediate Similarity	NPD3787	Discontinued
0.7805	Intermediate Similarity	NPD6190	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3027	Phase 3
0.7759	Intermediate Similarity	NPD7199	Phase 2
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD230	Phase 1
0.7683	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD6778	Approved
0.7672	Intermediate Similarity	NPD6777	Approved
0.7672	Intermediate Similarity	NPD6776	Approved
0.7672	Intermediate Similarity	NPD6779	Approved
0.7672	Intermediate Similarity	NPD6780	Approved
0.7672	Intermediate Similarity	NPD6781	Approved
0.7672	Intermediate Similarity	NPD6782	Approved
0.7644	Intermediate Similarity	NPD6234	Discontinued
0.7644	Intermediate Similarity	NPD919	Approved
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD3750	Approved
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.7579	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD447	Suspended
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7685	Pre-registration
0.7558	Intermediate Similarity	NPD37	Approved
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7696	Phase 3
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7552	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD7698	Approved
0.7551	Intermediate Similarity	NPD7783	Phase 2
0.7551	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7485	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.747	Intermediate Similarity	NPD2800	Approved
0.7457	Intermediate Similarity	NPD6844	Discontinued
0.7456	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD2532	Approved
0.7455	Intermediate Similarity	NPD2344	Approved
0.7439	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD9494	Approved
0.7418	Intermediate Similarity	NPD5953	Discontinued
0.7414	Intermediate Similarity	NPD8455	Phase 2
0.7409	Intermediate Similarity	NPD6823	Phase 2
0.7407	Intermediate Similarity	NPD6535	Approved
0.7407	Intermediate Similarity	NPD6534	Approved
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7700	Phase 2
0.7382	Intermediate Similarity	NPD7699	Phase 2
0.7377	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD920	Approved
0.7366	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7266	Discontinued
0.7337	Intermediate Similarity	NPD7549	Discontinued
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3748	Approved
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD7286	Phase 2
0.7289	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD6100	Approved
0.7286	Intermediate Similarity	NPD7801	Approved
0.7283	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7584	Approved
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2346	Discontinued
0.7243	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6233	Phase 2
0.7229	Intermediate Similarity	NPD2799	Discontinued
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7212	Intermediate Similarity	NPD6651	Approved
0.7182	Intermediate Similarity	NPD5242	Approved
0.7178	Intermediate Similarity	NPD6798	Discontinued
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7175	Intermediate Similarity	NPD5353	Approved
0.7173	Intermediate Similarity	NPD6212	Phase 3
0.7173	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6213	Phase 3
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD6832	Phase 2
0.716	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7680	Approved
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7097	Intermediate Similarity	NPD7039	Approved
0.7097	Intermediate Similarity	NPD7038	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD1203	Approved
0.7077	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7033	Intermediate Similarity	NPD5711	Approved
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD5710	Approved
0.7016	Intermediate Similarity	NPD4287	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6385	Approved
0.7006	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6971	Remote Similarity	NPD7907	Approved
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD2899	Discontinued
0.6957	Remote Similarity	NPD4111	Phase 1
0.6957	Remote Similarity	NPD4665	Approved
0.6957	Remote Similarity	NPD7784	Clinical (unspecified phase)

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