NPASS Compound

Structure

NPC112418 OpenBabel07101719522D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 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 -2.5981 -0.5000 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 -1.7321 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 1.7321 0.0000 0.0000 C 0 0 0 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 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 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 8 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 19 2 0 0 0 0 8 25 1 0 0 0 0 10 24 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 9 1 1 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	2.427
LogD:	2.056
LogS:	-3.972
# Rotatable Bonds:	4
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	3.375
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.475
MDCK Permeability:	1.5616131349815987e-05
Pgp-inhibitor:	0.616
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.338

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	94.79391479492188%
Volume Distribution (VD):	0.638
Pgp-substrate:	6.218271732330322%

ADMET: Metabolism

CYP1A2-inhibitor:	0.54
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.782
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	2.989
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.154
Rat Oral Acute Toxicity:	0.293
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.408
Carcinogencity:	0.271
Eye Corrosion:	0.003
Eye Irritation:	0.883
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: NPC112418

Natural Product ID:	NPC112418
*Common Name:**	3-O-Acetylpadmatin
IUPAC Name:	[(2R,3R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydrochromen-3-yl] acetate
Synonyms:	3-O-Acetylpadmatin
Standard InCHIKey:	WWYQJKVSCKMFCP-MSOLQXFVSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-8(19)25-18-16(23)15-13(22)6-10(24-2)7-14(15)26-17(18)9-3-4-11(20)12(21)5-9/h3-7,17-18,20-22H,1-2H3/t17-,18+/m1/s1
SMILES:	CC(=O)O[C@H]1C(=O)c2c(cc(cc2O[C@@H]1c1ccc(c(c1)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491542
PubChem CID:	10406203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated 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
NPO33456	inula viscosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217718]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	83.0	%	PMID[524251]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-1.0	%	PMID[524251]

☑ 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 NPC112418 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	374
0.1-0.2	1612
0.2-0.3	4195
0.3-0.4	9065
0.4-0.5	8726
0.5-0.6	3688
0.6-0.7	4727
0.7-0.8	5386
0.8-0.85	3031
0.85-0.9	1583
0.9-0.95	300
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC471745
0.9934	High Similarity	NPC471744
0.9737	High Similarity	NPC471500
0.9673	High Similarity	NPC471479
0.9673	High Similarity	NPC471515
0.9487	High Similarity	NPC471499
0.9484	High Similarity	NPC22192
0.9481	High Similarity	NPC250922
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9477	High Similarity	NPC18727
0.9437	High Similarity	NPC116864
0.9437	High Similarity	NPC244776
0.943	High Similarity	NPC88243
0.9423	High Similarity	NPC470326
0.9423	High Similarity	NPC287328
0.9423	High Similarity	NPC470183
0.9423	High Similarity	NPC282009
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC108456
0.9419	High Similarity	NPC67876
0.9416	High Similarity	NPC471746
0.9412	High Similarity	NPC9743
0.9412	High Similarity	NPC61506
0.9412	High Similarity	NPC260491
0.9412	High Similarity	NPC240476
0.9412	High Similarity	NPC236637
0.9412	High Similarity	NPC302950
0.9412	High Similarity	NPC219582
0.9412	High Similarity	NPC36835
0.9412	High Similarity	NPC19721
0.9412	High Similarity	NPC246162
0.9379	High Similarity	NPC190003
0.9379	High Similarity	NPC153755
0.9379	High Similarity	NPC175107
0.9375	High Similarity	NPC52382
0.9375	High Similarity	NPC270578
0.9363	High Similarity	NPC289771
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC35038
0.9355	High Similarity	NPC278778
0.9351	High Similarity	NPC141212
0.9351	High Similarity	NPC27532
0.9351	High Similarity	NPC270620
0.9351	High Similarity	NPC325028
0.9351	High Similarity	NPC192083
0.9351	High Similarity	NPC246328
0.9351	High Similarity	NPC236223
0.9351	High Similarity	NPC179126
0.9351	High Similarity	NPC162351
0.9351	High Similarity	NPC78326
0.9351	High Similarity	NPC58382
0.9351	High Similarity	NPC256346
0.9351	High Similarity	NPC213896
0.9346	High Similarity	NPC295650
0.9342	High Similarity	NPC477941
0.9321	High Similarity	NPC4390
0.9317	High Similarity	NPC235260
0.9317	High Similarity	NPC20505
0.9317	High Similarity	NPC155763
0.9313	High Similarity	NPC52550
0.9313	High Similarity	NPC173637
0.9313	High Similarity	NPC127546
0.9313	High Similarity	NPC317489
0.9313	High Similarity	NPC92565
0.9313	High Similarity	NPC84362
0.9313	High Similarity	NPC160156
0.9313	High Similarity	NPC223424
0.9308	High Similarity	NPC36
0.9308	High Similarity	NPC125039
0.9308	High Similarity	NPC7688
0.9308	High Similarity	NPC72787
0.9308	High Similarity	NPC58223
0.9308	High Similarity	NPC7154
0.9308	High Similarity	NPC36916
0.9304	High Similarity	NPC300537
0.9304	High Similarity	NPC127782
0.9299	High Similarity	NPC263449
0.9295	High Similarity	NPC474208
0.9295	High Similarity	NPC475267
0.9295	High Similarity	NPC48208
0.9295	High Similarity	NPC291508
0.9295	High Similarity	NPC474836
0.9295	High Similarity	NPC474055
0.9295	High Similarity	NPC27337
0.9295	High Similarity	NPC156057
0.9295	High Similarity	NPC162869
0.9295	High Similarity	NPC472598
0.929	High Similarity	NPC200761
0.929	High Similarity	NPC67396
0.929	High Similarity	NPC133392
0.929	High Similarity	NPC470327
0.929	High Similarity	NPC321779
0.929	High Similarity	NPC45849
0.929	High Similarity	NPC477503
0.9286	High Similarity	NPC106976
0.9286	High Similarity	NPC123886
0.9286	High Similarity	NPC279989
0.9286	High Similarity	NPC82325
0.9286	High Similarity	NPC472912
0.9281	High Similarity	NPC188871
0.9281	High Similarity	NPC149127
0.9281	High Similarity	NPC338131
0.9281	High Similarity	NPC286342
0.9276	High Similarity	NPC188679
0.9276	High Similarity	NPC321011
0.9276	High Similarity	NPC294852
0.9259	High Similarity	NPC476370
0.9255	High Similarity	NPC138927
0.9255	High Similarity	NPC219904
0.9255	High Similarity	NPC203050
0.9255	High Similarity	NPC120099
0.9255	High Similarity	NPC223747
0.9255	High Similarity	NPC225434
0.925	High Similarity	NPC73855
0.925	High Similarity	NPC179950
0.925	High Similarity	NPC277174
0.925	High Similarity	NPC145038
0.925	High Similarity	NPC281131
0.925	High Similarity	NPC88789
0.925	High Similarity	NPC135599
0.925	High Similarity	NPC253662
0.925	High Similarity	NPC118284
0.925	High Similarity	NPC113968
0.925	High Similarity	NPC13481
0.925	High Similarity	NPC328940
0.925	High Similarity	NPC471213
0.925	High Similarity	NPC308404
0.925	High Similarity	NPC274618
0.925	High Similarity	NPC56077
0.925	High Similarity	NPC276222
0.925	High Similarity	NPC207575
0.925	High Similarity	NPC477517
0.9245	High Similarity	NPC472625
0.9241	High Similarity	NPC142252
0.9241	High Similarity	NPC308992
0.9241	High Similarity	NPC472634
0.9241	High Similarity	NPC158188
0.9241	High Similarity	NPC26326
0.9241	High Similarity	NPC173137
0.9236	High Similarity	NPC105242
0.9236	High Similarity	NPC300943
0.9236	High Similarity	NPC9609
0.9236	High Similarity	NPC115798
0.9236	High Similarity	NPC25495
0.9236	High Similarity	NPC261004
0.9236	High Similarity	NPC19687
0.9236	High Similarity	NPC53545
0.9236	High Similarity	NPC143828
0.9236	High Similarity	NPC117418
0.9236	High Similarity	NPC176300
0.9236	High Similarity	NPC18607
0.9236	High Similarity	NPC152904
0.9236	High Similarity	NPC55738
0.9236	High Similarity	NPC4481
0.9236	High Similarity	NPC22472
0.9236	High Similarity	NPC253634
0.9236	High Similarity	NPC191459
0.9236	High Similarity	NPC288669
0.9236	High Similarity	NPC204854
0.9236	High Similarity	NPC130894
0.9236	High Similarity	NPC7846
0.9236	High Similarity	NPC18772
0.9236	High Similarity	NPC152166
0.9231	High Similarity	NPC24640
0.9231	High Similarity	NPC100916
0.9231	High Similarity	NPC474638
0.9231	High Similarity	NPC55619
0.9231	High Similarity	NPC200388
0.9231	High Similarity	NPC470328
0.9231	High Similarity	NPC235165
0.9231	High Similarity	NPC255106
0.9231	High Similarity	NPC227062
0.9231	High Similarity	NPC265511
0.9231	High Similarity	NPC472626
0.9231	High Similarity	NPC201837
0.9231	High Similarity	NPC209614
0.9226	High Similarity	NPC74924
0.9226	High Similarity	NPC298692
0.9221	High Similarity	NPC252933
0.9221	High Similarity	NPC54394
0.9221	High Similarity	NPC50403
0.9221	High Similarity	NPC76376
0.9221	High Similarity	NPC200740
0.9221	High Similarity	NPC236769
0.9221	High Similarity	NPC260895
0.9221	High Similarity	NPC125062
0.9221	High Similarity	NPC133953
0.9221	High Similarity	NPC28274
0.9216	High Similarity	NPC1612
0.9216	High Similarity	NPC270465
0.9216	High Similarity	NPC87125
0.9216	High Similarity	NPC183959
0.9207	High Similarity	NPC472380
0.9207	High Similarity	NPC471669
0.9207	High Similarity	NPC472384
0.9207	High Similarity	NPC268533
0.9207	High Similarity	NPC473862

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 NPC112418 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	920
0.2-0.3	1838
0.3-0.4	2541
0.4-0.5	1789
0.5-0.6	1040
0.6-0.7	478
0.7-0.8	134
0.8-0.85	40
0.85-0.9	17
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD3817	Phase 2
0.9412	High Similarity	NPD1934	Approved
0.9351	High Similarity	NPD2393	Clinical (unspecified phase)
0.9308	High Similarity	NPD6166	Phase 2
0.9308	High Similarity	NPD6167	Clinical (unspecified phase)
0.9308	High Similarity	NPD6168	Clinical (unspecified phase)
0.9295	High Similarity	NPD7075	Discontinued
0.9146	High Similarity	NPD4338	Clinical (unspecified phase)
0.9141	High Similarity	NPD6797	Phase 2
0.9108	High Similarity	NPD3882	Suspended
0.9108	High Similarity	NPD4868	Clinical (unspecified phase)
0.9103	High Similarity	NPD7096	Clinical (unspecified phase)
0.9085	High Similarity	NPD7251	Discontinued
0.902	High Similarity	NPD1512	Approved
0.8981	High Similarity	NPD2801	Approved
0.8963	High Similarity	NPD7074	Phase 3
0.8917	High Similarity	NPD6801	Discontinued
0.8916	High Similarity	NPD7808	Phase 3
0.8902	High Similarity	NPD7054	Approved
0.8889	High Similarity	NPD1511	Approved
0.8889	High Similarity	NPD6799	Approved
0.8848	High Similarity	NPD7472	Approved
0.8841	High Similarity	NPD3818	Discontinued
0.8795	High Similarity	NPD7993	Clinical (unspecified phase)
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.8688	High Similarity	NPD5402	Approved
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8671	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD6599	Discontinued
0.8625	High Similarity	NPD7819	Suspended
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8599	High Similarity	NPD5403	Approved
0.8562	High Similarity	NPD1549	Phase 2
0.85	High Similarity	NPD7411	Suspended
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8471	Intermediate Similarity	NPD5401	Approved
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8395	Intermediate Similarity	NPD1465	Phase 2
0.8364	Intermediate Similarity	NPD5494	Approved
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8312	Intermediate Similarity	NPD2796	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8303	Intermediate Similarity	NPD919	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8204	Intermediate Similarity	NPD6959	Discontinued
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6190	Approved
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD1613	Approved
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD230	Phase 1
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD1607	Approved
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD943	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.7962	Intermediate Similarity	NPD1551	Phase 2
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3749	Approved
0.791	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7866	Intermediate Similarity	NPD1653	Approved
0.7861	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD6798	Discontinued
0.7836	Intermediate Similarity	NPD3787	Discontinued
0.7821	Intermediate Similarity	NPD447	Suspended
0.7814	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5953	Discontinued
0.7711	Intermediate Similarity	NPD3226	Approved
0.7707	Intermediate Similarity	NPD6355	Discontinued
0.7707	Intermediate Similarity	NPD1933	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD6233	Phase 2
0.7679	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD8434	Phase 2
0.7657	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7613	Intermediate Similarity	NPD6832	Phase 2
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7593	Intermediate Similarity	NPD1243	Approved
0.7593	Intermediate Similarity	NPD2800	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7562	Intermediate Similarity	NPD7033	Discontinued
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1203	Approved
0.7532	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7266	Discontinued
0.7438	Intermediate Similarity	NPD6651	Approved
0.7429	Intermediate Similarity	NPD5710	Approved
0.7429	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7407	Intermediate Similarity	NPD6782	Approved
0.7405	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD2354	Approved
0.7394	Intermediate Similarity	NPD3887	Approved
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD5242	Approved
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5353	Approved
0.7378	Intermediate Similarity	NPD1652	Phase 2
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7362	Intermediate Similarity	NPD2344	Approved
0.7358	Intermediate Similarity	NPD4062	Phase 3
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7095	Approved
0.7338	Intermediate Similarity	NPD9269	Phase 2
0.7338	Intermediate Similarity	NPD9717	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.7325	Intermediate Similarity	NPD9494	Approved
0.7308	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD7390	Discontinued
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7247	Intermediate Similarity	NPD2403	Approved
0.7239	Intermediate Similarity	NPD4308	Phase 3
0.7239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD5049	Phase 3
0.7209	Intermediate Similarity	NPD6385	Approved
0.7209	Intermediate Similarity	NPD6386	Approved
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7202	Intermediate Similarity	NPD7697	Approved
0.7202	Intermediate Similarity	NPD7698	Approved
0.7202	Intermediate Similarity	NPD7696	Phase 3
0.7198	Intermediate Similarity	NPD7240	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD411	Approved
0.7186	Intermediate Similarity	NPD2309	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.7165	Intermediate Similarity	NPD7871	Phase 2
0.7165	Intermediate Similarity	NPD8320	Phase 1
0.7165	Intermediate Similarity	NPD8319	Approved
0.7165	Intermediate Similarity	NPD7870	Phase 2
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3146	Approved
0.716	Intermediate Similarity	NPD4340	Discontinued
0.7159	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD2355	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