NPASS Compound

Structure

CID101107 OpenBabel06191715442D 37 42 0 0 1 0 0 0 0 0999 V2000 -7.5060 -3.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7708 -3.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2471 -0.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7460 -0.8693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5705 2.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0260 1.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6387 -1.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7713 -1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4210 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2455 0.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4738 1.4277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6488 -1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6385 -2.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5964 0.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7715 -0.4771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2981 0.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 0.9518 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.4733 -1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8244 -1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6490 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4734 -0.4765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9472 0.9513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7719 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1228 1.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5961 -0.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9470 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8243 -0.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2453 -0.0016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8246 1.4279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3239 -1.9195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0262 -1.9194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7721 2.4290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1230 2.4294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1224 -0.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4206 -0.4774 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 29 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 14 23 2 0 0 0 0 14 25 1 0 0 0 0 15 25 2 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 16 27 2 0 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 18 31 1 0 0 0 0 19 28 2 0 0 0 0 19 32 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 26 2 0 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 25 36 1 0 0 0 0 26 35 1 0 0 0 0 27 35 1 0 0 0 0 28 37 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.2
Volume:	511.264
LogP:	7.799
LogD:	4.401
LogS:	-1.782
# Rotatable Bonds:	2
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	4.303
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	1.5990119209163822e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.544
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	99.03987121582031%
Volume Distribution (VD):	0.539
Pgp-substrate:	3.4702322483062744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.295
CYP2C19-inhibitor:	0.328
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.814
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	1.298
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.452
Carcinogencity:	0.636
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC101107

Natural Product ID:	NPC101107
*Common Name:**	Artonin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CYONWSIQFYQFOS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H30O7/c1-13(2)7-8-15-25-14(9-10-29(3,4)36-25)23(33)22-24(34)16-11-17-20-21(27(16)35-26(15)22)18(31)12-19(32)28(20)37-30(17,5)6/h7,9-10,12,17,31-33H,8,11H2,1-6H3
SMILES:	CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1oc1c3c(O)cc(c4c3C(Cc1c2=O)C(O4)(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516550
PubChem CID:	14557102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26579	Artocarpus fretessi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26579	Artocarpus fretessi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17767	Artocarpus heterophyllus	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	6.1	ug ml-1	PMID[512789]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	6.7	ug ml-1	PMID[512789]

☑ 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 NPC101107 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	478
0.1-0.2	1967
0.2-0.3	4268
0.3-0.4	11029
0.4-0.5	7172
0.5-0.6	3825
0.6-0.7	5379
0.7-0.8	5402
0.8-0.85	2098
0.85-0.9	912
0.9-0.95	150
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC475805
0.9812	High Similarity	NPC476637
0.975	High Similarity	NPC126204
0.9748	High Similarity	NPC156432
0.9444	High Similarity	NPC37870
0.9444	High Similarity	NPC472449
0.9441	High Similarity	NPC23298
0.9441	High Similarity	NPC189473
0.9437	High Similarity	NPC278427
0.9383	High Similarity	NPC239752
0.9383	High Similarity	NPC275780
0.9383	High Similarity	NPC472450
0.9325	High Similarity	NPC39091
0.9321	High Similarity	NPC207690
0.9317	High Similarity	NPC259456
0.9308	High Similarity	NPC276444
0.9308	High Similarity	NPC471985
0.9264	High Similarity	NPC303174
0.9259	High Similarity	NPC329760
0.9259	High Similarity	NPC229632
0.9259	High Similarity	NPC25152
0.9255	High Similarity	NPC471973
0.9255	High Similarity	NPC204290
0.9255	High Similarity	NPC139036
0.925	High Similarity	NPC476630
0.925	High Similarity	NPC218871
0.9222	High Similarity	NPC227906
0.9212	High Similarity	NPC188079
0.9207	High Similarity	NPC170245
0.9207	High Similarity	NPC272502
0.9207	High Similarity	NPC43319
0.9202	High Similarity	NPC186686
0.9202	High Similarity	NPC248638
0.9202	High Similarity	NPC152659
0.9202	High Similarity	NPC146134
0.9202	High Similarity	NPC270837
0.9202	High Similarity	NPC236521
0.9198	High Similarity	NPC61010
0.9198	High Similarity	NPC29876
0.9198	High Similarity	NPC167678
0.9193	High Similarity	NPC197856
0.9193	High Similarity	NPC474290
0.9193	High Similarity	NPC280680
0.9193	High Similarity	NPC100123
0.9182	High Similarity	NPC170492
0.9152	High Similarity	NPC218226
0.9152	High Similarity	NPC476306
0.9146	High Similarity	NPC326520
0.9141	High Similarity	NPC472448
0.9141	High Similarity	NPC294965
0.9141	High Similarity	NPC206605
0.9141	High Similarity	NPC194427
0.9141	High Similarity	NPC474162
0.9141	High Similarity	NPC78332
0.9141	High Similarity	NPC261470
0.9141	High Similarity	NPC474150
0.9141	High Similarity	NPC83922
0.9136	High Similarity	NPC14353
0.9136	High Similarity	NPC200746
0.9136	High Similarity	NPC476980
0.9136	High Similarity	NPC476280
0.9136	High Similarity	NPC320359
0.9136	High Similarity	NPC56085
0.9136	High Similarity	NPC228785
0.913	High Similarity	NPC136674
0.9096	High Similarity	NPC165456
0.9091	High Similarity	NPC120593
0.9085	High Similarity	NPC306321
0.9085	High Similarity	NPC236132
0.9085	High Similarity	NPC475985
0.9085	High Similarity	NPC303460
0.9085	High Similarity	NPC220313
0.9085	High Similarity	NPC12461
0.908	High Similarity	NPC40037
0.908	High Similarity	NPC40491
0.908	High Similarity	NPC198829
0.908	High Similarity	NPC66288
0.908	High Similarity	NPC278052
0.9074	High Similarity	NPC476242
0.9074	High Similarity	NPC46736
0.9074	High Similarity	NPC184755
0.9074	High Similarity	NPC74178
0.9068	High Similarity	NPC142339
0.9068	High Similarity	NPC68093
0.9068	High Similarity	NPC274730
0.9068	High Similarity	NPC191146
0.9053	High Similarity	NPC216307
0.9048	High Similarity	NPC310794
0.9042	High Similarity	NPC472276
0.9036	High Similarity	NPC117854
0.9036	High Similarity	NPC477154
0.9036	High Similarity	NPC6588
0.903	High Similarity	NPC293319
0.903	High Similarity	NPC85057
0.903	High Similarity	NPC130920
0.903	High Similarity	NPC50960
0.9024	High Similarity	NPC472402
0.9024	High Similarity	NPC81679
0.9024	High Similarity	NPC52204
0.9018	High Similarity	NPC118256
0.9018	High Similarity	NPC297212
0.9018	High Similarity	NPC119224
0.9018	High Similarity	NPC45146
0.9018	High Similarity	NPC328102
0.9018	High Similarity	NPC119209
0.9018	High Similarity	NPC192686
0.9018	High Similarity	NPC474960
0.9018	High Similarity	NPC235018
0.9018	High Similarity	NPC80375
0.9018	High Similarity	NPC472624
0.9018	High Similarity	NPC36217
0.9012	High Similarity	NPC241904
0.9012	High Similarity	NPC237418
0.9012	High Similarity	NPC273843
0.9012	High Similarity	NPC236796
0.9012	High Similarity	NPC218313
0.9012	High Similarity	NPC476981
0.9012	High Similarity	NPC78225
0.9012	High Similarity	NPC217677
0.9012	High Similarity	NPC474681
0.9012	High Similarity	NPC165977
0.9012	High Similarity	NPC300727
0.9006	High Similarity	NPC472280
0.9006	High Similarity	NPC234255
0.9006	High Similarity	NPC166054
0.9006	High Similarity	NPC55662
0.9	High Similarity	NPC471982
0.9	High Similarity	NPC237994
0.9	High Similarity	NPC249570
0.8994	High Similarity	NPC3825
0.8994	High Similarity	NPC88804
0.8988	High Similarity	NPC4200
0.8988	High Similarity	NPC475825
0.8988	High Similarity	NPC223375
0.8982	High Similarity	NPC288813
0.8976	High Similarity	NPC173292
0.8976	High Similarity	NPC472452
0.8976	High Similarity	NPC235610
0.897	High Similarity	NPC273959
0.897	High Similarity	NPC7483
0.8963	High Similarity	NPC266314
0.8963	High Similarity	NPC234644
0.8963	High Similarity	NPC32694
0.8963	High Similarity	NPC474038
0.8963	High Similarity	NPC258331
0.8963	High Similarity	NPC474187
0.8963	High Similarity	NPC472906
0.8957	High Similarity	NPC469658
0.8957	High Similarity	NPC204879
0.8957	High Similarity	NPC235448
0.8953	High Similarity	NPC150977
0.8951	High Similarity	NPC472907
0.8951	High Similarity	NPC133970
0.8951	High Similarity	NPC282307
0.8951	High Similarity	NPC470762
0.8951	High Similarity	NPC474167
0.8951	High Similarity	NPC13779
0.8951	High Similarity	NPC170026
0.8951	High Similarity	NPC6633
0.8951	High Similarity	NPC5322
0.8951	High Similarity	NPC475799
0.8951	High Similarity	NPC472455
0.8951	High Similarity	NPC138243
0.8944	High Similarity	NPC176775
0.8944	High Similarity	NPC231018
0.8944	High Similarity	NPC280530
0.8944	High Similarity	NPC183878
0.8944	High Similarity	NPC22519
0.8944	High Similarity	NPC69394
0.8944	High Similarity	NPC89474
0.8944	High Similarity	NPC274327
0.8944	High Similarity	NPC95842
0.8944	High Similarity	NPC255350
0.8944	High Similarity	NPC145379
0.8944	High Similarity	NPC178964
0.8944	High Similarity	NPC47781
0.8944	High Similarity	NPC160951
0.8944	High Similarity	NPC476631
0.8944	High Similarity	NPC472905
0.8938	High Similarity	NPC154345
0.8922	High Similarity	NPC150131
0.8922	High Similarity	NPC474024
0.8916	High Similarity	NPC473286
0.8916	High Similarity	NPC25361
0.8916	High Similarity	NPC259757
0.8909	High Similarity	NPC472635
0.8909	High Similarity	NPC8300
0.8909	High Similarity	NPC470694
0.8909	High Similarity	NPC201800
0.8902	High Similarity	NPC475886
0.8902	High Similarity	NPC246478
0.8902	High Similarity	NPC474287
0.8902	High Similarity	NPC476170
0.8902	High Similarity	NPC188433
0.8902	High Similarity	NPC475784
0.8902	High Similarity	NPC476283
0.8896	High Similarity	NPC472911
0.8896	High Similarity	NPC473272
0.8896	High Similarity	NPC36852
0.8896	High Similarity	NPC27337

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 NPC101107 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	1009
0.2-0.3	1741
0.3-0.4	2819
0.4-0.5	1774
0.5-0.6	891
0.6-0.7	340
0.7-0.8	127
0.8-0.85	22
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD2801	Approved
0.8712	High Similarity	NPD2393	Clinical (unspecified phase)
0.8675	High Similarity	NPD5494	Approved
0.865	High Similarity	NPD1934	Approved
0.8616	High Similarity	NPD1511	Approved
0.8509	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD3882	Suspended
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7473	Discontinued
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8353	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD5844	Phase 1
0.8324	Intermediate Similarity	NPD7054	Approved
0.8276	Intermediate Similarity	NPD7472	Approved
0.8276	Intermediate Similarity	NPD7074	Phase 3
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD3817	Phase 2
0.8193	Intermediate Similarity	NPD4380	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8136	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8079	Intermediate Similarity	NPD7251	Discontinued
0.8047	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD1465	Phase 2
0.8034	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD3750	Approved
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2800	Approved
0.791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3749	Approved
0.7907	Intermediate Similarity	NPD7075	Discontinued
0.7907	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2532	Approved
0.7892	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7759	Intermediate Similarity	NPD919	Approved
0.7744	Intermediate Similarity	NPD1549	Phase 2
0.773	Intermediate Similarity	NPD2796	Approved
0.7725	Intermediate Similarity	NPD7390	Discontinued
0.7719	Intermediate Similarity	NPD7411	Suspended
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.767	Intermediate Similarity	NPD7199	Phase 2
0.7669	Intermediate Similarity	NPD3748	Approved
0.7661	Intermediate Similarity	NPD6599	Discontinued
0.7654	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD943	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.7624	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD6799	Approved
0.7602	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3751	Discontinued
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7543	Intermediate Similarity	NPD4965	Approved
0.7541	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5403	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD2346	Discontinued
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3787	Discontinued
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7346	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD1613	Approved
0.7317	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7435	Discontinued
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3300	Phase 2
0.7251	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3027	Phase 3
0.7238	Intermediate Similarity	NPD7229	Phase 3
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7214	Intermediate Similarity	NPD7783	Phase 2
0.7214	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD7698	Approved
0.7208	Intermediate Similarity	NPD7696	Phase 3
0.7204	Intermediate Similarity	NPD7685	Pre-registration
0.7204	Intermediate Similarity	NPD7240	Approved
0.7202	Intermediate Similarity	NPD1551	Phase 2
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7195	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2309	Approved
0.7172	Intermediate Similarity	NPD7871	Phase 2
0.7172	Intermediate Similarity	NPD7870	Phase 2
0.7169	Intermediate Similarity	NPD230	Phase 1
0.7158	Intermediate Similarity	NPD2403	Approved
0.7157	Intermediate Similarity	NPD6823	Phase 2
0.715	Intermediate Similarity	NPD4360	Phase 2
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD7701	Phase 2
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD1653	Approved
0.7136	Intermediate Similarity	NPD4111	Phase 1
0.7136	Intermediate Similarity	NPD4665	Approved
0.7129	Intermediate Similarity	NPD7801	Approved
0.7114	Intermediate Similarity	NPD8151	Discontinued
0.7113	Intermediate Similarity	NPD4361	Phase 2
0.7113	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7095	Intermediate Similarity	NPD4288	Approved
0.7091	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD4749	Approved
0.7079	Intermediate Similarity	NPD7874	Approved
0.7079	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7549	Discontinued
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7069	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7907	Approved
0.7063	Intermediate Similarity	NPD1201	Approved
0.7062	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD5953	Discontinued
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7055	Intermediate Similarity	NPD2798	Approved
0.7043	Intermediate Similarity	NPD7286	Phase 2
0.7041	Intermediate Similarity	NPD7699	Phase 2
0.7041	Intermediate Similarity	NPD7700	Phase 2
0.7035	Intermediate Similarity	NPD7003	Approved
0.7035	Intermediate Similarity	NPD8166	Discontinued
0.7031	Intermediate Similarity	NPD4287	Approved
0.702	Intermediate Similarity	NPD2493	Approved
0.702	Intermediate Similarity	NPD2494	Approved
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD4582	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4583	Approved
0.6995	Remote Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD2797	Approved
0.6994	Remote Similarity	NPD1470	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5124	Phase 1
0.6964	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1933	Approved
0.695	Remote Similarity	NPD4004	Approved
0.695	Remote Similarity	NPD4002	Approved
0.6944	Remote Similarity	NPD5761	Phase 2
0.6944	Remote Similarity	NPD5760	Phase 2
0.6941	Remote Similarity	NPD4308	Phase 3
0.6941	Remote Similarity	NPD7033	Discontinued

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