NPASS Compound

Structure

NPC136278 OpenBabel07101719242D 27 29 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 5.1962 1.0000 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 -1.7321 -2.0000 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 2.5981 -0.5000 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 0.8660 -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 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -1.7321 0.0000 0.0000 C 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 4.3301 -0.5000 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 4.3301 1.5000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 18 2 0 0 0 0 13 21 2 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	3.075
LogD:	2.879
LogS:	-4.765
# Rotatable Bonds:	6
TPSA:	76.36
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.269
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.575
MDCK Permeability:	5.499178223544732e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	69.82254028320312%
Volume Distribution (VD):	0.847
Pgp-substrate:	25.572818756103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.364
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.49
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	6.633
Half-life (T1/2):	0.457

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.267
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.07
Skin Sensitization:	0.312
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC136278

Natural Product ID:	NPC136278
*Common Name:**	7,8,3',4',5'-Pentamethoxyflavone
IUPAC Name:	7,8-dimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:	7,8,3',4',5'-Pentamethoxyflavone
Standard InCHIKey:	IQXUAKMLDBLFJK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-22-14-7-6-12-13(21)10-15(27-18(12)20(14)26-5)11-8-16(23-2)19(25-4)17(9-11)24-3/h6-10H,1-5H3
SMILES:	COc1cc(cc(c1OC)OC)c1cc(=O)c2c(o1)c(OC)c(cc2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465255
PubChem CID:	24750458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-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
NPO8046	Muntingia calabura	Species	Muntingiaceae	Eukaryota	n.a.	root	n.a.	PMID[2045815]
NPO8046	Muntingia calabura	Species	Muntingiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[2045815]
NPO8046	Muntingia calabura	Species	Muntingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8046	Muntingia calabura	Species	Muntingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8046	Muntingia calabura	Species	Muntingiaceae	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	5
IC50	2

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[455163]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[455163]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[455163]
NPT916	Cell Line	SK-MEL	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[455163]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	>	25.0	ug ml-1	PMID[455163]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	>	800.0	ug.mL-1	PMID[455164]
NPT2	Others	Unspecified		IC50	>	800.0	ug.mL-1	PMID[455161]

☑ 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 NPC136278 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	515
0.1-0.2	2027
0.2-0.3	5277
0.3-0.4	11621
0.4-0.5	5553
0.5-0.6	4101
0.6-0.7	5549
0.7-0.8	4567
0.8-0.85	2150
0.85-0.9	897
0.9-0.95	394
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC113089
0.9857	High Similarity	NPC205522
0.9855	High Similarity	NPC70853
0.9855	High Similarity	NPC9966
0.9786	High Similarity	NPC106461
0.9786	High Similarity	NPC40818
0.9786	High Similarity	NPC110639
0.9786	High Similarity	NPC14958
0.9786	High Similarity	NPC215932
0.9783	High Similarity	NPC29536
0.9716	High Similarity	NPC85233
0.9716	High Similarity	NPC299923
0.9714	High Similarity	NPC471590
0.9648	High Similarity	NPC63256
0.9648	High Similarity	NPC10304
0.9645	High Similarity	NPC283002
0.9645	High Similarity	NPC310259
0.9645	High Similarity	NPC302408
0.9643	High Similarity	NPC23955
0.9643	High Similarity	NPC293201
0.958	High Similarity	NPC69752
0.9574	High Similarity	NPC165512
0.9517	High Similarity	NPC39732
0.9517	High Similarity	NPC60972
0.9514	High Similarity	NPC201547
0.9514	High Similarity	NPC259058
0.951	High Similarity	NPC195202
0.951	High Similarity	NPC261548
0.9507	High Similarity	NPC195919
0.9507	High Similarity	NPC216314
0.9507	High Similarity	NPC231013
0.9507	High Similarity	NPC120924
0.95	High Similarity	NPC214919
0.95	High Similarity	NPC124467
0.95	High Similarity	NPC185607
0.9493	High Similarity	NPC44573
0.9452	High Similarity	NPC186507
0.9452	High Similarity	NPC472408
0.9448	High Similarity	NPC308451
0.9448	High Similarity	NPC226973
0.9448	High Similarity	NPC208043
0.9444	High Similarity	NPC238366
0.9444	High Similarity	NPC181250
0.9441	High Similarity	NPC33265
0.9441	High Similarity	NPC117463
0.9441	High Similarity	NPC62536
0.9441	High Similarity	NPC470511
0.9441	High Similarity	NPC12200
0.9429	High Similarity	NPC58229
0.9388	High Similarity	NPC256612
0.9388	High Similarity	NPC20830
0.9384	High Similarity	NPC40033
0.9384	High Similarity	NPC166201
0.9384	High Similarity	NPC134677
0.9379	High Similarity	NPC189270
0.9379	High Similarity	NPC50728
0.9379	High Similarity	NPC5840
0.9379	High Similarity	NPC166753
0.9379	High Similarity	NPC306821
0.9375	High Similarity	NPC476342
0.9366	High Similarity	NPC182842
0.9348	High Similarity	NPC77955
0.9324	High Similarity	NPC265511
0.932	High Similarity	NPC145379
0.932	High Similarity	NPC128961
0.932	High Similarity	NPC274327
0.932	High Similarity	NPC69394
0.932	High Similarity	NPC176775
0.932	High Similarity	NPC280937
0.932	High Similarity	NPC183878
0.932	High Similarity	NPC86485
0.932	High Similarity	NPC47781
0.932	High Similarity	NPC231018
0.932	High Similarity	NPC22519
0.932	High Similarity	NPC472915
0.932	High Similarity	NPC160951
0.932	High Similarity	NPC255350
0.9315	High Similarity	NPC472535
0.9315	High Similarity	NPC474388
0.9315	High Similarity	NPC236769
0.9315	High Similarity	NPC474170
0.931	High Similarity	NPC52005
0.931	High Similarity	NPC137062
0.931	High Similarity	NPC48479
0.931	High Similarity	NPC177298
0.931	High Similarity	NPC474648
0.931	High Similarity	NPC328119
0.931	High Similarity	NPC223579
0.931	High Similarity	NPC159103
0.931	High Similarity	NPC287101
0.931	High Similarity	NPC183950
0.9296	High Similarity	NPC476054
0.9262	High Similarity	NPC19097
0.9262	High Similarity	NPC476981
0.9257	High Similarity	NPC241774
0.9257	High Similarity	NPC146165
0.9257	High Similarity	NPC34725
0.9257	High Similarity	NPC50715
0.9257	High Similarity	NPC128863
0.9257	High Similarity	NPC163780
0.9257	High Similarity	NPC189960
0.9257	High Similarity	NPC122623
0.9257	High Similarity	NPC183597
0.9257	High Similarity	NPC284353
0.9257	High Similarity	NPC167815
0.9257	High Similarity	NPC208197
0.9257	High Similarity	NPC227325
0.9257	High Similarity	NPC255807
0.9257	High Similarity	NPC2476
0.9257	High Similarity	NPC196439
0.9257	High Similarity	NPC276059
0.9257	High Similarity	NPC138360
0.9257	High Similarity	NPC280339
0.9257	High Similarity	NPC4455
0.9257	High Similarity	NPC213622
0.9257	High Similarity	NPC201136
0.9257	High Similarity	NPC32557
0.9257	High Similarity	NPC31018
0.9257	High Similarity	NPC92659
0.9252	High Similarity	NPC212678
0.9252	High Similarity	NPC71334
0.9252	High Similarity	NPC100887
0.9252	High Similarity	NPC301123
0.9252	High Similarity	NPC275836
0.9252	High Similarity	NPC301323
0.9252	High Similarity	NPC275722
0.9252	High Similarity	NPC239128
0.9252	High Similarity	NPC25270
0.9252	High Similarity	NPC83508
0.9252	High Similarity	NPC156222
0.9252	High Similarity	NPC57030
0.9252	High Similarity	NPC477231
0.9252	High Similarity	NPC55205
0.9252	High Similarity	NPC293183
0.9252	High Similarity	NPC256283
0.9252	High Similarity	NPC292460
0.9252	High Similarity	NPC187498
0.9252	High Similarity	NPC162313
0.9252	High Similarity	NPC198826
0.9252	High Similarity	NPC68882
0.9252	High Similarity	NPC257648
0.9252	High Similarity	NPC188203
0.9252	High Similarity	NPC131624
0.9252	High Similarity	NPC241498
0.9252	High Similarity	NPC120163
0.9252	High Similarity	NPC222830
0.9247	High Similarity	NPC177839
0.9247	High Similarity	NPC219330
0.9241	High Similarity	NPC183236
0.9241	High Similarity	NPC120464
0.9195	High Similarity	NPC49824
0.9195	High Similarity	NPC257277
0.9195	High Similarity	NPC180340
0.9195	High Similarity	NPC178854
0.9195	High Similarity	NPC472455
0.9195	High Similarity	NPC472916
0.9189	High Similarity	NPC270620
0.9189	High Similarity	NPC250822
0.9189	High Similarity	NPC75279
0.9189	High Similarity	NPC236223
0.9189	High Similarity	NPC476289
0.9189	High Similarity	NPC279930
0.9189	High Similarity	NPC179126
0.9189	High Similarity	NPC78326
0.9189	High Similarity	NPC276409
0.9184	High Similarity	NPC54394
0.9184	High Similarity	NPC117579
0.9184	High Similarity	NPC262623
0.9184	High Similarity	NPC149614
0.9184	High Similarity	NPC474663
0.9184	High Similarity	NPC31363
0.9184	High Similarity	NPC125062
0.9184	High Similarity	NPC76376
0.9184	High Similarity	NPC198615
0.9184	High Similarity	NPC200740
0.9184	High Similarity	NPC252933
0.9172	High Similarity	NPC119660
0.9172	High Similarity	NPC93034
0.9172	High Similarity	NPC474999
0.9172	High Similarity	NPC168803
0.9172	High Similarity	NPC108406
0.9161	High Similarity	NPC119663
0.9143	High Similarity	NPC254741
0.9139	High Similarity	NPC476980
0.9133	High Similarity	NPC224137
0.9133	High Similarity	NPC129684
0.9133	High Similarity	NPC227192
0.9133	High Similarity	NPC203891
0.9133	High Similarity	NPC101830
0.9133	High Similarity	NPC75215
0.9133	High Similarity	NPC93376
0.9133	High Similarity	NPC310206
0.9133	High Similarity	NPC189179
0.9133	High Similarity	NPC110070
0.9133	High Similarity	NPC299520
0.9133	High Similarity	NPC181960
0.9133	High Similarity	NPC470402
0.913	High Similarity	NPC473655
0.913	High Similarity	NPC101294
0.9128	High Similarity	NPC26227

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 NPC136278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	1004
0.2-0.3	1777
0.3-0.4	2728
0.4-0.5	1735
0.5-0.6	930
0.6-0.7	365
0.7-0.8	109
0.8-0.85	32
0.85-0.9	9
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.932	High Similarity	NPD2801	Approved
0.9128	High Similarity	NPD3817	Phase 2
0.9013	High Similarity	NPD5494	Approved
0.9007	High Similarity	NPD2796	Approved
0.8993	High Similarity	NPD1934	Approved
0.8966	High Similarity	NPD1511	Approved
0.894	High Similarity	NPD3882	Suspended
0.8844	High Similarity	NPD1512	Approved
0.8808	High Similarity	NPD2393	Clinical (unspecified phase)
0.8671	High Similarity	NPD3818	Discontinued
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8599	High Similarity	NPD3926	Phase 2
0.859	High Similarity	NPD1247	Approved
0.8581	High Similarity	NPD6799	Approved
0.8544	High Similarity	NPD6166	Phase 2
0.8544	High Similarity	NPD6168	Clinical (unspecified phase)
0.8544	High Similarity	NPD6167	Clinical (unspecified phase)
0.85	High Similarity	NPD7054	Approved
0.8462	Intermediate Similarity	NPD919	Approved
0.8447	Intermediate Similarity	NPD7472	Approved
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8411	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8366	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6232	Discontinued
0.8299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7808	Phase 3
0.8293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6797	Phase 2
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD5402	Approved
0.8264	Intermediate Similarity	NPD1240	Approved
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD6801	Discontinued
0.8247	Intermediate Similarity	NPD6599	Discontinued
0.8232	Intermediate Similarity	NPD7251	Discontinued
0.8207	Intermediate Similarity	NPD1933	Approved
0.817	Intermediate Similarity	NPD920	Approved
0.8165	Intermediate Similarity	NPD7075	Discontinued
0.8163	Intermediate Similarity	NPD3748	Approved
0.8151	Intermediate Similarity	NPD1607	Approved
0.8082	Intermediate Similarity	NPD447	Suspended
0.8077	Intermediate Similarity	NPD7411	Suspended
0.8067	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD5403	Approved
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD5401	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7925	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3750	Approved
0.7877	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6832	Phase 2
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5242	Approved
0.7791	Intermediate Similarity	NPD6959	Discontinued
0.777	Intermediate Similarity	NPD5536	Phase 2
0.7755	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7748	Intermediate Similarity	NPD1551	Phase 2
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6386	Approved
0.7736	Intermediate Similarity	NPD6385	Approved
0.7718	Intermediate Similarity	NPD230	Phase 1
0.7716	Intermediate Similarity	NPD3749	Approved
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2800	Approved
0.7702	Intermediate Similarity	NPD5353	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3226	Approved
0.7603	Intermediate Similarity	NPD2798	Approved
0.7597	Intermediate Similarity	NPD2654	Approved
0.7582	Intermediate Similarity	NPD2346	Discontinued
0.7582	Intermediate Similarity	NPD2344	Approved
0.758	Intermediate Similarity	NPD2532	Approved
0.758	Intermediate Similarity	NPD2533	Approved
0.758	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD7199	Phase 2
0.7566	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD2403	Approved
0.7533	Intermediate Similarity	NPD1613	Approved
0.7533	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3751	Discontinued
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3027	Phase 3
0.7448	Intermediate Similarity	NPD3972	Approved
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.744	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9494	Approved
0.7427	Intermediate Similarity	NPD5953	Discontinued
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.7415	Intermediate Similarity	NPD1203	Approved
0.7412	Intermediate Similarity	NPD7286	Phase 2
0.7403	Intermediate Similarity	NPD6099	Approved
0.7403	Intermediate Similarity	NPD6100	Approved
0.7397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7389	Intermediate Similarity	NPD2309	Approved
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7362	Intermediate Similarity	NPD6844	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7361	Intermediate Similarity	NPD17	Approved
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7341	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD1653	Approved
0.732	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD4357	Discontinued
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7278	Intermediate Similarity	NPD6190	Approved
0.7246	Intermediate Similarity	NPD6234	Discontinued
0.7234	Intermediate Similarity	NPD5283	Phase 1
0.7226	Intermediate Similarity	NPD7033	Discontinued
0.7226	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7390	Discontinued
0.7184	Intermediate Similarity	NPD7685	Pre-registration
0.7181	Intermediate Similarity	NPD2797	Approved
0.7172	Intermediate Similarity	NPD9268	Approved
0.7171	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD3887	Approved
0.7169	Intermediate Similarity	NPD5978	Approved
0.7169	Intermediate Similarity	NPD5977	Approved
0.7169	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD6280	Approved
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD6279	Approved
0.7143	Intermediate Similarity	NPD3146	Approved
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2353	Approved
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7114	Intermediate Similarity	NPD3225	Approved
0.7114	Intermediate Similarity	NPD1876	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7091	Intermediate Similarity	NPD5890	Approved
0.7091	Intermediate Similarity	NPD5889	Approved
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD3142	Approved
0.7078	Intermediate Similarity	NPD3140	Approved
0.707	Intermediate Similarity	NPD3539	Phase 1
0.7059	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7052	Intermediate Similarity	NPD2163	Approved
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1652	Phase 2
0.7043	Intermediate Similarity	NPD5006	Approved
0.7043	Intermediate Similarity	NPD5005	Approved
0.7039	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4662	Approved
0.7037	Intermediate Similarity	NPD4661	Approved
0.7033	Intermediate Similarity	NPD4363	Phase 3
0.7033	Intermediate Similarity	NPD4360	Phase 2
0.703	Intermediate Similarity	NPD6585	Discontinued
0.7027	Intermediate Similarity	NPD1610	Phase 2
0.7025	Intermediate Similarity	NPD3540	Phase 1
0.7018	Intermediate Similarity	NPD5710	Approved
0.7018	Intermediate Similarity	NPD6808	Phase 2

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