NPASS Compound

Structure

CID280493 OpenBabel06191716092D 35 38 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 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 4.3301 -1.5000 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 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 0.8660 2.5000 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 3.0000 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 -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 1.7321 0.0000 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 -1.7321 -0.0000 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 0.8660 -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 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 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 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 -1.5000 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 -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 -1.7321 4.0000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 26 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 30 1 0 0 0 0 17 35 1 0 0 0 0 18 20 1 0 0 0 0 18 34 1 0 0 0 0 19 24 2 0 0 0 0 19 31 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 2 0 0 0 0 23 25 2 0 0 0 0 23 34 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 29 2 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.13
Volume:	471.501
LogP:	4.084
LogD:	3.113
LogS:	-4.665
# Rotatable Bonds:	8
TPSA:	113.66
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	2.467
Fsp3:	0.154
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:	-4.788
MDCK Permeability:	6.899431173224002e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	87.72692108154297%
Volume Distribution (VD):	0.59
Pgp-substrate:	16.382734298706055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.243
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.848
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.681
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	3.573
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.332
Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.287
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.351
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC280493

Natural Product ID:	NPC280493
*Common Name:**	3'-Benzoyloxy-5-Hydroxy-3,6,7,4'-Tetramethoxyflavone
IUPAC Name:	[5-(5-hydroxy-3,6,7-trimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] benzoate
Synonyms:
Standard InCHIKey:	ZOSSZDQPAOYKCU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H22O9/c1-30-16-11-10-15(12-17(16)35-26(29)14-8-6-5-7-9-14)23-25(33-4)22(28)20-18(34-23)13-19(31-2)24(32-3)21(20)27/h5-13,27H,1-4H3
SMILES:	COc1ccc(cc1OC(=O)c1ccccc1)c1c(c(=O)c2c(cc(c(c2O)OC)OC)o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462317
PubChem CID:	10928896
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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	6

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[494425]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	20.0	ug ml-1	PMID[494425]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[494425]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[494425]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	16.5	ug ml-1	PMID[494425]
NPT27	Others	Unspecified		ED50	=	3.6	ug ml-1	PMID[494425]

☑ 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 NPC280493 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	411
0.1-0.2	1963
0.2-0.3	4989
0.3-0.4	10578
0.4-0.5	6948
0.5-0.6	3961
0.6-0.7	5375
0.7-0.8	4868
0.8-0.85	1767
0.85-0.9	1274
0.9-0.95	545
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC22472
0.9494	High Similarity	NPC115798
0.9494	High Similarity	NPC18772
0.9494	High Similarity	NPC152166
0.9494	High Similarity	NPC7846
0.9494	High Similarity	NPC204854
0.9494	High Similarity	NPC4481
0.9494	High Similarity	NPC130894
0.9494	High Similarity	NPC261004
0.9494	High Similarity	NPC18607
0.9494	High Similarity	NPC25495
0.9494	High Similarity	NPC300943
0.9494	High Similarity	NPC288669
0.9494	High Similarity	NPC105242
0.9494	High Similarity	NPC9609
0.9494	High Similarity	NPC191459
0.9494	High Similarity	NPC193842
0.9494	High Similarity	NPC176300
0.9494	High Similarity	NPC253634
0.9494	High Similarity	NPC19687
0.9494	High Similarity	NPC143828
0.943	High Similarity	NPC93376
0.943	High Similarity	NPC235215
0.943	High Similarity	NPC75215
0.943	High Similarity	NPC176665
0.943	High Similarity	NPC163524
0.943	High Similarity	NPC189179
0.943	High Similarity	NPC227192
0.943	High Similarity	NPC472438
0.943	High Similarity	NPC29841
0.943	High Similarity	NPC7973
0.943	High Similarity	NPC110070
0.943	High Similarity	NPC287979
0.943	High Similarity	NPC224137
0.943	High Similarity	NPC78302
0.943	High Similarity	NPC203891
0.943	High Similarity	NPC305663
0.943	High Similarity	NPC101830
0.939	High Similarity	NPC476370
0.9367	High Similarity	NPC43243
0.9367	High Similarity	NPC265511
0.9367	High Similarity	NPC245546
0.9367	High Similarity	NPC266960
0.9367	High Similarity	NPC200388
0.9367	High Similarity	NPC292107
0.9367	High Similarity	NPC98661
0.9367	High Similarity	NPC247017
0.9367	High Similarity	NPC55619
0.9367	High Similarity	NPC178854
0.9367	High Similarity	NPC268161
0.9367	High Similarity	NPC100916
0.9367	High Similarity	NPC49824
0.9367	High Similarity	NPC474520
0.9345	High Similarity	NPC36138
0.9333	High Similarity	NPC476374
0.9325	High Similarity	NPC295082
0.9321	High Similarity	NPC280893
0.9321	High Similarity	NPC142614
0.9304	High Similarity	NPC201136
0.9304	High Similarity	NPC196439
0.9304	High Similarity	NPC122623
0.9304	High Similarity	NPC4455
0.9304	High Similarity	NPC34725
0.9304	High Similarity	NPC201451
0.9304	High Similarity	NPC138360
0.9304	High Similarity	NPC280339
0.9304	High Similarity	NPC241774
0.9304	High Similarity	NPC146165
0.9304	High Similarity	NPC183597
0.9304	High Similarity	NPC92659
0.9304	High Similarity	NPC167815
0.9304	High Similarity	NPC20830
0.9304	High Similarity	NPC227325
0.9304	High Similarity	NPC26227
0.9304	High Similarity	NPC44079
0.9304	High Similarity	NPC189960
0.9304	High Similarity	NPC214138
0.9304	High Similarity	NPC163780
0.9304	High Similarity	NPC32557
0.9304	High Similarity	NPC256612
0.9304	High Similarity	NPC276059
0.9304	High Similarity	NPC128863
0.9304	High Similarity	NPC50715
0.9304	High Similarity	NPC208197
0.9304	High Similarity	NPC2476
0.929	High Similarity	NPC470416
0.9259	High Similarity	NPC272064
0.925	High Similarity	NPC190487
0.925	High Similarity	NPC195832
0.925	High Similarity	NPC154304
0.9245	High Similarity	NPC257277
0.9241	High Similarity	NPC183878
0.9241	High Similarity	NPC231018
0.9241	High Similarity	NPC250822
0.9241	High Similarity	NPC75279
0.9241	High Similarity	NPC160951
0.9241	High Similarity	NPC176775
0.9241	High Similarity	NPC86485
0.9241	High Similarity	NPC246204
0.9241	High Similarity	NPC58382
0.9241	High Similarity	NPC47781
0.9241	High Similarity	NPC255350
0.9241	High Similarity	NPC22519
0.9241	High Similarity	NPC145379
0.9241	High Similarity	NPC179126
0.9241	High Similarity	NPC236223
0.9241	High Similarity	NPC276409
0.9241	High Similarity	NPC274327
0.9241	High Similarity	NPC162351
0.9241	High Similarity	NPC78326
0.9241	High Similarity	NPC270620
0.9241	High Similarity	NPC69394
0.9222	High Similarity	NPC472385
0.9222	High Similarity	NPC198324
0.9207	High Similarity	NPC76482
0.9207	High Similarity	NPC243877
0.9198	High Similarity	NPC471745
0.9193	High Similarity	NPC130955
0.9193	High Similarity	NPC246478
0.9193	High Similarity	NPC188967
0.9187	High Similarity	NPC185526
0.9182	High Similarity	NPC213622
0.9177	High Similarity	NPC239128
0.9177	High Similarity	NPC293183
0.9177	High Similarity	NPC142540
0.9177	High Similarity	NPC60972
0.9177	High Similarity	NPC162313
0.9177	High Similarity	NPC82325
0.9177	High Similarity	NPC134677
0.9177	High Similarity	NPC188203
0.9177	High Similarity	NPC123886
0.9177	High Similarity	NPC156222
0.9177	High Similarity	NPC83508
0.9177	High Similarity	NPC275836
0.9177	High Similarity	NPC301323
0.9177	High Similarity	NPC198826
0.9177	High Similarity	NPC222830
0.9177	High Similarity	NPC289968
0.9177	High Similarity	NPC187498
0.9177	High Similarity	NPC57030
0.9177	High Similarity	NPC212678
0.9177	High Similarity	NPC279989
0.9177	High Similarity	NPC241498
0.9177	High Similarity	NPC120163
0.9177	High Similarity	NPC131624
0.9177	High Similarity	NPC25270
0.9177	High Similarity	NPC275722
0.9177	High Similarity	NPC100887
0.9177	High Similarity	NPC256283
0.9177	High Similarity	NPC71334
0.9177	High Similarity	NPC39732
0.9177	High Similarity	NPC301123
0.9177	High Similarity	NPC27208
0.9177	High Similarity	NPC55205
0.9167	High Similarity	NPC35167
0.9167	High Similarity	NPC476773
0.9167	High Similarity	NPC139571
0.9167	High Similarity	NPC98546
0.9167	High Similarity	NPC297807
0.9167	High Similarity	NPC217520
0.9162	High Similarity	NPC264735
0.9162	High Similarity	NPC237435
0.9162	High Similarity	NPC115760
0.9162	High Similarity	NPC477848
0.9162	High Similarity	NPC135277
0.9162	High Similarity	NPC43211
0.9162	High Similarity	NPC101191
0.9162	High Similarity	NPC49344
0.9162	High Similarity	NPC99591
0.9162	High Similarity	NPC210094
0.9141	High Similarity	NPC470459
0.9136	High Similarity	NPC196179
0.9136	High Similarity	NPC112418
0.9136	High Similarity	NPC34089
0.913	High Similarity	NPC172202
0.913	High Similarity	NPC476410
0.913	High Similarity	NPC284127
0.9125	High Similarity	NPC472916
0.9114	High Similarity	NPC474388
0.9114	High Similarity	NPC208043
0.9114	High Similarity	NPC472535
0.9114	High Similarity	NPC252933
0.9114	High Similarity	NPC474170
0.9114	High Similarity	NPC260895
0.9114	High Similarity	NPC76376
0.9114	High Similarity	NPC200740
0.9114	High Similarity	NPC133953
0.9114	High Similarity	NPC226973
0.9114	High Similarity	NPC50403
0.9114	High Similarity	NPC236769
0.9114	High Similarity	NPC54394
0.9114	High Similarity	NPC225731
0.9114	High Similarity	NPC308451
0.9114	High Similarity	NPC28274
0.9114	High Similarity	NPC125062
0.9107	High Similarity	NPC211532
0.9107	High Similarity	NPC61904
0.9107	High Similarity	NPC144097
0.9107	High Similarity	NPC154741
0.9107	High Similarity	NPC472992

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 NPC280493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	1003
0.2-0.3	1960
0.3-0.4	2637
0.4-0.5	1753
0.5-0.6	923
0.6-0.7	330
0.7-0.8	109
0.8-0.85	29
0.85-0.9	19
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD2801	Approved
0.9182	High Similarity	NPD3817	Phase 2
0.9162	High Similarity	NPD4338	Clinical (unspecified phase)
0.9006	High Similarity	NPD3882	Suspended
0.897	High Similarity	NPD6168	Clinical (unspecified phase)
0.897	High Similarity	NPD6166	Phase 2
0.897	High Similarity	NPD6167	Clinical (unspecified phase)
0.8889	High Similarity	NPD4868	Clinical (unspecified phase)
0.8827	High Similarity	NPD5402	Approved
0.8797	High Similarity	NPD1512	Approved
0.8706	High Similarity	NPD6797	Phase 2
0.8704	High Similarity	NPD1934	Approved
0.8671	High Similarity	NPD1511	Approved
0.8655	High Similarity	NPD7251	Discontinued
0.8639	High Similarity	NPD3818	Discontinued
0.8606	High Similarity	NPD7075	Discontinued
0.8605	High Similarity	NPD7808	Phase 3
0.8596	High Similarity	NPD7993	Clinical (unspecified phase)
0.8588	High Similarity	NPD7054	Approved
0.8553	High Similarity	NPD6799	Approved
0.8538	High Similarity	NPD7472	Approved
0.8537	High Similarity	NPD2393	Clinical (unspecified phase)
0.8512	High Similarity	NPD6232	Discontinued
0.848	Intermediate Similarity	NPD5844	Phase 1
0.8476	Intermediate Similarity	NPD6801	Discontinued
0.8471	Intermediate Similarity	NPD7473	Discontinued
0.843	Intermediate Similarity	NPD7074	Phase 3
0.8424	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD1465	Phase 2
0.8395	Intermediate Similarity	NPD5403	Approved
0.8385	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7411	Suspended
0.8284	Intermediate Similarity	NPD5494	Approved
0.8274	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD5401	Approved
0.8272	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4380	Phase 2
0.8242	Intermediate Similarity	NPD6599	Discontinued
0.8225	Intermediate Similarity	NPD919	Approved
0.8161	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1247	Approved
0.8111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8086	Intermediate Similarity	NPD6190	Approved
0.8061	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3749	Approved
0.8035	Intermediate Similarity	NPD3926	Phase 2
0.7989	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD447	Suspended
0.7941	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7931	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3750	Approved
0.7904	Intermediate Similarity	NPD1653	Approved
0.7901	Intermediate Similarity	NPD1549	Phase 2
0.7901	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7888	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD2796	Approved
0.7862	Intermediate Similarity	NPD230	Phase 1
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6559	Discontinued
0.7816	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD943	Approved
0.7797	Intermediate Similarity	NPD3751	Discontinued
0.7754	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3226	Approved
0.7744	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7199	Phase 2
0.7702	Intermediate Similarity	NPD1607	Approved
0.767	Intermediate Similarity	NPD3787	Discontinued
0.7669	Intermediate Similarity	NPD1551	Phase 2
0.7665	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD920	Approved
0.7625	Intermediate Similarity	NPD6233	Phase 2
0.7607	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3748	Approved
0.76	Intermediate Similarity	NPD6234	Discontinued
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1933	Approved
0.753	Intermediate Similarity	NPD1243	Approved
0.7527	Intermediate Similarity	NPD7685	Pre-registration
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7473	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD1203	Approved
0.7453	Intermediate Similarity	NPD6798	Discontinued
0.7453	Intermediate Similarity	NPD2313	Discontinued
0.7446	Intermediate Similarity	NPD8313	Approved
0.7446	Intermediate Similarity	NPD8312	Approved
0.7438	Intermediate Similarity	NPD6832	Phase 2
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8434	Phase 2
0.7419	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD37	Approved
0.7403	Intermediate Similarity	NPD7228	Approved
0.7396	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD7549	Discontinued
0.7389	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7286	Phase 2
0.7362	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD6777	Approved
0.7358	Intermediate Similarity	NPD6778	Approved
0.7358	Intermediate Similarity	NPD6782	Approved
0.7358	Intermediate Similarity	NPD6776	Approved
0.7358	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD6781	Approved
0.7358	Intermediate Similarity	NPD6780	Approved
0.7321	Intermediate Similarity	NPD2800	Approved
0.7317	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD2344	Approved
0.7286	Intermediate Similarity	NPD7874	Approved
0.7286	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD9717	Approved
0.7278	Intermediate Similarity	NPD9269	Phase 2
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9494	Approved
0.7251	Intermediate Similarity	NPD7390	Discontinued
0.725	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7783	Phase 2
0.7239	Intermediate Similarity	NPD3268	Approved
0.7238	Intermediate Similarity	NPD5242	Approved
0.7236	Intermediate Similarity	NPD8151	Discontinued
0.7233	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD422	Phase 1
0.7209	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7870	Phase 2
0.7208	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD3225	Approved
0.7186	Intermediate Similarity	NPD4308	Phase 3
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6385	Approved
0.7159	Intermediate Similarity	NPD6386	Approved
0.7158	Intermediate Similarity	NPD4287	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7698	Approved
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7135	Intermediate Similarity	NPD2354	Approved
0.7135	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD411	Approved
0.7127	Intermediate Similarity	NPD8127	Discontinued
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD7266	Discontinued
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7098	Intermediate Similarity	NPD6534	Approved
0.7098	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7073	Intermediate Similarity	NPD7095	Approved
0.7066	Intermediate Similarity	NPD6651	Approved
0.7056	Intermediate Similarity	NPD6971	Discontinued
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7045	Intermediate Similarity	NPD7458	Discontinued
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6099	Approved
0.7041	Intermediate Similarity	NPD5404	Approved
0.7041	Intermediate Similarity	NPD6100	Approved
0.7041	Intermediate Similarity	NPD5405	Approved
0.7041	Intermediate Similarity	NPD5406	Approved
0.7041	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD4288	Approved
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3764	Approved
0.7025	Intermediate Similarity	NPD9268	Approved
0.7021	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7011	Intermediate Similarity	NPD2403	Approved
0.6995	Remote Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD5710	Approved
0.6995	Remote Similarity	NPD5711	Approved
0.6994	Remote Similarity	NPD2798	Approved
0.699	Remote Similarity	NPD7699	Phase 2
0.699	Remote Similarity	NPD7700	Phase 2
0.6983	Remote Similarity	NPD8455	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