NPASS Compound

Structure

CID241774 OpenBabel06191716042D 37 39 0 0 0 0 0 0 0 0999 V2000 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 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 -5.1962 -6.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 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 -0.8660 -0.5000 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 -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 0.0000 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 -6.0622 -4.5000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 1.7321 -0.0000 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 -4.5000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 31 1 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 36 1 0 0 0 0 19 25 2 0 0 0 0 19 32 1 0 0 0 0 20 28 2 0 0 0 0 20 35 1 0 0 0 0 21 29 2 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 26 2 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 27 2 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 0 0 0 0 26 37 1 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.18
Volume:	511.416
LogP:	4.385
LogD:	3.455
LogS:	-5.689
# Rotatable Bonds:	13
TPSA:	119.73
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	2.745
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.88
MDCK Permeability:	2.7862262868438847e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	80.9913330078125%
Volume Distribution (VD):	0.636
Pgp-substrate:	18.101150512695312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	4.741
Half-life (T1/2):	0.634

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.005
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.687
Carcinogencity:	0.045
Eye Corrosion:	0.004
Eye Irritation:	0.19
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC241774

Natural Product ID:	NPC241774
*Common Name:**	5,3'-Dibutanoyloxy-3,6,7,4'-Tetramethoxyflavone
IUPAC Name:	[5-(5-butanoyloxy-3,6,7-trimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] butanoate
Synonyms:
Standard InCHIKey:	WEPRDNVSYAUHGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H30O10/c1-7-9-20(28)35-17-13-15(11-12-16(17)31-3)24-27(34-6)23(30)22-18(36-24)14-19(32-4)25(33-5)26(22)37-21(29)10-8-2/h11-14H,7-10H2,1-6H3
SMILES:	CCCC(=O)Oc1cc(ccc1OC)c1c(c(=O)c2c(cc(c(c2OC(=O)CCC)OC)OC)o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514284
PubChem CID:	10885755
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
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	=	11.7	ug ml-1	PMID[488712]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[488712]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.5	ug ml-1	PMID[488712]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[488712]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[488712]
NPT27	Others	Unspecified		ED50	=	0.6	ug ml-1	PMID[488712]

☑ 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 NPC241774 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	483
0.1-0.2	1949
0.2-0.3	5103
0.3-0.4	10750
0.4-0.5	6796
0.5-0.6	4006
0.6-0.7	5789
0.7-0.8	4816
0.8-0.85	1978
0.85-0.9	820
0.9-0.95	181
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122623
1.0	High Similarity	NPC276059
1.0	High Similarity	NPC34725
0.9932	High Similarity	NPC257277
0.9796	High Similarity	NPC474170
0.9796	High Similarity	NPC472535
0.9796	High Similarity	NPC474388
0.9728	High Similarity	NPC201547
0.9728	High Similarity	NPC177839
0.9728	High Similarity	NPC259058
0.966	High Similarity	NPC69752
0.966	High Similarity	NPC181250
0.9533	High Similarity	NPC186507
0.9524	High Similarity	NPC85233
0.9484	High Similarity	NPC280893
0.947	High Similarity	NPC471746
0.9467	High Similarity	NPC134677
0.9456	High Similarity	NPC110639
0.9456	High Similarity	NPC283002
0.9456	High Similarity	NPC302408
0.9456	High Similarity	NPC310259
0.9456	High Similarity	NPC14958
0.9456	High Similarity	NPC215932
0.9456	High Similarity	NPC40818
0.9456	High Similarity	NPC106461
0.9412	High Similarity	NPC257914
0.9412	High Similarity	NPC238405
0.9412	High Similarity	NPC104459
0.9408	High Similarity	NPC178854
0.94	High Similarity	NPC474663
0.94	High Similarity	NPC198615
0.9392	High Similarity	NPC299923
0.9392	High Similarity	NPC205522
0.9388	High Similarity	NPC165512
0.9342	High Similarity	NPC189960
0.9342	High Similarity	NPC32557
0.9333	High Similarity	NPC29056
0.932	High Similarity	NPC23955
0.9304	High Similarity	NPC280493
0.9286	High Similarity	NPC288669
0.9286	High Similarity	NPC18772
0.9286	High Similarity	NPC7846
0.9286	High Similarity	NPC105242
0.9286	High Similarity	NPC9609
0.9286	High Similarity	NPC204854
0.9286	High Similarity	NPC115798
0.9286	High Similarity	NPC191459
0.9286	High Similarity	NPC130894
0.9286	High Similarity	NPC152166
0.9286	High Similarity	NPC261004
0.9286	High Similarity	NPC25495
0.9286	High Similarity	NPC300943
0.9286	High Similarity	NPC143828
0.9286	High Similarity	NPC4481
0.9286	High Similarity	NPC19687
0.9286	High Similarity	NPC176300
0.9286	High Similarity	NPC253634
0.9286	High Similarity	NPC18607
0.9286	High Similarity	NPC22472
0.9276	High Similarity	NPC86485
0.9276	High Similarity	NPC476289
0.9276	High Similarity	NPC246204
0.9267	High Similarity	NPC474648
0.9257	High Similarity	NPC136278
0.9252	High Similarity	NPC70853
0.9252	High Similarity	NPC9966
0.9226	High Similarity	NPC131557
0.9221	High Similarity	NPC29841
0.9221	High Similarity	NPC305663
0.9221	High Similarity	NPC235215
0.9221	High Similarity	NPC78302
0.9221	High Similarity	NPC7973
0.9221	High Similarity	NPC93376
0.9221	High Similarity	NPC287979
0.9221	High Similarity	NPC224137
0.9221	High Similarity	NPC472438
0.9221	High Similarity	NPC110070
0.9221	High Similarity	NPC163524
0.9221	High Similarity	NPC75215
0.9221	High Similarity	NPC227192
0.9221	High Similarity	NPC203891
0.9221	High Similarity	NPC189179
0.9221	High Similarity	NPC176665
0.9221	High Similarity	NPC101830
0.9211	High Similarity	NPC301123
0.92	High Similarity	NPC183236
0.92	High Similarity	NPC63256
0.92	High Similarity	NPC261548
0.92	High Similarity	NPC10304
0.9189	High Similarity	NPC113089
0.9184	High Similarity	NPC124467
0.9184	High Similarity	NPC29536
0.9184	High Similarity	NPC214919
0.9161	High Similarity	NPC193842
0.9156	High Similarity	NPC245546
0.9156	High Similarity	NPC98661
0.9156	High Similarity	NPC247017
0.9156	High Similarity	NPC292107
0.9156	High Similarity	NPC268161
0.9156	High Similarity	NPC266960
0.9156	High Similarity	NPC100916
0.9156	High Similarity	NPC200388
0.9156	High Similarity	NPC55619
0.9156	High Similarity	NPC49824
0.9156	High Similarity	NPC474520
0.9156	High Similarity	NPC43243
0.9145	High Similarity	NPC236769
0.9145	High Similarity	NPC208043
0.9145	High Similarity	NPC76376
0.9145	High Similarity	NPC226973
0.9139	High Similarity	NPC238366
0.9133	High Similarity	NPC117463
0.9116	High Similarity	NPC474037
0.9091	High Similarity	NPC2476
0.9091	High Similarity	NPC201136
0.9091	High Similarity	NPC4455
0.9091	High Similarity	NPC92659
0.9091	High Similarity	NPC201451
0.9091	High Similarity	NPC26227
0.9091	High Similarity	NPC146165
0.9091	High Similarity	NPC138360
0.9091	High Similarity	NPC280339
0.9091	High Similarity	NPC44079
0.9091	High Similarity	NPC227325
0.9091	High Similarity	NPC50715
0.9091	High Similarity	NPC183597
0.9091	High Similarity	NPC214138
0.9091	High Similarity	NPC163780
0.9091	High Similarity	NPC196439
0.9091	High Similarity	NPC128863
0.9091	High Similarity	NPC167815
0.9091	High Similarity	NPC284353
0.9085	High Similarity	NPC292460
0.9079	High Similarity	NPC306821
0.9079	High Similarity	NPC50728
0.9079	High Similarity	NPC166753
0.9079	High Similarity	NPC219330
0.9067	High Similarity	NPC195919
0.9067	High Similarity	NPC216314
0.9067	High Similarity	NPC231013
0.9067	High Similarity	NPC120924
0.9057	High Similarity	NPC193881
0.9057	High Similarity	NPC155264
0.9057	High Similarity	NPC67450
0.9057	High Similarity	NPC475214
0.9057	High Similarity	NPC210460
0.9032	High Similarity	NPC265511
0.9032	High Similarity	NPC303255
0.9032	High Similarity	NPC474983
0.9026	High Similarity	NPC183878
0.9026	High Similarity	NPC255350
0.9026	High Similarity	NPC162351
0.9026	High Similarity	NPC145379
0.9026	High Similarity	NPC22519
0.9026	High Similarity	NPC236223
0.9026	High Similarity	NPC78326
0.9026	High Similarity	NPC75279
0.9026	High Similarity	NPC279930
0.9026	High Similarity	NPC472408
0.9026	High Similarity	NPC58382
0.9026	High Similarity	NPC160951
0.9026	High Similarity	NPC179126
0.9026	High Similarity	NPC274327
0.9026	High Similarity	NPC270620
0.9026	High Similarity	NPC47781
0.9026	High Similarity	NPC250822
0.9026	High Similarity	NPC231018
0.9026	High Similarity	NPC69394
0.9026	High Similarity	NPC276409
0.9026	High Similarity	NPC176775
0.902	High Similarity	NPC308451
0.9013	High Similarity	NPC328119
0.9013	High Similarity	NPC159103
0.9	High Similarity	NPC76482
0.9	High Similarity	NPC471590
0.8994	High Similarity	NPC475369
0.8987	High Similarity	NPC471745
0.8987	High Similarity	NPC108767
0.8986	High Similarity	NPC58229
0.8981	High Similarity	NPC246478
0.8981	High Similarity	NPC477164
0.8968	High Similarity	NPC213622
0.8968	High Similarity	NPC256612
0.8968	High Similarity	NPC20830
0.8968	High Similarity	NPC208197
0.8961	High Similarity	NPC188203
0.8961	High Similarity	NPC239128
0.8961	High Similarity	NPC162313
0.8961	High Similarity	NPC187498
0.8961	High Similarity	NPC71334
0.8961	High Similarity	NPC166201
0.8961	High Similarity	NPC156222
0.8961	High Similarity	NPC142540
0.8961	High Similarity	NPC83508
0.8961	High Similarity	NPC275836
0.8961	High Similarity	NPC100887
0.8961	High Similarity	NPC198826
0.8961	High Similarity	NPC241498
0.8961	High Similarity	NPC289968
0.8961	High Similarity	NPC82325

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 NPC241774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	1006
0.2-0.3	1903
0.3-0.4	2632
0.4-0.5	1797
0.5-0.6	892
0.6-0.7	358
0.7-0.8	108
0.8-0.85	31
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD3817	Phase 2
0.9026	High Similarity	NPD2801	Approved
0.8841	High Similarity	NPD4338	Clinical (unspecified phase)
0.8726	High Similarity	NPD5402	Approved
0.8684	High Similarity	NPD6799	Approved
0.8679	High Similarity	NPD919	Approved
0.8671	High Similarity	NPD3882	Suspended
0.8625	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD1247	Approved
0.8571	High Similarity	NPD1512	Approved
0.8481	Intermediate Similarity	NPD1934	Approved
0.8481	Intermediate Similarity	NPD6801	Discontinued
0.8442	Intermediate Similarity	NPD1511	Approved
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6166	Phase 2
0.8415	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7808	Phase 3
0.8387	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8383	Intermediate Similarity	NPD6797	Phase 2
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8354	Intermediate Similarity	NPD3926	Phase 2
0.8344	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8313	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.828	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5403	Approved
0.8269	Intermediate Similarity	NPD5401	Approved
0.8263	Intermediate Similarity	NPD7054	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8214	Intermediate Similarity	NPD7472	Approved
0.821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8107	Intermediate Similarity	NPD7074	Phase 3
0.805	Intermediate Similarity	NPD920	Approved
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD447	Suspended
0.7961	Intermediate Similarity	NPD1933	Approved
0.7953	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1243	Approved
0.7941	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3748	Approved
0.7901	Intermediate Similarity	NPD4380	Phase 2
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6832	Phase 2
0.7821	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1510	Phase 2
0.7799	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1549	Phase 2
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3750	Approved
0.7662	Intermediate Similarity	NPD1240	Approved
0.7661	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD3226	Approved
0.7619	Intermediate Similarity	NPD3749	Approved
0.7605	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5242	Approved
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD1607	Approved
0.7561	Intermediate Similarity	NPD1653	Approved
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6385	Approved
0.753	Intermediate Similarity	NPD6386	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7457	Intermediate Similarity	NPD2403	Approved
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.7453	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD943	Approved
0.7434	Intermediate Similarity	NPD3266	Approved
0.7434	Intermediate Similarity	NPD3267	Approved
0.7381	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3146	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7346	Intermediate Similarity	NPD4628	Phase 3
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.732	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7301	Intermediate Similarity	NPD3887	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD2353	Approved
0.7267	Intermediate Similarity	NPD17	Approved
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7208	Intermediate Similarity	NPD2797	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3225	Approved
0.7124	Intermediate Similarity	NPD2981	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7685	Pre-registration
0.7107	Intermediate Similarity	NPD1613	Approved
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD2982	Phase 2
0.7078	Intermediate Similarity	NPD2983	Phase 2
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.707	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2344	Approved
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7019	Intermediate Similarity	NPD6651	Approved
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6989	Remote Similarity	NPD8127	Discontinued
0.6983	Remote Similarity	NPD7228	Approved
0.6979	Remote Similarity	NPD5006	Approved
0.6979	Remote Similarity	NPD5005	Approved
0.6978	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD9268	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6777	Approved
0.6963	Remote Similarity	NPD6780	Approved
0.6963	Remote Similarity	NPD6781	Approved
0.6963	Remote Similarity	NPD6779	Approved
0.6963	Remote Similarity	NPD6776	Approved
0.6963	Remote Similarity	NPD6778	Approved
0.6963	Remote Similarity	NPD6782	Approved
0.6957	Remote Similarity	NPD4340	Discontinued
0.6949	Remote Similarity	NPD5710	Approved
0.6949	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD8313	Approved
0.694	Remote Similarity	NPD8312	Approved
0.6937	Remote Similarity	NPD4062	Phase 3
0.6933	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD7038	Approved
0.6923	Remote Similarity	NPD5049	Phase 3
0.6919	Remote Similarity	NPD5889	Approved
0.6919	Remote Similarity	NPD5890	Approved
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6971	Discontinued
0.6911	Remote Similarity	NPD8285	Discontinued
0.6905	Remote Similarity	NPD7390	Discontinued
0.6904	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7874	Approved
0.6903	Remote Similarity	NPD9269	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