NPASS Compound

Structure

CID275772 OpenBabel06191716082D 22 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 -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 -4.3301 -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 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 -5.1962 -2.0000 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 -1.5000 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 -0.8660 -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 -0.0000 -0.0000 0.0000 C 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 -6.0622 -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 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 0.0000 1.0000 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 1 2 2 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 4 11 2 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.04
Volume:	282.767
LogP:	2.33
LogD:	0.953
LogS:	-3.521
# Rotatable Bonds:	1
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	2.556
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203
MDCK Permeability:	7.860197001718916e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.165
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.14878845214844%
Volume Distribution (VD):	0.575
Pgp-substrate:	9.937505722045898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.552
CYP2C9-substrate:	0.368
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	7.368
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.562
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.956
Carcinogencity:	0.103
Eye Corrosion:	0.004
Eye Irritation:	0.934
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC275772

Natural Product ID:	NPC275772
*Common Name:**	6-Hydroxyluteolin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxychromen-4-one
Synonyms:	6-Hydroxyluteolin
Standard InCHIKey:	VYAKIUWQLHRZGK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H
SMILES:	Oc1ccc(cc1O)c1cc(=O)c2c(o1)cc(c(c2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464107
PubChem CID:	5281642
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Entire plants	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Whole Plant	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[24895551]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784154]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9240	Veronica spuria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9240	Veronica spuria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9295	Clerodendron fragrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19968	Millettia ovalifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO794	Lippia graveolens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20993	Bystropogon mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9240	Veronica spuria	Species	Plantaginaceae	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
NPO794	NPC275772	Dried Or Powder	n.a.	96.09090932	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

☑ 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
IC50	2
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	91.7	%	PMID[457249]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	204.17	nM	PMID[457247]
NPT2	Others	Unspecified		IC50	=	11600.0	nM	PMID[457248]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[457250]

☑ 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 NPC275772 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	566
0.1-0.2	2270
0.2-0.3	5840
0.3-0.4	11846
0.4-0.5	4567
0.5-0.6	4209
0.6-0.7	5137
0.7-0.8	4693
0.8-0.85	1929
0.85-0.9	1005
0.9-0.95	524
0.95-1	111

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239312
1.0	High Similarity	NPC130230
0.9929	High Similarity	NPC12367
0.9929	High Similarity	NPC118726
0.9859	High Similarity	NPC216318
0.9859	High Similarity	NPC17286
0.9859	High Similarity	NPC195351
0.9859	High Similarity	NPC296197
0.9859	High Similarity	NPC259713
0.979	High Similarity	NPC45873
0.979	High Similarity	NPC184136
0.979	High Similarity	NPC77858
0.9789	High Similarity	NPC276930
0.9786	High Similarity	NPC279121
0.9722	High Similarity	NPC225731
0.9716	High Similarity	NPC70136
0.9714	High Similarity	NPC175013
0.9655	High Similarity	NPC212678
0.9655	High Similarity	NPC188203
0.9655	High Similarity	NPC162313
0.9655	High Similarity	NPC241498
0.9655	High Similarity	NPC275836
0.9655	High Similarity	NPC131624
0.9655	High Similarity	NPC198826
0.9655	High Similarity	NPC57030
0.9655	High Similarity	NPC275722
0.9655	High Similarity	NPC83508
0.9655	High Similarity	NPC120163
0.9655	High Similarity	NPC71334
0.9655	High Similarity	NPC301323
0.9655	High Similarity	NPC187498
0.9655	High Similarity	NPC25270
0.9655	High Similarity	NPC156222
0.9655	High Similarity	NPC27208
0.9655	High Similarity	NPC100887
0.9655	High Similarity	NPC256283
0.9655	High Similarity	NPC293183
0.9655	High Similarity	NPC239128
0.9655	High Similarity	NPC222830
0.9653	High Similarity	NPC61620
0.9653	High Similarity	NPC62042
0.965	High Similarity	NPC194856
0.9648	High Similarity	NPC179271
0.9648	High Similarity	NPC20791
0.9589	High Similarity	NPC69394
0.9589	High Similarity	NPC274327
0.9589	High Similarity	NPC183878
0.9589	High Similarity	NPC145379
0.9589	High Similarity	NPC231018
0.9589	High Similarity	NPC160951
0.9589	High Similarity	NPC22519
0.9589	High Similarity	NPC176775
0.9589	High Similarity	NPC255350
0.9589	High Similarity	NPC47781
0.9586	High Similarity	NPC251110
0.9586	High Similarity	NPC204515
0.958	High Similarity	NPC207729
0.958	High Similarity	NPC74881
0.958	High Similarity	NPC168803
0.958	High Similarity	NPC51443
0.958	High Similarity	NPC108406
0.9524	High Similarity	NPC227325
0.9524	High Similarity	NPC2476
0.9524	High Similarity	NPC138360
0.9524	High Similarity	NPC280339
0.9524	High Similarity	NPC4455
0.9524	High Similarity	NPC201451
0.9524	High Similarity	NPC26227
0.9524	High Similarity	NPC163780
0.9524	High Similarity	NPC50715
0.9524	High Similarity	NPC146165
0.9524	High Similarity	NPC20830
0.9524	High Similarity	NPC128863
0.9524	High Similarity	NPC44079
0.9524	High Similarity	NPC214138
0.9524	High Similarity	NPC183597
0.9524	High Similarity	NPC201136
0.9524	High Similarity	NPC256612
0.9524	High Similarity	NPC213622
0.9524	High Similarity	NPC196439
0.9524	High Similarity	NPC167815
0.9524	High Similarity	NPC92659
0.9521	High Similarity	NPC180234
0.9521	High Similarity	NPC142540
0.9521	High Similarity	NPC199100
0.9521	High Similarity	NPC120537
0.9517	High Similarity	NPC248102
0.9517	High Similarity	NPC306821
0.9514	High Similarity	NPC218490
0.9514	High Similarity	NPC119059
0.951	High Similarity	NPC169749
0.9459	High Similarity	NPC266960
0.9459	High Similarity	NPC98661
0.9459	High Similarity	NPC245546
0.9459	High Similarity	NPC43243
0.9459	High Similarity	NPC247017
0.9459	High Similarity	NPC49824
0.9456	High Similarity	NPC167091
0.9456	High Similarity	NPC271779
0.9456	High Similarity	NPC292214
0.9456	High Similarity	NPC88645
0.9456	High Similarity	NPC206238
0.9456	High Similarity	NPC250822
0.9456	High Similarity	NPC276409
0.9456	High Similarity	NPC75279
0.9452	High Similarity	NPC226973
0.9452	High Similarity	NPC208043
0.9452	High Similarity	NPC202157
0.9448	High Similarity	NPC52005
0.9448	High Similarity	NPC183950
0.9448	High Similarity	NPC87125
0.9448	High Similarity	NPC270465
0.9448	High Similarity	NPC137062
0.9448	High Similarity	NPC287101
0.9448	High Similarity	NPC223579
0.9444	High Similarity	NPC61871
0.9444	High Similarity	NPC30647
0.9444	High Similarity	NPC55557
0.9396	High Similarity	NPC93376
0.9396	High Similarity	NPC110070
0.9396	High Similarity	NPC227192
0.9396	High Similarity	NPC203891
0.9396	High Similarity	NPC189179
0.9396	High Similarity	NPC163524
0.9396	High Similarity	NPC470402
0.9396	High Similarity	NPC75215
0.9396	High Similarity	NPC305663
0.9396	High Similarity	NPC101830
0.9396	High Similarity	NPC176665
0.9396	High Similarity	NPC224137
0.9396	High Similarity	NPC287979
0.9392	High Similarity	NPC208197
0.9392	High Similarity	NPC2928
0.9388	High Similarity	NPC101996
0.9388	High Similarity	NPC39732
0.9388	High Similarity	NPC161277
0.9388	High Similarity	NPC60972
0.9388	High Similarity	NPC249570
0.9388	High Similarity	NPC301123
0.9388	High Similarity	NPC39007
0.9384	High Similarity	NPC88804
0.9384	High Similarity	NPC3825
0.9384	High Similarity	NPC286342
0.9384	High Similarity	NPC188871
0.9384	High Similarity	NPC10467
0.9384	High Similarity	NPC149127
0.9379	High Similarity	NPC321011
0.9379	High Similarity	NPC120464
0.9379	High Similarity	NPC196277
0.9379	High Similarity	NPC43669
0.9379	High Similarity	NPC272721
0.9379	High Similarity	NPC188679
0.9379	High Similarity	NPC294852
0.9333	High Similarity	NPC204854
0.9333	High Similarity	NPC261004
0.9333	High Similarity	NPC19687
0.9333	High Similarity	NPC105242
0.9333	High Similarity	NPC9609
0.9333	High Similarity	NPC4481
0.9333	High Similarity	NPC7846
0.9333	High Similarity	NPC143828
0.9333	High Similarity	NPC18607
0.9333	High Similarity	NPC22472
0.9333	High Similarity	NPC18772
0.9333	High Similarity	NPC176300
0.9333	High Similarity	NPC253634
0.9333	High Similarity	NPC191459
0.9333	High Similarity	NPC288669
0.9333	High Similarity	NPC152166
0.9333	High Similarity	NPC130894
0.9333	High Similarity	NPC300943
0.9333	High Similarity	NPC115798
0.9333	High Similarity	NPC25495
0.9329	High Similarity	NPC201837
0.9329	High Similarity	NPC191146
0.9329	High Similarity	NPC235165
0.9329	High Similarity	NPC68093
0.9329	High Similarity	NPC292107
0.9329	High Similarity	NPC472916
0.9329	High Similarity	NPC276444
0.9329	High Similarity	NPC255106
0.9329	High Similarity	NPC474520
0.9324	High Similarity	NPC476631
0.9324	High Similarity	NPC89474
0.9324	High Similarity	NPC86485
0.932	High Similarity	NPC252933
0.932	High Similarity	NPC260895
0.932	High Similarity	NPC149614
0.932	High Similarity	NPC125062
0.932	High Similarity	NPC200740
0.932	High Similarity	NPC171010
0.932	High Similarity	NPC308451
0.932	High Similarity	NPC54394
0.932	High Similarity	NPC117579
0.9315	High Similarity	NPC48479
0.9315	High Similarity	NPC177298
0.9315	High Similarity	NPC183959
0.9315	High Similarity	NPC1612
0.9315	High Similarity	NPC328119
0.931	High Similarity	NPC12200

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 NPC275772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	498
0.1-0.2	1041
0.2-0.3	1900
0.3-0.4	2717
0.4-0.5	1632
0.5-0.6	917
0.6-0.7	297
0.7-0.8	96
0.8-0.85	35
0.85-0.9	12
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9786	High Similarity	NPD1511	Approved
0.9648	High Similarity	NPD1512	Approved
0.9589	High Similarity	NPD2801	Approved
0.9128	High Similarity	NPD1934	Approved
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8824	High Similarity	NPD3882	Suspended
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.8681	High Similarity	NPD1510	Phase 2
0.8679	High Similarity	NPD3818	Discontinued
0.8662	High Similarity	NPD943	Approved
0.8658	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD4338	Clinical (unspecified phase)
0.8636	High Similarity	NPD3817	Phase 2
0.863	High Similarity	NPD1549	Phase 2
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8509	High Similarity	NPD7054	Approved
0.8462	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7472	Approved
0.8405	Intermediate Similarity	NPD6797	Phase 2
0.8403	Intermediate Similarity	NPD1240	Approved
0.8377	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD7251	Discontinued
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD1465	Phase 2
0.8302	Intermediate Similarity	NPD5494	Approved
0.8291	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1607	Approved
0.828	Intermediate Similarity	NPD5402	Approved
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2796	Approved
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD3750	Approved
0.8137	Intermediate Similarity	NPD1247	Approved
0.8105	Intermediate Similarity	NPD6799	Approved
0.8095	Intermediate Similarity	NPD230	Phase 1
0.8086	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8027	Intermediate Similarity	NPD1613	Approved
0.8027	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7987	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7973	Intermediate Similarity	NPD447	Suspended
0.7964	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7862	Intermediate Similarity	NPD7411	Suspended
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7844	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD5403	Approved
0.7821	Intermediate Similarity	NPD5401	Approved
0.7815	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD6599	Discontinued
0.7793	Intermediate Similarity	NPD1203	Approved
0.7791	Intermediate Similarity	NPD919	Approved
0.777	Intermediate Similarity	NPD2313	Discontinued
0.7727	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7708	Intermediate Similarity	NPD9269	Phase 2
0.7707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1653	Approved
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3226	Approved
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.7595	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD2534	Approved
0.7595	Intermediate Similarity	NPD2532	Approved
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7568	Intermediate Similarity	NPD9494	Approved
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD3027	Phase 3
0.7466	Intermediate Similarity	NPD9717	Approved
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7431	Intermediate Similarity	NPD9268	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD3225	Approved
0.7356	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1481	Phase 2
0.7347	Intermediate Similarity	NPD1608	Approved
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7341	Intermediate Similarity	NPD5953	Discontinued
0.7338	Intermediate Similarity	NPD6651	Approved
0.7326	Intermediate Similarity	NPD7286	Phase 2
0.7315	Intermediate Similarity	NPD1470	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD411	Approved
0.7303	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD1535	Discovery
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2798	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7244	Intermediate Similarity	NPD4308	Phase 3
0.7233	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2797	Approved
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7186	Intermediate Similarity	NPD4288	Approved
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD17	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7102	Intermediate Similarity	NPD7685	Pre-registration
0.7086	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD3764	Approved
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD2654	Approved
0.7055	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4360	Phase 2
0.7049	Intermediate Similarity	NPD4363	Phase 3
0.7044	Intermediate Similarity	NPD1471	Phase 3
0.7041	Intermediate Similarity	NPD4967	Phase 2
0.7041	Intermediate Similarity	NPD4965	Approved
0.7041	Intermediate Similarity	NPD4966	Approved
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD5710	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7017	Intermediate Similarity	NPD4287	Approved
0.7013	Intermediate Similarity	NPD4625	Phase 3
0.7007	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD8434	Phase 2
0.6994	Remote Similarity	NPD5242	Approved
0.6987	Remote Similarity	NPD4307	Phase 2
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD9493	Approved
0.6982	Remote Similarity	NPD2296	Approved
0.6973	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD1652	Phase 2
0.6954	Remote Similarity	NPD2403	Approved
0.6954	Remote Similarity	NPD4749	Approved
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6936	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD1019	Discontinued
0.6919	Remote Similarity	NPD4361	Phase 2
0.6919	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6385	Approved
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6386	Approved
0.6897	Remote Similarity	NPD1241	Discontinued
0.689	Remote Similarity	NPD4357	Discontinued
0.6883	Remote Similarity	NPD3018	Phase 2
0.6882	Remote Similarity	NPD5353	Approved
0.6879	Remote Similarity	NPD1558	Phase 1
0.6875	Remote Similarity	NPD228	Approved
0.6875	Remote Similarity	NPD5404	Approved
0.6875	Remote Similarity	NPD5406	Approved
0.6875	Remote Similarity	NPD5408	Approved
0.6875	Remote Similarity	NPD5405	Approved
0.6871	Remote Similarity	NPD2354	Approved

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