NPASS Compound

Structure

CID162351 OpenBabel06191715532D 26 28 0 0 0 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -1.7321 1.0000 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 2.5981 -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 -1.7321 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 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 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 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 -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 -0.8660 -1.5000 0.0000 C 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 1.7321 -3.0000 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 0.0000 -3.0000 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 -4.3301 1.5000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 15 18 1 0 0 0 0 15 22 2 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	2.807
LogD:	2.645
LogS:	-3.693
# Rotatable Bonds:	4
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.582
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.988
MDCK Permeability:	1.4354423910845071e-05
Pgp-inhibitor:	0.827
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.49258422851562%
Volume Distribution (VD):	0.887
Pgp-substrate:	15.975895881652832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.557
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.507
CYP3A4-inhibitor:	0.594
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	6.395
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.426
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.471
Skin Sensitization:	0.519
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.885
Respiratory Toxicity:	0.216

Download Data

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

Natural Product: NPC162351

Natural Product ID:	NPC162351
*Common Name:**	Myricetin 3,3',4'-Trimethylether
IUPAC Name:	5,7-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3-methoxychromen-4-one
Synonyms:	Myricetin 3,3',4'-Trimethylether
Standard InCHIKey:	YTYFGDJADQYGLC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-23-13-5-8(4-11(21)17(13)24-2)16-18(25-3)15(22)14-10(20)6-9(19)7-12(14)26-16/h4-7,19-21H,1-3H3
SMILES:	COc1c(O)cc(cc1OC)c1oc2cc(O)cc(c2c(=O)c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689269
PubChem CID:	44259719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO32817	gardenia oudiepe	Species	Rubiaceae	Eukaryota	flowering buds and leaf bases	Foret Plate, New Caledonia	n.a.	PMID[25659770]
NPO32817	gardenia oudiepe	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29207340]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
IC50	3
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3892	Individual Protein	Tumor necrosis factor receptor superfamily member 10B	Homo sapiens	FC	=	2.2	n.a.	PMID[506997]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	90.0	nM	PMID[506998]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Ratio IC50	=	3.0	n.a.	PMID[506998]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	8100.0	nM	PMID[506999]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10300.0	nM	PMID[506999]

☑ 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 NPC162351 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	461
0.1-0.2	2066
0.2-0.3	5169
0.3-0.4	11268
0.4-0.5	5908
0.5-0.6	4037
0.6-0.7	5056
0.7-0.8	4683
0.8-0.85	2047
0.85-0.9	1186
0.9-0.95	563
0.95-1	253

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58382
0.9932	High Similarity	NPC123886
0.9865	High Similarity	NPC55619
0.9865	High Similarity	NPC100916
0.9865	High Similarity	NPC200388
0.9864	High Similarity	NPC270620
0.9864	High Similarity	NPC236223
0.9864	High Similarity	NPC78326
0.9864	High Similarity	NPC179126
0.9863	High Similarity	NPC28274
0.9863	High Similarity	NPC76376
0.9863	High Similarity	NPC50403
0.9863	High Similarity	NPC133953
0.9799	High Similarity	NPC472438
0.9799	High Similarity	NPC78302
0.9799	High Similarity	NPC235215
0.9799	High Similarity	NPC7973
0.9799	High Similarity	NPC29841
0.9796	High Similarity	NPC82325
0.9796	High Similarity	NPC279989
0.9795	High Similarity	NPC219330
0.9733	High Similarity	NPC25495
0.9733	High Similarity	NPC18607
0.9733	High Similarity	NPC261004
0.9733	High Similarity	NPC18772
0.9733	High Similarity	NPC105242
0.9733	High Similarity	NPC152166
0.9733	High Similarity	NPC130894
0.9733	High Similarity	NPC300943
0.9733	High Similarity	NPC204854
0.9733	High Similarity	NPC115798
0.9733	High Similarity	NPC9609
0.9733	High Similarity	NPC191459
0.9733	High Similarity	NPC22472
0.9733	High Similarity	NPC176300
0.9733	High Similarity	NPC288669
0.9733	High Similarity	NPC19687
0.9733	High Similarity	NPC4481
0.9733	High Similarity	NPC143828
0.9733	High Similarity	NPC7846
0.9733	High Similarity	NPC253634
0.9732	High Similarity	NPC265511
0.9732	High Similarity	NPC268161
0.9732	High Similarity	NPC474520
0.973	High Similarity	NPC246204
0.9728	High Similarity	NPC200740
0.9728	High Similarity	NPC125062
0.9728	High Similarity	NPC252933
0.9728	High Similarity	NPC236769
0.9728	High Similarity	NPC54394
0.9726	High Similarity	NPC177298
0.9726	High Similarity	NPC48479
0.9667	High Similarity	NPC189179
0.9667	High Similarity	NPC93376
0.9667	High Similarity	NPC305663
0.9667	High Similarity	NPC224137
0.9667	High Similarity	NPC163524
0.9667	High Similarity	NPC227192
0.9667	High Similarity	NPC203891
0.9667	High Similarity	NPC110070
0.9667	High Similarity	NPC101830
0.9667	High Similarity	NPC287979
0.9667	High Similarity	NPC176665
0.9667	High Similarity	NPC75215
0.9662	High Similarity	NPC55205
0.966	High Similarity	NPC166753
0.966	High Similarity	NPC50728
0.966	High Similarity	NPC149127
0.966	High Similarity	NPC286342
0.966	High Similarity	NPC188871
0.9658	High Similarity	NPC120464
0.9603	High Similarity	NPC193842
0.96	High Similarity	NPC266960
0.96	High Similarity	NPC247017
0.96	High Similarity	NPC292107
0.96	High Similarity	NPC245546
0.96	High Similarity	NPC49824
0.96	High Similarity	NPC98661
0.96	High Similarity	NPC43243
0.96	High Similarity	NPC178854
0.9597	High Similarity	NPC250822
0.9597	High Similarity	NPC75279
0.9597	High Similarity	NPC276409
0.9595	High Similarity	NPC260895
0.9592	High Similarity	NPC87125
0.9592	High Similarity	NPC137062
0.9592	High Similarity	NPC287101
0.9592	High Similarity	NPC223579
0.9592	High Similarity	NPC270465
0.9592	High Similarity	NPC183950
0.9592	High Similarity	NPC52005
0.9592	High Similarity	NPC159103
0.9589	High Similarity	NPC33265
0.9589	High Similarity	NPC62536
0.9539	High Similarity	NPC246478
0.9536	High Similarity	NPC471479
0.9536	High Similarity	NPC471515
0.9536	High Similarity	NPC174908
0.9533	High Similarity	NPC227325
0.9533	High Similarity	NPC32557
0.9533	High Similarity	NPC183597
0.9533	High Similarity	NPC133392
0.9533	High Similarity	NPC128863
0.9533	High Similarity	NPC44079
0.9533	High Similarity	NPC214138
0.9533	High Similarity	NPC201136
0.9533	High Similarity	NPC146165
0.9533	High Similarity	NPC167815
0.9533	High Similarity	NPC56786
0.9533	High Similarity	NPC92659
0.9533	High Similarity	NPC208197
0.9533	High Similarity	NPC138360
0.9533	High Similarity	NPC189960
0.9533	High Similarity	NPC2476
0.9533	High Similarity	NPC80534
0.9533	High Similarity	NPC280339
0.9533	High Similarity	NPC196439
0.9533	High Similarity	NPC4455
0.9533	High Similarity	NPC201451
0.9533	High Similarity	NPC26227
0.9533	High Similarity	NPC163780
0.9533	High Similarity	NPC50715
0.953	High Similarity	NPC39732
0.953	High Similarity	NPC471982
0.953	High Similarity	NPC60972
0.9524	High Similarity	NPC195202
0.9524	High Similarity	NPC261548
0.9521	High Similarity	NPC169749
0.9481	High Similarity	NPC470459
0.947	High Similarity	NPC250922
0.947	High Similarity	NPC471500
0.9467	High Similarity	NPC47781
0.9467	High Similarity	NPC22519
0.9467	High Similarity	NPC176775
0.9467	High Similarity	NPC160951
0.9467	High Similarity	NPC274327
0.9467	High Similarity	NPC255350
0.9467	High Similarity	NPC145379
0.9467	High Similarity	NPC69394
0.9467	High Similarity	NPC183878
0.9467	High Similarity	NPC86485
0.9467	High Similarity	NPC231018
0.9463	High Similarity	NPC304295
0.9463	High Similarity	NPC205046
0.9463	High Similarity	NPC59162
0.9459	High Similarity	NPC328119
0.9456	High Similarity	NPC12200
0.9456	High Similarity	NPC108406
0.9419	High Similarity	NPC470457
0.9412	High Similarity	NPC470326
0.9408	High Similarity	NPC67876
0.9404	High Similarity	NPC213622
0.9404	High Similarity	NPC256612
0.9404	High Similarity	NPC20830
0.94	High Similarity	NPC157784
0.94	High Similarity	NPC304954
0.94	High Similarity	NPC301323
0.94	High Similarity	NPC134677
0.94	High Similarity	NPC275836
0.94	High Similarity	NPC162313
0.94	High Similarity	NPC241498
0.94	High Similarity	NPC100887
0.94	High Similarity	NPC120163
0.94	High Similarity	NPC239128
0.94	High Similarity	NPC293183
0.94	High Similarity	NPC187498
0.94	High Similarity	NPC71334
0.94	High Similarity	NPC198826
0.94	High Similarity	NPC156222
0.94	High Similarity	NPC83508
0.94	High Similarity	NPC188203
0.94	High Similarity	NPC131624
0.94	High Similarity	NPC63187
0.94	High Similarity	NPC222830
0.94	High Similarity	NPC25270
0.94	High Similarity	NPC212678
0.94	High Similarity	NPC27208
0.94	High Similarity	NPC142540
0.94	High Similarity	NPC37684
0.94	High Similarity	NPC275722
0.94	High Similarity	NPC57030
0.94	High Similarity	NPC256283
0.94	High Similarity	NPC301123
0.9388	High Similarity	NPC20791
0.9388	High Similarity	NPC310259
0.9388	High Similarity	NPC179271
0.9359	High Similarity	NPC470462
0.9351	High Similarity	NPC112418
0.9351	High Similarity	NPC471499
0.9346	High Similarity	NPC280680
0.9346	High Similarity	NPC195832
0.9346	High Similarity	NPC284127
0.9346	High Similarity	NPC172202
0.9346	High Similarity	NPC476410
0.9342	High Similarity	NPC326037
0.9342	High Similarity	NPC320825
0.9342	High Similarity	NPC13858
0.9338	High Similarity	NPC18727
0.9333	High Similarity	NPC208043
0.9333	High Similarity	NPC225731

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 NPC162351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	442
0.1-0.2	1017
0.2-0.3	1934
0.3-0.4	2649
0.4-0.5	1677
0.5-0.6	949
0.6-0.7	329
0.7-0.8	96
0.8-0.85	35
0.85-0.9	13
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9467	High Similarity	NPD2801	Approved
0.9404	High Similarity	NPD3817	Phase 2
0.9388	High Similarity	NPD1512	Approved
0.9342	High Similarity	NPD3882	Suspended
0.9272	High Similarity	NPD1934	Approved
0.9252	High Similarity	NPD1511	Approved
0.9172	High Similarity	NPD6168	Clinical (unspecified phase)
0.9172	High Similarity	NPD6166	Phase 2
0.9172	High Similarity	NPD6167	Clinical (unspecified phase)
0.9085	High Similarity	NPD2393	Clinical (unspecified phase)
0.9006	High Similarity	NPD6797	Phase 2
0.8951	High Similarity	NPD7251	Discontinued
0.8933	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD7808	Phase 3
0.8896	High Similarity	NPD4338	Clinical (unspecified phase)
0.8882	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7472	Approved
0.882	High Similarity	NPD3818	Discontinued
0.8712	High Similarity	NPD7074	Phase 3
0.8671	High Similarity	NPD7075	Discontinued
0.8618	High Similarity	NPD6799	Approved
0.8608	High Similarity	NPD4868	Clinical (unspecified phase)
0.8535	High Similarity	NPD6801	Discontinued
0.8526	High Similarity	NPD4380	Phase 2
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD5402	Approved
0.8424	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD6599	Discontinued
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.825	Intermediate Similarity	NPD1465	Phase 2
0.8221	Intermediate Similarity	NPD5494	Approved
0.8205	Intermediate Similarity	NPD5401	Approved
0.8188	Intermediate Similarity	NPD1240	Approved
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8171	Intermediate Similarity	NPD1247	Approved
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1607	Approved
0.8067	Intermediate Similarity	NPD943	Approved
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7973	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD230	Phase 1
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7834	Intermediate Similarity	NPD3750	Approved
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD2800	Approved
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.7613	Intermediate Similarity	NPD6651	Approved
0.7607	Intermediate Similarity	NPD1653	Approved
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.7588	Intermediate Similarity	NPD3787	Discontinued
0.7584	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3749	Approved
0.7548	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3226	Approved
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2403	Approved
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD1203	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7317	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.7301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7244	Intermediate Similarity	NPD3268	Approved
0.7239	Intermediate Similarity	NPD2309	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7171	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD2354	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7119	Intermediate Similarity	NPD2163	Approved
0.7114	Intermediate Similarity	NPD5536	Phase 2
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6780	Approved
0.7086	Intermediate Similarity	NPD5710	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7078	Intermediate Similarity	NPD3225	Approved
0.7072	Intermediate Similarity	NPD8312	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.707	Intermediate Similarity	NPD7095	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD6385	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD6386	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7048	Intermediate Similarity	NPD4357	Discontinued
0.7047	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD411	Approved
0.702	Intermediate Similarity	NPD9268	Approved
0.7018	Intermediate Similarity	NPD6844	Discontinued
0.7013	Intermediate Similarity	NPD4749	Approved
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3146	Approved
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4340	Discontinued
0.6994	Remote Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD7266	Discontinued
0.6981	Remote Similarity	NPD4062	Phase 3
0.6974	Remote Similarity	NPD8151	Discontinued
0.6968	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4361	Phase 2
0.6964	Remote Similarity	NPD5049	Phase 3
0.6962	Remote Similarity	NPD4625	Phase 3
0.6939	Remote Similarity	NPD228	Approved
0.6936	Remote Similarity	NPD4288	Approved
0.6928	Remote Similarity	NPD3887	Approved
0.6923	Remote Similarity	NPD3266	Approved
0.6923	Remote Similarity	NPD3267	Approved
0.6893	Remote Similarity	NPD7229	Phase 3
0.6891	Remote Similarity	NPD7697	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