NPASS Compound

Structure

CID18727 OpenBabel06191715342D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -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 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 1.5000 0.0000 C 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 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 3.4641 -0.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 22 1 0 0 0 0 15 9 1 6 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	3.027
LogD:	2.986
LogS:	-4.696
# Rotatable Bonds:	3
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.905
Synthetic Accessibility Score:	2.832
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	2.9742417609668337e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.231

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	92.24417877197266%
Volume Distribution (VD):	0.777
Pgp-substrate:	9.179655075073242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.622
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	14.281
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.611
Skin Sensitization:	0.688
Carcinogencity:	0.459
Eye Corrosion:	0.008
Eye Irritation:	0.91
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC18727

Natural Product ID:	NPC18727
*Common Name:**	7-Methoxyhesperetin
IUPAC Name:	(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	LWBHKKLWSUFUNZ-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3/t15-/m0/s1
SMILES:	COc1cc2O[C@@H](CC(=O)c2c(c1)O)c1ccc(c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2234487
PubChem CID:	14157910
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
NPO6444	Humulus scandens	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1821	Kopsia albiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14809	Talaromyces avellaneus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5497	Stachys chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2741	Ribes sanguineum	Species	Grossulariaceae	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
MIC	4
Others	4

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	ug.mL-1	PMID[554470]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	50.0	ug.mL-1	PMID[554470]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[554470]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	200.0	ug.mL-1	PMID[554470]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0.7	mm	PMID[554470]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	IZ	=	2.2	mm	PMID[554470]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	1.8	mm	PMID[554470]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.7	mm	PMID[554470]

☑ 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 NPC18727 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	398
0.1-0.2	1606
0.2-0.3	4253
0.3-0.4	10242
0.4-0.5	7684
0.5-0.6	3296
0.6-0.7	4641
0.7-0.8	5332
0.8-0.85	2810
0.85-0.9	1685
0.9-0.95	600
0.95-1	150

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC302950
0.9932	High Similarity	NPC219582
0.9932	High Similarity	NPC236637
0.9865	High Similarity	NPC195796
0.9865	High Similarity	NPC278778
0.9865	High Similarity	NPC291878
0.9865	High Similarity	NPC35038
0.9799	High Similarity	NPC156057
0.9799	High Similarity	NPC472598
0.9799	High Similarity	NPC474836
0.9799	High Similarity	NPC162869
0.9799	High Similarity	NPC471479
0.9799	High Similarity	NPC27337
0.9799	High Similarity	NPC291508
0.9799	High Similarity	NPC471515
0.9799	High Similarity	NPC475267
0.9799	High Similarity	NPC474208
0.9799	High Similarity	NPC48208
0.9799	High Similarity	NPC474055
0.9797	High Similarity	NPC45849
0.9797	High Similarity	NPC200761
0.9797	High Similarity	NPC470327
0.9797	High Similarity	NPC477503
0.9796	High Similarity	NPC472912
0.9795	High Similarity	NPC338131
0.9732	High Similarity	NPC255106
0.9732	High Similarity	NPC320825
0.9732	High Similarity	NPC209614
0.9732	High Similarity	NPC326037
0.9732	High Similarity	NPC235165
0.9732	High Similarity	NPC13858
0.9732	High Similarity	NPC471500
0.9732	High Similarity	NPC470328
0.9732	High Similarity	NPC472626
0.973	High Similarity	NPC213896
0.973	High Similarity	NPC192083
0.9669	High Similarity	NPC192686
0.9669	High Similarity	NPC287328
0.9669	High Similarity	NPC118256
0.9669	High Similarity	NPC282009
0.9669	High Similarity	NPC472624
0.9669	High Similarity	NPC36217
0.9669	High Similarity	NPC119209
0.9667	High Similarity	NPC472914
0.9667	High Similarity	NPC52530
0.9667	High Similarity	NPC67876
0.9667	High Similarity	NPC96167
0.9667	High Similarity	NPC299520
0.9667	High Similarity	NPC472913
0.9667	High Similarity	NPC223787
0.9667	High Similarity	NPC472911
0.9667	High Similarity	NPC472910
0.9667	High Similarity	NPC245758
0.9667	High Similarity	NPC129684
0.9667	High Similarity	NPC222814
0.9667	High Similarity	NPC99597
0.9667	High Similarity	NPC210084
0.9664	High Similarity	NPC37392
0.9664	High Similarity	NPC226025
0.9664	High Similarity	NPC321779
0.9664	High Similarity	NPC67396
0.9662	High Similarity	NPC257648
0.9662	High Similarity	NPC477231
0.9662	High Similarity	NPC106976
0.9662	High Similarity	NPC260979
0.9658	High Similarity	NPC294852
0.9658	High Similarity	NPC321011
0.9658	High Similarity	NPC188679
0.9605	High Similarity	NPC158188
0.9605	High Similarity	NPC26326
0.9605	High Similarity	NPC472632
0.9605	High Similarity	NPC471499
0.9605	High Similarity	NPC471210
0.9605	High Similarity	NPC472634
0.9605	High Similarity	NPC474038
0.9603	High Similarity	NPC95936
0.9603	High Similarity	NPC22192
0.9603	High Similarity	NPC250214
0.96	High Similarity	NPC24640
0.96	High Similarity	NPC250922
0.96	High Similarity	NPC472916
0.9597	High Similarity	NPC74924
0.9597	High Similarity	NPC298692
0.9597	High Similarity	NPC469550
0.9595	High Similarity	NPC31363
0.9592	High Similarity	NPC48479
0.9592	High Similarity	NPC177298
0.9592	High Similarity	NPC137062
0.9592	High Similarity	NPC1612
0.9592	High Similarity	NPC287101
0.9592	High Similarity	NPC183950
0.9592	High Similarity	NPC183959
0.9592	High Similarity	NPC223579
0.9592	High Similarity	NPC52005
0.9542	High Similarity	NPC472635
0.9542	High Similarity	NPC474034
0.9542	High Similarity	NPC201800
0.9542	High Similarity	NPC476247
0.9542	High Similarity	NPC474033
0.9542	High Similarity	NPC472964
0.9539	High Similarity	NPC263449
0.9539	High Similarity	NPC472630
0.9539	High Similarity	NPC472902
0.9539	High Similarity	NPC470183
0.9539	High Similarity	NPC470326
0.9539	High Similarity	NPC174953
0.9539	High Similarity	NPC472631
0.9539	High Similarity	NPC475784
0.9536	High Similarity	NPC470402
0.9536	High Similarity	NPC473272
0.9536	High Similarity	NPC78225
0.9536	High Similarity	NPC471209
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC108456
0.9536	High Similarity	NPC284820
0.9533	High Similarity	NPC472909
0.9533	High Similarity	NPC2928
0.9533	High Similarity	NPC255807
0.9533	High Similarity	NPC117992
0.9533	High Similarity	NPC213622
0.9533	High Similarity	NPC57674
0.9533	High Similarity	NPC168247
0.9533	High Similarity	NPC31018
0.9533	High Similarity	NPC152951
0.9533	High Similarity	NPC230149
0.953	High Similarity	NPC36835
0.953	High Similarity	NPC39732
0.953	High Similarity	NPC246162
0.953	High Similarity	NPC260491
0.953	High Similarity	NPC180234
0.953	High Similarity	NPC199100
0.953	High Similarity	NPC120537
0.953	High Similarity	NPC240476
0.953	High Similarity	NPC9743
0.953	High Similarity	NPC60972
0.953	High Similarity	NPC61506
0.953	High Similarity	NPC471982
0.9527	High Similarity	NPC29231
0.9524	High Similarity	NPC195202
0.9524	High Similarity	NPC3036
0.9524	High Similarity	NPC120464
0.9481	High Similarity	NPC124038
0.9481	High Similarity	NPC186686
0.9481	High Similarity	NPC472625
0.9477	High Similarity	NPC113163
0.9477	High Similarity	NPC471212
0.9477	High Similarity	NPC112418
0.9477	High Similarity	NPC66618
0.9477	High Similarity	NPC266314
0.9477	High Similarity	NPC288131
0.9477	High Similarity	NPC84324
0.9477	High Similarity	NPC305987
0.9477	High Similarity	NPC142252
0.9477	High Similarity	NPC165970
0.9477	High Similarity	NPC134783
0.9477	High Similarity	NPC308992
0.9477	High Similarity	NPC471211
0.9477	High Similarity	NPC173137
0.9474	High Similarity	NPC117418
0.9474	High Similarity	NPC210459
0.9474	High Similarity	NPC473990
0.9474	High Similarity	NPC172202
0.9474	High Similarity	NPC284127
0.9474	High Similarity	NPC53545
0.9474	High Similarity	NPC152904
0.9474	High Similarity	NPC55738
0.9474	High Similarity	NPC476410
0.947	High Similarity	NPC474638
0.947	High Similarity	NPC68093
0.947	High Similarity	NPC191146
0.9467	High Similarity	NPC167091
0.9467	High Similarity	NPC70433
0.9467	High Similarity	NPC179126
0.9467	High Similarity	NPC270620
0.9467	High Similarity	NPC325028
0.9467	High Similarity	NPC47781
0.9467	High Similarity	NPC49402
0.9467	High Similarity	NPC22519
0.9467	High Similarity	NPC176775
0.9467	High Similarity	NPC33051
0.9467	High Similarity	NPC160951
0.9467	High Similarity	NPC274327
0.9467	High Similarity	NPC141212
0.9467	High Similarity	NPC292214
0.9467	High Similarity	NPC227337
0.9467	High Similarity	NPC271779
0.9467	High Similarity	NPC255350
0.9467	High Similarity	NPC472915
0.9467	High Similarity	NPC145379
0.9467	High Similarity	NPC69394
0.9467	High Similarity	NPC27532
0.9467	High Similarity	NPC88645
0.9467	High Similarity	NPC183878
0.9467	High Similarity	NPC273462
0.9467	High Similarity	NPC78326
0.9467	High Similarity	NPC231018
0.9467	High Similarity	NPC236223
0.9467	High Similarity	NPC256346
0.9467	High Similarity	NPC246328
0.9467	High Similarity	NPC206238

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 NPC18727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	926
0.2-0.3	1755
0.3-0.4	2616
0.4-0.5	1743
0.5-0.6	1010
0.6-0.7	538
0.7-0.8	136
0.8-0.85	42
0.85-0.9	12
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9932	High Similarity	NPD1934	Approved
0.973	High Similarity	NPD2393	Clinical (unspecified phase)
0.9467	High Similarity	NPD2801	Approved
0.9419	High Similarity	NPD6167	Clinical (unspecified phase)
0.9419	High Similarity	NPD6168	Clinical (unspecified phase)
0.9419	High Similarity	NPD6166	Phase 2
0.9252	High Similarity	NPD1511	Approved
0.9216	High Similarity	NPD3882	Suspended
0.9182	High Similarity	NPD7074	Phase 3
0.9128	High Similarity	NPD1512	Approved
0.9119	High Similarity	NPD7054	Approved
0.9062	High Similarity	NPD7472	Approved
0.9057	High Similarity	NPD3818	Discontinued
0.9026	High Similarity	NPD3817	Phase 2
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8968	High Similarity	NPD4868	Clinical (unspecified phase)
0.8912	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD4380	Phase 2
0.8834	High Similarity	NPD7251	Discontinued
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD5494	Approved
0.879	High Similarity	NPD7075	Discontinued
0.879	High Similarity	NPD4381	Clinical (unspecified phase)
0.878	High Similarity	NPD4338	Clinical (unspecified phase)
0.878	High Similarity	NPD7808	Phase 3
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8649	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD1510	Phase 2
0.8544	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6799	Approved
0.8481	Intermediate Similarity	NPD7819	Suspended
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8435	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1613	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8434	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD5844	Phase 1
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8395	Intermediate Similarity	NPD6959	Discontinued
0.8365	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1607	Approved
0.8311	Intermediate Similarity	NPD943	Approved
0.8291	Intermediate Similarity	NPD6599	Discontinued
0.8288	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6559	Discontinued
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5402	Approved
0.8101	Intermediate Similarity	NPD5403	Approved
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8061	Intermediate Similarity	NPD1247	Approved
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD919	Approved
0.8024	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD230	Phase 1
0.7987	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5401	Approved
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7949	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7768	Phase 2
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD447	Suspended
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2800	Approved
0.7879	Intermediate Similarity	NPD3749	Approved
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7831	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD1653	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7806	Intermediate Similarity	NPD6100	Approved
0.7799	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1933	Approved
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD9494	Approved
0.7719	Intermediate Similarity	NPD3751	Discontinued
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4908	Phase 1
0.7673	Intermediate Similarity	NPD6190	Approved
0.767	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD920	Approved
0.7643	Intermediate Similarity	NPD2344	Approved
0.7636	Intermediate Similarity	NPD37	Approved
0.7628	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD7228	Approved
0.7613	Intermediate Similarity	NPD6651	Approved
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.7582	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7561	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1243	Approved
0.7543	Intermediate Similarity	NPD7685	Pre-registration
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1203	Approved
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7468	Intermediate Similarity	NPD6798	Discontinued
0.7458	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7453	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.7442	Intermediate Similarity	NPD5242	Approved
0.744	Intermediate Similarity	NPD5353	Approved
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.7384	Intermediate Similarity	NPD5710	Approved
0.7384	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.732	Intermediate Similarity	NPD2798	Approved
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7584	Approved
0.7312	Intermediate Similarity	NPD7266	Discontinued
0.7308	Intermediate Similarity	NPD6233	Phase 2
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7285	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7262	Intermediate Similarity	NPD6386	Approved
0.7262	Intermediate Similarity	NPD6385	Approved
0.7255	Intermediate Similarity	NPD2797	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD4749	Approved
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7215	Intermediate Similarity	NPD5124	Phase 1
0.7215	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4662	Approved
0.7212	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7178	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4110	Phase 3
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD4357	Discontinued
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD7240	Approved
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD411	Approved
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7119	Intermediate Similarity	NPD2163	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