NPASS Compound

Structure

NPC24043 OpenBabel07101718312D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -3.4641 -0.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -0.0000 4.0000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 0.8660 2.5000 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -0.0000 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 1 31 1 0 0 0 0 2 32 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 24 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 33 1 0 0 0 0 12 21 2 0 0 0 0 12 31 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 34 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 6 0 0 0 16 21 1 0 0 0 0 16 27 1 0 0 0 0 17 22 1 0 0 0 0 17 28 2 0 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 23 1 0 0 0 0 19 30 1 1 0 0 0 20 22 2 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 22 35 1 0 0 0 0 23 34 1 0 0 0 0 23 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.13
Volume:	456.529
LogP:	1.077
LogD:	0.567
LogS:	-3.586
# Rotatable Bonds:	6
TPSA:	188.51
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	3.928
Fsp3:	0.348
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.046
MDCK Permeability:	1.5987485312507488e-05
Pgp-inhibitor:	0.426
Pgp-substrate:	0.896
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.287

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	80.4144287109375%
Volume Distribution (VD):	0.986
Pgp-substrate:	17.858530044555664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.467
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	4.153
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.254
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.738
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.226
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC24043

Natural Product ID:	NPC24043
*Common Name:**	Eupalitin 3-O-Beta-D-Galactopyranoside
IUPAC Name:	5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	FFRYQAOUWMJQCX-LTGKLFRMSA-N
Standard InCHI:	InChI=1S/C23H24O12/c1-31-12-7-11-14(16(27)21(12)32-2)17(28)22(20(33-11)9-3-5-10(25)6-4-9)35-23-19(30)18(29)15(26)13(8-24)34-23/h3-7,13,15,18-19,23-27,29-30H,8H2,1-2H3/t13-,15+,18+,19-,23+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)c(c(c3)OC)OC)c2ccc(cc2)O)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518337
PubChem CID:	9805669
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO32923	boerhaavia repens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8946741]

☑ 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
Others	3

Activity Type	# Activity
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	23.1	%	PMID[500057]
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	55.3	%	PMID[500057]
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	20.6	%	PMID[500057]

☑ 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 NPC24043 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	444
0.1-0.2	1773
0.2-0.3	4156
0.3-0.4	9775
0.4-0.5	8387
0.5-0.6	4259
0.6-0.7	5245
0.7-0.8	5274
0.8-0.85	1537
0.85-0.9	1157
0.9-0.95	503
0.95-1	187

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169977
1.0	High Similarity	NPC101026
1.0	High Similarity	NPC21666
1.0	High Similarity	NPC42773
1.0	High Similarity	NPC45522
0.9938	High Similarity	NPC117260
0.9938	High Similarity	NPC476405
0.9877	High Similarity	NPC472385
0.9877	High Similarity	NPC198324
0.9876	High Similarity	NPC282987
0.9876	High Similarity	NPC245014
0.9876	High Similarity	NPC84265
0.9817	High Similarity	NPC168584
0.9816	High Similarity	NPC101191
0.9816	High Similarity	NPC49344
0.9816	High Similarity	NPC264735
0.9816	High Similarity	NPC43211
0.9816	High Similarity	NPC477848
0.9816	High Similarity	NPC210094
0.9816	High Similarity	NPC237435
0.9816	High Similarity	NPC115760
0.9816	High Similarity	NPC135277
0.9814	High Similarity	NPC201292
0.9814	High Similarity	NPC203050
0.9814	High Similarity	NPC469931
0.9814	High Similarity	NPC120099
0.9814	High Similarity	NPC219904
0.9814	High Similarity	NPC58053
0.9814	High Similarity	NPC186807
0.9814	High Similarity	NPC225434
0.9814	High Similarity	NPC45638
0.9814	High Similarity	NPC475942
0.9814	High Similarity	NPC223747
0.9814	High Similarity	NPC93337
0.9814	High Similarity	NPC105025
0.9814	High Similarity	NPC226294
0.9758	High Similarity	NPC241423
0.9758	High Similarity	NPC473682
0.9758	High Similarity	NPC110941
0.9758	High Similarity	NPC473571
0.9758	High Similarity	NPC470443
0.9758	High Similarity	NPC126784
0.9758	High Similarity	NPC470444
0.9756	High Similarity	NPC211532
0.9756	High Similarity	NPC233994
0.9756	High Similarity	NPC470949
0.9756	High Similarity	NPC8573
0.9756	High Similarity	NPC65563
0.9756	High Similarity	NPC169733
0.9755	High Similarity	NPC4390
0.9753	High Similarity	NPC206123
0.9752	High Similarity	NPC325555
0.9752	High Similarity	NPC226304
0.9752	High Similarity	NPC223424
0.9752	High Similarity	NPC52550
0.9752	High Similarity	NPC127546
0.9752	High Similarity	NPC317489
0.9752	High Similarity	NPC146792
0.9752	High Similarity	NPC45618
0.9752	High Similarity	NPC265530
0.9752	High Similarity	NPC173637
0.9752	High Similarity	NPC58716
0.9752	High Similarity	NPC84362
0.9699	High Similarity	NPC473073
0.9699	High Similarity	NPC473071
0.9693	High Similarity	NPC205076
0.9693	High Similarity	NPC211594
0.9693	High Similarity	NPC172807
0.9693	High Similarity	NPC307518
0.9693	High Similarity	NPC48773
0.9693	High Similarity	NPC175107
0.9693	High Similarity	NPC153755
0.9693	High Similarity	NPC190003
0.9693	High Similarity	NPC254540
0.9689	High Similarity	NPC145038
0.9689	High Similarity	NPC21100
0.9689	High Similarity	NPC197285
0.9689	High Similarity	NPC88789
0.9689	High Similarity	NPC274618
0.9689	High Similarity	NPC113968
0.9689	High Similarity	NPC135599
0.9689	High Similarity	NPC277174
0.9689	High Similarity	NPC308404
0.9689	High Similarity	NPC73855
0.9689	High Similarity	NPC328940
0.9689	High Similarity	NPC281131
0.9689	High Similarity	NPC56077
0.9689	High Similarity	NPC276222
0.9689	High Similarity	NPC179950
0.9689	High Similarity	NPC118284
0.9689	High Similarity	NPC253662
0.9641	High Similarity	NPC470447
0.9641	High Similarity	NPC470445
0.9641	High Similarity	NPC36138
0.9641	High Similarity	NPC470446
0.9641	High Similarity	NPC470449
0.9641	High Similarity	NPC473072
0.9636	High Similarity	NPC472384
0.9636	High Similarity	NPC268533
0.9636	High Similarity	NPC472382
0.9636	High Similarity	NPC472380
0.9634	High Similarity	NPC204693
0.9632	High Similarity	NPC155763
0.9632	High Similarity	NPC244776
0.9632	High Similarity	NPC116864
0.9632	High Similarity	NPC105511
0.9632	High Similarity	NPC183357
0.9632	High Similarity	NPC21190
0.9632	High Similarity	NPC95866
0.9632	High Similarity	NPC235260
0.9632	High Similarity	NPC20505
0.9632	High Similarity	NPC224462
0.9632	High Similarity	NPC22195
0.9627	High Similarity	NPC55786
0.9627	High Similarity	NPC19388
0.9627	High Similarity	NPC240431
0.9627	High Similarity	NPC311830
0.9627	High Similarity	NPC277205
0.9627	High Similarity	NPC22832
0.9583	High Similarity	NPC148710
0.9583	High Similarity	NPC470451
0.9583	High Similarity	NPC470416
0.9583	High Similarity	NPC470455
0.9581	High Similarity	NPC222674
0.9576	High Similarity	NPC476472
0.9576	High Similarity	NPC220173
0.9576	High Similarity	NPC294815
0.9576	High Similarity	NPC16194
0.9576	High Similarity	NPC473327
0.9576	High Similarity	NPC19108
0.9573	High Similarity	NPC155877
0.9573	High Similarity	NPC3583
0.9573	High Similarity	NPC60735
0.9573	High Similarity	NPC471725
0.9573	High Similarity	NPC134532
0.9573	High Similarity	NPC245452
0.9573	High Similarity	NPC259152
0.9573	High Similarity	NPC203259
0.9573	High Similarity	NPC33054
0.9573	High Similarity	NPC176740
0.9573	High Similarity	NPC471748
0.9573	High Similarity	NPC26230
0.9571	High Similarity	NPC138927
0.9571	High Similarity	NPC270578
0.9571	High Similarity	NPC471457
0.9571	High Similarity	NPC472383
0.9571	High Similarity	NPC112755
0.9571	High Similarity	NPC210042
0.9571	High Similarity	NPC95855
0.9571	High Similarity	NPC170675
0.9571	High Similarity	NPC52382
0.9571	High Similarity	NPC472381
0.9568	High Similarity	NPC99957
0.9568	High Similarity	NPC181616
0.9565	High Similarity	NPC88023
0.9565	High Similarity	NPC222936
0.9565	High Similarity	NPC94777
0.9565	High Similarity	NPC270335
0.9565	High Similarity	NPC243930
0.9565	High Similarity	NPC284960
0.9565	High Similarity	NPC309025
0.9565	High Similarity	NPC191306
0.9565	High Similarity	NPC19709
0.9524	High Similarity	NPC107987
0.9515	High Similarity	NPC51774
0.9515	High Similarity	NPC239549
0.9515	High Similarity	NPC236191
0.9512	High Similarity	NPC259896
0.9512	High Similarity	NPC67105
0.9512	High Similarity	NPC72249
0.9512	High Similarity	NPC29958
0.9512	High Similarity	NPC136042
0.9512	High Similarity	NPC34287
0.9512	High Similarity	NPC255157
0.9512	High Similarity	NPC156869
0.9512	High Similarity	NPC471416
0.9512	High Similarity	NPC285197
0.9512	High Similarity	NPC67326
0.9512	High Similarity	NPC254855
0.9512	High Similarity	NPC44558
0.9512	High Similarity	NPC474434
0.9509	High Similarity	NPC76482
0.9509	High Similarity	NPC135345
0.9509	High Similarity	NPC92565
0.9509	High Similarity	NPC160156
0.9509	High Similarity	NPC93099
0.9509	High Similarity	NPC229729
0.9503	High Similarity	NPC473043
0.9503	High Similarity	NPC189142
0.9503	High Similarity	NPC77660
0.9461	High Similarity	NPC35167
0.9461	High Similarity	NPC89052
0.9461	High Similarity	NPC251417
0.9461	High Similarity	NPC173837
0.9461	High Similarity	NPC139571
0.9461	High Similarity	NPC217520
0.9458	High Similarity	NPC253685
0.9458	High Similarity	NPC472607
0.9458	High Similarity	NPC294629
0.9455	High Similarity	NPC472386

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 NPC24043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	942
0.2-0.3	1978
0.3-0.4	2688
0.4-0.5	1794
0.5-0.6	894
0.6-0.7	301
0.7-0.8	117
0.8-0.85	17
0.85-0.9	14
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9816	High Similarity	NPD4338	Clinical (unspecified phase)
0.9573	High Similarity	NPD6797	Phase 2
0.9515	High Similarity	NPD7251	Discontinued
0.9458	High Similarity	NPD7808	Phase 3
0.9451	High Similarity	NPD7054	Approved
0.9394	High Similarity	NPD7472	Approved
0.9277	High Similarity	NPD7074	Phase 3
0.9273	High Similarity	NPD3818	Discontinued
0.9068	High Similarity	NPD2801	Approved
0.9036	High Similarity	NPD6167	Clinical (unspecified phase)
0.9036	High Similarity	NPD6168	Clinical (unspecified phase)
0.9036	High Similarity	NPD6166	Phase 2
0.9018	High Similarity	NPD4381	Clinical (unspecified phase)
0.8988	High Similarity	NPD7804	Clinical (unspecified phase)
0.8896	High Similarity	NPD3817	Phase 2
0.8889	High Similarity	NPD1934	Approved
0.8841	High Similarity	NPD3882	Suspended
0.872	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD5402	Approved
0.8634	High Similarity	NPD1512	Approved
0.8509	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD4380	Phase 2
0.8353	Intermediate Similarity	NPD5494	Approved
0.8343	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8303	Intermediate Similarity	NPD1653	Approved
0.8295	Intermediate Similarity	NPD6559	Discontinued
0.8287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD3751	Discontinued
0.815	Intermediate Similarity	NPD3787	Discontinued
0.8125	Intermediate Similarity	NPD5844	Phase 1
0.8121	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD1549	Phase 2
0.7953	Intermediate Similarity	NPD1465	Phase 2
0.7943	Intermediate Similarity	NPD6232	Discontinued
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7473	Discontinued
0.7907	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD6776	Approved
0.7884	Intermediate Similarity	NPD6780	Approved
0.7884	Intermediate Similarity	NPD6781	Approved
0.7884	Intermediate Similarity	NPD6778	Approved
0.7884	Intermediate Similarity	NPD6777	Approved
0.7884	Intermediate Similarity	NPD6782	Approved
0.7884	Intermediate Similarity	NPD6779	Approved
0.7882	Intermediate Similarity	NPD6599	Discontinued
0.788	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7228	Approved
0.7853	Intermediate Similarity	NPD7435	Discontinued
0.7853	Intermediate Similarity	NPD2796	Approved
0.7849	Intermediate Similarity	NPD7819	Suspended
0.7836	Intermediate Similarity	NPD7411	Suspended
0.7831	Intermediate Similarity	NPD6190	Approved
0.7811	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7784	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7771	Intermediate Similarity	NPD919	Approved
0.7705	Intermediate Similarity	NPD8313	Approved
0.7705	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7688	Intermediate Similarity	NPD37	Approved
0.7668	Intermediate Similarity	NPD7697	Approved
0.7668	Intermediate Similarity	NPD7698	Approved
0.7668	Intermediate Similarity	NPD7696	Phase 3
0.7665	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD4966	Approved
0.7657	Intermediate Similarity	NPD4967	Phase 2
0.7654	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1613	Approved
0.7629	Intermediate Similarity	NPD7871	Phase 2
0.7629	Intermediate Similarity	NPD7870	Phase 2
0.7619	Intermediate Similarity	NPD6534	Approved
0.7619	Intermediate Similarity	NPD6535	Approved
0.7614	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7874	Approved
0.7602	Intermediate Similarity	NPD7701	Phase 2
0.759	Intermediate Similarity	NPD7266	Discontinued
0.7556	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7584	Approved
0.7546	Intermediate Similarity	NPD943	Approved
0.7546	Intermediate Similarity	NPD1240	Approved
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1933	Approved
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7801	Approved
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7475	Intermediate Similarity	NPD8151	Discontinued
0.7469	Intermediate Similarity	NPD3027	Phase 3
0.7456	Intermediate Similarity	NPD3750	Approved
0.7455	Intermediate Similarity	NPD1607	Approved
0.7448	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6823	Phase 2
0.7425	Intermediate Similarity	NPD2935	Discontinued
0.7416	Intermediate Similarity	NPD3749	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7240	Approved
0.7394	Intermediate Similarity	NPD447	Suspended
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7768	Phase 2
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8455	Phase 2
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7317	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8150	Discontinued
0.7302	Intermediate Similarity	NPD8434	Phase 2
0.7288	Intermediate Similarity	NPD6844	Discontinued
0.7283	Intermediate Similarity	NPD2534	Approved
0.7283	Intermediate Similarity	NPD2532	Approved
0.7283	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD8320	Phase 1
0.7273	Intermediate Similarity	NPD8319	Approved
0.7246	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6213	Phase 3
0.7202	Intermediate Similarity	NPD6212	Phase 3
0.7202	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD920	Approved
0.7193	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2800	Approved
0.7174	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5953	Discontinued
0.7164	Intermediate Similarity	NPD7585	Approved
0.716	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD9494	Approved
0.7119	Intermediate Similarity	NPD3226	Approved
0.7114	Intermediate Similarity	NPD7583	Approved
0.7108	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6674	Discontinued
0.709	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1091	Approved
0.7077	Intermediate Similarity	NPD4360	Phase 2
0.7077	Intermediate Similarity	NPD4363	Phase 3
0.7065	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.705	Intermediate Similarity	NPD7680	Approved
0.7022	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD6099	Approved
0.7018	Intermediate Similarity	NPD6100	Approved
0.7017	Intermediate Similarity	NPD5353	Approved
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.6994	Remote Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD1652	Phase 2
0.6994	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6832	Phase 2
0.6988	Remote Similarity	NPD4908	Phase 1
0.6982	Remote Similarity	NPD6355	Discontinued
0.6977	Remote Similarity	NPD2346	Discontinued
0.6977	Remote Similarity	NPD2344	Approved
0.6971	Remote Similarity	NPD643	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2798	Approved
0.6959	Remote Similarity	NPD2799	Discontinued
0.6941	Remote Similarity	NPD6651	Approved
0.6935	Remote Similarity	NPD5242	Approved
0.6932	Remote Similarity	NPD7390	Discontinued
0.6919	Remote Similarity	NPD7907	Approved
0.6915	Remote Similarity	NPD2163	Approved
0.6915	Remote Similarity	NPD5006	Approved
0.6915	Remote Similarity	NPD5005	Approved
0.6911	Remote Similarity	NPD7549	Discontinued
0.6909	Remote Similarity	NPD1203	Approved
0.6905	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2403	Approved
0.6893	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5124	Phase 1
0.6882	Remote Similarity	NPD5710	Approved
0.6882	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5711	Approved
0.6882	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2493	Approved
0.6866	Remote Similarity	NPD2494	Approved
0.686	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7615	Clinical (unspecified phase)

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