NPASS Compound

Structure

NPC284960 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 2 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 -7.7942 2.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 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 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0.0000 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 33 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 25 1 0 0 0 0 10 14 1 0 0 0 0 11 31 1 0 0 0 0 12 19 1 0 0 0 0 12 26 2 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 34 1 0 0 0 0 15 19 2 0 0 0 0 15 34 1 0 0 0 0 16 19 1 0 0 0 0 16 35 1 0 0 0 0 17 23 1 0 0 0 0 17 32 1 0 0 0 0 18 9 1 6 0 0 0 18 20 1 0 0 0 0 18 36 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 1 0 0 0 23 33 1 0 0 0 0 24 35 1 6 0 0 0 24 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.14
Volume:	473.825
LogP:	1.543
LogD:	1.401
LogS:	-3.903
# Rotatable Bonds:	7
TPSA:	177.51
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	3.983
Fsp3:	0.375
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.968
MDCK Permeability:	4.0289971366291866e-05
Pgp-inhibitor:	0.109
Pgp-substrate:	0.852
Human Intestinal Absorption (HIA):	0.556
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254
Plasma Protein Binding (PPB):	71.44139862060547%
Volume Distribution (VD):	0.84
Pgp-substrate:	25.730741500854492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.625
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.552
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	6.254
Half-life (T1/2):	0.681

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.478
AMES Toxicity:	0.477
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.348
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC284960

Natural Product ID:	NPC284960
*Common Name:**	Lethedoside C
IUPAC Name:	2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Lethedoside C
Standard InCHIKey:	WGZGLIQYUYIVRX-BKSKZGTRSA-N
Standard InCHI:	InChI=1S/C24H26O12/c1-31-11-6-15-19(16(7-11)35-24-22(30)21(29)20(28)18(9-25)36-24)12(26)8-14(34-15)10-4-13(27)23(33-3)17(5-10)32-2/h4-8,18,20-22,24-25,27-30H,9H2,1-3H3/t18-,20-,21+,22-,24-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc3c2c(=O)cc(o3)c2cc(O)c(c(c2)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455082
PubChem CID:	10391471
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	43.0	ug.mL-1	PMID[543574]

☑ 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 NPC284960 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	424
0.1-0.2	1751
0.2-0.3	3854
0.3-0.4	9314
0.4-0.5	9005
0.5-0.6	4172
0.6-0.7	5029
0.7-0.8	5361
0.8-0.85	1816
0.85-0.9	1373
0.9-0.95	445
0.95-1	153

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC222936
0.9935	High Similarity	NPC22832
0.9935	High Similarity	NPC311830
0.9935	High Similarity	NPC473043
0.9871	High Similarity	NPC270335
0.9871	High Similarity	NPC88023
0.9871	High Similarity	NPC19709
0.9871	High Similarity	NPC309025
0.9871	High Similarity	NPC243930
0.9871	High Similarity	NPC191306
0.9809	High Similarity	NPC226304
0.9809	High Similarity	NPC325555
0.9809	High Similarity	NPC229729
0.9809	High Similarity	NPC265530
0.9806	High Similarity	NPC77660
0.9806	High Similarity	NPC189142
0.9805	High Similarity	NPC110349
0.9747	High Similarity	NPC45638
0.9747	High Similarity	NPC93337
0.9747	High Similarity	NPC203050
0.9747	High Similarity	NPC58053
0.9747	High Similarity	NPC120099
0.9747	High Similarity	NPC219904
0.9747	High Similarity	NPC225434
0.9747	High Similarity	NPC475942
0.9747	High Similarity	NPC226294
0.9747	High Similarity	NPC186807
0.9747	High Similarity	NPC201292
0.9747	High Similarity	NPC209296
0.9747	High Similarity	NPC195257
0.9747	High Similarity	NPC469931
0.9747	High Similarity	NPC223747
0.9747	High Similarity	NPC105025
0.9745	High Similarity	NPC115674
0.9745	High Similarity	NPC5778
0.9745	High Similarity	NPC135599
0.9745	High Similarity	NPC21100
0.9745	High Similarity	NPC113968
0.9745	High Similarity	NPC210073
0.9745	High Similarity	NPC277174
0.9745	High Similarity	NPC236934
0.9745	High Similarity	NPC197285
0.9745	High Similarity	NPC73855
0.9745	High Similarity	NPC328940
0.9744	High Similarity	NPC168822
0.9742	High Similarity	NPC182045
0.9686	High Similarity	NPC51326
0.9686	High Similarity	NPC224462
0.9686	High Similarity	NPC206123
0.9686	High Similarity	NPC231194
0.9684	High Similarity	NPC45618
0.9684	High Similarity	NPC127546
0.9684	High Similarity	NPC58716
0.9684	High Similarity	NPC52550
0.9684	High Similarity	NPC173637
0.9684	High Similarity	NPC477502
0.9684	High Similarity	NPC146792
0.9684	High Similarity	NPC84362
0.9684	High Similarity	NPC223424
0.9684	High Similarity	NPC317489
0.9682	High Similarity	NPC19388
0.9682	High Similarity	NPC240431
0.9682	High Similarity	NPC55786
0.9682	High Similarity	NPC277205
0.9679	High Similarity	NPC300537
0.9679	High Similarity	NPC127782
0.9625	High Similarity	NPC153755
0.9625	High Similarity	NPC254540
0.9625	High Similarity	NPC48773
0.9625	High Similarity	NPC172807
0.9625	High Similarity	NPC256760
0.9625	High Similarity	NPC235575
0.9625	High Similarity	NPC205076
0.9625	High Similarity	NPC476405
0.9625	High Similarity	NPC211594
0.9625	High Similarity	NPC117260
0.9625	High Similarity	NPC307518
0.9623	High Similarity	NPC229687
0.9623	High Similarity	NPC86008
0.9623	High Similarity	NPC227508
0.962	High Similarity	NPC145038
0.962	High Similarity	NPC179950
0.962	High Similarity	NPC281131
0.962	High Similarity	NPC8856
0.962	High Similarity	NPC253662
0.962	High Similarity	NPC88789
0.962	High Similarity	NPC308404
0.962	High Similarity	NPC99957
0.962	High Similarity	NPC118284
0.962	High Similarity	NPC274618
0.962	High Similarity	NPC276222
0.962	High Similarity	NPC56077
0.962	High Similarity	NPC181616
0.9618	High Similarity	NPC94777
0.9618	High Similarity	NPC88043
0.9618	High Similarity	NPC29830
0.961	High Similarity	NPC261866
0.9565	High Similarity	NPC24043
0.9565	High Similarity	NPC21666
0.9565	High Similarity	NPC101026
0.9565	High Similarity	NPC169977
0.9565	High Similarity	NPC204693
0.9565	High Similarity	NPC42773
0.9565	High Similarity	NPC208668
0.9565	High Similarity	NPC472993
0.9565	High Similarity	NPC4390
0.9565	High Similarity	NPC45522
0.9563	High Similarity	NPC183357
0.9563	High Similarity	NPC67105
0.9563	High Similarity	NPC245014
0.9563	High Similarity	NPC177731
0.9563	High Similarity	NPC285197
0.9563	High Similarity	NPC21190
0.9563	High Similarity	NPC84265
0.9563	High Similarity	NPC150767
0.9563	High Similarity	NPC78734
0.9563	High Similarity	NPC282987
0.9563	High Similarity	NPC105511
0.9563	High Similarity	NPC244776
0.9563	High Similarity	NPC105095
0.9563	High Similarity	NPC22195
0.9563	High Similarity	NPC116864
0.9563	High Similarity	NPC79056
0.9563	High Similarity	NPC95866
0.9563	High Similarity	NPC44328
0.956	High Similarity	NPC275454
0.956	High Similarity	NPC116745
0.956	High Similarity	NPC45400
0.9557	High Similarity	NPC284277
0.9557	High Similarity	NPC475366
0.9557	High Similarity	NPC165720
0.9557	High Similarity	NPC475497
0.9557	High Similarity	NPC15358
0.9506	High Similarity	NPC198199
0.9506	High Similarity	NPC476472
0.9506	High Similarity	NPC294815
0.9506	High Similarity	NPC19108
0.9506	High Similarity	NPC477848
0.9506	High Similarity	NPC220173
0.9506	High Similarity	NPC473327
0.9506	High Similarity	NPC16194
0.9503	High Similarity	NPC259152
0.9503	High Similarity	NPC33054
0.9503	High Similarity	NPC203259
0.9503	High Similarity	NPC471748
0.9503	High Similarity	NPC471725
0.9503	High Similarity	NPC26230
0.9503	High Similarity	NPC261254
0.9503	High Similarity	NPC245452
0.9503	High Similarity	NPC176740
0.9503	High Similarity	NPC180918
0.9503	High Similarity	NPC155877
0.9503	High Similarity	NPC190003
0.9503	High Similarity	NPC60735
0.9503	High Similarity	NPC3583
0.9503	High Similarity	NPC175107
0.9503	High Similarity	NPC134532
0.95	High Similarity	NPC43587
0.95	High Similarity	NPC293629
0.95	High Similarity	NPC52382
0.95	High Similarity	NPC183036
0.95	High Similarity	NPC170675
0.95	High Similarity	NPC95855
0.95	High Similarity	NPC471457
0.95	High Similarity	NPC112755
0.95	High Similarity	NPC138927
0.95	High Similarity	NPC210042
0.95	High Similarity	NPC270578
0.95	High Similarity	NPC472383
0.95	High Similarity	NPC472381
0.9497	High Similarity	NPC254306
0.9448	High Similarity	NPC255799
0.9448	High Similarity	NPC169733
0.9448	High Similarity	NPC472385
0.9448	High Similarity	NPC198324
0.9448	High Similarity	NPC233994
0.9448	High Similarity	NPC211532
0.9444	High Similarity	NPC175230
0.9444	High Similarity	NPC239549
0.9444	High Similarity	NPC236191
0.9444	High Similarity	NPC88560
0.9444	High Similarity	NPC172033
0.9444	High Similarity	NPC51774
0.9444	High Similarity	NPC25724
0.9441	High Similarity	NPC474434
0.9441	High Similarity	NPC44558
0.9441	High Similarity	NPC67326
0.9441	High Similarity	NPC155763
0.9441	High Similarity	NPC255157
0.9441	High Similarity	NPC212748
0.9441	High Similarity	NPC156869
0.9441	High Similarity	NPC471416
0.9441	High Similarity	NPC204937
0.9441	High Similarity	NPC254855
0.9441	High Similarity	NPC29958
0.9441	High Similarity	NPC149011
0.9441	High Similarity	NPC136042
0.9441	High Similarity	NPC259896
0.9441	High Similarity	NPC235260
0.9441	High Similarity	NPC218488

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 NPC284960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	952
0.2-0.3	1920
0.3-0.4	2664
0.4-0.5	1832
0.5-0.6	906
0.6-0.7	313
0.7-0.8	138
0.8-0.85	21
0.85-0.9	16
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9747	High Similarity	NPD7054	Approved
0.9686	High Similarity	NPD7472	Approved
0.9563	High Similarity	NPD7074	Phase 3
0.9503	High Similarity	NPD6797	Phase 2
0.9444	High Similarity	NPD7251	Discontinued
0.9437	High Similarity	NPD3818	Discontinued
0.9387	High Similarity	NPD7808	Phase 3
0.9387	High Similarity	NPD4338	Clinical (unspecified phase)
0.9299	High Similarity	NPD4381	Clinical (unspecified phase)
0.9167	High Similarity	NPD1934	Approved
0.9074	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD6166	Phase 2
0.9074	High Similarity	NPD6167	Clinical (unspecified phase)
0.8987	High Similarity	NPD2801	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8909	High Similarity	NPD7804	Clinical (unspecified phase)
0.8812	High Similarity	NPD3817	Phase 2
0.8774	High Similarity	NPD1511	Approved
0.8758	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD4380	Phase 2
0.8662	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD3882	Suspended
0.8529	High Similarity	NPD6559	Discontinued
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1653	Approved
0.8269	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5402	Approved
0.8232	Intermediate Similarity	NPD6801	Discontinued
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5403	Approved
0.814	Intermediate Similarity	NPD5844	Phase 1
0.8133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6959	Discontinued
0.8103	Intermediate Similarity	NPD7685	Pre-registration
0.8089	Intermediate Similarity	NPD2796	Approved
0.8081	Intermediate Similarity	NPD7228	Approved
0.8075	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7904	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1613	Approved
0.7875	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7849	Intermediate Similarity	NPD3787	Discontinued
0.7812	Intermediate Similarity	NPD7266	Discontinued
0.7809	Intermediate Similarity	NPD8313	Approved
0.7809	Intermediate Similarity	NPD8312	Approved
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1240	Approved
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7584	Approved
0.7722	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD919	Approved
0.7673	Intermediate Similarity	NPD1607	Approved
0.7669	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD943	Approved
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.7628	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD7240	Approved
0.7586	Intermediate Similarity	NPD1247	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7544	Intermediate Similarity	NPD8455	Phase 2
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD6190	Approved
0.7514	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7697	Approved
0.7394	Intermediate Similarity	NPD6674	Discontinued
0.7394	Intermediate Similarity	NPD2800	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7354	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD7585	Approved
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD920	Approved
0.729	Intermediate Similarity	NPD1091	Approved
0.7289	Intermediate Similarity	NPD1243	Approved
0.7282	Intermediate Similarity	NPD7583	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7253	Intermediate Similarity	NPD5953	Discontinued
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7239	Intermediate Similarity	NPD6651	Approved
0.7233	Intermediate Similarity	NPD9494	Approved
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7222	Intermediate Similarity	NPD7801	Approved
0.7219	Intermediate Similarity	NPD7390	Discontinued
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD5353	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7176	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7680	Approved
0.7112	Intermediate Similarity	NPD8434	Phase 2
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.7107	Intermediate Similarity	NPD1203	Approved
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6841	Approved
0.7074	Intermediate Similarity	NPD6843	Phase 3
0.7074	Intermediate Similarity	NPD6842	Approved
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5124	Phase 1
0.7072	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2344	Approved
0.7066	Intermediate Similarity	NPD2346	Discontinued
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2799	Discontinued
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7017	Intermediate Similarity	NPD5242	Approved
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD3268	Approved
0.6994	Remote Similarity	NPD6798	Discontinued
0.699	Remote Similarity	NPD5006	Approved
0.699	Remote Similarity	NPD5005	Approved
0.6962	Remote Similarity	NPD1610	Phase 2
0.6962	Remote Similarity	NPD422	Phase 1
0.6951	Remote Similarity	NPD6233	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data