NPASS Compound

Structure

NPC160991 OpenBabel07101719522D 29 30 0 0 1 0 0 0 0 0999 V2000 -6.0622 -1.5000 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 -0.8660 2.5000 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 2.5981 1.5000 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 -4.3301 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 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 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 1.7321 1.0000 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 -5.1962 -0.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 -6.0622 1.5000 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 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 23 1 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 19 12 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 25 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.16
Volume:	406.526
LogP:	0.756
LogD:	1.236
LogS:	-2.363
# Rotatable Bonds:	10
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	3.349
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
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:	-4.987
MDCK Permeability:	9.355827387480531e-06
Pgp-inhibitor:	0.633
Pgp-substrate:	0.624
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.794
Plasma Protein Binding (PPB):	78.16191101074219%
Volume Distribution (VD):	0.56
Pgp-substrate:	18.950902938842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.451
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.738
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	8.139
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.204
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.658
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC160991

Natural Product ID:	NPC160991
*Common Name:**	(+)-Threo-Guaiacylglycerol-Beta-O-4'-Sinapyl Ether
IUPAC Name:	(1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]propane-1,3-diol
Synonyms:
Standard InCHIKey:	JVQPMSYMHZSFNV-WEPWYQGCSA-N
Standard InCHI:	InChI=1S/C21H26O8/c1-26-16-11-14(6-7-15(16)24)20(25)19(12-23)29-21-17(27-2)9-13(5-4-8-22)10-18(21)28-3/h4-7,9-11,19-20,22-25H,8,12H2,1-3H3/b5-4+/t19-,20-/m1/s1
SMILES:	OC/C=C/c1cc(OC)c(c(c1)OC)O[C@@H]([C@@H](c1ccc(c(c1)OC)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2268766
PubChem CID:	76326750
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO9642	Brassica fruticulosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14518939]
NPO9642	Brassica fruticulosa	Species	Brassicaceae	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
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	=	120.2	%	PMID[523983]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23530.0	nM	PMID[523983]

☑ 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 NPC160991 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	402
0.1-0.2	1499
0.2-0.3	4939
0.3-0.4	12456
0.4-0.5	5412
0.5-0.6	4365
0.6-0.7	6613
0.7-0.8	5034
0.8-0.85	1133
0.85-0.9	537
0.9-0.95	249
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC16208
1.0	High Similarity	NPC35932
1.0	High Similarity	NPC184447
1.0	High Similarity	NPC7903
0.992	High Similarity	NPC472597
0.9843	High Similarity	NPC170694
0.9843	High Similarity	NPC310854
0.984	High Similarity	NPC472338
0.9762	High Similarity	NPC469613
0.9762	High Similarity	NPC469625
0.9762	High Similarity	NPC470095
0.9762	High Similarity	NPC30043
0.9762	High Similarity	NPC470096
0.976	High Similarity	NPC273295
0.976	High Similarity	NPC210623
0.976	High Similarity	NPC202582
0.976	High Similarity	NPC222004
0.976	High Similarity	NPC218856
0.976	High Similarity	NPC226788
0.976	High Similarity	NPC470258
0.976	High Similarity	NPC190629
0.976	High Similarity	NPC3439
0.976	High Similarity	NPC285339
0.9685	High Similarity	NPC470752
0.9683	High Similarity	NPC469612
0.9683	High Similarity	NPC469614
0.9612	High Similarity	NPC472337
0.9609	High Similarity	NPC475840
0.9606	High Similarity	NPC309787
0.9603	High Similarity	NPC170844
0.9603	High Similarity	NPC476968
0.96	High Similarity	NPC118787
0.96	High Similarity	NPC319625
0.96	High Similarity	NPC163332
0.96	High Similarity	NPC41706
0.96	High Similarity	NPC183181
0.96	High Similarity	NPC147821
0.96	High Similarity	NPC210355
0.96	High Similarity	NPC111247
0.96	High Similarity	NPC474119
0.96	High Similarity	NPC292056
0.9542	High Similarity	NPC22517
0.9538	High Similarity	NPC306441
0.9538	High Similarity	NPC472336
0.9538	High Similarity	NPC472334
0.9538	High Similarity	NPC16435
0.9531	High Similarity	NPC201587
0.9531	High Similarity	NPC253105
0.9524	High Similarity	NPC470213
0.9524	High Similarity	NPC98631
0.9524	High Similarity	NPC186843
0.9524	High Similarity	NPC206615
0.952	High Similarity	NPC191037
0.952	High Similarity	NPC58607
0.952	High Similarity	NPC178284
0.947	High Similarity	NPC267291
0.947	High Similarity	NPC291101
0.947	High Similarity	NPC266197
0.9462	High Similarity	NPC61946
0.9462	High Similarity	NPC47398
0.9462	High Similarity	NPC260898
0.9462	High Similarity	NPC234333
0.9462	High Similarity	NPC470356
0.9462	High Similarity	NPC474206
0.9462	High Similarity	NPC121812
0.9462	High Similarity	NPC112939
0.9462	High Similarity	NPC112246
0.9462	High Similarity	NPC94750
0.9457	High Similarity	NPC229442
0.9457	High Similarity	NPC168059
0.9453	High Similarity	NPC474017
0.9449	High Similarity	NPC86030
0.9449	High Similarity	NPC5851
0.944	High Similarity	NPC194519
0.9389	High Similarity	NPC227503
0.9389	High Similarity	NPC474639
0.9389	High Similarity	NPC302701
0.9389	High Similarity	NPC230734
0.9389	High Similarity	NPC269091
0.9389	High Similarity	NPC471719
0.9385	High Similarity	NPC244983
0.9385	High Similarity	NPC287745
0.9385	High Similarity	NPC326095
0.937	High Similarity	NPC72529
0.936	High Similarity	NPC114901
0.936	High Similarity	NPC293701
0.936	High Similarity	NPC94276
0.936	High Similarity	NPC122792
0.936	High Similarity	NPC48990
0.936	High Similarity	NPC109822
0.936	High Similarity	NPC228972
0.9328	High Similarity	NPC469559
0.9328	High Similarity	NPC193722
0.9328	High Similarity	NPC189115
0.9328	High Similarity	NPC278469
0.9318	High Similarity	NPC107551
0.9318	High Similarity	NPC474282
0.9318	High Similarity	NPC474390
0.9318	High Similarity	NPC102904
0.9318	High Similarity	NPC176051
0.9318	High Similarity	NPC211549
0.9318	High Similarity	NPC326797
0.9318	High Similarity	NPC103976
0.9313	High Similarity	NPC164787
0.9313	High Similarity	NPC151224
0.9308	High Similarity	NPC263064
0.9308	High Similarity	NPC158331
0.9308	High Similarity	NPC11060
0.9297	High Similarity	NPC212015
0.9291	High Similarity	NPC470699
0.9286	High Similarity	NPC472093
0.9286	High Similarity	NPC208950
0.9286	High Similarity	NPC203133
0.9286	High Similarity	NPC475169
0.9286	High Similarity	NPC17943
0.9286	High Similarity	NPC251855
0.9286	High Similarity	NPC233410
0.9286	High Similarity	NPC193544
0.9286	High Similarity	NPC298757
0.9286	High Similarity	NPC116907
0.9286	High Similarity	NPC221077
0.9286	High Similarity	NPC57490
0.9286	High Similarity	NPC117214
0.928	High Similarity	NPC165375
0.928	High Similarity	NPC220598
0.9254	High Similarity	NPC224876
0.9254	High Similarity	NPC471389
0.9254	High Similarity	NPC311530
0.9254	High Similarity	NPC263261
0.9254	High Similarity	NPC469661
0.9254	High Similarity	NPC83375
0.9254	High Similarity	NPC87725
0.9248	High Similarity	NPC98777
0.9248	High Similarity	NPC212770
0.9242	High Similarity	NPC470802
0.9242	High Similarity	NPC248727
0.9242	High Similarity	NPC270456
0.9242	High Similarity	NPC265433
0.9242	High Similarity	NPC162659
0.9242	High Similarity	NPC172818
0.9242	High Similarity	NPC25695
0.9237	High Similarity	NPC309744
0.9237	High Similarity	NPC317380
0.9231	High Similarity	NPC185604
0.9231	High Similarity	NPC78770
0.9231	High Similarity	NPC261619
0.9231	High Similarity	NPC219876
0.9231	High Similarity	NPC61477
0.9231	High Similarity	NPC127624
0.9231	High Similarity	NPC175067
0.9231	High Similarity	NPC86655
0.9231	High Similarity	NPC15658
0.9231	High Similarity	NPC126029
0.9231	High Similarity	NPC204215
0.9231	High Similarity	NPC202762
0.9225	High Similarity	NPC91291
0.9225	High Similarity	NPC214860
0.9219	High Similarity	NPC252307
0.9219	High Similarity	NPC245826
0.9219	High Similarity	NPC474178
0.9213	High Similarity	NPC103823
0.9213	High Similarity	NPC44748
0.9213	High Similarity	NPC18924
0.9213	High Similarity	NPC181361
0.9213	High Similarity	NPC78974
0.9213	High Similarity	NPC214406
0.9213	High Similarity	NPC223136
0.9213	High Similarity	NPC28730
0.92	High Similarity	NPC71579
0.92	High Similarity	NPC261661
0.92	High Similarity	NPC71090
0.92	High Similarity	NPC262253
0.92	High Similarity	NPC473411
0.9191	High Similarity	NPC470097
0.9191	High Similarity	NPC25292
0.9191	High Similarity	NPC473045
0.9191	High Similarity	NPC471415
0.9191	High Similarity	NPC114119
0.9185	High Similarity	NPC475084
0.9179	High Similarity	NPC160283
0.9179	High Similarity	NPC262189
0.9179	High Similarity	NPC184797
0.9179	High Similarity	NPC254759
0.9179	High Similarity	NPC22317
0.9179	High Similarity	NPC309124
0.9173	High Similarity	NPC276490
0.9173	High Similarity	NPC59324
0.9173	High Similarity	NPC65530
0.9167	High Similarity	NPC134968
0.9167	High Similarity	NPC24490
0.9167	High Similarity	NPC473413
0.9167	High Similarity	NPC126409
0.9167	High Similarity	NPC256262
0.9167	High Similarity	NPC141765
0.9167	High Similarity	NPC99572
0.9167	High Similarity	NPC34103
0.9167	High Similarity	NPC165155
0.9154	High Similarity	NPC268266
0.9154	High Similarity	NPC220825
0.9154	High Similarity	NPC268342

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 NPC160991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	863
0.2-0.3	1981
0.3-0.4	2702
0.4-0.5	1555
0.5-0.6	913
0.6-0.7	630
0.7-0.8	156
0.8-0.85	14
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9603	High Similarity	NPD3027	Phase 3
0.9231	High Similarity	NPD1612	Clinical (unspecified phase)
0.9231	High Similarity	NPD1613	Approved
0.8923	High Similarity	NPD1529	Clinical (unspecified phase)
0.8846	High Similarity	NPD1530	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2982	Phase 2
0.8397	Intermediate Similarity	NPD2983	Phase 2
0.8321	Intermediate Similarity	NPD2981	Phase 2
0.8284	Intermediate Similarity	NPD3018	Phase 2
0.8243	Intermediate Similarity	NPD1934	Approved
0.824	Intermediate Similarity	NPD228	Approved
0.8222	Intermediate Similarity	NPD4908	Phase 1
0.8219	Intermediate Similarity	NPD1653	Approved
0.8217	Intermediate Similarity	NPD1548	Phase 1
0.8106	Intermediate Similarity	NPD1610	Phase 2
0.8102	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2801	Approved
0.8065	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6166	Phase 2
0.7986	Intermediate Similarity	NPD1558	Phase 1
0.7985	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD5283	Phase 1
0.7961	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3882	Suspended
0.7911	Intermediate Similarity	NPD7054	Approved
0.7902	Intermediate Similarity	NPD7266	Discontinued
0.7891	Intermediate Similarity	NPD7843	Approved
0.7883	Intermediate Similarity	NPD2861	Phase 2
0.7867	Intermediate Similarity	NPD4678	Approved
0.7867	Intermediate Similarity	NPD4675	Approved
0.7862	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD2684	Approved
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7846	Intermediate Similarity	NPD7157	Approved
0.7836	Intermediate Similarity	NPD1091	Approved
0.7823	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4625	Phase 3
0.7763	Intermediate Similarity	NPD37	Approved
0.773	Intermediate Similarity	NPD3620	Phase 2
0.773	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4966	Approved
0.7727	Intermediate Similarity	NPD4965	Approved
0.7727	Intermediate Similarity	NPD4967	Phase 2
0.7721	Intermediate Similarity	NPD4749	Approved
0.7718	Intermediate Similarity	NPD1512	Approved
0.7714	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3705	Approved
0.7702	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD4538	Approved
0.7692	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4536	Approved
0.7687	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3060	Approved
0.7656	Intermediate Similarity	NPD3021	Approved
0.7656	Intermediate Similarity	NPD3022	Approved
0.7655	Intermediate Similarity	NPD3540	Phase 1
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD7199	Phase 2
0.7638	Intermediate Similarity	NPD290	Approved
0.7625	Intermediate Similarity	NPD7228	Approved
0.7612	Intermediate Similarity	NPD1357	Approved
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7808	Phase 3
0.7606	Intermediate Similarity	NPD4060	Phase 1
0.7586	Intermediate Similarity	NPD3539	Phase 1
0.7574	Intermediate Similarity	NPD422	Phase 1
0.7568	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD968	Approved
0.7551	Intermediate Similarity	NPD4237	Approved
0.7551	Intermediate Similarity	NPD4162	Approved
0.7551	Intermediate Similarity	NPD4236	Phase 3
0.7551	Intermediate Similarity	NPD1652	Phase 2
0.7551	Intermediate Similarity	NPD6674	Discontinued
0.7533	Intermediate Similarity	NPD4123	Phase 3
0.752	Intermediate Similarity	NPD291	Approved
0.7517	Intermediate Similarity	NPD5960	Phase 3
0.7517	Intermediate Similarity	NPD5588	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5844	Phase 1
0.7467	Intermediate Similarity	NPD4357	Discontinued
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4005	Discontinued
0.745	Intermediate Similarity	NPD2677	Approved
0.7447	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6671	Approved
0.744	Intermediate Similarity	NPD1242	Phase 1
0.7438	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD230	Phase 1
0.7429	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6584	Phase 3
0.7426	Intermediate Similarity	NPD6516	Phase 2
0.7426	Intermediate Similarity	NPD5846	Approved
0.7413	Intermediate Similarity	NPD6233	Phase 2
0.741	Intermediate Similarity	NPD8651	Approved
0.74	Intermediate Similarity	NPD5058	Phase 3
0.7391	Intermediate Similarity	NPD2235	Phase 2
0.7391	Intermediate Similarity	NPD2231	Phase 2
0.7386	Intermediate Similarity	NPD3686	Approved
0.7386	Intermediate Similarity	NPD3687	Approved
0.7383	Intermediate Similarity	NPD4628	Phase 3
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7372	Intermediate Similarity	NPD2977	Approved
0.7372	Intermediate Similarity	NPD2978	Approved
0.7368	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7213	Phase 3
0.7351	Intermediate Similarity	NPD7212	Phase 2
0.7342	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD2219	Phase 1
0.7325	Intermediate Similarity	NPD5402	Approved
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.731	Intermediate Similarity	NPD5735	Approved
0.731	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7447	Phase 1
0.7297	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1375	Discontinued
0.7297	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2674	Phase 3
0.7292	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7124	Phase 2
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD4110	Phase 3
0.7267	Intermediate Similarity	NPD6331	Phase 2
0.7267	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7261	Intermediate Similarity	NPD5773	Approved
0.7261	Intermediate Similarity	NPD5772	Approved
0.726	Intermediate Similarity	NPD6653	Approved
0.7255	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5494	Approved
0.7248	Intermediate Similarity	NPD1549	Phase 2
0.7241	Intermediate Similarity	NPD2238	Phase 2
0.7237	Intermediate Similarity	NPD6799	Approved
0.7237	Intermediate Similarity	NPD1774	Approved
0.7237	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7214	Intermediate Similarity	NPD6583	Phase 3
0.7214	Intermediate Similarity	NPD6582	Phase 2
0.7214	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD6801	Discontinued
0.7192	Intermediate Similarity	NPD4340	Discontinued
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD5763	Approved
0.7181	Intermediate Similarity	NPD5762	Approved
0.7172	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD3180	Approved
0.7153	Intermediate Similarity	NPD3179	Approved
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4535	Phase 3
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3052	Approved
0.7143	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD52	Approved
0.7143	Intermediate Similarity	NPD3054	Approved
0.7143	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7473	Discontinued
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD7240	Approved
0.7123	Intermediate Similarity	NPD3062	Approved
0.7123	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3059	Approved
0.7123	Intermediate Similarity	NPD3061	Approved
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.7114	Intermediate Similarity	NPD6100	Approved
0.7114	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD2796	Approved
0.7114	Intermediate Similarity	NPD2161	Phase 2
0.7109	Intermediate Similarity	NPD940	Approved
0.7109	Intermediate Similarity	NPD846	Approved
0.7107	Intermediate Similarity	NPD2560	Approved
0.7107	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2563	Approved
0.7105	Intermediate Similarity	NPD5241	Discontinued
0.7103	Intermediate Similarity	NPD3144	Approved
0.7103	Intermediate Similarity	NPD3145	Approved
0.7101	Intermediate Similarity	NPD8053	Approved
0.7101	Intermediate Similarity	NPD8054	Approved
0.7095	Intermediate Similarity	NPD6111	Discontinued
0.709	Intermediate Similarity	NPD821	Approved
0.709	Intermediate Similarity	NPD5535	Approved
0.7083	Intermediate Similarity	NPD7549	Discontinued

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