NPASS Compound

Structure

NPC469698 OpenBabel07101718332D 36 38 0 0 1 0 0 0 0 0999 V2000 -0.0000 3.0000 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 9.5263 -1.5000 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 1.7321 3.0000 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 3.4641 -0.0000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 3.4641 -2.0000 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 6.9282 0.0000 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 1.7321 -3.0000 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 1.0000 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 1 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 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 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 2.5981 1.5000 0.0000 O 0 0 0 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 0.8660 -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 28 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 22 2 0 0 0 0 21 31 1 0 0 0 0 22 35 1 0 0 0 0 23 16 1 6 0 0 0 23 24 1 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 25 26 1 0 0 0 0 25 33 1 6 0 0 0 26 27 1 0 0 0 0 26 34 1 1 0 0 0 27 35 1 6 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.24
Volume:	510.536
LogP:	3.088
LogD:	3.41
LogS:	-4.543
# Rotatable Bonds:	12
TPSA:	83.07
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	3.887
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	5.445553324534558e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	83.59019470214844%
Volume Distribution (VD):	0.595
Pgp-substrate:	8.663780212402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	8.779
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.985
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.892
Carcinogencity:	0.035
Eye Corrosion:	0.026
Eye Irritation:	0.102
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC469698

Natural Product ID:	NPC469698
*Common Name:**	(2S,3R,4S,5R,6R)-2-[5-[(E)-2-(3,5-Dimethoxyphenyl)Ethenyl]-2-Methoxyphenoxy]-3,4,5-Trimethoxy-6-(Methoxymethyl)Oxane
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[5-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-2-methoxyphenoxy]-3,4,5-trimethoxy-6-(methoxymethyl)oxane
Synonyms:
Standard InCHIKey:	SUCVNWYOBRSXKG-XWKSYUBDSA-N
Standard InCHI:	InChI=1S/C27H36O9/c1-28-16-23-24(32-5)25(33-6)26(34-7)27(36-23)35-22-14-17(10-11-21(22)31-4)8-9-18-12-19(29-2)15-20(13-18)30-3/h8-15,23-27H,16H2,1-7H3/b9-8+/t23-,24-,25+,26-,27-/m1/s1
SMILES:	COC[C@H]1O[C@@H](Oc2cc(/C=C/c3cc(OC)cc(c3)OC)ccc2OC)[C@@H]([C@H]([C@@H]1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL113074
PubChem CID:	44339880
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO88	Rheum undulatum	Species	Polygonaceae	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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	27000.0	nM	PMID[470807]

☑ 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 NPC469698 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	504
0.1-0.2	1808
0.2-0.3	5902
0.3-0.4	11951
0.4-0.5	5353
0.5-0.6	5728
0.6-0.7	7398
0.7-0.8	3369
0.8-0.85	518
0.85-0.9	125
0.9-0.95	38
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473412
0.9385	High Similarity	NPC470236
0.9318	High Similarity	NPC212770
0.9318	High Similarity	NPC98777
0.9313	High Similarity	NPC164857
0.9302	High Similarity	NPC162093
0.9254	High Similarity	NPC469559
0.9242	High Similarity	NPC65530
0.9242	High Similarity	NPC59324
0.9231	High Similarity	NPC49074
0.9167	High Similarity	NPC242028
0.9167	High Similarity	NPC203230
0.916	High Similarity	NPC187194
0.9111	High Similarity	NPC475084
0.9111	High Similarity	NPC189115
0.9084	High Similarity	NPC69513
0.9084	High Similarity	NPC115022
0.9084	High Similarity	NPC215833
0.9084	High Similarity	NPC294166
0.9051	High Similarity	NPC475096
0.9037	High Similarity	NPC469661
0.9023	High Similarity	NPC40664
0.9023	High Similarity	NPC165482
0.9023	High Similarity	NPC138350
0.9023	High Similarity	NPC3293
0.9023	High Similarity	NPC197723
0.9015	High Similarity	NPC476411
0.9015	High Similarity	NPC48863
0.9015	High Similarity	NPC13745
0.9015	High Similarity	NPC251981
0.9008	High Similarity	NPC165686
0.9008	High Similarity	NPC85799
0.9008	High Similarity	NPC303422
0.9008	High Similarity	NPC26080
0.9008	High Similarity	NPC299144
0.9	High Similarity	NPC307042
0.9	High Similarity	NPC79184
0.8992	High Similarity	NPC302378
0.8992	High Similarity	NPC31707
0.8978	High Similarity	NPC473045
0.8978	High Similarity	NPC25292
0.8968	High Similarity	NPC261661
0.8955	High Similarity	NPC470413
0.8955	High Similarity	NPC138738
0.8947	High Similarity	NPC238243
0.8939	High Similarity	NPC132895
0.8931	High Similarity	NPC121376
0.8923	High Similarity	NPC248355
0.8921	High Similarity	NPC39657
0.8921	High Similarity	NPC227902
0.8905	High Similarity	NPC473044
0.8905	High Similarity	NPC252169
0.8881	High Similarity	NPC25695
0.8881	High Similarity	NPC172818
0.8872	High Similarity	NPC188555
0.8872	High Similarity	NPC130496
0.8857	High Similarity	NPC270751
0.8855	High Similarity	NPC472024
0.8855	High Similarity	NPC80600
0.8849	High Similarity	NPC190714
0.8849	High Similarity	NPC125755
0.8849	High Similarity	NPC99515
0.8846	High Similarity	NPC210674
0.8832	High Similarity	NPC174522
0.8832	High Similarity	NPC80326
0.8832	High Similarity	NPC5262
0.8832	High Similarity	NPC472714
0.8824	High Similarity	NPC210478
0.8815	High Similarity	NPC124149
0.8815	High Similarity	NPC195196
0.881	High Similarity	NPC472596
0.8806	High Similarity	NPC224941
0.8806	High Similarity	NPC311430
0.8797	High Similarity	NPC266848
0.8797	High Similarity	NPC136750
0.8794	High Similarity	NPC55158
0.8794	High Similarity	NPC51328
0.8794	High Similarity	NPC106138
0.8794	High Similarity	NPC286235
0.8788	High Similarity	NPC469613
0.8788	High Similarity	NPC9912
0.8788	High Similarity	NPC30043
0.8788	High Similarity	NPC469625
0.8779	High Similarity	NPC166040
0.8779	High Similarity	NPC270849
0.8779	High Similarity	NPC218003
0.8779	High Similarity	NPC26653
0.8777	High Similarity	NPC277867
0.8777	High Similarity	NPC161700
0.8759	High Similarity	NPC257095
0.8759	High Similarity	NPC273932
0.8759	High Similarity	NPC300798
0.8759	High Similarity	NPC58137
0.8759	High Similarity	NPC89686
0.875	High Similarity	NPC292487
0.8741	High Similarity	NPC199459
0.8741	High Similarity	NPC177035
0.8741	High Similarity	NPC143895
0.8741	High Similarity	NPC104167
0.8741	High Similarity	NPC52277
0.8731	High Similarity	NPC309744
0.8731	High Similarity	NPC170694
0.8731	High Similarity	NPC107478
0.8723	High Similarity	NPC478237
0.8723	High Similarity	NPC130449
0.8723	High Similarity	NPC93924
0.8723	High Similarity	NPC175976
0.8723	High Similarity	NPC248132
0.8722	High Similarity	NPC72046
0.8722	High Similarity	NPC65183
0.8722	High Similarity	NPC470270
0.8722	High Similarity	NPC261812
0.8712	High Similarity	NPC476399
0.8712	High Similarity	NPC469612
0.8712	High Similarity	NPC477804
0.8712	High Similarity	NPC469614
0.871	High Similarity	NPC123948
0.8705	High Similarity	NPC118385
0.8705	High Similarity	NPC472713
0.8705	High Similarity	NPC469313
0.8705	High Similarity	NPC472712
0.8705	High Similarity	NPC76176
0.8705	High Similarity	NPC138227
0.8705	High Similarity	NPC187774
0.8705	High Similarity	NPC473046
0.8705	High Similarity	NPC168579
0.8696	High Similarity	NPC473873
0.8696	High Similarity	NPC473792
0.8696	High Similarity	NPC246947
0.8686	High Similarity	NPC226547
0.8686	High Similarity	NPC106944
0.8667	High Similarity	NPC49235
0.8667	High Similarity	NPC148893
0.8667	High Similarity	NPC236522
0.8667	High Similarity	NPC25333
0.8667	High Similarity	NPC189474
0.8662	High Similarity	NPC95392
0.8662	High Similarity	NPC55715
0.8662	High Similarity	NPC35877
0.8657	High Similarity	NPC263064
0.8657	High Similarity	NPC25821
0.8657	High Similarity	NPC1474
0.8652	High Similarity	NPC15538
0.8652	High Similarity	NPC473480
0.8647	High Similarity	NPC475067
0.8647	High Similarity	NPC192255
0.8636	High Similarity	NPC202582
0.8636	High Similarity	NPC222004
0.8636	High Similarity	NPC226788
0.8636	High Similarity	NPC190629
0.8636	High Similarity	NPC307110
0.8636	High Similarity	NPC470258
0.8636	High Similarity	NPC210623
0.8636	High Similarity	NPC285339
0.8636	High Similarity	NPC273295
0.8636	High Similarity	NPC3439
0.8636	High Similarity	NPC218856
0.8633	High Similarity	NPC37793
0.8633	High Similarity	NPC81638
0.8633	High Similarity	NPC185307
0.8633	High Similarity	NPC470950
0.8633	High Similarity	NPC46092
0.8626	High Similarity	NPC474119
0.8623	High Similarity	NPC76871
0.8623	High Similarity	NPC210192
0.8611	High Similarity	NPC302610
0.8603	High Similarity	NPC121651
0.8603	High Similarity	NPC471719
0.8601	High Similarity	NPC472709
0.8601	High Similarity	NPC472710
0.8593	High Similarity	NPC474478
0.8593	High Similarity	NPC31530
0.8593	High Similarity	NPC35731
0.8592	High Similarity	NPC280945
0.8582	High Similarity	NPC16208
0.8582	High Similarity	NPC7903
0.8582	High Similarity	NPC184447
0.8582	High Similarity	NPC35932
0.8582	High Similarity	NPC160991
0.8571	High Similarity	NPC470235
0.8571	High Similarity	NPC471063
0.8571	High Similarity	NPC471667
0.8571	High Similarity	NPC129417
0.8571	High Similarity	NPC79429
0.8571	High Similarity	NPC217635
0.8571	High Similarity	NPC283995
0.8561	High Similarity	NPC311057
0.8561	High Similarity	NPC472562
0.8561	High Similarity	NPC474651
0.8561	High Similarity	NPC474623
0.8561	High Similarity	NPC476356
0.8561	High Similarity	NPC60249
0.8561	High Similarity	NPC157816
0.855	High Similarity	NPC9891
0.855	High Similarity	NPC244364
0.855	High Similarity	NPC112571
0.855	High Similarity	NPC88297
0.855	High Similarity	NPC285725
0.855	High Similarity	NPC50683
0.855	High Similarity	NPC186845

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 NPC469698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	918
0.2-0.3	2050
0.3-0.4	2772
0.4-0.5	1572
0.5-0.6	907
0.6-0.7	462
0.7-0.8	77
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD2981	Phase 2
0.8321	Intermediate Similarity	NPD2983	Phase 2
0.8321	Intermediate Similarity	NPD2982	Phase 2
0.8222	Intermediate Similarity	NPD3027	Phase 3
0.8175	Intermediate Similarity	NPD1613	Approved
0.8175	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD3705	Approved
0.8151	Intermediate Similarity	NPD1653	Approved
0.8074	Intermediate Similarity	NPD3018	Phase 2
0.8015	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1091	Approved
0.7848	Intermediate Similarity	NPD7054	Approved
0.7847	Intermediate Similarity	NPD6674	Discontinued
0.7832	Intermediate Similarity	NPD7266	Discontinued
0.7799	Intermediate Similarity	NPD7472	Approved
0.7799	Intermediate Similarity	NPD7074	Phase 3
0.7752	Intermediate Similarity	NPD5283	Phase 1
0.7718	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7669	Intermediate Similarity	NPD1357	Approved
0.7662	Intermediate Similarity	NPD4967	Phase 2
0.7662	Intermediate Similarity	NPD4966	Approved
0.7662	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7626	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7251	Discontinued
0.758	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD6234	Discontinued
0.7562	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD3818	Discontinued
0.7531	Intermediate Similarity	NPD6797	Phase 2
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3817	Phase 2
0.7484	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1934	Approved
0.7466	Intermediate Similarity	NPD3540	Phase 1
0.7463	Intermediate Similarity	NPD1548	Phase 1
0.7439	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3454	Phase 3
0.7394	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7240	Approved
0.7376	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4678	Approved
0.7338	Intermediate Similarity	NPD4675	Approved
0.7333	Intermediate Similarity	NPD5058	Phase 3
0.7325	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2861	Phase 2
0.7303	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5494	Approved
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7843	Approved
0.7254	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3383	Approved
0.7244	Intermediate Similarity	NPD3384	Approved
0.7244	Intermediate Similarity	NPD3382	Approved
0.7241	Intermediate Similarity	NPD1933	Approved
0.7239	Intermediate Similarity	NPD7157	Approved
0.723	Intermediate Similarity	NPD1375	Discontinued
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7124	Phase 2
0.7203	Intermediate Similarity	NPD4625	Phase 3
0.7197	Intermediate Similarity	NPD8455	Phase 2
0.7197	Intermediate Similarity	NPD2801	Approved
0.7195	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5677	Discontinued
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.7153	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD4749	Approved
0.7133	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7132	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2684	Approved
0.7095	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.7091	Intermediate Similarity	NPD5844	Phase 1
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7534	Approved
0.708	Intermediate Similarity	NPD7533	Approved
0.7068	Intermediate Similarity	NPD228	Approved
0.7066	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD4357	Discontinued
0.7047	Intermediate Similarity	NPD2796	Approved
0.7044	Intermediate Similarity	NPD5353	Approved
0.7034	Intermediate Similarity	NPD5718	Phase 2
0.7029	Intermediate Similarity	NPD5585	Approved
0.7027	Intermediate Similarity	NPD6111	Discontinued
0.7023	Intermediate Similarity	NPD1358	Approved
0.7021	Intermediate Similarity	NPD5327	Phase 3
0.7018	Intermediate Similarity	NPD6843	Phase 3
0.7018	Intermediate Similarity	NPD6841	Approved
0.7018	Intermediate Similarity	NPD6842	Approved
0.7013	Intermediate Similarity	NPD4123	Phase 3
0.7	Intermediate Similarity	NPD3882	Suspended
0.6994	Remote Similarity	NPD3787	Discontinued
0.6986	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6233	Phase 2
0.6981	Remote Similarity	NPD7819	Suspended
0.6981	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5588	Approved
0.698	Remote Similarity	NPD5960	Phase 3
0.6974	Remote Similarity	NPD7466	Approved
0.6972	Remote Similarity	NPD8651	Approved
0.6968	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD7075	Discontinued
0.6948	Remote Similarity	NPD5297	Approved
0.6948	Remote Similarity	NPD1511	Approved
0.6943	Remote Similarity	NPD4005	Discontinued
0.6943	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1558	Phase 1
0.6918	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD556	Approved
0.6908	Remote Similarity	NPD4236	Phase 3
0.6908	Remote Similarity	NPD4162	Approved
0.6908	Remote Similarity	NPD4237	Approved
0.6903	Remote Similarity	NPD7447	Phase 1
0.6899	Remote Similarity	NPD291	Approved
0.6894	Remote Similarity	NPD290	Approved
0.6892	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5124	Phase 1
0.6886	Remote Similarity	NPD8156	Discontinued
0.6879	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD2977	Approved
0.6875	Remote Similarity	NPD2978	Approved
0.6871	Remote Similarity	NPD3530	Approved
0.6871	Remote Similarity	NPD3531	Approved
0.6871	Remote Similarity	NPD3532	Approved
0.6863	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4110	Phase 3
0.6863	Remote Similarity	NPD6331	Phase 2
0.6861	Remote Similarity	NPD6671	Approved
0.6859	Remote Similarity	NPD1512	Approved
0.6857	Remote Similarity	NPD5846	Approved
0.6857	Remote Similarity	NPD6516	Phase 2
0.6855	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2922	Phase 1
0.6846	Remote Similarity	NPD2492	Phase 1
0.6839	Remote Similarity	NPD6799	Approved
0.6839	Remote Similarity	NPD7213	Phase 3
0.6839	Remote Similarity	NPD7212	Phase 2
0.6835	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1182	Approved
0.6832	Remote Similarity	NPD5402	Approved
0.6826	Remote Similarity	NPD8251	Approved
0.6826	Remote Similarity	NPD8252	Approved
0.6826	Remote Similarity	NPD8099	Discontinued
0.6824	Remote Similarity	NPD7549	Discontinued
0.6824	Remote Similarity	NPD4060	Phase 1
0.6822	Remote Similarity	NPD1242	Phase 1
0.6818	Remote Similarity	NPD3134	Approved
0.6818	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD2219	Phase 1
0.6818	Remote Similarity	NPD968	Approved
0.6805	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5110	Phase 2
0.6803	Remote Similarity	NPD5111	Phase 2
0.6803	Remote Similarity	NPD5109	Approved
0.6803	Remote Similarity	NPD6798	Discontinued
0.6802	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5177	Phase 3
0.6797	Remote Similarity	NPD3060	Approved
0.6792	Remote Similarity	NPD4380	Phase 2
0.6791	Remote Similarity	NPD5451	Approved
0.6788	Remote Similarity	NPD6232	Discontinued
0.6786	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6382	Discontinued
0.6783	Remote Similarity	NPD4359	Approved
0.6779	Remote Similarity	NPD4340	Discontinued
0.6779	Remote Similarity	NPD3657	Discovery
0.6779	Remote Similarity	NPD6355	Discontinued
0.6779	Remote Similarity	NPD5735	Approved
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3686	Approved
0.6772	Remote Similarity	NPD3687	Approved
0.677	Remote Similarity	NPD1465	Phase 2
0.677	Remote Similarity	NPD5772	Approved
0.677	Remote Similarity	NPD5773	Approved
0.6766	Remote Similarity	NPD7473	Discontinued
0.676	Remote Similarity	NPD7237	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