NPASS Compound

Structure

CID294166 OpenBabel06191716102D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.1962 5.0000 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 -5.1962 -0.0000 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 -5.1962 2.0000 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 -5.1962 3.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 0.8660 0.5000 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 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 -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 -3.4641 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 0.0000 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 -6.0622 4.5000 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 27 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 22 1 0 0 0 0 14 23 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 11 1 1 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.15
Volume:	397.969
LogP:	1.72
LogD:	1.976
LogS:	-3.057
# Rotatable Bonds:	6
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	3.607
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.872
MDCK Permeability:	1.4076501429372001e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.703
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	96.57794952392578%
Volume Distribution (VD):	0.539
Pgp-substrate:	3.0198075771331787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.481
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.154
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	11.852
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.668
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.597
Carcinogencity:	0.34
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC294166

Natural Product ID:	NPC294166
*Common Name:**	(Z)-3,5-Dihydroxy-4'-Methoxystilbene 3-O-Beta-D-Glucopyranoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	MFMQRDLLSRLUJY-JGOUSXGWSA-N
Standard InCHI:	InChI=1S/C21H24O8/c1-27-15-6-4-12(5-7-15)2-3-13-8-14(23)10-16(9-13)28-21-20(26)19(25)18(24)17(11-22)29-21/h2-10,17-26H,11H2,1H3/b3-2-/t17-,18-,19+,20-,21-/m1/s1
SMILES:	COc1ccc(/C=Cc2cc(cc(c2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464004
PubChem CID:	11795500
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
NPO20665	Erythrophleum lasianthum	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[9392877]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20665	Erythrophleum lasianthum	Species	Fabaceae	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	2

Activity Type	# Activity
CELL-LINE	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	300.0	ug	PMID[519468]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	198.0	ug	PMID[519468]

☑ 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 NPC294166 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	364
0.1-0.2	1568
0.2-0.3	4534
0.3-0.4	11027
0.4-0.5	7270
0.5-0.6	5001
0.6-0.7	7681
0.7-0.8	4247
0.8-0.85	741
0.85-0.9	180
0.9-0.95	60
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC115022
0.9921	High Similarity	NPC303422
0.9921	High Similarity	NPC26080
0.9921	High Similarity	NPC165686
0.9921	High Similarity	NPC85799
0.9844	High Similarity	NPC238243
0.9841	High Similarity	NPC121376
0.9767	High Similarity	NPC40664
0.9767	High Similarity	NPC138350
0.9767	High Similarity	NPC3293
0.9767	High Similarity	NPC165482
0.9767	High Similarity	NPC197723
0.9766	High Similarity	NPC188555
0.9766	High Similarity	NPC130496
0.9692	High Similarity	NPC124149
0.9683	High Similarity	NPC218003
0.9618	High Similarity	NPC98777
0.9618	High Similarity	NPC212770
0.9615	High Similarity	NPC203230
0.9615	High Similarity	NPC242028
0.9542	High Similarity	NPC59324
0.9542	High Similarity	NPC65530
0.9474	High Similarity	NPC273932
0.9474	High Similarity	NPC210192
0.9474	High Similarity	NPC89686
0.9474	High Similarity	NPC257095
0.9403	High Similarity	NPC475084
0.9403	High Similarity	NPC469559
0.9403	High Similarity	NPC189115
0.9385	High Similarity	NPC49074
0.938	High Similarity	NPC475067
0.9365	High Similarity	NPC12308
0.9333	High Similarity	NPC473044
0.9328	High Similarity	NPC469661
0.9318	High Similarity	NPC164857
0.9308	High Similarity	NPC162093
0.9265	High Similarity	NPC25292
0.9265	High Similarity	NPC473045
0.9248	High Similarity	NPC87777
0.9248	High Similarity	NPC262328
0.9248	High Similarity	NPC134260
0.9242	High Similarity	NPC470236
0.9237	High Similarity	NPC132895
0.9197	High Similarity	NPC475096
0.9191	High Similarity	NPC252169
0.9167	High Similarity	NPC251981
0.9167	High Similarity	NPC13745
0.9167	High Similarity	NPC48863
0.916	High Similarity	NPC299144
0.9154	High Similarity	NPC262606
0.913	High Similarity	NPC125755
0.913	High Similarity	NPC190714
0.913	High Similarity	NPC99515
0.9124	High Similarity	NPC168579
0.9124	High Similarity	NPC469313
0.9124	High Similarity	NPC76176
0.9124	High Similarity	NPC138227
0.9104	High Similarity	NPC470413
0.9104	High Similarity	NPC138738
0.9098	High Similarity	NPC185778
0.9091	High Similarity	NPC215833
0.9091	High Similarity	NPC69513
0.9084	High Similarity	NPC469698
0.9084	High Similarity	NPC473412
0.9077	High Similarity	NPC248355
0.9065	High Similarity	NPC15538
0.9065	High Similarity	NPC473480
0.9065	High Similarity	NPC227902
0.9065	High Similarity	NPC39657
0.9058	High Similarity	NPC161700
0.9058	High Similarity	NPC277867
0.9051	High Similarity	NPC37793
0.903	High Similarity	NPC25695
0.903	High Similarity	NPC172818
0.9023	High Similarity	NPC187194
0.9023	High Similarity	NPC107478
0.9023	High Similarity	NPC170694
0.9015	High Similarity	NPC470270
0.9	High Similarity	NPC175976
0.9	High Similarity	NPC302378
0.9	High Similarity	NPC478237
0.8978	High Similarity	NPC5253
0.8978	High Similarity	NPC472353
0.8978	High Similarity	NPC139976
0.8978	High Similarity	NPC472714
0.8978	High Similarity	NPC84207
0.8978	High Similarity	NPC128337
0.8978	High Similarity	NPC49542
0.8978	High Similarity	NPC5262
0.8978	High Similarity	NPC230718
0.8963	High Similarity	NPC195196
0.8936	High Similarity	NPC55158
0.8936	High Similarity	NPC106138
0.8936	High Similarity	NPC286235
0.8936	High Similarity	NPC51328
0.8931	High Similarity	NPC166040
0.8931	High Similarity	NPC307110
0.8905	High Similarity	NPC108674
0.8889	High Similarity	NPC177035
0.8889	High Similarity	NPC104167
0.8889	High Similarity	NPC52277
0.8889	High Similarity	NPC199459
0.8881	High Similarity	NPC476411
0.8872	High Similarity	NPC7903
0.8872	High Similarity	NPC160991
0.8872	High Similarity	NPC35932
0.8872	High Similarity	NPC184447
0.8872	High Similarity	NPC16208
0.8865	High Similarity	NPC280945
0.8865	High Similarity	NPC248132
0.8865	High Similarity	NPC130449
0.8864	High Similarity	NPC472024
0.8864	High Similarity	NPC80600
0.8855	High Similarity	NPC40377
0.8849	High Similarity	NPC187774
0.8849	High Similarity	NPC472713
0.8849	High Similarity	NPC118385
0.8849	High Similarity	NPC473046
0.8849	High Similarity	NPC225445
0.8849	High Similarity	NPC472712
0.8841	High Similarity	NPC157816
0.8841	High Similarity	NPC145319
0.8832	High Similarity	NPC106944
0.8832	High Similarity	NPC210478
0.8819	High Similarity	NPC269242
0.8819	High Similarity	NPC198734
0.8819	High Similarity	NPC469412
0.8815	High Similarity	NPC61946
0.8815	High Similarity	NPC79957
0.8811	High Similarity	NPC473621
0.8806	High Similarity	NPC25821
0.8806	High Similarity	NPC215037
0.8797	High Similarity	NPC103799
0.8797	High Similarity	NPC9912
0.8797	High Similarity	NPC30043
0.8797	High Similarity	NPC469625
0.8797	High Similarity	NPC65942
0.8797	High Similarity	NPC248307
0.8797	High Similarity	NPC469613
0.8797	High Similarity	NPC472597
0.8788	High Similarity	NPC97326
0.8788	High Similarity	NPC210623
0.8788	High Similarity	NPC218856
0.8788	High Similarity	NPC470258
0.8788	High Similarity	NPC226788
0.8788	High Similarity	NPC26653
0.8788	High Similarity	NPC222004
0.8788	High Similarity	NPC202582
0.8788	High Similarity	NPC190629
0.8788	High Similarity	NPC273295
0.8788	High Similarity	NPC3439
0.8788	High Similarity	NPC285339
0.8788	High Similarity	NPC270849
0.8786	High Similarity	NPC226722
0.8777	High Similarity	NPC185307
0.8777	High Similarity	NPC46092
0.8777	High Similarity	NPC116922
0.8777	High Similarity	NPC478239
0.8777	High Similarity	NPC470950
0.8777	High Similarity	NPC81638
0.8768	High Similarity	NPC186406
0.8759	High Similarity	NPC292487
0.875	High Similarity	NPC16435
0.875	High Similarity	NPC53587
0.875	High Similarity	NPC166180
0.875	High Similarity	NPC21902
0.875	High Similarity	NPC176186
0.875	High Similarity	NPC306441
0.875	High Similarity	NPC169404
0.8741	High Similarity	NPC472709
0.8741	High Similarity	NPC310854
0.8741	High Similarity	NPC472710
0.8741	High Similarity	NPC87696
0.8741	High Similarity	NPC35731
0.874	High Similarity	NPC469708
0.874	High Similarity	NPC60589
0.8732	High Similarity	NPC93924
0.8732	High Similarity	NPC270751
0.8731	High Similarity	NPC201587
0.8731	High Similarity	NPC252833
0.8731	High Similarity	NPC253105
0.8723	High Similarity	NPC199928
0.8723	High Similarity	NPC74320
0.8723	High Similarity	NPC107120
0.8722	High Similarity	NPC469612
0.8722	High Similarity	NPC474491
0.8722	High Similarity	NPC472338
0.8722	High Similarity	NPC469614
0.8714	High Similarity	NPC292443
0.8714	High Similarity	NPC129417
0.8714	High Similarity	NPC177597
0.8714	High Similarity	NPC470235
0.8714	High Similarity	NPC283995
0.8712	High Similarity	NPC87224
0.8712	High Similarity	NPC222572
0.8705	High Similarity	NPC60249
0.8705	High Similarity	NPC476356
0.8692	High Similarity	NPC287429
0.869	High Similarity	NPC150442
0.869	High Similarity	NPC78809

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 NPC294166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	852
0.2-0.3	1879
0.3-0.4	2819
0.4-0.5	1684
0.5-0.6	963
0.6-0.7	556
0.7-0.8	96
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD1091	Approved
0.8593	High Similarity	NPD1612	Clinical (unspecified phase)
0.8593	High Similarity	NPD1613	Approved
0.8507	High Similarity	NPD3027	Phase 3
0.8414	Intermediate Similarity	NPD1653	Approved
0.8296	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.8099	Intermediate Similarity	NPD7266	Discontinued
0.8092	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1610	Phase 2
0.8043	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.7975	Intermediate Similarity	NPD7054	Approved
0.7925	Intermediate Similarity	NPD7074	Phase 3
0.7925	Intermediate Similarity	NPD7472	Approved
0.7875	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD6559	Discontinued
0.7826	Intermediate Similarity	NPD2861	Phase 2
0.7826	Intermediate Similarity	NPD7251	Discontinued
0.7823	Intermediate Similarity	NPD5058	Phase 3
0.7799	Intermediate Similarity	NPD3818	Discontinued
0.7794	Intermediate Similarity	NPD2983	Phase 2
0.7794	Intermediate Similarity	NPD2982	Phase 2
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.775	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6674	Discontinued
0.7721	Intermediate Similarity	NPD2981	Phase 2
0.7714	Intermediate Similarity	NPD4625	Phase 3
0.7712	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7688	Intermediate Similarity	NPD7228	Approved
0.7687	Intermediate Similarity	NPD1357	Approved
0.7677	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD4966	Approved
0.7677	Intermediate Similarity	NPD4965	Approved
0.7669	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4749	Approved
0.766	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4538	Approved
0.7639	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4536	Approved
0.7619	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1652	Phase 2
0.7597	Intermediate Similarity	NPD1934	Approved
0.7595	Intermediate Similarity	NPD7199	Phase 2
0.7571	Intermediate Similarity	NPD3018	Phase 2
0.7564	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7843	Approved
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8455	Phase 2
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7157	Approved
0.7519	Intermediate Similarity	NPD2684	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7466	Intermediate Similarity	NPD5588	Approved
0.7466	Intermediate Similarity	NPD5960	Phase 3
0.7453	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6166	Phase 2
0.7453	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD290	Approved
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD7075	Discontinued
0.7391	Intermediate Similarity	NPD422	Phase 1
0.7391	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1242	Phase 1
0.7379	Intermediate Similarity	NPD5124	Phase 1
0.7379	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD968	Approved
0.7361	Intermediate Similarity	NPD6233	Phase 2
0.7329	Intermediate Similarity	NPD3787	Discontinued
0.7325	Intermediate Similarity	NPD2801	Approved
0.7303	Intermediate Similarity	NPD7213	Phase 3
0.7303	Intermediate Similarity	NPD7212	Phase 2
0.7289	Intermediate Similarity	NPD7240	Approved
0.7286	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD5402	Approved
0.7259	Intermediate Similarity	NPD6671	Approved
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7254	Intermediate Similarity	NPD6584	Phase 3
0.7248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5846	Approved
0.7246	Intermediate Similarity	NPD5126	Approved
0.7246	Intermediate Similarity	NPD5125	Phase 3
0.7246	Intermediate Similarity	NPD6516	Phase 2
0.7244	Intermediate Similarity	NPD4675	Approved
0.7244	Intermediate Similarity	NPD4678	Approved
0.7234	Intermediate Similarity	NPD8651	Approved
0.723	Intermediate Similarity	NPD4108	Discontinued
0.7222	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7218	Intermediate Similarity	NPD228	Approved
0.7215	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1511	Approved
0.7188	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7685	Pre-registration
0.7172	Intermediate Similarity	NPD6798	Discontinued
0.7171	Intermediate Similarity	NPD6190	Approved
0.7161	Intermediate Similarity	NPD5403	Approved
0.7161	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7152	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5735	Approved
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7108	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD2977	Approved
0.7107	Intermediate Similarity	NPD2978	Approved
0.7107	Intermediate Similarity	NPD7819	Suspended
0.7105	Intermediate Similarity	NPD4535	Phase 3
0.7097	Intermediate Similarity	NPD1512	Approved
0.7095	Intermediate Similarity	NPD6653	Approved
0.7092	Intermediate Similarity	NPD2235	Phase 2
0.7092	Intermediate Similarity	NPD2231	Phase 2
0.7089	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6799	Approved
0.7075	Intermediate Similarity	NPD1558	Phase 1
0.7067	Intermediate Similarity	NPD6100	Approved
0.7067	Intermediate Similarity	NPD6099	Approved
0.7063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2677	Approved
0.7047	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3685	Discontinued
0.7042	Intermediate Similarity	NPD6582	Phase 2
0.7042	Intermediate Similarity	NPD6583	Phase 3
0.7037	Intermediate Similarity	NPD5535	Approved
0.7032	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD5763	Approved
0.702	Intermediate Similarity	NPD3540	Phase 1
0.7007	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6993	Remote Similarity	NPD3750	Approved
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3892	Phase 2
0.6986	Remote Similarity	NPD3180	Approved
0.6986	Remote Similarity	NPD3179	Approved
0.6981	Remote Similarity	NPD7411	Suspended
0.6974	Remote Similarity	NPD2424	Discontinued
0.6968	Remote Similarity	NPD4357	Discontinued
0.6962	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3620	Phase 2
0.6959	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2238	Phase 2
0.6959	Remote Similarity	NPD4140	Approved
0.6954	Remote Similarity	NPD3539	Phase 1
0.6954	Remote Similarity	NPD1551	Phase 2
0.6954	Remote Similarity	NPD2796	Approved
0.6951	Remote Similarity	NPD6959	Discontinued
0.695	Remote Similarity	NPD3496	Discontinued
0.6948	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6841	Approved
0.6936	Remote Similarity	NPD6843	Phase 3
0.6936	Remote Similarity	NPD6842	Approved
0.6929	Remote Similarity	NPD5585	Approved
0.6928	Remote Similarity	NPD3060	Approved
0.6923	Remote Similarity	NPD4123	Phase 3
0.6923	Remote Similarity	NPD3536	Discontinued
0.6923	Remote Similarity	NPD291	Approved
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1358	Approved
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD1375	Discontinued
0.6906	Remote Similarity	NPD5536	Phase 2
0.6894	Remote Similarity	NPD1465	Phase 2
0.6887	Remote Similarity	NPD1510	Phase 2
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD3225	Approved
0.6872	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3054	Approved
0.6867	Remote Similarity	NPD3052	Approved
0.6857	Remote Similarity	NPD1182	Approved
0.6855	Remote Similarity	NPD4005	Discontinued
0.6853	Remote Similarity	NPD1608	Approved
0.6842	Remote Similarity	NPD3454	Phase 3
0.6842	Remote Similarity	NPD6032	Approved
0.6828	Remote Similarity	NPD3094	Phase 2
0.6824	Remote Similarity	NPD7007	Discovery
0.6821	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4162	Approved
0.6818	Remote Similarity	NPD4236	Phase 3
0.6818	Remote Similarity	NPD4237	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data