NPASS Compound

Structure

NPC25292 OpenBabel07101718322D 30 32 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 -7.7942 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 -2.5981 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 -5.1962 3.0000 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 1.7321 -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 -0.0000 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 -6.0622 3.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -7.7942 1.5000 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 28 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 8 1 1 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 29 1 1 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.14
Volume:	400.89
LogP:	0.297
LogD:	0.455
LogS:	-2.836
# Rotatable Bonds:	6
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	3.632
Fsp3:	0.4
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:	-6.317
MDCK Permeability:	2.8339649361441843e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.543
Human Intestinal Absorption (HIA):	0.658
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.779

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	89.44080352783203%
Volume Distribution (VD):	0.414
Pgp-substrate:	13.125835418701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.432
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.26
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.488
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	8.863
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.917
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC25292

Natural Product ID:	NPC25292
*Common Name:**	Fortuneanoside E
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Fortuneanoside E
Standard InCHIKey:	LNEZLIPXCBMQAT-XIKSMUEASA-N
Standard InCHI:	InChI=1S/C20H24O10/c1-27-13-6-10(7-14(28-2)16(13)23)9-3-4-12(11(22)5-9)29-20-19(26)18(25)17(24)15(8-21)30-20/h3-7,15,17-26H,8H2,1-2H3/t15-,17-,18+,19-,20-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2O)c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498291
PubChem CID:	11844494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO27360	Pyracantha fortuneana	Species	Rosaceae	Eukaryota	fruit	n.a.	n.a.	PMID[16872137]
NPO27360	Pyracantha fortuneana	Species	Rosaceae	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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	140000.0	nM	PMID[500064]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	140000.0	nM	PMID[500063]

☑ 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 NPC25292 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	431
0.1-0.2	1548
0.2-0.3	4060
0.3-0.4	10510
0.4-0.5	8002
0.5-0.6	4599
0.6-0.7	6684
0.7-0.8	5000
0.8-0.85	1156
0.85-0.9	537
0.9-0.95	144
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473045
0.9926	High Similarity	NPC473044
0.9855	High Similarity	NPC190714
0.9855	High Similarity	NPC99515
0.9853	High Similarity	NPC189115
0.9779	High Similarity	NPC469661
0.9714	High Similarity	NPC175976
0.9708	High Similarity	NPC469559
0.9643	High Similarity	NPC39657
0.964	High Similarity	NPC475096
0.9632	High Similarity	NPC98777
0.9632	High Similarity	NPC212770
0.9571	High Similarity	NPC125755
0.9565	High Similarity	NPC472714
0.9565	High Similarity	NPC5262
0.9565	High Similarity	NPC475084
0.9559	High Similarity	NPC59324
0.9559	High Similarity	NPC65530
0.9507	High Similarity	NPC55158
0.9507	High Similarity	NPC286235
0.9507	High Similarity	NPC51328
0.9504	High Similarity	NPC227902
0.95	High Similarity	NPC277867
0.95	High Similarity	NPC161700
0.9485	High Similarity	NPC203230
0.9485	High Similarity	NPC242028
0.9444	High Similarity	NPC21902
0.9437	High Similarity	NPC248132
0.9437	High Similarity	NPC130449
0.9429	High Similarity	NPC472713
0.9429	High Similarity	NPC472712
0.9429	High Similarity	NPC76176
0.9429	High Similarity	NPC138227
0.9429	High Similarity	NPC118385
0.9429	High Similarity	NPC469313
0.9429	High Similarity	NPC473046
0.9429	High Similarity	NPC187774
0.9429	High Similarity	NPC168579
0.9416	High Similarity	NPC470413
0.9416	High Similarity	NPC138738
0.9379	High Similarity	NPC78809
0.9366	High Similarity	NPC473480
0.9366	High Similarity	NPC15538
0.9357	High Similarity	NPC470950
0.9357	High Similarity	NPC252169
0.9357	High Similarity	NPC37793
0.9357	High Similarity	NPC185307
0.9357	High Similarity	NPC46092
0.9348	High Similarity	NPC22517
0.9343	High Similarity	NPC199459
0.9343	High Similarity	NPC52277
0.9343	High Similarity	NPC177035
0.9338	High Similarity	NPC48863
0.9338	High Similarity	NPC107478
0.9338	High Similarity	NPC170694
0.9338	High Similarity	NPC13745
0.9338	High Similarity	NPC251981
0.9306	High Similarity	NPC472710
0.9306	High Similarity	NPC472709
0.9291	High Similarity	NPC283995
0.9291	High Similarity	NPC129417
0.9291	High Similarity	NPC470235
0.9286	High Similarity	NPC48309
0.9286	High Similarity	NPC476356
0.9286	High Similarity	NPC60249
0.9281	High Similarity	NPC106944
0.9265	High Similarity	NPC132895
0.9265	High Similarity	NPC49074
0.9265	High Similarity	NPC294166
0.9265	High Similarity	NPC115022
0.9265	High Similarity	NPC69513
0.9265	High Similarity	NPC215833
0.9236	High Similarity	NPC106138
0.9225	High Similarity	NPC18979
0.9225	High Similarity	NPC22150
0.9225	High Similarity	NPC279298
0.9225	High Similarity	NPC38041
0.922	High Similarity	NPC81638
0.9214	High Similarity	NPC76871
0.9214	High Similarity	NPC210192
0.9214	High Similarity	NPC472711
0.9203	High Similarity	NPC164857
0.9203	High Similarity	NPC16435
0.9203	High Similarity	NPC306441
0.9203	High Similarity	NPC25695
0.9203	High Similarity	NPC172818
0.9197	High Similarity	NPC476411
0.9197	High Similarity	NPC187194
0.9191	High Similarity	NPC160991
0.9191	High Similarity	NPC184447
0.9191	High Similarity	NPC26080
0.9191	High Similarity	NPC16208
0.9191	High Similarity	NPC162093
0.9191	High Similarity	NPC85799
0.9191	High Similarity	NPC303422
0.9191	High Similarity	NPC7903
0.9191	High Similarity	NPC201587
0.9191	High Similarity	NPC299144
0.9191	High Similarity	NPC470270
0.9191	High Similarity	NPC253105
0.9191	High Similarity	NPC165686
0.9191	High Similarity	NPC35932
0.9167	High Similarity	NPC280945
0.9167	High Similarity	NPC270751
0.9161	High Similarity	NPC112861
0.9143	High Similarity	NPC266197
0.9143	High Similarity	NPC291101
0.9137	High Similarity	NPC304152
0.9137	High Similarity	NPC474039
0.913	High Similarity	NPC234333
0.913	High Similarity	NPC94750
0.913	High Similarity	NPC47398
0.913	High Similarity	NPC238243
0.913	High Similarity	NPC121812
0.913	High Similarity	NPC470236
0.913	High Similarity	NPC260898
0.913	High Similarity	NPC61946
0.913	High Similarity	NPC112939
0.913	High Similarity	NPC474206
0.913	High Similarity	NPC112246
0.913	High Similarity	NPC470356
0.9118	High Similarity	NPC65942
0.9118	High Similarity	NPC121376
0.9118	High Similarity	NPC475067
0.9118	High Similarity	NPC248307
0.9118	High Similarity	NPC472597
0.9116	High Similarity	NPC150442
0.911	High Similarity	NPC473621
0.9097	High Similarity	NPC31325
0.9097	High Similarity	NPC15956
0.9097	High Similarity	NPC275284
0.9097	High Similarity	NPC213074
0.9097	High Similarity	NPC193473
0.9097	High Similarity	NPC224674
0.9097	High Similarity	NPC114505
0.9091	High Similarity	NPC307466
0.9091	High Similarity	NPC469586
0.9085	High Similarity	NPC113680
0.9085	High Similarity	NPC477898
0.9085	High Similarity	NPC278961
0.9078	High Similarity	NPC471389
0.9071	High Similarity	NPC292487
0.9065	High Similarity	NPC269091
0.9065	High Similarity	NPC138350
0.9065	High Similarity	NPC165482
0.9065	High Similarity	NPC230734
0.9065	High Similarity	NPC3293
0.9065	High Similarity	NPC40664
0.9065	High Similarity	NPC265433
0.9065	High Similarity	NPC270456
0.9065	High Similarity	NPC162659
0.9065	High Similarity	NPC227503
0.9065	High Similarity	NPC474639
0.9065	High Similarity	NPC302701
0.9065	High Similarity	NPC197723
0.9065	High Similarity	NPC248727
0.9058	High Similarity	NPC130496
0.9058	High Similarity	NPC188555
0.9058	High Similarity	NPC310854
0.9058	High Similarity	NPC35731
0.9051	High Similarity	NPC470752
0.9048	High Similarity	NPC169404
0.9048	High Similarity	NPC53587
0.9048	High Similarity	NPC176186
0.9044	High Similarity	NPC472338
0.9044	High Similarity	NPC472024
0.9044	High Similarity	NPC80600
0.9041	High Similarity	NPC225815
0.9041	High Similarity	NPC185955
0.9041	High Similarity	NPC218041
0.9041	High Similarity	NPC214326
0.9041	High Similarity	NPC145979
0.9041	High Similarity	NPC260781
0.9041	High Similarity	NPC9933
0.9041	High Similarity	NPC469707
0.9041	High Similarity	NPC182368
0.9041	High Similarity	NPC469706
0.9034	High Similarity	NPC301961
0.9034	High Similarity	NPC478237
0.9034	High Similarity	NPC166584
0.9021	High Similarity	NPC84181
0.9014	High Similarity	NPC41782
0.9014	High Similarity	NPC246947
0.9007	High Similarity	NPC226547
0.9007	High Similarity	NPC309124
0.9007	High Similarity	NPC177868
0.9007	High Similarity	NPC184797
0.9	High Similarity	NPC176051
0.9	High Similarity	NPC474282
0.9	High Similarity	NPC124149
0.9	High Similarity	NPC87777
0.9	High Similarity	NPC134260
0.9	High Similarity	NPC195196
0.9	High Similarity	NPC211549
0.9	High Similarity	NPC107551
0.9	High Similarity	NPC326797
0.9	High Similarity	NPC262328
0.9	High Similarity	NPC102904
0.9	High Similarity	NPC103976
0.8993	High Similarity	NPC101624

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 NPC25292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	856
0.2-0.3	1830
0.3-0.4	2769
0.4-0.5	1699
0.5-0.6	942
0.6-0.7	573
0.7-0.8	121
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8971	High Similarity	NPD3027	Phase 3
0.8913	High Similarity	NPD1613	Approved
0.8913	High Similarity	NPD1612	Clinical (unspecified phase)
0.8623	High Similarity	NPD1529	Clinical (unspecified phase)
0.8591	High Similarity	NPD1653	Approved
0.8551	High Similarity	NPD1530	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8288	Intermediate Similarity	NPD7266	Discontinued
0.8261	Intermediate Similarity	NPD7054	Approved
0.8217	Intermediate Similarity	NPD6234	Discontinued
0.821	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD3818	Discontinued
0.8199	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD6674	Discontinued
0.8129	Intermediate Similarity	NPD37	Approved
0.8116	Intermediate Similarity	NPD1091	Approved
0.8099	Intermediate Similarity	NPD4908	Phase 1
0.8089	Intermediate Similarity	NPD4966	Approved
0.8089	Intermediate Similarity	NPD4967	Phase 2
0.8089	Intermediate Similarity	NPD4965	Approved
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8013	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1610	Phase 2
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.7925	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3705	Approved
0.7853	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4625	Phase 3
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.7746	Intermediate Similarity	NPD2983	Phase 2
0.7746	Intermediate Similarity	NPD2982	Phase 2
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7679	Intermediate Similarity	NPD7240	Approved
0.7676	Intermediate Similarity	NPD2981	Phase 2
0.7662	Intermediate Similarity	NPD5058	Phase 3
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.7643	Intermediate Similarity	NPD1357	Approved
0.7625	Intermediate Similarity	NPD8455	Phase 2
0.7625	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD4749	Approved
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD228	Approved
0.7517	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3620	Phase 2
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7482	Intermediate Similarity	NPD7157	Approved
0.7471	Intermediate Similarity	NPD7685	Pre-registration
0.7469	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3882	Suspended
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3787	Discontinued
0.7407	Intermediate Similarity	NPD2977	Approved
0.7407	Intermediate Similarity	NPD2978	Approved
0.74	Intermediate Similarity	NPD4060	Phase 1
0.74	Intermediate Similarity	NPD1558	Phase 1
0.7391	Intermediate Similarity	NPD7843	Approved
0.7389	Intermediate Similarity	NPD1511	Approved
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1652	Phase 2
0.7353	Intermediate Similarity	NPD2684	Approved
0.7338	Intermediate Similarity	NPD1375	Discontinued
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4678	Approved
0.7329	Intermediate Similarity	NPD4380	Phase 2
0.7329	Intermediate Similarity	NPD4675	Approved
0.732	Intermediate Similarity	NPD5960	Phase 3
0.732	Intermediate Similarity	NPD5588	Approved
0.732	Intermediate Similarity	NPD4108	Discontinued
0.7314	Intermediate Similarity	NPD6841	Approved
0.7314	Intermediate Similarity	NPD6842	Approved
0.7314	Intermediate Similarity	NPD6843	Phase 3
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7299	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3021	Approved
0.7299	Intermediate Similarity	NPD3022	Approved
0.7296	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7268	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4005	Discontinued
0.7267	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7226	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5126	Approved
0.7222	Intermediate Similarity	NPD5125	Phase 3
0.7211	Intermediate Similarity	NPD8651	Approved
0.72	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7188	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.717	Intermediate Similarity	NPD7212	Phase 2
0.717	Intermediate Similarity	NPD7213	Phase 3
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7134	Intermediate Similarity	NPD3384	Approved
0.7134	Intermediate Similarity	NPD3382	Approved
0.7134	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7134	Intermediate Similarity	NPD3383	Approved
0.7126	Intermediate Similarity	NPD7549	Discontinued
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7447	Phase 1
0.7124	Intermediate Similarity	NPD5735	Approved
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7115	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.7115	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6584	Phase 3
0.7113	Intermediate Similarity	NPD6671	Approved
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7103	Intermediate Similarity	NPD5846	Approved
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7091	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6331	Phase 2
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.707	Intermediate Similarity	NPD1549	Phase 2
0.7059	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6099	Approved
0.7051	Intermediate Similarity	NPD6100	Approved
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5402	Approved
0.7045	Intermediate Similarity	NPD8053	Approved
0.7045	Intermediate Similarity	NPD8054	Approved
0.7044	Intermediate Similarity	NPD2677	Approved
0.7041	Intermediate Similarity	NPD6959	Discontinued
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7029	Intermediate Similarity	NPD290	Approved
0.7025	Intermediate Similarity	NPD4237	Approved
0.7025	Intermediate Similarity	NPD4236	Phase 3
0.7025	Intermediate Similarity	NPD4162	Approved
0.7019	Intermediate Similarity	NPD4123	Phase 3
0.7019	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD230	Phase 1
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD7124	Phase 2
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6989	Remote Similarity	NPD8313	Approved
0.6989	Remote Similarity	NPD8312	Approved
0.6987	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3892	Phase 2
0.6981	Remote Similarity	NPD4535	Phase 3
0.6981	Remote Similarity	NPD3750	Approved
0.6975	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6653	Approved
0.6957	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD968	Approved
0.6948	Remote Similarity	NPD2238	Phase 2
0.6948	Remote Similarity	NPD4140	Approved
0.6941	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD5403	Approved
0.6928	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7906	Approved
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD27	Approved
0.6919	Remote Similarity	NPD2489	Approved
0.6913	Remote Similarity	NPD6583	Phase 3
0.6913	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6582	Phase 2
0.6913	Remote Similarity	NPD3685	Discontinued
0.6912	Remote Similarity	NPD291	Approved
0.6908	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7879	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