NPASS Compound

Structure

NPC165119 OpenBabel07101718282D 23 24 0 0 1 0 0 0 0 0999 V2000 2.8535 2.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8046 2.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2215 -1.1160 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 2.6456 1.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 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 1.8366 0.0055 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3147 0.6636 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0125 3.6720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6337 -1.9250 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 1.0934 -0.6637 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 -2.5981 1.5000 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 -0.0000 -0.0000 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 1 2 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 1 1 1 0 0 0 5 12 1 0 0 0 0 5 14 1 0 0 0 0 6 3 1 6 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 4 1 6 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 1 0 0 0 9 10 1 0 0 0 0 9 19 1 1 0 0 0 10 11 1 0 0 0 0 10 20 1 6 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 23 1 6 0 0 0 13 22 1 0 0 0 0 13 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.15
Volume:	306.4
LogP:	-2.708
LogD:	-2.338
LogS:	-0.122
# Rotatable Bonds:	6
TPSA:	172.1
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	4.622
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.026
MDCK Permeability:	0.00017448136350139976
Pgp-inhibitor:	0.0
Pgp-substrate:	0.529
Human Intestinal Absorption (HIA):	0.956
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	14.436901092529297%
Volume Distribution (VD):	0.296
Pgp-substrate:	76.66424560546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	1.229
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.677
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.217
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.026
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: NPC165119

Natural Product ID:	NPC165119
*Common Name:**	(2R,3S,4S,5S,6R)-2-[(2R,3R,4R,5R)-4-Hydroxy-2-(2-Hydroxyethyl)-5-(Hydroxymethyl)Pyrrolidin-3-Yl]Oxy-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2R,3S,4S,5S,6R)-2-[(2R,3R,4R,5R)-4-hydroxy-2-(2-hydroxyethyl)-5-(hydroxymethyl)pyrrolidin-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	IUJDTJSEAKUOOC-KEGYGLKMSA-N
Standard InCHI:	InChI=1S/C13H25NO9/c15-2-1-5-12(8(18)6(3-16)14-5)23-13-11(21)10(20)9(19)7(4-17)22-13/h5-21H,1-4H2/t5-,6-,7-,8-,9-,10+,11+,12-,13+/m1/s1
SMILES:	C(CO)[C@@H]1[C@H]([C@@H]([C@@H](CO)N1)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519261
PubChem CID:	10246556
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:0002207] O-glycosyl 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
NPO33353	scilla sibirica	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502331]

☑ 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
Others	4

Activity Type	# Activity
Individual Protein	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT506	Individual Protein	Beta-mannosidase	Rattus norvegicus	IC50	=	160000.0	nM	PMID[550325]
NPT496	Individual Protein	Alpha-L-fucosidase 1	Bos taurus	IC50	=	78000.0	nM	PMID[550325]
NPT1648	Individual Protein	Oligo-1,6-glucosidase	Saccharomyces cerevisiae S288c	Inhibition	<	50.0	%	PMID[550325]
NPT2	Others	Unspecified		Inhibition	<	50.0	%	PMID[550325]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	<	50.0	%	PMID[550325]

☑ 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 NPC165119 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	247
0.1-0.2	9752
0.2-0.3	20446
0.3-0.4	9827
0.4-0.5	1919
0.5-0.6	324
0.6-0.7	101
0.7-0.8	68
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC83248
0.9605	High Similarity	NPC100204
0.95	High Similarity	NPC306838
0.8875	High Similarity	NPC271772
0.8875	High Similarity	NPC36927
0.8625	High Similarity	NPC70574
0.85	High Similarity	NPC98750
0.8049	Intermediate Similarity	NPC150557
0.7975	Intermediate Similarity	NPC474468
0.7949	Intermediate Similarity	NPC473710
0.7949	Intermediate Similarity	NPC475694
0.7895	Intermediate Similarity	NPC77191
0.7895	Intermediate Similarity	NPC101746
0.7895	Intermediate Similarity	NPC116377
0.7895	Intermediate Similarity	NPC69798
0.7895	Intermediate Similarity	NPC473952
0.7857	Intermediate Similarity	NPC471420
0.7848	Intermediate Similarity	NPC137554
0.7848	Intermediate Similarity	NPC255535
0.7848	Intermediate Similarity	NPC299603
0.7848	Intermediate Similarity	NPC285014
0.7848	Intermediate Similarity	NPC28959
0.7792	Intermediate Similarity	NPC291650
0.7792	Intermediate Similarity	NPC129100
0.7792	Intermediate Similarity	NPC322801
0.7738	Intermediate Similarity	NPC318258
0.7532	Intermediate Similarity	NPC474928
0.7528	Intermediate Similarity	NPC313552
0.75	Intermediate Similarity	NPC315036
0.7468	Intermediate Similarity	NPC471418
0.7444	Intermediate Similarity	NPC214376
0.7444	Intermediate Similarity	NPC470282
0.7375	Intermediate Similarity	NPC268922
0.7368	Intermediate Similarity	NPC8087
0.7368	Intermediate Similarity	NPC62507
0.7356	Intermediate Similarity	NPC315969
0.732	Intermediate Similarity	NPC56298
0.732	Intermediate Similarity	NPC471628
0.7308	Intermediate Similarity	NPC198341
0.7308	Intermediate Similarity	NPC471780
0.7308	Intermediate Similarity	NPC471892
0.7308	Intermediate Similarity	NPC223386
0.7308	Intermediate Similarity	NPC75435
0.7308	Intermediate Similarity	NPC142290
0.7283	Intermediate Similarity	NPC176381
0.7283	Intermediate Similarity	NPC195969
0.7273	Intermediate Similarity	NPC263058
0.725	Intermediate Similarity	NPC171850
0.7215	Intermediate Similarity	NPC286851
0.7215	Intermediate Similarity	NPC315980
0.7215	Intermediate Similarity	NPC303798
0.7209	Intermediate Similarity	NPC316807
0.7195	Intermediate Similarity	NPC476696
0.7195	Intermediate Similarity	NPC476694
0.7195	Intermediate Similarity	NPC476695
0.7143	Intermediate Similarity	NPC30126
0.7143	Intermediate Similarity	NPC474014
0.7143	Intermediate Similarity	NPC57846
0.7111	Intermediate Similarity	NPC253975
0.7111	Intermediate Similarity	NPC192025
0.7111	Intermediate Similarity	NPC125253
0.7073	Intermediate Similarity	NPC223174
0.7073	Intermediate Similarity	NPC327753
0.7073	Intermediate Similarity	NPC327486
0.7065	Intermediate Similarity	NPC43850
0.7065	Intermediate Similarity	NPC314007
0.7065	Intermediate Similarity	NPC314408
0.7065	Intermediate Similarity	NPC477060
0.7065	Intermediate Similarity	NPC123746
0.7053	Intermediate Similarity	NPC315334
0.7051	Intermediate Similarity	NPC218150
0.7051	Intermediate Similarity	NPC150680
0.7051	Intermediate Similarity	NPC2432
0.7051	Intermediate Similarity	NPC306462
0.7051	Intermediate Similarity	NPC69669
0.7051	Intermediate Similarity	NPC22774
0.7037	Intermediate Similarity	NPC34291
0.7037	Intermediate Similarity	NPC126664
0.7033	Intermediate Similarity	NPC83839
0.6867	Remote Similarity	NPC115800
0.6867	Remote Similarity	NPC163538
0.6857	Remote Similarity	NPC57436
0.6857	Remote Similarity	NPC121479
0.6842	Remote Similarity	NPC65832
0.6842	Remote Similarity	NPC10262
0.6842	Remote Similarity	NPC311668
0.6809	Remote Similarity	NPC470284
0.6765	Remote Similarity	NPC221148
0.675	Remote Similarity	NPC163134
0.675	Remote Similarity	NPC471419
0.6739	Remote Similarity	NPC476523
0.6735	Remote Similarity	NPC330590
0.6707	Remote Similarity	NPC141156
0.6707	Remote Similarity	NPC184150
0.6705	Remote Similarity	NPC314772
0.6705	Remote Similarity	NPC314968
0.6667	Remote Similarity	NPC193593
0.6667	Remote Similarity	NPC143809
0.6667	Remote Similarity	NPC233034
0.6667	Remote Similarity	NPC290106
0.6667	Remote Similarity	NPC76726
0.6627	Remote Similarity	NPC306763
0.6627	Remote Similarity	NPC474469
0.6627	Remote Similarity	NPC266242
0.6627	Remote Similarity	NPC74555
0.6627	Remote Similarity	NPC254617
0.6625	Remote Similarity	NPC17455
0.6598	Remote Similarity	NPC208537
0.6598	Remote Similarity	NPC270005
0.6585	Remote Similarity	NPC12514
0.6585	Remote Similarity	NPC294883
0.6574	Remote Similarity	NPC314306
0.6548	Remote Similarity	NPC475127
0.6548	Remote Similarity	NPC473419
0.6548	Remote Similarity	NPC475715
0.6535	Remote Similarity	NPC315170
0.6506	Remote Similarity	NPC59221
0.6489	Remote Similarity	NPC469363
0.6465	Remote Similarity	NPC470283
0.6447	Remote Similarity	NPC130683
0.6447	Remote Similarity	NPC272396
0.6447	Remote Similarity	NPC323361
0.6429	Remote Similarity	NPC328646
0.6415	Remote Similarity	NPC317534
0.6396	Remote Similarity	NPC313813
0.6329	Remote Similarity	NPC204709
0.6263	Remote Similarity	NPC61894
0.6263	Remote Similarity	NPC475603
0.625	Remote Similarity	NPC170172
0.625	Remote Similarity	NPC471421
0.625	Remote Similarity	NPC233364
0.6216	Remote Similarity	NPC241597
0.6207	Remote Similarity	NPC94319
0.6207	Remote Similarity	NPC20035
0.6184	Remote Similarity	NPC326533
0.6176	Remote Similarity	NPC313821
0.6154	Remote Similarity	NPC275727
0.6132	Remote Similarity	NPC314413
0.6132	Remote Similarity	NPC314398
0.6132	Remote Similarity	NPC239705
0.6125	Remote Similarity	NPC219040
0.6122	Remote Similarity	NPC292345
0.6098	Remote Similarity	NPC472026
0.6095	Remote Similarity	NPC188453
0.6095	Remote Similarity	NPC42320
0.6075	Remote Similarity	NPC62845
0.6075	Remote Similarity	NPC189854
0.6075	Remote Similarity	NPC166242
0.6075	Remote Similarity	NPC322449
0.6075	Remote Similarity	NPC92874
0.6053	Remote Similarity	NPC323574
0.6049	Remote Similarity	NPC34877
0.6049	Remote Similarity	NPC290179
0.6026	Remote Similarity	NPC145112
0.6026	Remote Similarity	NPC107914
0.6026	Remote Similarity	NPC242073
0.6026	Remote Similarity	NPC58629
0.6026	Remote Similarity	NPC269166
0.6026	Remote Similarity	NPC157514
0.6026	Remote Similarity	NPC246558
0.6026	Remote Similarity	NPC165198
0.6026	Remote Similarity	NPC67660
0.6026	Remote Similarity	NPC89145
0.6019	Remote Similarity	NPC10897
0.6019	Remote Similarity	NPC325900
0.6019	Remote Similarity	NPC160066
0.6016	Remote Similarity	NPC262050
0.6	Remote Similarity	NPC293551
0.6	Remote Similarity	NPC148424
0.6	Remote Similarity	NPC8979
0.5976	Remote Similarity	NPC143326
0.5974	Remote Similarity	NPC233726
0.5974	Remote Similarity	NPC124963
0.5974	Remote Similarity	NPC23134
0.5949	Remote Similarity	NPC303727
0.5926	Remote Similarity	NPC472025
0.5904	Remote Similarity	NPC477763
0.5904	Remote Similarity	NPC477757
0.5904	Remote Similarity	NPC477755
0.5904	Remote Similarity	NPC477753
0.5904	Remote Similarity	NPC477762
0.5904	Remote Similarity	NPC477750
0.5888	Remote Similarity	NPC227622
0.5872	Remote Similarity	NPC475918
0.5842	Remote Similarity	NPC43074
0.5842	Remote Similarity	NPC242503
0.5842	Remote Similarity	NPC139782
0.5842	Remote Similarity	NPC209047
0.5842	Remote Similarity	NPC74672
0.5823	Remote Similarity	NPC178263
0.5823	Remote Similarity	NPC277072
0.5818	Remote Similarity	NPC59589
0.5798	Remote Similarity	NPC471262
0.5789	Remote Similarity	NPC219340
0.5784	Remote Similarity	NPC263545
0.5784	Remote Similarity	NPC473950
0.5784	Remote Similarity	NPC475125
0.5784	Remote Similarity	NPC111567
0.5784	Remote Similarity	NPC473604
0.5784	Remote Similarity	NPC473581

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 NPC165119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	85
0.1-0.2	2863
0.2-0.3	4447
0.3-0.4	1350
0.4-0.5	227
0.5-0.6	94
0.6-0.7	65
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7792	Intermediate Similarity	NPD9032	Approved
0.7792	Intermediate Similarity	NPD9030	Approved
0.7792	Intermediate Similarity	NPD9033	Approved
0.7792	Intermediate Similarity	NPD9031	Approved
0.7444	Intermediate Similarity	NPD2698	Approved
0.7439	Intermediate Similarity	NPD67	Phase 2
0.7439	Intermediate Similarity	NPD9034	Approved
0.732	Intermediate Similarity	NPD4836	Approved
0.732	Intermediate Similarity	NPD4838	Approved
0.732	Intermediate Similarity	NPD4837	Approved
0.732	Intermediate Similarity	NPD4835	Approved
0.7283	Intermediate Similarity	NPD5798	Approved
0.7283	Intermediate Similarity	NPD5797	Approved
0.7283	Intermediate Similarity	NPD5795	Approved
0.7283	Intermediate Similarity	NPD5796	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5794	Approved
0.7273	Intermediate Similarity	NPD882	Phase 2
0.7273	Intermediate Similarity	NPD883	Phase 2
0.7143	Intermediate Similarity	NPD3200	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4282	Approved
0.71	Intermediate Similarity	NPD8045	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9445	Approved
0.7065	Intermediate Similarity	NPD3208	Approved
0.7065	Intermediate Similarity	NPD3209	Approved
0.7065	Intermediate Similarity	NPD3202	Approved
0.7065	Intermediate Similarity	NPD3201	Approved
0.7065	Intermediate Similarity	NPD3207	Approved
0.7065	Intermediate Similarity	NPD3203	Approved
0.7051	Intermediate Similarity	NPD9029	Phase 3
0.7051	Intermediate Similarity	NPD9027	Phase 3
0.7051	Intermediate Similarity	NPD9028	Phase 2
0.7051	Intermediate Similarity	NPD9026	Phase 2
0.7037	Intermediate Similarity	NPD9443	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2700	Approved
0.6977	Remote Similarity	NPD372	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1457	Discontinued
0.6857	Remote Similarity	NPD4833	Approved
0.6857	Remote Similarity	NPD35	Approved
0.6829	Remote Similarity	NPD9444	Discontinued
0.6796	Remote Similarity	NPD5376	Approved
0.6765	Remote Similarity	NPD1449	Approved
0.6765	Remote Similarity	NPD1450	Approved
0.6735	Remote Similarity	NPD5381	Approved
0.6735	Remote Similarity	NPD5378	Approved
0.6735	Remote Similarity	NPD5377	Approved
0.6705	Remote Similarity	NPD9435	Approved
0.6705	Remote Similarity	NPD9434	Approved
0.6667	Remote Similarity	NPD9440	Discontinued
0.6667	Remote Similarity	NPD6428	Approved
0.6636	Remote Similarity	NPD2690	Discontinued
0.6606	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD9240	Approved
0.6582	Remote Similarity	NPD9239	Approved
0.6582	Remote Similarity	NPD9455	Approved
0.6574	Remote Similarity	NPD6429	Approved
0.6574	Remote Similarity	NPD6430	Approved
0.6542	Remote Similarity	NPD8087	Discontinued
0.65	Remote Similarity	NPD393	Approved
0.646	Remote Similarity	NPD8345	Approved
0.646	Remote Similarity	NPD8347	Approved
0.646	Remote Similarity	NPD8346	Approved
0.6447	Remote Similarity	NPD895	Approved
0.6447	Remote Similarity	NPD894	Approved
0.6447	Remote Similarity	NPD889	Approved
0.6447	Remote Similarity	NPD887	Approved
0.6436	Remote Similarity	NPD881	Approved
0.6392	Remote Similarity	NPD3716	Discontinued
0.6316	Remote Similarity	NPD394	Phase 3
0.6296	Remote Similarity	NPD6941	Approved
0.625	Remote Similarity	NPD4830	Approved
0.625	Remote Similarity	NPD4832	Approved
0.625	Remote Similarity	NPD4831	Approved
0.6216	Remote Similarity	NPD3731	Phase 3
0.6211	Remote Similarity	NPD9401	Discovery
0.6207	Remote Similarity	NPD4826	Approved
0.6207	Remote Similarity	NPD4828	Approved
0.6207	Remote Similarity	NPD4827	Approved
0.62	Remote Similarity	NPD1446	Phase 3
0.62	Remote Similarity	NPD1447	Phase 3
0.6186	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD904	Phase 3
0.6184	Remote Similarity	NPD905	Approved
0.6176	Remote Similarity	NPD3191	Approved
0.6176	Remote Similarity	NPD3190	Approved
0.6176	Remote Similarity	NPD3189	Approved
0.6136	Remote Similarity	NPD6704	Discontinued
0.6122	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8307	Discontinued
0.6111	Remote Similarity	NPD8140	Approved
0.6068	Remote Similarity	NPD6436	Phase 3
0.6042	Remote Similarity	NPD361	Discontinued
0.6026	Remote Similarity	NPD892	Phase 3
0.6026	Remote Similarity	NPD891	Phase 3
0.6026	Remote Similarity	NPD888	Phase 3
0.6026	Remote Similarity	NPD893	Approved
0.6026	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2267	Suspended
0.5981	Remote Similarity	NPD8275	Approved
0.5981	Remote Similarity	NPD8276	Approved
0.593	Remote Similarity	NPD374	Approved
0.593	Remote Similarity	NPD373	Approved
0.5905	Remote Similarity	NPD2255	Approved
0.5904	Remote Similarity	NPD9022	Phase 2
0.5904	Remote Similarity	NPD9024	Phase 2
0.5897	Remote Similarity	NPD2269	Approved
0.5889	Remote Similarity	NPD389	Phase 3
0.5888	Remote Similarity	NPD8086	Approved
0.5888	Remote Similarity	NPD8082	Approved
0.5888	Remote Similarity	NPD8139	Approved
0.5888	Remote Similarity	NPD8084	Approved
0.5888	Remote Similarity	NPD8085	Approved
0.5888	Remote Similarity	NPD8083	Approved
0.5888	Remote Similarity	NPD8138	Approved
0.5872	Remote Similarity	NPD8393	Approved
0.5842	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.578	Remote Similarity	NPD8081	Approved
0.5765	Remote Similarity	NPD847	Phase 1
0.5747	Remote Similarity	NPD8868	Approved
0.5741	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7139	Approved
0.5741	Remote Similarity	NPD7140	Approved
0.5714	Remote Similarity	NPD9653	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD9429	Discontinued
0.5625	Remote Similarity	NPD8174	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data