NPASS Compound

Structure

NPC475760 OpenBabel07101719152D 26 26 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 0.0000 -3.0000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 5 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 7 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 6 0 0 0 15 26 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.16
Volume:	368.467
LogP:	2.516
LogD:	1.423
LogS:	-3.12
# Rotatable Bonds:	12
TPSA:	105.2
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	4.249
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	8.817101479507983e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.728
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.563
Plasma Protein Binding (PPB):	26.04559898376465%
Volume Distribution (VD):	1.159
Pgp-substrate:	44.58915328979492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.584
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.967
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.427
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	2.261
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.332
Carcinogencity:	0.061
Eye Corrosion:	0.053
Eye Irritation:	0.084
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC475760

Natural Product ID:	NPC475760
*Common Name:**	Boronolide
IUPAC Name:	[(1R,2R,3S)-1,2-diacetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]heptan-3-yl] acetate
Synonyms:	Boronolide
Standard InCHIKey:	BRBSZFBUFZWHCT-BURFUSLBSA-N
Standard InCHI:	InChI=1S/C18H26O8/c1-5-6-8-14(23-11(2)19)17(24-12(3)20)18(25-13(4)21)15-9-7-10-16(22)26-15/h7,10,14-15,17-18H,5-6,8-9H2,1-4H3/t14-,15+,17+,18+/m0/s1
SMILES:	CCCCC(C(C(C1CC=CC(=O)O1)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514754
PubChem CID:	10474298
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496706]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO28865	Hyptis pectinata	Species	Lamiaceae	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
ED50	11

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	4.5	ug ml-1	PMID[508808]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[508808]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[508808]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.0	ug ml-1	PMID[508808]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	6.5	ug ml-1	PMID[508808]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.2	ug ml-1	PMID[508808]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	8.7	ug ml-1	PMID[508808]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.8	ug ml-1	PMID[508808]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.9	ug ml-1	PMID[508808]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.0	ug ml-1	PMID[508808]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.6	ug ml-1	PMID[508808]

☑ 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 NPC475760 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	191
0.1-0.2	2157
0.2-0.3	7693
0.3-0.4	18527
0.4-0.5	8923
0.5-0.6	3884
0.6-0.7	1158
0.7-0.8	133
0.8-0.85	12
0.85-0.9	15
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC475762
0.9365	High Similarity	NPC25747
0.9365	High Similarity	NPC148233
0.9077	High Similarity	NPC124586
0.8889	High Similarity	NPC26223
0.8873	High Similarity	NPC474026
0.8769	High Similarity	NPC308457
0.873	High Similarity	NPC22897
0.873	High Similarity	NPC159650
0.863	High Similarity	NPC473947
0.863	High Similarity	NPC180725
0.8514	High Similarity	NPC470147
0.8514	High Similarity	NPC133226
0.8493	Intermediate Similarity	NPC248775
0.8378	Intermediate Similarity	NPC470148
0.8378	Intermediate Similarity	NPC470149
0.8333	Intermediate Similarity	NPC285840
0.8333	Intermediate Similarity	NPC327041
0.831	Intermediate Similarity	NPC327383
0.831	Intermediate Similarity	NPC185186
0.8108	Intermediate Similarity	NPC475711
0.8088	Intermediate Similarity	NPC96414
0.7971	Intermediate Similarity	NPC201356
0.7895	Intermediate Similarity	NPC1180
0.7879	Intermediate Similarity	NPC474267
0.7826	Intermediate Similarity	NPC19769
0.7808	Intermediate Similarity	NPC329914
0.7808	Intermediate Similarity	NPC329890
0.7714	Intermediate Similarity	NPC248125
0.7714	Intermediate Similarity	NPC284447
0.7714	Intermediate Similarity	NPC276299
0.7692	Intermediate Similarity	NPC469469
0.7681	Intermediate Similarity	NPC477456
0.7681	Intermediate Similarity	NPC477457
0.7662	Intermediate Similarity	NPC139712
0.7654	Intermediate Similarity	NPC208473
0.7647	Intermediate Similarity	NPC26810
0.7639	Intermediate Similarity	NPC151481
0.7632	Intermediate Similarity	NPC233071
0.7534	Intermediate Similarity	NPC476037
0.7534	Intermediate Similarity	NPC469660
0.7534	Intermediate Similarity	NPC476012
0.75	Intermediate Similarity	NPC188860
0.75	Intermediate Similarity	NPC177668
0.75	Intermediate Similarity	NPC218477
0.75	Intermediate Similarity	NPC44261
0.7465	Intermediate Similarity	NPC146811
0.7407	Intermediate Similarity	NPC473308
0.7381	Intermediate Similarity	NPC133450
0.7375	Intermediate Similarity	NPC475690
0.7375	Intermediate Similarity	NPC251026
0.7333	Intermediate Similarity	NPC474705
0.7333	Intermediate Similarity	NPC284006
0.7324	Intermediate Similarity	NPC182794
0.7308	Intermediate Similarity	NPC182292
0.7302	Intermediate Similarity	NPC275316
0.7294	Intermediate Similarity	NPC3952
0.7286	Intermediate Similarity	NPC54925
0.7286	Intermediate Similarity	NPC44343
0.7286	Intermediate Similarity	NPC179087
0.7286	Intermediate Similarity	NPC210303
0.7284	Intermediate Similarity	NPC315559
0.7284	Intermediate Similarity	NPC142111
0.7284	Intermediate Similarity	NPC473315
0.7273	Intermediate Similarity	NPC301525
0.7273	Intermediate Similarity	NPC49392
0.7273	Intermediate Similarity	NPC190400
0.726	Intermediate Similarity	NPC63873
0.725	Intermediate Similarity	NPC184208
0.725	Intermediate Similarity	NPC315731
0.725	Intermediate Similarity	NPC8538
0.7246	Intermediate Similarity	NPC299730
0.7241	Intermediate Similarity	NPC256368
0.7237	Intermediate Similarity	NPC474280
0.7237	Intermediate Similarity	NPC107654
0.7237	Intermediate Similarity	NPC477204
0.7215	Intermediate Similarity	NPC473980
0.7215	Intermediate Similarity	NPC473981
0.72	Intermediate Similarity	NPC293114
0.72	Intermediate Similarity	NPC84038
0.7195	Intermediate Similarity	NPC41856
0.7195	Intermediate Similarity	NPC474251
0.7183	Intermediate Similarity	NPC470808
0.7179	Intermediate Similarity	NPC97516
0.7179	Intermediate Similarity	NPC474278
0.7164	Intermediate Similarity	NPC86948
0.7162	Intermediate Similarity	NPC475982
0.7162	Intermediate Similarity	NPC475004
0.716	Intermediate Similarity	NPC474252
0.716	Intermediate Similarity	NPC313677
0.7143	Intermediate Similarity	NPC271282
0.7143	Intermediate Similarity	NPC476600
0.7143	Intermediate Similarity	NPC325929
0.7143	Intermediate Similarity	NPC66460
0.7143	Intermediate Similarity	NPC207815
0.7143	Intermediate Similarity	NPC260396
0.7143	Intermediate Similarity	NPC178215
0.7143	Intermediate Similarity	NPC477421
0.7123	Intermediate Similarity	NPC472266
0.7123	Intermediate Similarity	NPC122627
0.7123	Intermediate Similarity	NPC203335
0.7108	Intermediate Similarity	NPC470124
0.7108	Intermediate Similarity	NPC182383
0.7108	Intermediate Similarity	NPC477014
0.7108	Intermediate Similarity	NPC477013
0.7105	Intermediate Similarity	NPC16349
0.7105	Intermediate Similarity	NPC470435
0.7105	Intermediate Similarity	NPC222244
0.7101	Intermediate Similarity	NPC302564
0.7093	Intermediate Similarity	NPC473311
0.7089	Intermediate Similarity	NPC477314
0.7089	Intermediate Similarity	NPC475699
0.7083	Intermediate Similarity	NPC273600
0.7073	Intermediate Similarity	NPC170286
0.7067	Intermediate Similarity	NPC202011
0.7059	Intermediate Similarity	NPC233551
0.7059	Intermediate Similarity	NPC471279
0.7059	Intermediate Similarity	NPC280621
0.7059	Intermediate Similarity	NPC40376
0.7059	Intermediate Similarity	NPC20339
0.7059	Intermediate Similarity	NPC48338
0.7059	Intermediate Similarity	NPC21208
0.7059	Intermediate Similarity	NPC471277
0.7051	Intermediate Similarity	NPC469880
0.7051	Intermediate Similarity	NPC477202
0.7051	Intermediate Similarity	NPC326661
0.7042	Intermediate Similarity	NPC474774
0.7042	Intermediate Similarity	NPC217940
0.7042	Intermediate Similarity	NPC29697
0.7037	Intermediate Similarity	NPC473339
0.7037	Intermediate Similarity	NPC471552
0.7037	Intermediate Similarity	NPC297440
0.7027	Intermediate Similarity	NPC474823
0.7027	Intermediate Similarity	NPC238223
0.7024	Intermediate Similarity	NPC134865
0.7024	Intermediate Similarity	NPC477428
0.7024	Intermediate Similarity	NPC469483
0.7024	Intermediate Similarity	NPC47937
0.7024	Intermediate Similarity	NPC69082
0.7024	Intermediate Similarity	NPC311163
0.7024	Intermediate Similarity	NPC477015
0.7024	Intermediate Similarity	NPC103523
0.7024	Intermediate Similarity	NPC204048
0.7024	Intermediate Similarity	NPC279267
0.7013	Intermediate Similarity	NPC474321
0.7013	Intermediate Similarity	NPC315843
0.7013	Intermediate Similarity	NPC476355
0.7	Intermediate Similarity	NPC55304
0.7	Intermediate Similarity	NPC475332
0.7	Intermediate Similarity	NPC226872
0.7	Intermediate Similarity	NPC158368
0.7	Intermediate Similarity	NPC226226
0.7	Intermediate Similarity	NPC471537
0.7	Intermediate Similarity	NPC79756
0.7	Intermediate Similarity	NPC229252
0.7	Intermediate Similarity	NPC143857
0.7	Intermediate Similarity	NPC270126
0.7	Intermediate Similarity	NPC252851
0.7	Intermediate Similarity	NPC154908
0.7	Intermediate Similarity	NPC475210
0.6988	Remote Similarity	NPC160517
0.6988	Remote Similarity	NPC186155
0.6988	Remote Similarity	NPC78673
0.6988	Remote Similarity	NPC163093
0.6986	Remote Similarity	NPC475675
0.6986	Remote Similarity	NPC475555
0.6974	Remote Similarity	NPC186531
0.6974	Remote Similarity	NPC316185
0.6962	Remote Similarity	NPC477203
0.6962	Remote Similarity	NPC471225
0.6962	Remote Similarity	NPC141789
0.6962	Remote Similarity	NPC171204
0.6962	Remote Similarity	NPC476028
0.6957	Remote Similarity	NPC23418
0.6951	Remote Similarity	NPC10080
0.6951	Remote Similarity	NPC11383
0.6951	Remote Similarity	NPC474959
0.6951	Remote Similarity	NPC123908
0.6951	Remote Similarity	NPC475046
0.6951	Remote Similarity	NPC310450
0.6933	Remote Similarity	NPC476591
0.6933	Remote Similarity	NPC470436
0.6933	Remote Similarity	NPC101622
0.6933	Remote Similarity	NPC88877
0.6932	Remote Similarity	NPC472195
0.6932	Remote Similarity	NPC238090
0.6932	Remote Similarity	NPC472196
0.6923	Remote Similarity	NPC469414
0.6923	Remote Similarity	NPC473948
0.6923	Remote Similarity	NPC329826
0.6914	Remote Similarity	NPC281132
0.6914	Remote Similarity	NPC474739
0.6914	Remote Similarity	NPC233332
0.6912	Remote Similarity	NPC245002
0.6905	Remote Similarity	NPC283085
0.6905	Remote Similarity	NPC471567
0.6905	Remote Similarity	NPC473478
0.6905	Remote Similarity	NPC471494
0.6905	Remote Similarity	NPC286338
0.6905	Remote Similarity	NPC322529

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 NPC475760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2698
0.2-0.3	3913
0.3-0.4	1878
0.4-0.5	387
0.5-0.6	99
0.6-0.7	16
0.7-0.8	0
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
0.7093	Intermediate Similarity	NPD7838	Discovery
0.7083	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6698	Approved
0.6897	Remote Similarity	NPD46	Approved
0.6559	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6648	Approved
0.6421	Remote Similarity	NPD5344	Discontinued
0.6395	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5209	Approved
0.631	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4225	Approved
0.6176	Remote Similarity	NPD6927	Phase 3
0.6163	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4756	Discovery
0.6136	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8039	Approved
0.6087	Remote Similarity	NPD7983	Approved
0.6081	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4268	Approved
0.6071	Remote Similarity	NPD4271	Approved
0.6053	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3197	Phase 1
0.6027	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD9119	Approved
0.6027	Remote Similarity	NPD69	Approved
0.6027	Remote Similarity	NPD6109	Phase 1
0.5978	Remote Similarity	NPD5785	Approved
0.597	Remote Similarity	NPD5343	Approved
0.5955	Remote Similarity	NPD1694	Approved
0.5942	Remote Similarity	NPD28	Approved
0.5942	Remote Similarity	NPD29	Approved
0.5941	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4819	Approved
0.593	Remote Similarity	NPD4821	Approved
0.593	Remote Similarity	NPD4820	Approved
0.593	Remote Similarity	NPD4822	Approved
0.5909	Remote Similarity	NPD7154	Phase 3
0.5897	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.589	Remote Similarity	NPD9118	Approved
0.5889	Remote Similarity	NPD4249	Approved
0.5882	Remote Similarity	NPD6686	Approved
0.5833	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4250	Approved
0.5824	Remote Similarity	NPD4251	Approved
0.5823	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5363	Approved
0.5775	Remote Similarity	NPD3172	Approved
0.5758	Remote Similarity	NPD6097	Approved
0.5758	Remote Similarity	NPD6096	Approved
0.5714	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD1695	Approved
0.5694	Remote Similarity	NPD4266	Approved
0.5694	Remote Similarity	NPD3194	Approved
0.5694	Remote Similarity	NPD3196	Approved
0.5694	Remote Similarity	NPD3195	Phase 2
0.5672	Remote Similarity	NPD3174	Discontinued
0.5619	Remote Similarity	NPD6371	Approved
0.5619	Remote Similarity	NPD2067	Discontinued
0.5618	Remote Similarity	NPD6435	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