NPASS Compound

Structure

CID26223 OpenBabel06191715352D 22 22 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 4.3301 -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 2.5981 -0.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 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 0.8660 -0.5000 0.0000 C 0 0 1 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 3.4641 1.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 6 1 1 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 8 1 1 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.14
Volume:	316.295
LogP:	2.149
LogD:	1.901
LogS:	-2.923
# Rotatable Bonds:	9
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.027
Fsp3:	0.562
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:	-4.668
MDCK Permeability:	6.922172178747132e-05
Pgp-inhibitor:	0.215
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.283
20% Bioavailability (F20%):	0.482
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	28.90802764892578%
Volume Distribution (VD):	1.183
Pgp-substrate:	50.2495002746582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.203
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.472
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	3.333
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.793
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.776
Carcinogencity:	0.134
Eye Corrosion:	0.068
Eye Irritation:	0.063
Respiratory Toxicity:	0.663

Download Data

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

Natural Product: NPC26223

Natural Product ID:	NPC26223
*Common Name:**	Pectinolide A
IUPAC Name:	[(2S,3S)-2-[(Z,3S)-3-acetyloxyhept-1-enyl]-6-oxo-2,3-dihydropyran-3-yl] acetate
Synonyms:
Standard InCHIKey:	ALTFKBHIGVQJSX-RTJHIJBXSA-N
Standard InCHI:	InChI=1S/C16H22O6/c1-4-5-6-13(20-11(2)17)7-8-15-14(21-12(3)18)9-10-16(19)22-15/h7-10,13-15H,4-6H2,1-3H3/b8-7-/t13-,14-,15-/m0/s1
SMILES:	CCCC[C@@H](/C=C[C@H]1[C@H](C=CC(=O)O1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519474
PubChem CID:	10041041
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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
NPO40549	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30601004]
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
IC50	3
MIC	5
Others	2

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	4
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[521906]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.7	ug ml-1	PMID[521906]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[521906]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.9	ug ml-1	PMID[521906]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[521906]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.7	ug ml-1	PMID[521906]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[521906]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	5700.0	nM	PMID[521907]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3200.0	nM	PMID[521907]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3200.0	nM	PMID[521907]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[521906]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[521906]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug.mL-1	PMID[521906]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[521906]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	ug.mL-1	PMID[521906]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	200.0	ug.mL-1	PMID[521906]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[521906]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	ug ml-1	PMID[521906]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.9	ug ml-1	PMID[521906]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.8	ug ml-1	PMID[521906]

☑ 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 NPC26223 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	164
0.1-0.2	3160
0.2-0.3	13267
0.3-0.4	16484
0.4-0.5	6307
0.5-0.6	2523
0.6-0.7	635
0.7-0.8	128
0.8-0.85	15
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9492	High Similarity	NPC308457
0.9492	High Similarity	NPC148233
0.9492	High Similarity	NPC25747
0.918	High Similarity	NPC124586
0.9016	High Similarity	NPC96414
0.8889	High Similarity	NPC475760
0.8871	High Similarity	NPC201356
0.8814	High Similarity	NPC159650
0.8814	High Similarity	NPC22897
0.8485	Intermediate Similarity	NPC475762
0.8413	Intermediate Similarity	NPC19769
0.8226	Intermediate Similarity	NPC26810
0.8214	Intermediate Similarity	NPC275316
0.8182	Intermediate Similarity	NPC151481
0.8	Intermediate Similarity	NPC146811
0.8	Intermediate Similarity	NPC276299
0.791	Intermediate Similarity	NPC475982
0.7903	Intermediate Similarity	NPC302564
0.7887	Intermediate Similarity	NPC474026
0.7879	Intermediate Similarity	NPC203335
0.7846	Intermediate Similarity	NPC273600
0.7826	Intermediate Similarity	NPC185186
0.7826	Intermediate Similarity	NPC327383
0.7812	Intermediate Similarity	NPC474774
0.7778	Intermediate Similarity	NPC248775
0.7778	Intermediate Similarity	NPC79756
0.7727	Intermediate Similarity	NPC475675
0.7727	Intermediate Similarity	NPC248125
0.7727	Intermediate Similarity	NPC475555
0.7714	Intermediate Similarity	NPC107654
0.7705	Intermediate Similarity	NPC86948
0.7705	Intermediate Similarity	NPC245002
0.7692	Intermediate Similarity	NPC470808
0.7671	Intermediate Similarity	NPC470149
0.7671	Intermediate Similarity	NPC470148
0.7671	Intermediate Similarity	NPC180725
0.7671	Intermediate Similarity	NPC473947
0.7656	Intermediate Similarity	NPC151648
0.7639	Intermediate Similarity	NPC475711
0.7619	Intermediate Similarity	NPC478095
0.7619	Intermediate Similarity	NPC474267
0.7612	Intermediate Similarity	NPC122627
0.7612	Intermediate Similarity	NPC478100
0.7606	Intermediate Similarity	NPC327041
0.7606	Intermediate Similarity	NPC285840
0.7576	Intermediate Similarity	NPC182794
0.7568	Intermediate Similarity	NPC470147
0.7568	Intermediate Similarity	NPC133226
0.7541	Intermediate Similarity	NPC474913
0.7538	Intermediate Similarity	NPC210303
0.7538	Intermediate Similarity	NPC44343
0.7538	Intermediate Similarity	NPC179087
0.7536	Intermediate Similarity	NPC476037
0.7536	Intermediate Similarity	NPC202011
0.7536	Intermediate Similarity	NPC476012
0.75	Intermediate Similarity	NPC63873
0.7465	Intermediate Similarity	NPC315843
0.7463	Intermediate Similarity	NPC478101
0.746	Intermediate Similarity	NPC478096
0.7429	Intermediate Similarity	NPC293114
0.7429	Intermediate Similarity	NPC316185
0.7424	Intermediate Similarity	NPC477457
0.7424	Intermediate Similarity	NPC477456
0.7385	Intermediate Similarity	NPC15193
0.7377	Intermediate Similarity	NPC151761
0.7377	Intermediate Similarity	NPC159535
0.7353	Intermediate Similarity	NPC478097
0.7353	Intermediate Similarity	NPC194871
0.7344	Intermediate Similarity	NPC97570
0.7344	Intermediate Similarity	NPC286189
0.7324	Intermediate Similarity	NPC329914
0.7324	Intermediate Similarity	NPC284006
0.7324	Intermediate Similarity	NPC329890
0.7313	Intermediate Similarity	NPC478098
0.7313	Intermediate Similarity	NPC478099
0.7313	Intermediate Similarity	NPC282760
0.7302	Intermediate Similarity	NPC471279
0.7302	Intermediate Similarity	NPC294938
0.7302	Intermediate Similarity	NPC471277
0.7302	Intermediate Similarity	NPC129150
0.7288	Intermediate Similarity	NPC236338
0.7288	Intermediate Similarity	NPC15789
0.7286	Intermediate Similarity	NPC469660
0.7273	Intermediate Similarity	NPC44261
0.7273	Intermediate Similarity	NPC315559
0.7273	Intermediate Similarity	NPC217940
0.7246	Intermediate Similarity	NPC238223
0.7246	Intermediate Similarity	NPC218477
0.7246	Intermediate Similarity	NPC470256
0.7237	Intermediate Similarity	NPC297440
0.7206	Intermediate Similarity	NPC284447
0.72	Intermediate Similarity	NPC271632
0.72	Intermediate Similarity	NPC1180
0.72	Intermediate Similarity	NPC139712
0.7188	Intermediate Similarity	NPC254095
0.7188	Intermediate Similarity	NPC474084
0.7188	Intermediate Similarity	NPC223679
0.7143	Intermediate Similarity	NPC313677
0.7143	Intermediate Similarity	NPC472808
0.7143	Intermediate Similarity	NPC476591
0.7143	Intermediate Similarity	NPC324224
0.7143	Intermediate Similarity	NPC88877
0.7143	Intermediate Similarity	NPC251026
0.7123	Intermediate Similarity	NPC260396
0.7101	Intermediate Similarity	NPC225272
0.7101	Intermediate Similarity	NPC132286
0.7097	Intermediate Similarity	NPC478120
0.7083	Intermediate Similarity	NPC474705
0.7083	Intermediate Similarity	NPC16349
0.7083	Intermediate Similarity	NPC222244
0.7077	Intermediate Similarity	NPC82465
0.7077	Intermediate Similarity	NPC222852
0.7069	Intermediate Similarity	NPC128280
0.7069	Intermediate Similarity	NPC197467
0.7067	Intermediate Similarity	NPC318481
0.7067	Intermediate Similarity	NPC279532
0.7059	Intermediate Similarity	NPC471565
0.7059	Intermediate Similarity	NPC471556
0.7059	Intermediate Similarity	NPC471566
0.7059	Intermediate Similarity	NPC470123
0.7059	Intermediate Similarity	NPC476589
0.7051	Intermediate Similarity	NPC142111
0.7051	Intermediate Similarity	NPC473315
0.7049	Intermediate Similarity	NPC106531
0.7042	Intermediate Similarity	NPC59558
0.7042	Intermediate Similarity	NPC473361
0.7042	Intermediate Similarity	NPC329904
0.7031	Intermediate Similarity	NPC212730
0.7031	Intermediate Similarity	NPC293437
0.7031	Intermediate Similarity	NPC135863
0.7031	Intermediate Similarity	NPC265551
0.7031	Intermediate Similarity	NPC249850
0.7027	Intermediate Similarity	NPC188860
0.7027	Intermediate Similarity	NPC203277
0.7015	Intermediate Similarity	NPC68110
0.7015	Intermediate Similarity	NPC473737
0.7013	Intermediate Similarity	NPC469469
0.7	Intermediate Similarity	NPC310210
0.7	Intermediate Similarity	NPC474823
0.7	Intermediate Similarity	NPC477117
0.6986	Remote Similarity	NPC476355
0.6974	Remote Similarity	NPC473981
0.6974	Remote Similarity	NPC473980
0.697	Remote Similarity	NPC309408
0.697	Remote Similarity	NPC19241
0.697	Remote Similarity	NPC321919
0.697	Remote Similarity	NPC81896
0.697	Remote Similarity	NPC299730
0.6964	Remote Similarity	NPC57923
0.6962	Remote Similarity	NPC473308
0.6962	Remote Similarity	NPC474251
0.6957	Remote Similarity	NPC37382
0.6944	Remote Similarity	NPC84038
0.6935	Remote Similarity	NPC477780
0.6935	Remote Similarity	NPC477781
0.6933	Remote Similarity	NPC233071
0.6933	Remote Similarity	NPC471225
0.6923	Remote Similarity	NPC475690
0.6923	Remote Similarity	NPC21946
0.6912	Remote Similarity	NPC114464
0.6901	Remote Similarity	NPC475004
0.6901	Remote Similarity	NPC470693
0.6897	Remote Similarity	NPC47946
0.6897	Remote Similarity	NPC26600
0.6897	Remote Similarity	NPC270706
0.6892	Remote Similarity	NPC473948
0.6875	Remote Similarity	NPC150717
0.6875	Remote Similarity	NPC327388
0.6875	Remote Similarity	NPC470124
0.6875	Remote Similarity	NPC221763
0.6866	Remote Similarity	NPC66460
0.6866	Remote Similarity	NPC55376
0.6866	Remote Similarity	NPC271282
0.6866	Remote Similarity	NPC325929
0.6857	Remote Similarity	NPC472266
0.6857	Remote Similarity	NPC25298
0.6849	Remote Similarity	NPC287878
0.6842	Remote Similarity	NPC473471
0.6842	Remote Similarity	NPC182292
0.6842	Remote Similarity	NPC477314
0.6842	Remote Similarity	NPC28049
0.6842	Remote Similarity	NPC475699
0.6835	Remote Similarity	NPC16488
0.6835	Remote Similarity	NPC161045
0.6833	Remote Similarity	NPC207815
0.6833	Remote Similarity	NPC135698
0.6825	Remote Similarity	NPC269615
0.6818	Remote Similarity	NPC329249
0.6818	Remote Similarity	NPC133600
0.6812	Remote Similarity	NPC220766
0.6812	Remote Similarity	NPC470688
0.68	Remote Similarity	NPC301207
0.68	Remote Similarity	NPC123360
0.68	Remote Similarity	NPC326661
0.68	Remote Similarity	NPC127118
0.68	Remote Similarity	NPC209113
0.679	Remote Similarity	NPC208473
0.6769	Remote Similarity	NPC323597
0.6769	Remote Similarity	NPC44542
0.6769	Remote Similarity	NPC323498

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 NPC26223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	3253
0.2-0.3	4035
0.3-0.4	1432
0.4-0.5	222
0.5-0.6	60
0.6-0.7	14
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
0.7059	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6927	Phase 3
0.6667	Remote Similarity	NPD5343	Approved
0.6667	Remote Similarity	NPD6109	Phase 1
0.6441	Remote Similarity	NPD6097	Approved
0.6441	Remote Similarity	NPD6096	Approved
0.6418	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5209	Approved
0.6279	Remote Similarity	NPD7838	Discovery
0.6232	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD69	Approved
0.6176	Remote Similarity	NPD9119	Approved
0.6164	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6698	Approved
0.6092	Remote Similarity	NPD46	Approved
0.6071	Remote Similarity	NPD9115	Approved
0.6066	Remote Similarity	NPD3174	Discontinued
0.6032	Remote Similarity	NPD4220	Pre-registration
0.6029	Remote Similarity	NPD9118	Approved
0.5978	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6648	Approved
0.5904	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4756	Discovery
0.5851	Remote Similarity	NPD5344	Discontinued
0.5823	Remote Similarity	NPD8039	Approved
0.5806	Remote Similarity	NPD4225	Approved
0.5806	Remote Similarity	NPD39	Approved
0.5806	Remote Similarity	NPD4222	Approved
0.5797	Remote Similarity	NPD8779	Phase 3
0.5781	Remote Similarity	NPD3173	Approved
0.5753	Remote Similarity	NPD3197	Phase 1
0.573	Remote Similarity	NPD5785	Approved
0.5698	Remote Similarity	NPD1694	Approved
0.5698	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1452	Discontinued
0.5606	Remote Similarity	NPD28	Approved
0.5606	Remote Similarity	NPD29	Approved
0.56	Remote Similarity	NPD6108	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