NPASS Compound

Structure

CID126518 OpenBabel06191715482D 30 32 0 0 1 0 0 0 0 0999 V2000 6.2788 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3769 6.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8769 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 6.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8769 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 17 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 19 1 6 0 0 0 21 29 1 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.26
Volume:	446.056
LogP:	5.444
LogD:	3.956
LogS:	-3.868
# Rotatable Bonds:	7
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	4.56
Fsp3:	0.6
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:	-5.103
MDCK Permeability:	1.5733039617771283e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	94.82269287109375%
Volume Distribution (VD):	2.627
Pgp-substrate:	2.409729480743408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.392
CYP2C9-inhibitor:	0.376
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.385
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	3.518
Half-life (T1/2):	0.221

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.767
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.272
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC126518

Natural Product ID:	NPC126518
*Common Name:**	Manoalide
IUPAC Name:	(2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
Synonyms:	Manoalide
Standard InCHIKey:	FGJIDQWRRLDGDB-CPIXEKRISA-N
Standard InCHI:	InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1
SMILES:	C/C(=CCCC1=CC[C@@H](O[C@H]1O)C1=CC(=O)O[C@H]1O)/CCC1=C(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463914
PubChem CID:	6437368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO5099	Luffariella variabilis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)77766-5]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514323]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402955]
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1624940]
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[8482949]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594155]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677277]
NPO33053	laffaariella variabilis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]
NPO12514	Fasciospongia cavernosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5099	Luffariella variabilis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	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	1
IC50	26
Others	19

Activity Type	# Activity
Cell Line	2
Individual Protein	38
Organism	1
Others	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4421	Individual Protein	Group IID secretory phospholipase A2	Homo sapiens	IC50	=	0.34	ug.mL-1	PMID[482545]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	17.0	%	PMID[482546]
NPT2945	Individual Protein	Phospholipase A2 group 1B	Sus scrofa	Inhibition	=	32.3	%	PMID[482546]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	Inhibition	=	93.2	%	PMID[482546]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	3900.0	nM	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	62.5	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	7500.0	nM	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	42.4	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	21.0	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	49.5	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	44.2	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	28.0	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	63.3	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	47.3	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	43.1	%	PMID[482546]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	91.1	%	PMID[482546]
NPT4062	Individual Protein	Phospholipase A2 group IIA	Rattus norvegicus	IC50	=	2000000.0	nM	PMID[482547]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	1500000.0	nM	PMID[482547]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Inhibition	=	17.0	%	PMID[482548]
NPT2945	Individual Protein	Phospholipase A2 group 1B	Sus scrofa	Inhibition	=	32.3	%	PMID[482548]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	Inhibition	=	93.2	%	PMID[482548]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	3900.0	nM	PMID[482548]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Inhibition	=	62.5	%	PMID[482548]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	7500.0	nM	PMID[482548]
NPT4423	Individual Protein	Cytosolic phospholipase A2	Mus musculus	Inhibition	=	44.6	%	PMID[482548]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	7500.0	nM	PMID[482550]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	IC50	=	3900.0	nM	PMID[482550]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	IC50	=	17000.0	nM	PMID[482551]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	93200.0	nM	PMID[482551]
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	3900.0	nM	PMID[482551]
NPT4062	Individual Protein	Phospholipase A2 group IIA	Rattus norvegicus	IC50	=	38400.0	nM	PMID[482551]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	62500.0	nM	PMID[482551]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	7500.0	nM	PMID[482551]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.032	ug.mL-1	PMID[482553]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.31	ug.mL-1	PMID[482553]
NPT4425	Individual Protein	Phospholipase A2 alpha	Crotalus adamanteus	IC50	=	400.0	nM	PMID[482556]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	500.0	nM	PMID[482557]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	500.0	nM	PMID[482558]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	=	5600.0	nM	PMID[482560]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	=	3400.0	nM	PMID[482560]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[482549]
NPT2	Others	Unspecified		IC50	=	32300.0	nM	PMID[482551]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	100.0	ug	PMID[482552]
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	IC50	=	40.0	nM	PMID[482555]
NPT2	Others	Unspecified		IC50	=	15000.0	nM	PMID[482559]
NPT2	Others	Unspecified		IC50	=	70000.0	nM	PMID[482559]

☑ 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 NPC126518 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	172
0.1-0.2	1248
0.2-0.3	5665
0.3-0.4	15943
0.4-0.5	9486
0.5-0.6	7291
0.6-0.7	2599
0.7-0.8	253
0.8-0.85	23
0.85-0.9	8
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC163606
0.9744	High Similarity	NPC323251
0.925	High Similarity	NPC471298
0.9231	High Similarity	NPC209135
0.9231	High Similarity	NPC474816
0.9136	High Similarity	NPC471297
0.9103	High Similarity	NPC473756
0.9103	High Similarity	NPC262747
0.9048	High Similarity	NPC474629
0.9012	High Similarity	NPC324170
0.8966	High Similarity	NPC104925
0.8966	High Similarity	NPC298973
0.8889	High Similarity	NPC475944
0.8795	High Similarity	NPC471301
0.875	High Similarity	NPC469697
0.8721	High Similarity	NPC470734
0.869	High Similarity	NPC471300
0.869	High Similarity	NPC474860
0.8675	High Similarity	NPC474809
0.8605	High Similarity	NPC472809
0.8605	High Similarity	NPC472810
0.859	High Similarity	NPC16349
0.859	High Similarity	NPC222244
0.8571	High Similarity	NPC31086
0.8571	High Similarity	NPC471302
0.8571	High Similarity	NPC474865
0.8556	High Similarity	NPC162346
0.8452	Intermediate Similarity	NPC42476
0.8427	Intermediate Similarity	NPC472812
0.8391	Intermediate Similarity	NPC472378
0.8354	Intermediate Similarity	NPC476490
0.8354	Intermediate Similarity	NPC476489
0.8333	Intermediate Similarity	NPC471296
0.8315	Intermediate Similarity	NPC472811
0.8256	Intermediate Similarity	NPC473251
0.8256	Intermediate Similarity	NPC42586
0.8161	Intermediate Similarity	NPC211892
0.814	Intermediate Similarity	NPC470800
0.8132	Intermediate Similarity	NPC470255
0.8111	Intermediate Similarity	NPC477122
0.8065	Intermediate Similarity	NPC477718
0.8065	Intermediate Similarity	NPC477719
0.8046	Intermediate Similarity	NPC329630
0.8023	Intermediate Similarity	NPC472377
0.8023	Intermediate Similarity	NPC311070
0.8	Intermediate Similarity	NPC78973
0.8	Intermediate Similarity	NPC232426
0.8	Intermediate Similarity	NPC281942
0.7976	Intermediate Similarity	NPC471299
0.7917	Intermediate Similarity	NPC201191
0.7912	Intermediate Similarity	NPC141831
0.7895	Intermediate Similarity	NPC477721
0.7895	Intermediate Similarity	NPC477716
0.7872	Intermediate Similarity	NPC475709
0.7849	Intermediate Similarity	NPC472441
0.7841	Intermediate Similarity	NPC472442
0.7826	Intermediate Similarity	NPC242069
0.7816	Intermediate Similarity	NPC472440
0.7812	Intermediate Similarity	NPC477717
0.7802	Intermediate Similarity	NPC469403
0.7802	Intermediate Similarity	NPC477782
0.7789	Intermediate Similarity	NPC474440
0.7766	Intermediate Similarity	NPC165632
0.7753	Intermediate Similarity	NPC131813
0.7742	Intermediate Similarity	NPC474554
0.7742	Intermediate Similarity	NPC324078
0.7717	Intermediate Similarity	NPC477783
0.7717	Intermediate Similarity	NPC329842
0.7708	Intermediate Similarity	NPC324841
0.7701	Intermediate Similarity	NPC471218
0.7692	Intermediate Similarity	NPC282760
0.7684	Intermediate Similarity	NPC98112
0.7667	Intermediate Similarity	NPC312561
0.7654	Intermediate Similarity	NPC4299
0.764	Intermediate Similarity	NPC217394
0.7634	Intermediate Similarity	NPC469939
0.7634	Intermediate Similarity	NPC53555
0.7619	Intermediate Similarity	NPC477202
0.7614	Intermediate Similarity	NPC474193
0.7614	Intermediate Similarity	NPC12283
0.7609	Intermediate Similarity	NPC202886
0.7604	Intermediate Similarity	NPC473154
0.7579	Intermediate Similarity	NPC240673
0.7579	Intermediate Similarity	NPC17578
0.7561	Intermediate Similarity	NPC257618
0.7558	Intermediate Similarity	NPC139712
0.7558	Intermediate Similarity	NPC242767
0.7553	Intermediate Similarity	NPC474555
0.7553	Intermediate Similarity	NPC475572
0.7551	Intermediate Similarity	NPC472815
0.7531	Intermediate Similarity	NPC151481
0.7531	Intermediate Similarity	NPC101622
0.7529	Intermediate Similarity	NPC477203
0.7528	Intermediate Similarity	NPC78673
0.7528	Intermediate Similarity	NPC160517
0.7528	Intermediate Similarity	NPC186155
0.7526	Intermediate Similarity	NPC477720
0.7525	Intermediate Similarity	NPC470024
0.7525	Intermediate Similarity	NPC38948
0.75	Intermediate Similarity	NPC251528
0.75	Intermediate Similarity	NPC477748
0.7475	Intermediate Similarity	NPC120009
0.7474	Intermediate Similarity	NPC476488
0.7474	Intermediate Similarity	NPC476487
0.7474	Intermediate Similarity	NPC276110
0.7473	Intermediate Similarity	NPC199382
0.7473	Intermediate Similarity	NPC316138
0.7473	Intermediate Similarity	NPC313658
0.7451	Intermediate Similarity	NPC206618
0.7449	Intermediate Similarity	NPC198992
0.7449	Intermediate Similarity	NPC471075
0.7447	Intermediate Similarity	NPC472196
0.7447	Intermediate Similarity	NPC472195
0.7447	Intermediate Similarity	NPC152778
0.7447	Intermediate Similarity	NPC205034
0.7447	Intermediate Similarity	NPC238090
0.7447	Intermediate Similarity	NPC156553
0.7447	Intermediate Similarity	NPC115021
0.7447	Intermediate Similarity	NPC162615
0.7444	Intermediate Similarity	NPC471494
0.7444	Intermediate Similarity	NPC35933
0.7444	Intermediate Similarity	NPC471795
0.7439	Intermediate Similarity	NPC469660
0.7426	Intermediate Similarity	NPC109376
0.7419	Intermediate Similarity	NPC182136
0.7419	Intermediate Similarity	NPC253186
0.7419	Intermediate Similarity	NPC280149
0.7419	Intermediate Similarity	NPC221111
0.7416	Intermediate Similarity	NPC161045
0.7416	Intermediate Similarity	NPC44261
0.7412	Intermediate Similarity	NPC27205
0.7412	Intermediate Similarity	NPC469880
0.7396	Intermediate Similarity	NPC16967
0.7374	Intermediate Similarity	NPC238397
0.7374	Intermediate Similarity	NPC471363
0.7368	Intermediate Similarity	NPC159698
0.7368	Intermediate Similarity	NPC256368
0.7368	Intermediate Similarity	NPC477722
0.7363	Intermediate Similarity	NPC311163
0.7363	Intermediate Similarity	NPC471219
0.7363	Intermediate Similarity	NPC61527
0.7363	Intermediate Similarity	NPC474062
0.7356	Intermediate Similarity	NPC321728
0.7353	Intermediate Similarity	NPC224660
0.7349	Intermediate Similarity	NPC316185
0.7349	Intermediate Similarity	NPC472254
0.7347	Intermediate Similarity	NPC476299
0.7347	Intermediate Similarity	NPC227865
0.7347	Intermediate Similarity	NPC219285
0.7347	Intermediate Similarity	NPC477972
0.7347	Intermediate Similarity	NPC472644
0.7347	Intermediate Similarity	NPC20113
0.7347	Intermediate Similarity	NPC161527
0.7347	Intermediate Similarity	NPC477971
0.7347	Intermediate Similarity	NPC477968
0.7347	Intermediate Similarity	NPC38855
0.7347	Intermediate Similarity	NPC474012
0.7347	Intermediate Similarity	NPC228251
0.734	Intermediate Similarity	NPC72845
0.734	Intermediate Similarity	NPC177037
0.734	Intermediate Similarity	NPC477749
0.734	Intermediate Similarity	NPC472814
0.7327	Intermediate Similarity	NPC239961
0.7327	Intermediate Similarity	NPC82251
0.7327	Intermediate Similarity	NPC172867
0.7327	Intermediate Similarity	NPC153095
0.7326	Intermediate Similarity	NPC315394
0.732	Intermediate Similarity	NPC53844
0.732	Intermediate Similarity	NPC205143
0.7312	Intermediate Similarity	NPC174342
0.7312	Intermediate Similarity	NPC50488
0.7312	Intermediate Similarity	NPC79027
0.7312	Intermediate Similarity	NPC5509
0.7312	Intermediate Similarity	NPC474396
0.7312	Intermediate Similarity	NPC133450
0.7312	Intermediate Similarity	NPC293044
0.7308	Intermediate Similarity	NPC17791
0.7303	Intermediate Similarity	NPC256112
0.73	Intermediate Similarity	NPC127933
0.73	Intermediate Similarity	NPC134270
0.73	Intermediate Similarity	NPC475889
0.73	Intermediate Similarity	NPC45897
0.73	Intermediate Similarity	NPC7613
0.73	Intermediate Similarity	NPC7644
0.7292	Intermediate Similarity	NPC13924
0.7284	Intermediate Similarity	NPC472266
0.7283	Intermediate Similarity	NPC166857
0.7283	Intermediate Similarity	NPC476600
0.7283	Intermediate Similarity	NPC475678
0.7283	Intermediate Similarity	NPC45409
0.7273	Intermediate Similarity	NPC472643
0.7273	Intermediate Similarity	NPC63249
0.7273	Intermediate Similarity	NPC10636
0.7263	Intermediate Similarity	NPC472641
0.7263	Intermediate Similarity	NPC472640
0.7263	Intermediate Similarity	NPC166346
0.7263	Intermediate Similarity	NPC139692
0.7263	Intermediate Similarity	NPC472954
0.7262	Intermediate Similarity	NPC477085
0.7255	Intermediate Similarity	NPC475074

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 NPC126518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1698
0.2-0.3	4152
0.3-0.4	2392
0.4-0.5	490
0.5-0.6	242
0.6-0.7	35
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6400	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6686	Approved
0.7071	Intermediate Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD7637	Suspended
0.6914	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6829	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6698	Approved
0.6701	Remote Similarity	NPD46	Approved
0.6701	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6607	Remote Similarity	NPD7328	Approved
0.6607	Remote Similarity	NPD7327	Approved
0.6579	Remote Similarity	NPD8033	Approved
0.6579	Remote Similarity	NPD7503	Approved
0.6566	Remote Similarity	NPD5778	Approved
0.6566	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD7516	Approved
0.6531	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD8039	Approved
0.6517	Remote Similarity	NPD8264	Approved
0.6491	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD8377	Approved
0.6489	Remote Similarity	NPD6695	Phase 3
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD5344	Discontinued
0.6435	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD8296	Approved
0.6435	Remote Similarity	NPD8380	Approved
0.6435	Remote Similarity	NPD8335	Approved
0.6435	Remote Similarity	NPD8379	Approved
0.6429	Remote Similarity	NPD6051	Approved
0.6421	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6925	Approved
0.6374	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7332	Phase 2
0.6344	Remote Similarity	NPD4822	Approved
0.6344	Remote Similarity	NPD4819	Approved
0.6344	Remote Similarity	NPD7514	Phase 3
0.6344	Remote Similarity	NPD4821	Approved
0.6344	Remote Similarity	NPD4820	Approved
0.6316	Remote Similarity	NPD5362	Discontinued
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.6306	Remote Similarity	NPD6053	Discontinued
0.6304	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD4271	Approved
0.6304	Remote Similarity	NPD7145	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6277	Remote Similarity	NPD6902	Approved
0.6275	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6101	Approved
0.6238	Remote Similarity	NPD6399	Phase 3
0.6237	Remote Similarity	NPD6929	Approved
0.6226	Remote Similarity	NPD7632	Discontinued
0.6224	Remote Similarity	NPD7750	Discontinued
0.6224	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD7507	Approved
0.6216	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7839	Suspended
0.6211	Remote Similarity	NPD5209	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6186	Remote Similarity	NPD5363	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.617	Remote Similarity	NPD6930	Phase 2
0.617	Remote Similarity	NPD6931	Approved
0.6154	Remote Similarity	NPD8513	Phase 3
0.6146	Remote Similarity	NPD5332	Approved
0.6146	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD6923	Approved
0.6136	Remote Similarity	NPD6922	Approved
0.6126	Remote Similarity	NPD6371	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6117	Remote Similarity	NPD5695	Phase 3
0.6105	Remote Similarity	NPD6898	Phase 1
0.6105	Remote Similarity	NPD4790	Discontinued
0.6067	Remote Similarity	NPD7143	Approved
0.6067	Remote Similarity	NPD7144	Approved
0.6066	Remote Similarity	NPD7319	Approved
0.6061	Remote Similarity	NPD4251	Approved
0.6061	Remote Similarity	NPD4250	Approved
0.6058	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6675	Approved
0.6055	Remote Similarity	NPD6402	Approved
0.6055	Remote Similarity	NPD7128	Approved
0.6055	Remote Similarity	NPD5739	Approved
0.6049	Remote Similarity	NPD4219	Approved
0.6044	Remote Similarity	NPD6926	Approved
0.6044	Remote Similarity	NPD6924	Approved
0.6042	Remote Similarity	NPD4269	Approved
0.6042	Remote Similarity	NPD4270	Approved
0.6036	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6932	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6017	Remote Similarity	NPD8517	Approved
0.6017	Remote Similarity	NPD8515	Approved
0.6017	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6903	Approved
0.598	Remote Similarity	NPD7087	Discontinued
0.598	Remote Similarity	NPD7983	Approved
0.5978	Remote Similarity	NPD6942	Approved
0.5978	Remote Similarity	NPD7339	Approved
0.596	Remote Similarity	NPD5786	Approved
0.596	Remote Similarity	NPD4249	Approved
0.5946	Remote Similarity	NPD6899	Approved
0.5946	Remote Similarity	NPD7320	Approved
0.5946	Remote Similarity	NPD6881	Approved
0.5943	Remote Similarity	NPD5696	Approved
0.5941	Remote Similarity	NPD689	Discontinued
0.5918	Remote Similarity	NPD3665	Phase 1
0.5918	Remote Similarity	NPD4786	Approved
0.5918	Remote Similarity	NPD3666	Approved
0.5918	Remote Similarity	NPD3133	Approved
0.5914	Remote Similarity	NPD6933	Approved
0.5914	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4211	Phase 1
0.5895	Remote Similarity	NPD6683	Phase 2
0.5895	Remote Similarity	NPD7645	Phase 2
0.5893	Remote Similarity	NPD6373	Approved
0.5893	Remote Similarity	NPD6372	Approved
0.5882	Remote Similarity	NPD368	Approved
0.5876	Remote Similarity	NPD3667	Approved
0.5876	Remote Similarity	NPD6435	Approved
0.5859	Remote Similarity	NPD6893	Approved
0.5859	Remote Similarity	NPD1696	Phase 3
0.5856	Remote Similarity	NPD5697	Approved
0.5856	Remote Similarity	NPD5701	Approved
0.5851	Remote Similarity	NPD4756	Discovery
0.5841	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7102	Approved
0.5841	Remote Similarity	NPD6883	Approved
0.5841	Remote Similarity	NPD7290	Approved
0.5825	Remote Similarity	NPD5693	Phase 1
0.5812	Remote Similarity	NPD7505	Discontinued
0.58	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD6650	Approved
0.5789	Remote Similarity	NPD6649	Approved
0.5789	Remote Similarity	NPD6847	Approved
0.5789	Remote Similarity	NPD6869	Approved
0.5789	Remote Similarity	NPD8130	Phase 1
0.5789	Remote Similarity	NPD6617	Approved
0.5784	Remote Similarity	NPD4753	Phase 2
0.5784	Remote Similarity	NPD5328	Approved
0.5773	Remote Similarity	NPD5369	Approved
0.5766	Remote Similarity	NPD6640	Phase 3
0.5765	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4732	Discontinued
0.5752	Remote Similarity	NPD6014	Approved
0.5752	Remote Similarity	NPD6012	Approved
0.5752	Remote Similarity	NPD6013	Approved
0.5743	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8297	Approved
0.5728	Remote Similarity	NPD7136	Phase 2
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.569	Remote Similarity	NPD8133	Approved
0.5673	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6079	Approved
0.567	Remote Similarity	NPD7525	Registered
0.567	Remote Similarity	NPD4695	Discontinued
0.567	Remote Similarity	NPD5368	Approved
0.567	Remote Similarity	NPD7509	Discontinued
0.5664	Remote Similarity	NPD6011	Approved
0.5657	Remote Similarity	NPD6110	Phase 1
0.5656	Remote Similarity	NPD7830	Approved
0.5656	Remote Similarity	NPD7829	Approved
0.5656	Remote Similarity	NPD8328	Phase 3
0.5652	Remote Similarity	NPD7116	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