NPASS Compound

Natural Product: NPC537303

Natural Product ID	NPC537303
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	oxacyclooctadecan-2-one
IUPAC Name	oxacyclooctadecan-2-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 51 51 0 0 0 0 0 0 0 0999 V2000 -3.0627 -3.0266 -2.0516 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -2.5192 -0.9602 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5553 -1.5781 -0.2999 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0486 -0.8358 0.8623 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0352 0.2306 0.6718 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5598 1.4518 -0.0826 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5466 2.5571 -0.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3106 2.2723 -0.8566 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7365 3.3712 -0.7483 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1989 3.5545 0.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7471 2.2200 1.2135 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9635 1.7987 0.4844 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3174 0.3167 0.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2443 -0.5290 0.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3877 -2.0559 0.3493 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1332 -2.5156 -0.3327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7634 -3.9267 -0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5779 -3.8620 -1.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4060 -2.9203 -0.5355 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4733 -2.1424 0.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9571 -0.8712 -1.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9518 -0.3312 1.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6989 -1.5267 1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6566 0.6251 1.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1282 -0.1243 0.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8851 1.1784 -1.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4909 1.7854 0.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3354 2.7933 0.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0920 3.4626 -0.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5797 2.2625 -1.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0643 1.2757 -0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5455 3.1349 -1.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2231 4.3115 -1.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3329 3.9105 1.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9777 4.3120 0.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9136 1.5345 1.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0567 2.4628 2.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8345 2.3728 0.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9077 1.9557 -0.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4869 0.1455 1.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2796 0.1502 0.2418 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2177 -0.2659 0.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1195 -0.3544 -0.8756 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4110 -2.3307 1.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2571 -2.4263 -0.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2950 -1.9887 0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 -2.0236 -1.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4162 -4.3760 0.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4412 -4.5985 -0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2997 -3.4932 -2.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0702 -4.8239 -1.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 2 1 0 3 20 1 0 3 21 1 0 4 22 1 0 4 23 1 0 5 24 1 0 5 25 1 0 6 26 1 0 6 27 1 0 7 28 1 0 7 29 1 0 8 30 1 0 8 31 1 0 9 32 1 0 9 33 1 0 10 34 1 0 10 35 1 0 11 36 1 0 11 37 1 0 12 38 1 0 12 39 1 0 13 40 1 0 13 41 1 0 14 42 1 0 14 43 1 0 15 44 1 0 15 45 1 0 16 46 1 0 16 47 1 0 17 48 1 0 17 49 1 0 18 50 1 0 18 51 1 0 M END

Standard InCHIKey	FXQOOHFUXNQCKQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C17H32O2/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-19-17/h1-16H2
SMILES	O=C1CCCCCCCCCCCCCCCCO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	268.24	Volume:	308.976 ? Van der Waals volume.
Dense:	0.868	LogP:	5.741 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.7 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.658 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	19.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.55	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.286	Fsp³:	0.941
MCE-18:	7.879 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.119	Fluc inhibitor:	0.229 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.996	Promiscuous compounds:	0.654

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.914
Pgp-inhibitor:	0.788	Pgp-substrate:	0.0
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	0.931
Plasma Protein Binding (PPB):	78.702%	Volume Distribution (VD):	0.062
Fu:	7.301% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.765
OATP1B3 inhibitor:	0.947	BCRP inhibitor:	0.054
BSEP inhibitor:	0.947

ADMET: Metabolism

CYP1A2-inhibitor:	0.382	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.468
HLM stability:	1.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.111

Half-life (T1/2):

0.22

ADMET: Toxicity

hERG Blockers:	0.378	hERG Blockers (10um):	0.717
Human Hepatotoxicity (H-HT):	0.103	Drug-induced Liver Injury (DILI):	0.058
AMES Toxicity:	0.005	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.657	Skin Sensitization:	0.805
Carcinogencity:	0.046	Eye Corrosion:	0.905
Eye Irritation:	0.993	Respiratory Toxicity:	0.269
Drug-induced Neurotoxicity:	0.093	Ototoxicity:	0.132
Hematotoxicity:	0.071	Drug-induced Nephrotoxicity:	0.047
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.25	Hek293 Cytotoxicity:	0.207
BCF:	2.002 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	2.948 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.411 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	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	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO26622	Taraxacum officinale	Oil	n.a.	0.95	n.a.	n.a.	%	PMID[36235013]

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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC537303 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	32561
0.1-0.2	16372
0.2-0.3	731
0.3-0.4	112
0.4-0.5	42
0.5-0.6	18
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223249
0.875	High Similarity	NPC149299
0.8333	Intermediate Similarity	NPC80396
0.7778	Intermediate Similarity	NPC71761
0.76	Intermediate Similarity	NPC154642
0.76	Intermediate Similarity	NPC80641
0.76	Intermediate Similarity	NPC603612
0.72	Intermediate Similarity	NPC154396
0.72	Intermediate Similarity	NPC286695
0.7143	Intermediate Similarity	NPC99700
0.68	Remote Similarity	NPC12904
0.68	Remote Similarity	NPC476550
0.625	Remote Similarity	NPC53541
0.619	Remote Similarity	NPC327450
0.619	Remote Similarity	NPC234005
0.6154	Remote Similarity	NPC322892
0.6129	Remote Similarity	NPC223677
0.5769	Remote Similarity	NPC250028
0.5769	Remote Similarity	NPC236579
0.5769	Remote Similarity	NPC80234
0.5769	Remote Similarity	NPC86545
0.5769	Remote Similarity	NPC286498
0.5769	Remote Similarity	NPC223374
0.5769	Remote Similarity	NPC203531
0.5769	Remote Similarity	NPC196442
0.5769	Remote Similarity	NPC256163
0.5769	Remote Similarity	NPC301398
0.5769	Remote Similarity	NPC40597
0.5769	Remote Similarity	NPC608162
0.5769	Remote Similarity	NPC609004
0.5517	Remote Similarity	NPC223675
0.5517	Remote Similarity	NPC68577
0.5484	Remote Similarity	NPC163345
0.5385	Remote Similarity	NPC40965
0.5185	Remote Similarity	NPC81263

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC537303 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7416
0.1-0.2	1614
0.2-0.3	95
0.3-0.4	18
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
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
0.6	Remote Similarity	NPD900	Pre-clinical
0.5758	Remote Similarity	NPD631	Phase 4
0.5588	Remote Similarity	NPD630	Approved

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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