Natural Product: NPC35026

Natural Product IDNPC35026
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 KUZABABLVHWUGR-MRXNPFEDSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 124511461
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0002949] Long-chain fatty acids

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

  Chemical Representations

Standard InCHIKey KUZABABLVHWUGR-MRXNPFEDSA-N
Standard InCHI InChI=1S/C17H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(18)17(19)20/h16,18H,2-15H2,1H3,(H,19,20)/t16-/m1/s1
SMILES CCCCCCCCCCCCCCC[C@H](C(=O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   286.25 Volume:   326.322
?
Van der Waals volume.
Dense:   0.877 LogP:   5.908
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The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.575
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The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -5.009
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The logarithm of aqueous solubility value.
Rotatable Bonds:   15.0 Rigid Bonds:   1.0
TPSA:   57.53
?
Topological Polar Surface Area.
 H-Bond Acceptor:   3.0
H-Bond Donor:   2.0 Rings:   0.0
Heavy Atoms:   3.0

MedChem Properties

QED Drug-Likeness Score:   0.42 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.401 Fsp3:   0.941
MCE-18:   2.0
?
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:   1
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.375 Fluc inhibitor:   0.014
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The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.003
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The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
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The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.986 Promiscuous compounds:   0.491

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.125 MDCK Permeability:   -4.838
Pgp-inhibitor:   0.0 Pgp-substrate:   0.109
PAMPA:   0.039
?
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):   0.044
20% Bioavailability (F20%):   0.566 30% Bioavailability (F30%):   0.943
50% Bioavailability (F50%):   0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.076 MRP1:   0.936
Plasma Protein Binding (PPB):   98.618% Volume Distribution (VD):   0.898
Fu: 1.543%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.59
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.468
BSEP inhibitor:   0.022

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.071
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.011
CYP2C9-inhibitor:   0.814 CYP2C9-substrate:   0.063
CYP2D6-inhibitor:   0.893 CYP2D6-substrate:   0.004
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.999
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.92
HLM stability:   0.11
?
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):  2.734 Half-life (T1/2):  1.306

ADMET: Toxicity

hERG Blockers:  0.096 hERG Blockers (10um):  0.354
Human Hepatotoxicity (H-HT):  0.425 Drug-induced Liver Injury (DILI):  0.084
AMES Toxicity:  0.032 Rat Oral Acute Toxicity:  0.104
Maximum Recommended Daily Dose:  0.138 Skin Sensitization:  0.984
Carcinogencity:  0.131 Eye Corrosion:  0.981
Eye Irritation:  0.997 Respiratory Toxicity:  0.858
Drug-induced Neurotoxicity:  0.007 Ototoxicity:  0.228
Hematotoxicity:  0.121 Drug-induced Nephrotoxicity:  0.409
Genotoxicity:  0.0 RPMI-8226 Immunitoxicity:  0.047
A549 Cytotoxicity:  0.318 Hek293 Cytotoxicity:  0.04
BCF:   1.067
?
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:   4.363
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48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.763
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48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.354
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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
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s10529-013-1178-6]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/14786419.2014.986657]
NPO23553 Abies sachalinensis Species Pinaceae Eukaryota Barks n.a. n.a. PMID[12444693]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[12502309]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota whole plant Zhangzhou, Fujian Province, China n.a. PMID[17343408]
NPO23553 Abies sachalinensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1097 Bacopa monnieri Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23553 Abies sachalinensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1097 Bacopa monnieri Species Plantaginaceae 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

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
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 NPC35026 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.6087 Remote Similarity NPC5505
0.6 Remote Similarity NPC319680
0.5455 Remote Similarity NPC307739
0.5455 Remote Similarity NPC76217
0.5455 Remote Similarity NPC178595

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC35026 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7857 Intermediate Similarity NPD3197 Phase 1
0.5455 Remote Similarity NPD8202 Phase 4
0.5455 Remote Similarity NPD8205 Phase 4

Bioactivity similarity

  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