Natural Product: NPC213918

Natural Product IDNPC213918
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 NSMIMJYEKVSYMT-TWGQIWQCSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 5352452
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001127] Acyclic monoterpenoids

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 NSMIMJYEKVSYMT-TWGQIWQCSA-N
Standard InCHI InChI=1S/C10H18O2/c1-4-10(3,12)7-5-6-9(2)8-11/h4,6,11-12H,1,5,7-8H2,2-3H3/b9-6-
SMILES C=CC(C)(CC/C=C(/C)CO)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   170.13 Volume:   193.824
?
Van der Waals volume.
Dense:   0.878 LogP:   1.396
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.427
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.079
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   5.0 Rigid Bonds:   2.0
TPSA:   40.46
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   2.0 Rings:   0.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.616 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.647 Fsp3:   0.6
MCE-18:   4.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.001 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.001
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.998 Promiscuous compounds:   0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.725 MDCK Permeability:   -4.804
Pgp-inhibitor:   0.063 Pgp-substrate:   0.204
PAMPA:   0.438
?
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):   0.23
20% Bioavailability (F20%):   0.811 30% Bioavailability (F30%):   0.924
50% Bioavailability (F50%):   0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.077 MRP1:   0.698
Plasma Protein Binding (PPB):   54.729% Volume Distribution (VD):   -0.168
Fu: 47.606%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.904
OATP1B3 inhibitor:   0.921 BCRP inhibitor:   0.963
BSEP inhibitor:   0.142

ADMET: Metabolism

CYP1A2-inhibitor:   0.006 CYP1A2-substrate:   0.002
CYP2C19-inhibitor:   0.901 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.312 CYP2C9-substrate:   0.001
CYP2D6-inhibitor:   0.183 CYP2D6-substrate:   0.02
CYP3A4-inhibitor:   0.214 CYP3A4-substrate:   0.002
CYP2B6-substrate:   0.001 CYP2C8-inhibitor:   0.041
HLM stability:   0.017
?
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):  9.38 Half-life (T1/2):  1.099

ADMET: Toxicity

hERG Blockers:  0.032 hERG Blockers (10um):  0.266
Human Hepatotoxicity (H-HT):  0.466 Drug-induced Liver Injury (DILI):  0.016
AMES Toxicity:  0.287 Rat Oral Acute Toxicity:  0.039
Maximum Recommended Daily Dose:  0.083 Skin Sensitization:  0.955
Carcinogencity:  0.395 Eye Corrosion:  0.96
Eye Irritation:  0.997 Respiratory Toxicity:  0.75
Drug-induced Neurotoxicity:  0.219 Ototoxicity:  0.366
Hematotoxicity:  0.17 Drug-induced Nephrotoxicity:  0.172
Genotoxicity:  0.01 RPMI-8226 Immunitoxicity:  0.032
A549 Cytotoxicity:  0.011 Hek293 Cytotoxicity:  0.037
BCF:   0.413
?
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:   2.576
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.28
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.112
?
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
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.5897/AJB11.1524]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17689080]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[32456033]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[33937995]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[34771092]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[35143705]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[35268681]
NPO54134 Croton linearis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[36551370]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[37049761]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[37111302]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38159180]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38308284]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[39410132]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9445 Crocus sativus Species Iridaceae 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
NPO54134 Croton linearis Oil Stems 0.54 n.a. n.a. % PMID[36551370]

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 NPC213918 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
0.7083 Intermediate Similarity NPC68889
0.7083 Intermediate Similarity NPC180871
0.6538 Remote Similarity NPC88079
0.5667 Remote Similarity NPC67761
0.5667 Remote Similarity NPC209279
0.5667 Remote Similarity NPC194586
0.5667 Remote Similarity NPC108494
0.5667 Remote Similarity NPC51758
0.5152 Remote Similarity NPC227135

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC213918 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
NPD

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