Natural Product: NPC118210

Natural Product IDNPC118210
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 XDUXBBDRILEIEZ-IBGZPJMESA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 56967682
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

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 XDUXBBDRILEIEZ-IBGZPJMESA-N
Standard InCHI InChI=1S/C19H18O4/c1-10-8-23-18-12-5-6-13-11(4-3-7-19(13,2)9-20)15(12)17(22)16(21)14(10)18/h5-6,8,20H,3-4,7,9H2,1-2H3/t19-/m0/s1
SMILES Cc1coc2-c3ccc4c(CCC[C@@]4(C)CO)c3C(=O)C(=O)c12

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   310.12 Volume:   319.66
?
Van der Waals volume.
Dense:   0.97 LogP:   2.669
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.499
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.755
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   22.0
TPSA:   67.51
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   1.0 Rings:   4.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.821 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.626 Fsp3:   0.368
MCE-18:   79.385
?
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:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   1
Colloidal aggregators:   0.131 Fluc inhibitor:   0.343
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.756
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.451
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.033 Promiscuous compounds:   0.112

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.477 MDCK Permeability:   -4.654
Pgp-inhibitor:   0.763 Pgp-substrate:   0.009
PAMPA:   0.972
?
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):   0.944
20% Bioavailability (F20%):   0.149 30% Bioavailability (F30%):   0.871
50% Bioavailability (F50%):   0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.0 MRP1:   0.511
Plasma Protein Binding (PPB):   98.226% Volume Distribution (VD):   0.282
Fu: 1.57%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.944
OATP1B3 inhibitor:   0.978 BCRP inhibitor:   0.009
BSEP inhibitor:   0.953

ADMET: Metabolism

CYP1A2-inhibitor:   0.991 CYP1A2-substrate:   0.135
CYP2C19-inhibitor:   0.914 CYP2C19-substrate:   0.637
CYP2C9-inhibitor:   0.107 CYP2C9-substrate:   0.973
CYP2D6-inhibitor:   0.005 CYP2D6-substrate:   0.457
CYP3A4-inhibitor:   0.115 CYP3A4-substrate:   0.374
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.436
?
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):  4.96 Half-life (T1/2):  0.595

ADMET: Toxicity

hERG Blockers:  0.056 hERG Blockers (10um):  0.285
Human Hepatotoxicity (H-HT):  0.899 Drug-induced Liver Injury (DILI):  0.721
AMES Toxicity:  0.816 Rat Oral Acute Toxicity:  0.519
Maximum Recommended Daily Dose:  0.885 Skin Sensitization:  0.987
Carcinogencity:  0.912 Eye Corrosion:  0.0
Eye Irritation:  0.806 Respiratory Toxicity:  0.379
Drug-induced Neurotoxicity:  0.449 Ototoxicity:  0.637
Hematotoxicity:  0.815 Drug-induced Nephrotoxicity:  0.865
Genotoxicity:  0.795 RPMI-8226 Immunitoxicity:  0.137
A549 Cytotoxicity:  0.251 Hek293 Cytotoxicity:  0.57
BCF:   1.682
?
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:   4.452
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.926
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.426
?
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
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12880325]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[1567426]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[17217287]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[37570961]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25779 Vicia sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12476 Delphinium cyphoplectrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23417 Rhabdia lycioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6346 Phallusia fumigata Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25974 Streptomyces lateritius Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO415 Deguelia hatschbachii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24988 Viburnum sieboldi Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4009 Allochromatium minutissimum Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22016 Notholaena dealbata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26054 Palmaria palmata Species Palmariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24740 Uvaria klaineana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25868 Decachaeta ovatifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26087 Euphorbia retusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28257 Dioscorea communis Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25701 Amentotaxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26223 Cladonia bellidiflora Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25813 Salvia przewalskii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10497 Hydrolithon reinboldii Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23960 Artemisia siversiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27437 Camptothecium lutescens Species Brachytheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25212 Ritterella rubra n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10155 Stauntonia obovatifoliola Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26316 Pleurophycus gardneri Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25779 Vicia sativa Species Fabaceae 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 NPC118210 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
1.0 High Similarity NPC145830
0.8 Intermediate Similarity NPC281398
0.7333 Intermediate Similarity NPC144010
0.7 Intermediate Similarity NPC179170
0.6885 Remote Similarity NPC221992
0.5938 Remote Similarity NPC10051
0.5938 Remote Similarity NPC299094
0.5806 Remote Similarity NPC605467
0.5714 Remote Similarity NPC117674
0.5588 Remote Similarity NPC23559
0.5469 Remote Similarity NPC307672
0.5362 Remote Similarity NPC608807

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC118210 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