Natural Product: NPC196459

Natural Product IDNPC196459
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Mammea A/Ab
IUPAC Name 5,7-dihydroxy-6-[(2S)-2-methylbutanoyl]-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1689185
PubChem CID 53321420
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001614] Neoflavonoids
        • [CHEMONTID:0003650] Prenylated neoflavonoids

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 YALRCXHVQYBSJC-HNNXBMFYSA-N
Standard InCHI InChI=1S/C25H26O5/c1-5-15(4)22(27)21-23(28)17(12-11-14(2)3)25-20(24(21)29)18(13-19(26)30-25)16-9-7-6-8-10-16/h6-11,13,15,28-29H,5,12H2,1-4H3/t15-/m0/s1
SMILES CC[C@H](C)C(=O)c1c(c(CC=C(C)C)c2c(c(cc(=O)o2)c2ccccc2)c1O)O

  Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[21214226]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[21214226]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21645 Mammea americana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21645 Mammea americana Species Calophyllaceae 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
NPT396 Cell line T47D Homo sapiens IC50 = 2880.0 nM PMID[21214226]
NPT306 Cell line PC-3 Homo sapiens IC50 = 3820.0 nM PMID[21214226]
NPT21802 Protein family Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 4630.0 nM PMID[21214226]
NPT21802 Protein family Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 4820.0 nM PMID[21214226]

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 NPC196459 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 NPC470296
0.8281 Intermediate Similarity NPC1886
0.8125 Intermediate Similarity NPC36181
0.7761 Intermediate Similarity NPC36705
0.7313 Intermediate Similarity NPC188632
0.7313 Intermediate Similarity NPC112791
0.6957 Remote Similarity NPC73776
0.6765 Remote Similarity NPC87609
0.6479 Remote Similarity NPC196137
0.6438 Remote Similarity NPC474735
0.6364 Remote Similarity NPC32463
0.6338 Remote Similarity NPC94794
0.6324 Remote Similarity NPC138047
0.6316 Remote Similarity NPC469935
0.6216 Remote Similarity NPC483434
0.6216 Remote Similarity NPC470322
0.6143 Remote Similarity NPC474939
0.5974 Remote Similarity NPC178627
0.5972 Remote Similarity NPC470083
0.5921 Remote Similarity NPC19238
0.5658 Remote Similarity NPC474738
0.5625 Remote Similarity NPC181388
0.5325 Remote Similarity NPC140120
0.5316 Remote Similarity NPC249942
0.5195 Remote Similarity NPC329215
0.519 Remote Similarity NPC290671
0.5139 Remote Similarity NPC154217
0.5135 Remote Similarity NPC199458
0.5132 Remote Similarity NPC262011
0.5128 Remote Similarity NPC78554

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC196459 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