Natural Product: NPC297797

Natural Product IDNPC297797
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Guttiferone E
IUPAC Name n.a.
Synonyms (+)-Guttiferone D; Guttiferone E
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL447153
PubChem CID n.a.
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic 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 PERYNTNSURMRNO-AAXMREPPSA-N
Standard InCHI InChI=1S/C37H48O6/c1-21(2)11-13-27-20-36(19-26(24(7)8)17-23(5)6)32(41)30(31(40)25-12-14-28(38)29(39)18-25)33(42)37(34(36)43,35(27,9)10)16-15-22(3)4/h11-12,14-15,17-18,26-27,38-39,41H,7,13,16,19-20H2,1-6,8-10H3/t26-,27-,36-,37+/m0/s1
SMILES CC(=CC[C@@]12C(=O)C(=C([C@](C1=O)(C[C@@H](C(=C)C)C=C(C)C)C[C@@H](C2(C)C)CC=C(C)C)O)C(=O)c1ccc(c(c1)O)O)C

  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
NPO7574 Garcinia pyrifera Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[10978200]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. xylem n.a. PMID[14600386]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota fruits n.a. n.a. PMID[15787435]
NPO15264 Garcinia paucinervis Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20594858]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15264 Garcinia paucinervis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7574 Garcinia pyrifera Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15264 Garcinia paucinervis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21424 Garcinia xanthochymus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7574 Garcinia pyrifera Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae 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
NPT660 Cell line SW480 Homo sapiens IC50 = 7500.0 nM PMID[8229017]
NPT1 Others Radical scavenging activity n.a. IC50 = 68000.0 nM Open TG-GATES in vivo data: Biochemistry
NPT2 Others Unspecified n.a. IC50 = 1500.0 nM PMID[15844934]
NPT2 Others Unspecified n.a. Ratio <= 3.0 n.a. PMID[14987072]

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 NPC297797 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
0.8636 High Similarity NPC46242
0.8636 High Similarity NPC91887
0.8636 High Similarity NPC93556
0.8438 Intermediate Similarity NPC149773
0.8261 Intermediate Similarity NPC469857
0.8261 Intermediate Similarity NPC245760
0.8028 Intermediate Similarity NPC471971
0.8028 Intermediate Similarity NPC471972
0.8028 Intermediate Similarity NPC469855
0.75 Intermediate Similarity NPC165191
0.75 Intermediate Similarity NPC30846
0.75 Intermediate Similarity NPC177501
0.7432 Intermediate Similarity NPC469856
0.7397 Intermediate Similarity NPC294330
0.7361 Intermediate Similarity NPC114333
0.7361 Intermediate Similarity NPC28592
0.7361 Intermediate Similarity NPC51531
0.7333 Intermediate Similarity NPC471970
0.7297 Intermediate Similarity NPC469854
0.726 Intermediate Similarity NPC473479
0.726 Intermediate Similarity NPC50615
0.726 Intermediate Similarity NPC141650
0.7067 Intermediate Similarity NPC603871
0.6944 Remote Similarity NPC289358
0.6944 Remote Similarity NPC4289
0.6944 Remote Similarity NPC42384
0.6933 Remote Similarity NPC479151
0.6753 Remote Similarity NPC237441
0.6579 Remote Similarity NPC479148
0.6522 Remote Similarity NPC259400
0.6522 Remote Similarity NPC130591
0.6522 Remote Similarity NPC234637
0.641 Remote Similarity NPC5014
0.6338 Remote Similarity NPC611064
0.6301 Remote Similarity NPC473779
0.6282 Remote Similarity NPC23667
0.6282 Remote Similarity NPC157284
0.625 Remote Similarity NPC479146
0.6104 Remote Similarity NPC473527
0.6076 Remote Similarity NPC482621
0.6024 Remote Similarity NPC482617
0.6024 Remote Similarity NPC482616
0.5904 Remote Similarity NPC482618
0.5897 Remote Similarity NPC198803
0.5375 Remote Similarity NPC479147
0.5366 Remote Similarity NPC8493
0.5366 Remote Similarity NPC469375
0.5366 Remote Similarity NPC110855
0.5366 Remote Similarity NPC144247
0.5357 Remote Similarity NPC264229
0.5357 Remote Similarity NPC25736
0.5357 Remote Similarity NPC46549
0.5357 Remote Similarity NPC606601
0.5325 Remote Similarity NPC474715
0.5309 Remote Similarity NPC48949
0.5294 Remote Similarity NPC294679
0.5294 Remote Similarity NPC145301
0.5294 Remote Similarity NPC302044
0.5294 Remote Similarity NPC600911
0.5233 Remote Similarity NPC231479
0.5125 Remote Similarity NPC600618
0.5059 Remote Similarity NPC482619

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC297797 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