Structure

Physi-Chem Properties

Molecular Weight:  236.18
Volume:  263.191
LogP:  2.648
LogD:  2.668
LogS:  -2.502
# Rotatable Bonds:  3
TPSA:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.752
Synthetic Accessibility Score:  4.161
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.831
MDCK Permeability:  1.754406184772961e-05
Pgp-inhibitor:  0.471
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.759
Plasma Protein Binding (PPB):  69.62254333496094%
Volume Distribution (VD):  0.553
Pgp-substrate:  36.75374984741211%

ADMET: Metabolism

CYP1A2-inhibitor:  0.043
CYP1A2-substrate:  0.608
CYP2C19-inhibitor:  0.209
CYP2C19-substrate:  0.928
CYP2C9-inhibitor:  0.219
CYP2C9-substrate:  0.611
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.693
CYP3A4-inhibitor:  0.097
CYP3A4-substrate:  0.282

ADMET: Excretion

Clearance (CL):  12.308
Half-life (T1/2):  0.555

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.198
Drug-inuced Liver Injury (DILI):  0.209
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.199
Maximum Recommended Daily Dose:  0.217
Skin Sensitization:  0.089
Carcinogencity:  0.127
Eye Corrosion:  0.397
Eye Irritation:  0.362
Respiratory Toxicity:  0.077

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Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC118453

Natural Product ID:  NPC118453
Common Name*:   GTUMAHOVZNSHNI-ZLDLUXBVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GTUMAHOVZNSHNI-ZLDLUXBVSA-N
Standard InCHI:  InChI=1S/C15H24O2/c1-10(16)5-6-11-13-12(17)7-8-15(13,4)9-14(11,2)3/h11,13H,5-9H2,1-4H3/t11-,13+,15+/m1/s1
SMILES:  CC(=O)CC[C@@H]1[C@H]2C(=O)CC[C@@]2(C)CC1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   101690795
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO8246 Lantana involucrata Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[15217280]
NPO4890 Streptomyces rimosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17631493]
NPO13607 Arenaria kansuensis Species Scolopacidae Eukaryota n.a. n.a. n.a. PMID[17655145]
NPO4890 Streptomyces rimosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1833366]
NPO9032 Geotrichum candidum Species Dipodascaceae Eukaryota n.a. n.a. n.a. PMID[20488699]
NPO14190 Streptopelia orientalis Species Columbidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13305 Mammea africana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14190 Streptopelia orientalis Species Columbidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13607 Arenaria kansuensis Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13305 Mammea africana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8246 Lantana involucrata Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13201 Diphasiastrum tristachyum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14882 Collariella gracilis Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14190 Streptopelia orientalis Species Columbidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8655 Wendlandia tinctoria Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13607 Arenaria kansuensis Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7119 Endospermum diadenum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7350 Sitotroga cerealella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2510 Pteris argentea Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13305 Mammea africana Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5412 Tedania anhelans Species Tedaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4890 Streptomyces rimosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6089 Metacalypogeia alternifolia Species Calypogeiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9032 Geotrichum candidum Species Dipodascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11341 Eucalyptus piperita Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13497 Senecio trichopterygius Species Asteraceae 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC118453 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC118453 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  Bioactivity similarity: Similar Natural Products in NPASS

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