Structure

Physi-Chem Properties

Molecular Weight:  218.17
Volume:  251.764
LogP:  3.093
LogD:  2.338
LogS:  -3.696
# Rotatable Bonds:  1
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.61
Synthetic Accessibility Score:  4.443
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.565
MDCK Permeability:  1.5979167073965073e-05
Pgp-inhibitor:  0.211
Pgp-substrate:  0.015
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.338

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.934
Plasma Protein Binding (PPB):  81.8367919921875%
Volume Distribution (VD):  2.215
Pgp-substrate:  13.522507667541504%

ADMET: Metabolism

CYP1A2-inhibitor:  0.112
CYP1A2-substrate:  0.872
CYP2C19-inhibitor:  0.134
CYP2C19-substrate:  0.894
CYP2C9-inhibitor:  0.116
CYP2C9-substrate:  0.22
CYP2D6-inhibitor:  0.07
CYP2D6-substrate:  0.859
CYP3A4-inhibitor:  0.527
CYP3A4-substrate:  0.418

ADMET: Excretion

Clearance (CL):  7.969
Half-life (T1/2):  0.605

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.151
Drug-inuced Liver Injury (DILI):  0.137
AMES Toxicity:  0.062
Rat Oral Acute Toxicity:  0.614
Maximum Recommended Daily Dose:  0.733
Skin Sensitization:  0.06
Carcinogencity:  0.849
Eye Corrosion:  0.148
Eye Irritation:  0.207
Respiratory Toxicity:  0.963

Download Data

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

  Natural Product: NPC138972

Natural Product ID:  NPC138972
Common Name*:   KUFXJZXMWHNCEH-SWLSCSKDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KUFXJZXMWHNCEH-SWLSCSKDSA-N
Standard InCHI:  InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m0/s1
SMILES:  C=C(C)[C@H]1CC[C@]2(C)CCC(=O)C(=C2C1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   12303268
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO4815 Cladonia coccifera Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9810 Keteleeria davidiana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18489 Pinus serotina Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10053 Peperomia blanda Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3223 Aristolochia esperanzae Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO999 Trigonostemon cherrieri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11639 Chlorogloeopsis fritschii Species Chlorogloeopsidaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11518 Strophanthus sarmentosus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11007 Ophiomastix annulosa Species Ophiocomidae 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 NPC138972 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 NPC138972 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