Structure

Physi-Chem Properties

Molecular Weight:  178.14
Volume:  208.433
LogP:  3.034
LogD:  2.144
LogS:  -3.129
# Rotatable Bonds:  2
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.468
Synthetic Accessibility Score:  3.326
Fsp3:  0.583
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.394
MDCK Permeability:  2.7229132683714852e-05
Pgp-inhibitor:  0.017
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.101
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.195
Plasma Protein Binding (PPB):  95.06660461425781%
Volume Distribution (VD):  2.543
Pgp-substrate:  4.61022424697876%

ADMET: Metabolism

CYP1A2-inhibitor:  0.486
CYP1A2-substrate:  0.475
CYP2C19-inhibitor:  0.746
CYP2C19-substrate:  0.847
CYP2C9-inhibitor:  0.291
CYP2C9-substrate:  0.678
CYP2D6-inhibitor:  0.08
CYP2D6-substrate:  0.324
CYP3A4-inhibitor:  0.038
CYP3A4-substrate:  0.35

ADMET: Excretion

Clearance (CL):  5.978
Half-life (T1/2):  0.689

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.636
Drug-inuced Liver Injury (DILI):  0.071
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.872
Skin Sensitization:  0.94
Carcinogencity:  0.944
Eye Corrosion:  0.924
Eye Irritation:  0.979
Respiratory Toxicity:  0.825

Download Data

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

  Natural Product: NPC92148

Natural Product ID:  NPC92148
Common Name*:   SSDLCRAPQKJETK-ZJNQMXKESA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SSDLCRAPQKJETK-ZJNQMXKESA-N
Standard InCHI:  InChI=1S/C12H18O/c1-9-4-6-12(7-5-9)10(2)8-11(3)13/h4,8,12H,5-7H2,1-3H3/b10-8+/t12-/m1/s1
SMILES:  CC1=CC[C@H](CC1)/C(=C/C(=O)C)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
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:0001401] Menthane monoterpenoids

*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
NPO21179 Streptomyces griseoaurantiacus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10048567]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14307 Rhizopus oryzae Species Rhizopodaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18881 Loropetalum chinense Species Hamamelidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22147 Goniothalamus macrophyllus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21894 Psychotria granadensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22968 Elaeocarpus serratus Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15469 Myodocarpus gracilis Species Myodocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6953.1 Aconitum sachalinense subsp. yezoense Subspecies Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20425 Epimedium macranthum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23194 Berberis beaniana Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21704 Papaver suaveolens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23157 Wigandia kunthii Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14307 Rhizopus oryzae Species Rhizopodaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13308 Polycitor adriaticus Species Polycitoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21179 Streptomyces griseoaurantiacus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22530 Vigna luteola 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 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 NPC92148 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 NPC92148 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