Structure

Physi-Chem Properties

Molecular Weight:  194.06
Volume:  194.938
LogP:  1.807
LogD:  2.861
LogS:  -1.796
# Rotatable Bonds:  3
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.715
Synthetic Accessibility Score:  1.91
Fsp3:  0.1
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.908
MDCK Permeability:  1.492413503001444e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.097
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.039
30% Bioavailability (F30%):  0.551

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.325
Plasma Protein Binding (PPB):  89.48690795898438%
Volume Distribution (VD):  0.34
Pgp-substrate:  6.454893112182617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.077
CYP1A2-substrate:  0.544
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.161
CYP2C9-substrate:  0.377
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.21
CYP3A4-inhibitor:  0.03
CYP3A4-substrate:  0.074

ADMET: Excretion

Clearance (CL):  7.361
Half-life (T1/2):  0.92

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.331
Drug-inuced Liver Injury (DILI):  0.556
AMES Toxicity:  0.124
Rat Oral Acute Toxicity:  0.704
Maximum Recommended Daily Dose:  0.069
Skin Sensitization:  0.934
Carcinogencity:  0.396
Eye Corrosion:  0.339
Eye Irritation:  0.972
Respiratory Toxicity:  0.75

Download Data

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

  Natural Product: NPC136702

Natural Product ID:  NPC136702
Common Name*:   QURCVMIEKCOAJU-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QURCVMIEKCOAJU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)
SMILES:  COc1ccc(C=CC(=O)O)cc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   92126
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0002503] Hydroxycinnamic acids

*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
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[11558608]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12542353]
NPO11507 Entada africana Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16989528]
NPO2687 Baphia bancoensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[19007285]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[20149652]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[7775983]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7043 Fuligo candida Species Physaraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14865 Vitex limonifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11684 Iberis sempervirens Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18291 Idea leuconoe Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1033 Plectranthus nummularius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4360 Hendersonula toruloidea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2687 Baphia bancoensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21409 Populus angustifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21758 Thiocystis gelatinosa Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12994 Choriaster granulatus Species Oreasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22304 Morinda morindoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14297 Dioscorea gracillima Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21028 Sasa paniculata Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11507 Entada africana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9786 Monomeria barbata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14049 Fumaria indica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7043 Fuligo candida Species Physaraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22434 Cryptosporium pinicola n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13383 Schumanniophyton magnificum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6370 Roemeria carica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15167 Eichhornia crassipes Species Pontederiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8401 Pteris setuloso-costulata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21276 Sedum forsteri Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11153 Entada polystachya Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9358 Pseuduvaria indochinensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15449 Echium rubrum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22176 Lasiosiphon kraussianus Species Thymelaeaceae 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 NPC136702 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 NPC136702 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