Structure

Physi-Chem Properties

Molecular Weight:  290.08
Volume:  279.249
LogP:  2.666
LogD:  2.937
LogS:  -3.634
# Rotatable Bonds:  3
TPSA:  81.29
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.771
Synthetic Accessibility Score:  2.476
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.957
MDCK Permeability:  3.141030902042985e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.017
Plasma Protein Binding (PPB):  86.98944091796875%
Volume Distribution (VD):  0.757
Pgp-substrate:  21.554214477539062%

ADMET: Metabolism

CYP1A2-inhibitor:  0.959
CYP1A2-substrate:  0.973
CYP2C19-inhibitor:  0.117
CYP2C19-substrate:  0.517
CYP2C9-inhibitor:  0.254
CYP2C9-substrate:  0.858
CYP2D6-inhibitor:  0.242
CYP2D6-substrate:  0.86
CYP3A4-inhibitor:  0.435
CYP3A4-substrate:  0.405

ADMET: Excretion

Clearance (CL):  12.925
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.229
Drug-inuced Liver Injury (DILI):  0.962
AMES Toxicity:  0.575
Rat Oral Acute Toxicity:  0.451
Maximum Recommended Daily Dose:  0.871
Skin Sensitization:  0.848
Carcinogencity:  0.057
Eye Corrosion:  0.004
Eye Irritation:  0.832
Respiratory Toxicity:  0.652

Download Data

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

  Natural Product: NPC24681

Natural Product ID:  NPC24681
Common Name*:   BUJOWQKLLDUNTC-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BUJOWQKLLDUNTC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H14O6/c1-18-12-6-11-7(4-9(12)16)8-5-10(17)14(19-2)15(20-3)13(8)21-11/h4-6,16-17H,1-3H3
SMILES:  COc1cc2c(cc1O)c1cc(c(c(c1o2)OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   441782
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans
        • [CHEMONTID:0000015] Dibenzofurans

*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
NPO22761 Gentiana cruciata Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88887-1]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1071/CH03175]
NPO14117 Diplodia sapinea Species Botryosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[10075753]
NPO24512 Xestospongia testudinaria Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[10543913]
NPO25046 Aplidium meridianum Species Polyclinidae Eukaryota n.a. South Georgia Islands, South Atlantic n.a. PMID[15026054]
NPO20590 Justicia patentiflora Species Acanthaceae Eukaryota n.a. Vietnamese n.a. PMID[15921419]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO25391 Vitex glabrata Species Lamiaceae Eukaryota leaves Chantaburi Province, Thailand 2007-Nov PMID[19943620]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20058933]
NPO21423 Botryllus tuberatus Species Styelidae Eukaryota n.a. n.a. n.a. PMID[21142112]
NPO21423 Botryllus tuberatus Species Styelidae Eukaryota n.a. Korean n.a. PMID[21142112]
NPO28887 Eupomatia laurina Species Eupomatiaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO24745 Salvia cavaleriei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24256484]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota flowers Pakook, Muang District, Chiang Rai Province, Thailand 2013-Feb PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota young fruits Khokkhon, Tha Bo District, Nong Khai Province, Thailand 2011-Aug PMID[25651042]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27128898]
NPO22780 Sphaeranthus africanus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[30074787]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota Leaves n.a. n.a. PMID[31860303]
NPO25046 Aplidium meridianum Species Polyclinidae Eukaryota n.a. n.a. n.a. PMID[9748381]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO27436 Ribes uva-crispa Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13767 Woodfordia fruticosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24077 Astragalus pterocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13588 Sanguinaria canadensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13767 Woodfordia fruticosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13588 Sanguinaria canadensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24077 Astragalus pterocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20590 Justicia patentiflora Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25625 Hymenophyllum recurvum Species Hymenophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23568 Guatteria pogonopus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27436 Ribes uva-crispa Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18812 Vicia narbonensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21423 Botryllus tuberatus Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25364 Didemnum candidum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22761 Gentiana cruciata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20335 Nassauvia pygmaea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25391 Vitex glabrata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24077 Astragalus pterocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22293 Bryobium hyacinthoides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13767 Woodfordia fruticosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25145 Cydonia oblonga Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22780 Sphaeranthus africanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24512 Xestospongia testudinaria Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14117 Diplodia sapinea Species Botryosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28887 Eupomatia laurina Species Eupomatiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25046 Aplidium meridianum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5027 Peniophora polygonia Species Peniophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25091 Samadera bidwillii Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13588 Sanguinaria canadensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25700 Psiadia punctulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18842 Gnaphalium gaudichaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24745 Salvia cavaleriei Species Lamiaceae 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 NPC24681 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 NPC24681 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