Structure

Physi-Chem Properties

Molecular Weight:  338.1
Volume:  322.682
LogP:  0.652
LogD:  -0.11
LogS:  -1.295
# Rotatable Bonds:  5
TPSA:  144.52
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.37
Synthetic Accessibility Score:  3.743
Fsp3:  0.375
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:  -6.128
MDCK Permeability:  1.954993604158517e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.831
Human Intestinal Absorption (HIA):  0.57
20% Bioavailability (F20%):  0.506
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.284
Plasma Protein Binding (PPB):  79.11012268066406%
Volume Distribution (VD):  0.249
Pgp-substrate:  21.537612915039062%

ADMET: Metabolism

CYP1A2-inhibitor:  0.121
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.033
CYP2C9-substrate:  0.783
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.139
CYP3A4-inhibitor:  0.048
CYP3A4-substrate:  0.056

ADMET: Excretion

Clearance (CL):  1.749
Half-life (T1/2):  0.855

ADMET: Toxicity

hERG Blockers:  0.069
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.245
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.075
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.426
Carcinogencity:  0.278
Eye Corrosion:  0.004
Eye Irritation:  0.08
Respiratory Toxicity:  0.039

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General Info & Identifiers & Properties  
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  Natural Product: NPC282348

Natural Product ID:  NPC282348
Common Name*:   BMRSEYFENKXDIS-ZARITIHLSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BMRSEYFENKXDIS-ZARITIHLSA-N
Standard InCHI:  InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3-/t11-,12-,14+,16-/m1/s1
SMILES:  c1cc(ccc1/C=CC(=O)O[C@@H]1C[C@](C[C@H]([C@@H]1O)O)(C(=O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   92135690
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols and derivatives
            • [CHEMONTID:0002509] Cyclitols and derivatives
              • [CHEMONTID:0002512] Quinic acids and derivatives

*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
NPO8171 Artocarpus altilis Species Moraceae Eukaryota bud covers n.a. n.a. PMID[11975520]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. root n.a. PMID[12662107]
NPO5870 Xenia florida Species n.a. n.a. n.a. n.a. n.a. PMID[16643051]
NPO12386 Russula japonica Species Russulaceae Eukaryota fruiting body n.a. n.a. PMID[16989517]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[3839140]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[7684040]
NPO5870 Xenia florida Species n.a. n.a. n.a. n.a. n.a. PMID[9868153]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO7731 Lactuca serriola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2469 Erythrophleum couminga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7731 Lactuca serriola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2469 Erythrophleum couminga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2469 Erythrophleum couminga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10594 Centaurea solstitialis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12726 Piptostigma fugax Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12035 Rhododendron ungerni Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5380 Eucalyptus australiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20585 Urochloa decumbens Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16306 Curcuma caesia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12207 Lagochilus leiacanthus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13683 Cosmos diversifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14075 Streptomyces viridogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9342 Solenopsis punctaticeps Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10928 Xenia obscuronata Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO206 Ormosia nobilis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3059 Erythrina pallida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12386 Russula japonica Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2046 Cathormion altissimum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO875 Cryptocarya oblata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11046 Ocimum pilosum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2469 Erythrophleum couminga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12557 Strychnos tricalysioides Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5870 Xenia florida Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7608 Phelline lucida Species Phellinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1398 Trichodesma incanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7731 Lactuca serriola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13192 Chara ceratophylla Species Characeae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10892 Xanthorrhoea resinosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16013 Inga velutina 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 NPC282348 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 NPC282348 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