Structure

Physi-Chem Properties

Molecular Weight:  326.1
Volume:  308.023
LogP:  -0.043
LogD:  -0.51
LogS:  -1.058
# Rotatable Bonds:  5
TPSA:  136.68
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.341
Synthetic Accessibility Score:  3.633
Fsp3:  0.4
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:  -6.203
MDCK Permeability:  9.20655220397748e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.861
20% Bioavailability (F20%):  0.045
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.197
Plasma Protein Binding (PPB):  83.88365173339844%
Volume Distribution (VD):  0.283
Pgp-substrate:  16.393259048461914%

ADMET: Metabolism

CYP1A2-inhibitor:  0.15
CYP1A2-substrate:  0.027
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  1.362
Half-life (T1/2):  0.806

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.857
Drug-inuced Liver Injury (DILI):  0.961
AMES Toxicity:  0.436
Rat Oral Acute Toxicity:  0.043
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.524
Carcinogencity:  0.031
Eye Corrosion:  0.004
Eye Irritation:  0.26
Respiratory Toxicity:  0.013

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

  Natural Product: NPC258236

Natural Product ID:  NPC258236
Common Name*:   IFJZNZBKGRGNSP-HOCDIANWSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  IFJZNZBKGRGNSP-HOCDIANWSA-N
Standard InCHI:  InChI=1S/C15H18O8/c16-7-10-11(17)12(18)13(19)15(23-10)22-9(14(20)21)6-8-4-2-1-3-5-8/h1-6,10-13,15-19H,7H2,(H,20,21)/p-1/b9-6-/t10-,11-,12+,13-,15-/m1/s1
SMILES:  c1ccc(cc1)/C=C(/C(=O)[O-])O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   53385591
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001766] Fatty acyl glycosides
          • [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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]
NPO27025 Erylus trisphaerus Species Geodiidae Eukaryota n.a. Dominican n.a. PMID[12713417]
NPO27007 Cunonia macrophylla Species Cunoniaceae Eukaryota n.a. New Caledonia n.a. PMID[15652581]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. PMID[16499326]
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]
NPO27576 Lysiana subfalcata Species Loranthaceae Eukaryota n.a. n.a. n.a. PMID[18222087]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[1955887]
NPO19202 Phaeolus schweinitzii Species Hymenochaetaceae Eukaryota fruits Tibetan Plateau n.a. PMID[23869482]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[2878063]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[3839140]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7130988]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota bark n.a. n.a. PMID[7623034]
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 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]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
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]
NPO27640 Sorbus tianschanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27675 Platycarya strobilacea Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27237 Aucuba chinensis Species Garryaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27007 Cunonia macrophylla Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27376 Curculigo pilosa Species Hypoxidaceae 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[HerDing]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27640 Sorbus tianschanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27376 Curculigo pilosa Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27612 Peperomia vulcanica Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2469 Erythrophleum couminga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7731 Lactuca serriola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27840 Stephania elegans Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27675 Platycarya strobilacea Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9698 Parablechnum minus Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27007 Cunonia macrophylla Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30034 Onobrychis vicllfolia Species Fabaceae 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]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27675 Platycarya strobilacea Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27640 Sorbus tianschanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27215 Gracilaria textorii Species Gracilariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27712 Helichrysum mixtum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19202 Phaeolus schweinitzii Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22520 Felimida luteorosea Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5380 Eucalyptus australiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16013 Inga velutina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27800 Usnea undulata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27440 Osteospermum muricatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10928 Xenia obscuronata Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9342 Solenopsis punctaticeps Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27732 Cynometra lujae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19173 Gleditsia caspica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27237 Aucuba chinensis Species Garryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29217 Brickellia vernicosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27597 Haplophyllum ramosissimum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3059 Erythrina pallida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27254 Utricularia australis Species Lentibulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14449 Cedronella canariensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27312 Citrus tangerina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27274 Amsinckia tessellata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO206 Ormosia nobilis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27345 Crocus minimus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12726 Piptostigma fugax Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27761 Aspalathus linearis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27394 Sideritis euboea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6917 Kali turgidum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15868 0stoc spongiaeforme Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27612 Peperomia vulcanica Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27788 Eupatorium areolare Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27290 Carica dodecaphylla Species Caricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26969 Sagittaria sagittifolia Species Alismataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12035 Rhododendron ungerni Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2046 Cathormion altissimum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27419 Aurelia aurita Species Ulmaridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18100 Physalis edulis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29241 Macaranga peltata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14274 Rhododendron mucronatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26882 Swertia swertopsis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27495 Sisyrinchium californicum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO875 Cryptocarya oblata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27675 Platycarya strobilacea Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27025 Erylus trisphaerus Species Geodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20585 Urochloa decumbens Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8171 Artocarpus altilis Species Moraceae 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]
NPO12386 Russula japonica Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27815 Sia ferox Species Stenopelmatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16306 Curcuma caesia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27453 Trichoderma koningi Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27007 Cunonia macrophylla Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27076 Aspergillus mutabilis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11046 Ocimum pilosum Species Lamiaceae 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]
NPO10892 Xanthorrhoea resinosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7608 Phelline lucida Species Phellinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26912 Premna tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27099 Virgilia divaricata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14075 Streptomyces viridogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15795 Humata pectinata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27525 Saussurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7731 Lactuca serriola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27576 Lysiana subfalcata Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27376 Curculigo pilosa Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27640 Sorbus tianschanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9698 Parablechnum minus Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10594 Centaurea solstitialis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1398 Trichodesma incanum Species Boraginaceae 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]
NPO27696 Anolis lineatopus Species Iguanidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27470 Centaurea huber-morathii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25349 Bistorta vivipara Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13192 Chara ceratophylla Species Characeae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27840 Stephania elegans Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27050 Tsuga chinensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27138 Entada rheedei 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 NPC258236 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 NPC258236 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