Structure

Physi-Chem Properties

Molecular Weight:  374.12
Volume:  339.616
LogP:  -1.54
LogD:  -0.348
LogS:  -0.555
# Rotatable Bonds:  5
TPSA:  166.14
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.288
Synthetic Accessibility Score:  4.675
Fsp3:  0.688
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:  -6.208
MDCK Permeability:  0.0001269396161660552
Pgp-inhibitor:  0.0
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.846
20% Bioavailability (F20%):  0.861
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.248
Plasma Protein Binding (PPB):  28.28606414794922%
Volume Distribution (VD):  0.287
Pgp-substrate:  57.26707077026367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.041
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.087
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.038

ADMET: Excretion

Clearance (CL):  1.456
Half-life (T1/2):  0.906

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.351
Maximum Recommended Daily Dose:  0.044
Skin Sensitization:  0.116
Carcinogencity:  0.865
Eye Corrosion:  0.003
Eye Irritation:  0.112
Respiratory Toxicity:  0.031

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  Natural Product: NPC47182

Natural Product ID:  NPC47182
Common Name*:   ZJDOESGVOWAULF-CCSCWUBBSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZJDOESGVOWAULF-CCSCWUBBSA-N
Standard InCHI:  InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9+,10-,11+,12-,13+,15+,16-/m0/s1
SMILES:  C1=C(CO)[C@H]2[C@@H](C1)C(=CO[C@@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   129362042
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11858748]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1367520]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15974609]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[19093848]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21381678]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22118684]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[24840014]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26692349]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[31180680]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33089690]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8626236]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8556 Eucalyptus kitsoniana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21851 Chaetomella raphigera Species Chaetomellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10527 Cyathula tomentosa Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26381 Bombus pascuorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22101 Himantoglossum hircinum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15513 Pseudocyphellaria rubella Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13225 Spergula japonica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15806 Rhododendron campylocarpum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO255 Solanum pseudopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26951 Gymnopus androsaceus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1777 Toddalia aculeata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29322 Rhodanthe maryonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9299.3 Hordeum vulgare var. distichon Varieties Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28240 0tholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11243 Exochorda giraldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15718 Lindera sericea Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15621 Lethasterias fusca Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13460 Asphodeline damascena Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2667 Acacia lasiopetala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27134 Euphrasia rubra Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9917 Plagiomnium cuspidatum Species Mniaceae 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 NPC47182 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 NPC47182 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