Structure

Physi-Chem Properties

Molecular Weight:  279.08
Volume:  249.934
LogP:  -0.467
LogD:  -1.101
LogS:  -0.568
# Rotatable Bonds:  5
TPSA:  122.74
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.145
Synthetic Accessibility Score:  4.511
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.676
MDCK Permeability:  2.8773454687325284e-05
Pgp-inhibitor:  0.202
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.875
20% Bioavailability (F20%):  0.273
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.185
Plasma Protein Binding (PPB):  57.61868667602539%
Volume Distribution (VD):  0.55
Pgp-substrate:  42.18859100341797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.032
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.243
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.121
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.029

ADMET: Excretion

Clearance (CL):  1.483
Half-life (T1/2):  0.895

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.105
Drug-inuced Liver Injury (DILI):  0.37
AMES Toxicity:  0.243
Rat Oral Acute Toxicity:  0.152
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.111
Carcinogencity:  0.684
Eye Corrosion:  0.004
Eye Irritation:  0.078
Respiratory Toxicity:  0.197

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  Natural Product: NPC294419

Natural Product ID:  NPC294419
Common Name*:   ULXVHDBQEPWLDR-PPUWAGDWSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ULXVHDBQEPWLDR-PPUWAGDWSA-N
Standard InCHI:  InChI=1S/C21H28O6/c1-20-8-16(23)15(22)7-12(20)4-5-13-14(20)6-3-11-9-25-21(2)18(11)17(10-26-21)27-19(13)24/h4,9,13-18,22-23H,3,5-8,10H2,1-2H3/t13-,14+,15+,16+,17+,18+,20-,21-/m0/s1
SMILES:  C[C@]12C[C@H]([C@@H](CC1=CC[C@H]1[C@H]2CCC2=CO[C@]3(C)[C@H]2[C@@H](CO3)OC1=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001816] Furofurans

*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
NPO27831 Phakellia flabellata Species Bubaridae Eukaryota n.a. n.a. n.a. DOI[10.1021/jo00445a028]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota Roots n.a. n.a. PMID[11374953]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15056914]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15270557]
NPO27850 Trichilia catigua Species Meliaceae Eukaryota n.a. bark n.a. PMID[18020420]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[19948405]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20415462]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. seed n.a. PMID[23672042]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24024763]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28176 Russula lepida Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28507 Hymenoxys grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27850 Trichilia catigua Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28494 Hydroclathrus tenuis Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28214 Phyllosticta cirsii Species Phyllostictaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9245 Ventilago madraspatana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28333 Syzygium levinei Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28316 Scandix pecten-veneris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28651 Othonna tagetes Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28479 Campanula hypopolia Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28158 Polygala fruticosa Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28300 Sorbaria arborea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29373 Trichoplusia ni Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28197 Huperzia selago Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28443 Larix lyallii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28461 Crepis czerepanovii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28525 Urginea riparia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29042 Vincetoxicum atratum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27918 Pterocarpus macrocarpus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28404 Chasmanthera dependens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28611 Phragmatobia fuliginosa Species Erebidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28228 Kielmeyera rubriflora Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28176 Russula lepida Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28668 Agave cocui Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27956 Eupatoriastrum nelsonii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27973 Simaba cuneata Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28543 Alcyonium coralloides Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25330 Maackia floribunda Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28372 Corydalis pallida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27906 Philadelphus coronarius Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10135 Tripteris microcarpa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28050 Thalictrum podocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28507 Hymenoxys grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11786 Cylindropuntia leptocaulis Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28282 Turbina corymbosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28593 Pteris pedata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27891 Lethariella sinensis Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27938 Meliosma wightii Species Sabiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28071 Dendrobates auratus Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28009 Pellina semitubulosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28425 Senecio miser Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27831 Phakellia flabellata Species Bubaridae 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 NPC294419 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 NPC294419 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