Yuanhuandine - Compound Card

Yuanhuandine

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Yuanhuandine

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daphnane Diterpene Ester
Canonical Smiles CCCCC/C=C/C=C/[C@@]12O[C@H]3[C@](O1)(C(=C)C)[C@@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)OC(=O)C
InChI InChI=1S/C32H42O10/c1-7-8-9-10-11-12-13-14-29-40-26-22-25-28(16-33,39-25)27(36)30(37)21(15-18(4)23(30)35)32(22,42-29)19(5)24(38-20(6)34)31(26,41-29)17(2)3/h11-15,19,21-22,24-27,33,36-37H,2,7-10,16H2,1,3-6H3/b12-11+,14-13+/t19-,21-,22+,24-,25+,26-,27-,28+,29-,30-,31+,32+/m1/s1
InChIKey NHELFTYSELEEFD-SVAWBNMMSA-N
Formula C32H42O10
HBA 10
HBD 3
MW 586.68
Rotatable Bonds 9
TPSA 144.28
LogP 2.41
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 586.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Synaptolepis kirkii Thymelaeaceae Plantae 2896602
2 Synaptolepis kirkii Thymelaeaceae Plantae 2896602

Showing of synonyms

  • He W, Cik M, et al. (2002). Neurotrophic and antileukemic daphnane diterpenoids from Synaptolepis kirkii. Bioorganic and Medicinal Chemistry,2002,10(10),3245-3255. [View] [PubMed]
  • He W, De Kimpe N. (2000). Study of biological active principles from Kenyan medicinal plants. PhD Thesis, University of Ghent, Belgium, 2000-2001. [View]
Pubchem: 6440572
Chebi: 69565
Metabolights: MTBLC69565
CPRiL: 106418
Structure

SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6

Level: 0

Mol. Weight: 586.68 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.78
Plasma Protein Binding
71.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.24
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.14
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-11836.07
Rat (Acute)
4.83
Rat (Chronic Oral)
3.06
Fathead Minnow
29.98
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
297.61
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.74
Log(P)
4.04
Log S
-4.36
Log(Vapor Pressure)
-12.34
Melting Point
144.88
pKa Acid
4.11
pKa Basic
1.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7682
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7682
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7137
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7137
Glycolate oxidase P05414 GOX_SPIOL Spinacia oleracea 3 0.7036
Glycolate oxidase P05414 GOX_SPIOL Spinacia oleracea 3 0.7036

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