(-)-6alpha-hydroxy-5alpha,8alpha,9alpha,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid - Compound Card

(-)-6alpha-hydroxy-5alpha,8alpha,9alpha,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid

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(-)-6alpha-hydroxy-5alpha,8alpha,9alpha,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Sapindaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Clerodane Diterpenoid
Canonical Smiles OC(=O)C1=CCCC2[C@@]1(C)[C@@H](O)C[C@H]([C@]2(C)CCC1=CCOC1=O)C
InChI InChI=1S/C20H28O5/c1-12-11-16(21)20(3)14(17(22)23)5-4-6-15(20)19(12,2)9-7-13-8-10-25-18(13)24/h5,8,12,15-16,21H,4,6-7,9-11H2,1-3H3,(H,22,23)/t12-,15?,16+,19+,20+/m1/s1
InChIKey VIZZFMPBFLWOFS-VJXOHGMASA-N
Formula C20H28O5
HBA 4
HBD 2
MW 348.44
Rotatable Bonds 4
TPSA 83.83
LogP 3.08
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 348.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dodonaea viscosa Sapindaceae Plantae 151065

Showing of synonyms

  • Mostafa AE, El-Hela AA, et al. (2014). New secondary metabolites from Dodonaea viscosa. Phytochemistry Letters,2014,8,10-15. [View]
Pubchem: 162982335
Nmrshiftdb2: 70062568

No compound-protein relationship available.

Structure

SMILES: O=C1OCC=C1CCC(CCC2)C(C23)CCC=C3

Level: 1

Mol. Weight: 348.44 g/mol

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 348.44 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 348.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
63.06
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.7
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.18
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.08
Rat (Acute)
2.09
Rat (Chronic Oral)
1.95
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.77
Hydration Free Energy
-6.59
Log(D) at pH=7.4
0.16
Log(P)
2.6
Log S
-4.04
Log(Vapor Pressure)
-8.44
Melting Point
176.52
pKa Acid
3.19
pKa Basic
6.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8545
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8545
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8090
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8090
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7942
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7942
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 4 0.7858
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 4 0.7858
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7632
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7632
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7603
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7603
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7578
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7578
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7474
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7474
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7452
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7452
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7395
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7395
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7311
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7311
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7292
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7292
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7223
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7223
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7173
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7173
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7143
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7143
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7099
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7053
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7053

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