Ent-16beta-hydroxykauran-19-oic acid - Compound Card

Ent-16beta-hydroxykauran-19-oic acid

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Ent-16beta-hydroxykauran-19-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Kaurane Diterpene
Canonical Smiles OC(=O)[C@]1(C)CCC[C@]2([C@H]1CC[C@@]13[C@@H]2CC[C@@H](C1)[C@@](C3)(C)O)C
InChI InChI=1S/C20H32O3/c1-17-8-4-9-18(2,16(21)22)14(17)7-10-20-11-13(5-6-15(17)20)19(3,23)12-20/h13-15,23H,4-12H2,1-3H3,(H,21,22)/t13-,14+,15+,17-,18+,19-,20+/m0/s1
InChIKey XJSSRXITQUJZLO-REWVTSRDSA-N
Formula C20H32O3
HBA 2
HBD 2
MW 320.47
Rotatable Bonds 1
TPSA 57.53
LogP 4.23
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 320.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zanthoxylum leprieurii Rutaceae Plantae 992815

Showing of synonyms

  • Guetchueng ST, Nahar L, et al. (2017). Kaurane diterpenes from the fruits of Zanthoxylum leprieurii (Rutaceae). Rec. Nat. Prod., (2017), 11(3) 304-309. [View]
Pubchem: 21123960

No compound-protein relationship available.

Structure

SMILES: C1CC(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 320.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
78.3
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
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
4.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.38
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.35
Rat (Acute)
2.21
Rat (Chronic Oral)
1.89
Fathead Minnow
3.87
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
392.4
Hydration Free Energy
-3.59
Log(D) at pH=7.4
1.9
Log(P)
3.61
Log S
-4.84
Log(Vapor Pressure)
-7.48
Melting Point
216.34
pKa Acid
4.77
pKa Basic
8.94
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 0.8829
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8761
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8020
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7995
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7631
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7438
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7359

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