Ent-16beta-hydroxykauran-19-al - Compound Card

Ent-16beta-hydroxykauran-19-al

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Ent-16beta-hydroxykauran-19-al

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Kaurane Diterpene
Canonical Smiles O=C[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/C20H32O2/c1-17(13-21)8-4-9-18(2)15(17)7-10-20-11-14(5-6-16(18)20)19(3,22)12-20/h13-16,22H,4-12H2,1-3H3/t14-,15-,16+,17-,18-,19-,20+/m0/s1
InChIKey RXXOJGKRNHHLDL-UZEMSBSCSA-N
Formula C20H32O2
HBA 2
HBD 1
MW 304.47
Rotatable Bonds 1
TPSA 37.3
LogP 4.35
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 304.24
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: 22216258

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 304.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.18
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
65.03
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
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
17.37
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.59
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.18
Rat (Acute)
2.02
Rat (Chronic Oral)
1.22
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
370.79
Hydration Free Energy
-3.12
Log(D) at pH=7.4
4.32
Log(P)
3.98
Log S
-4.64
Log(Vapor Pressure)
-6.37
Melting Point
148.66
pKa Acid
10.26
pKa Basic
8.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8582
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7628
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7476
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7424
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7201
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7012
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7007

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