Ent-3beta,7alpha,18-trihydroxykaur-16-ene - Compound Card

Ent-3beta,7alpha,18-trihydroxykaur-16-ene

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Ent-3beta,7alpha,18-trihydroxykaur-16-ene

Structure
Zoomed Structure
  • Family: Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@@]1(C)[C@H](O)CC[C@@]2(C1C[C@H](O)[C@]13C2CC[C@H](C1)C(=C)C3)C
InChI InChI=1S/C20H32O3/c1-12-9-20-10-13(12)4-5-14(20)18(2)7-6-16(22)19(3,11-21)15(18)8-17(20)23/h13-17,21-23H,1,4-11H2,2-3H3/t13-,14?,15?,16-,17+,18+,19-,20+/m1/s1
InChIKey ZHAIQJLGKAVXSD-JYDIYQMOSA-N
Formula C20H32O3
HBA 3
HBD 3
MW 320.47
Rotatable Bonds 1
TPSA 60.69
LogP 2.89
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 320.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sideritis moorei Lamiaceae Plantae 3394641

Showing of synonyms

  • Ghoumari H, Benajiba MH, et al. (2005). ent-Kauranoid derivatives from Sideritis moorei. Phytochemistry,2005,66(12),1492-1498. [View] [PubMed]
Pubchem: 162995958

No compound-protein relationship available.

Structure

SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 230.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
55.57
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.73
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
-2.0
Rat (Acute)
2.62
Rat (Chronic Oral)
2.03
Fathead Minnow
3.83
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
401.04
Hydration Free Energy
-7.14
Log(D) at pH=7.4
2.54
Log(P)
2.81
Log S
-3.48
Log(Vapor Pressure)
-7.76
Melting Point
184.79
pKa Acid
10.65
pKa Basic
8.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8462
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8462
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8262
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8262
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8259
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8259
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8008
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8008
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7923
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7923
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7905
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7905
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7518
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7478
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7478
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7472
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7472
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7463
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7463
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7402
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7402
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7388
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7253
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7088
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7088
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7078
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7078
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7075
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7075
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7016
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7016

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