16-acetoxy-12(R),15-epoxy-15-hydroxylabda-8(17),13(16)-diene - Compound Card

16-acetoxy-12(R),15-epoxy-15-hydroxylabda-8(17),13(16)-diene

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16-acetoxy-12(R),15-epoxy-15-hydroxylabda-8(17),13(16)-diene

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Labdane Diterpenoid
Canonical Smiles CC(=O)O/C=C/1\C[C@H](O[C@H]1C[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CCCC2(C)C)O
InChI InChI=1S/C22H34O4/c1-14-7-8-19-21(3,4)9-6-10-22(19,5)17(14)12-18-16(11-20(24)26-18)13-25-15(2)23/h13,17-20,24H,1,6-12H2,2-5H3/b16-13+/t17-,18+,19-,20+,22+/m1/s1
InChIKey IOSDVPGBKLNUBH-IHBDHQCXSA-N
Formula C22H34O4
HBA 4
HBD 1
MW 362.51
Rotatable Bonds 3
TPSA 55.76
LogP 4.73
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 362.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Turraeanthus africanus Meliaceae Plantae 1672009

Showing of synonyms

  • Chenda LBN, Kouam SF, et al. (2014). Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus.. Phytochemistry,2014, 103, 137-144. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1COC(C1=C)CC2C(=C)CCC(C23)CCCC3

Level: 1

Mol. Weight: 362.51 g/mol

Structure

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 362.51 g/mol

Structure

SMILES: C=C1CCOC1

Level: 0

Mol. Weight: 362.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.06
Plasma Protein Binding
66.14
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
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
9.64
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.36
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
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
-4.48
Rat (Acute)
3.5
Rat (Chronic Oral)
1.75
Fathead Minnow
4.02
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
389.85
Hydration Free Energy
-4.39
Log(D) at pH=7.4
3.55
Log(P)
4.11
Log S
-5.06
Log(Vapor Pressure)
-6.69
Melting Point
101.72
pKa Acid
9.45
pKa Basic
5.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8565
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8460
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8356
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8329
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7900
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7827
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7767
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7699
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7553
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7512
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7398
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7258
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7237
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7158
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7057
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7022
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7020

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