13,14,15,16-tetranorlabdane-8alpha,12,14-triol - Compound Card

13,14,15,16-tetranorlabdane-8alpha,12,14-triol

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13,14,15,16-tetranorlabdane-8alpha,12,14-triol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OCC[C@H]1[C@](C)(O)CCC2[C@]1(C)CCC[C@@]2(C)CO
InChI InChI=1S/C16H30O3/c1-14(11-18)7-4-8-15(2)12(14)5-9-16(3,19)13(15)6-10-17/h12-13,17-19H,4-11H2,1-3H3/t12?,13-,14+,15+,16-/m1/s1
InChIKey OSLJXGPVHCLGHU-WGXCOWCCSA-N
Formula C16H30O3
HBA 3
HBD 3
MW 270.41
Rotatable Bonds 3
TPSA 60.69
LogP 2.33
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 270.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crassocephalum mannii Asteraceae Plantae 189252

Showing of synonyms

  • Hegazy MEF, Ohta S, et al. (2008). Cyclooxygenase (COX)-1 and -2 Inhibitory Labdane Diterpenes from Crassocephalum mannii. Journal of Natural Products,2008,71,1070-1073. [View] [PubMed]
Pubchem: 162944601
Nmrshiftdb2: 70121414

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 270.41 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.320
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.430
Plasma Protein Binding
48.87
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
15.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.380
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.310
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.680
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-2.450
Rat (Acute)
1.750
Rat (Chronic Oral)
1.910
Fathead Minnow
3.530
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
344.740
Hydration Free Energy
-6.980
Log(D) at pH=7.4
1.550
Log(P)
1.98
Log S
-2.38
Log(Vapor Pressure)
-5.95
Melting Point
126.88
pKa Acid
10.84
pKa Basic
8.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8593
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8593
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8429
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8429
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8199
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8199
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8117
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8117
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8077
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8077
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7961
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7961
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7808
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7808
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7800
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7800
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7592
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7592
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7587
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7587
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7312
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7312
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7266
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7266
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7098
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7098
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7066
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7066

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