13,14,15- trihydroxylabd-8,17-ene - Compound Card

13,14,15- trihydroxylabd-8,17-ene

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13,14,15- trihydroxylabd-8,17-ene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@@H](C(CC[C@H]1C(=CCC2[C@]1(C)CCCC2(C)C)C)(O)C)O
InChI InChI=1S/C20H36O3/c1-14-7-8-16-18(2,3)10-6-11-19(16,4)15(14)9-12-20(5,23)17(22)13-21/h7,15-17,21-23H,6,8-13H2,1-5H3/t15-,16?,17-,19+,20?/m0/s1
InChIKey WWUAKADIANYYEA-BFGUNEOZSA-N
Formula C20H36O3
HBA 3
HBD 3
MW 324.5
Rotatable Bonds 5
TPSA 60.69
LogP 3.67
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 324.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Madia anomala Asteraceae Plantae 71817
2 Madia capitata Asteraceae Plantae 576756
3 Madia citrigracilis Asteraceae Plantae 4253
4 Madia dissitiflora Asteraceae Plantae 907201
5 Madia elegans Asteraceae Plantae 4255

Showing of synonyms

  • Wollenweber E, Dörr M, et al. (2003). Flavonoids and terpenoids from the resinous exudates of Madia species (Asteraceae, Helenieae). Zeitschrift fur Naturforschung C,2003,58,153-160. [View] [PubMed]
Pubchem: 162962549

No compound-protein relationship available.

Structure

SMILES: C1C=CCC(C12)CCCC2

Level: 0

Mol. Weight: 324.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
63.12
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
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
7.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.45
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
-0.53
Rat (Acute)
1.79
Rat (Chronic Oral)
1.98
Fathead Minnow
3.78
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
382.47
Hydration Free Energy
-9.01
Log(D) at pH=7.4
3.53
Log(P)
4.55
Log S
-4.16
Log(Vapor Pressure)
-7.01
Melting Point
119.72
pKa Acid
11.04
pKa Basic
8.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9386
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9386
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8396
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8396
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7985
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7985
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7950
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7950
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7861
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7861
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7762
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7762
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7757
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7757
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7737
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7737
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7612
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7612
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7597
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7597
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7594
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7594
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7532
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7532
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7527
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7466
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7466
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7387
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7387
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7359
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7359
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7190
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7190
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7043
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7043

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