13,14,15-trihydroxylabd-7-ene - Compound Card

13,14,15-trihydroxylabd-7-ene

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13,14,15-trihydroxylabd-7-ene

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC[C@@H](C(CC[C@H]1C(=C)CCC2[C@]1(C)CCCC2(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/h15-17,21-23H,1,6-13H2,2-5H3/t15-,16?,17-,19+,20?/m0/s1
InChIKey JVDYHDMFSILONM-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-Compositae Plantae 71817
2 Madia capitata Asteraceae-Compositae Plantae 576756
3 Madia citrigracilis Asteraceae-Compositae Plantae 4253
4 Madia dissitiflora Asteraceae-Compositae Plantae 907201
5 Madia elegans Asteraceae-Compositae 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: 162879521
Nmrshiftdb2: 70054844

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 150.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
66.64
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
7.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.29
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.3
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
-0.33
Rat (Acute)
2.35
Rat (Chronic Oral)
2.1
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
379.22
Hydration Free Energy
-8.44
Log(D) at pH=7.4
3.35
Log(P)
3.92
Log S
-4.23
Log(Vapor Pressure)
-7.31
Melting Point
123.32
pKa Acid
10.75
pKa Basic
8.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8878
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8878
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8780
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8780
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8626
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8626
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8456
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8456
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7982
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7982
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7968
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7968
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7964
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7964
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7851
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7851
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7845
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7845
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7647
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7647
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7612
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7612
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7598
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7598
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7593
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7593
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7534
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7534
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7498
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7498
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7370
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7370
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7308
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7308
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7303
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7303
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7290
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7290
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7285
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7285
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7147
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7147
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7146
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7146
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7144
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7144
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7127
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7127
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7046
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7046
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7001
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7001

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