3-alpha-hydroxycativic acid methyl esther - Compound Card

3-alpha-hydroxycativic acid methyl esther

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3-alpha-hydroxycativic acid methyl esther

Structure
Zoomed Structure
  • Family: Plantae - Eupatorieae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Labdane Diterpenoid
Canonical Smiles COC(=O)C[C@H](CC[C@H]1C(=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C
InChI InChI=1S/C21H36O3/c1-14(13-19(23)24-6)7-9-16-15(2)8-10-17-20(3,4)18(22)11-12-21(16,17)5/h8,14,16-18,22H,7,9-13H2,1-6H3/t14-,16-,17-,18+,21+/m0/s1
InChIKey POYDSQYENWJRER-MOMZRRJVSA-N
Formula C21H36O3
HBA 3
HBD 1
MW 336.52
Rotatable Bonds 5
TPSA 46.53
LogP 4.74
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 336.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brickellia vernicosa Eupatorieae Plantae 1550870

Showing of synonyms

  • Ahmed AA, Gage DA, et al. (1986). Labdane diterpenes from Brickellia vernicosa. Phytochemistry,1986,25(6),1385-1388. [View]
Pubchem: 163090413
Nmrshiftdb2: 70056717

No compound-protein relationship available.

Structure

SMILES: C1C=CCC(C12)CCCC2

Level: 0

Mol. Weight: 336.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.430
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
67.97
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.490
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
-2.760
Rat (Acute)
1.770
Rat (Chronic Oral)
1.760
Fathead Minnow
3.920
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
377.840
Hydration Free Energy
-3.310
Log(D) at pH=7.4
4.620
Log(P)
5.8
Log S
-5.19
Log(Vapor Pressure)
-5.65
Melting Point
71.0
pKa Acid
11.94
pKa Basic
6.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8627
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8627
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8451
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8451
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8372
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8372
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8341
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8341
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8142
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8142
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7914
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7914
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7913
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7913
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7868
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7868
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7816
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7816
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7801
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7801
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7631
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7631
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7572
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7572
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7532
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7532
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7532
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7532
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7525
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7525
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7494
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7494
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7491
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7491
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7412
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7412
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7380
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7380
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7371
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7371
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7289
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7289
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7237
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7237
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7201
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7201
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7166
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7166
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7158
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7158
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7153
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7153
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7125
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7125
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7098
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7098
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7074
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7074
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7054
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7054
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7038
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7038
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7028
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7028

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