Hirsein A - Compound Card

Hirsein A

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Hirsein A

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daphnane Diterpenoid
Canonical Smiles CCCCC/C=C/C12O[C@H]3[C@](O2)(C(=C)C)[C@@H]([C@H](C2(O1)[C@H]3[C@@H]1O[C@@]1([C@H]([C@]1([C@H]2C=C(C1=O)C)O)O)CO)C)OC(=O)/C=C/c1ccccc1
InChI InChI=1S/C37H44O10/c1-6-7-8-9-13-18-34-45-31-27-30-33(20-38,44-30)32(41)35(42)25(19-22(4)28(35)40)37(27,47-34)23(5)29(36(31,46-34)21(2)3)43-26(39)17-16-24-14-11-10-12-15-24/h10-19,23,25,27,29-32,38,41-42H,2,6-9,20H2,1,3-5H3/b17-16+,18-13+/t23-,25-,27+,29-,30+,31-,32-,33+,34?,35-,36+,37?/m1/s1
InChIKey SBKXRMYYKDQAMZ-PKXAVDEZSA-N
Formula C37H44O10
HBA 10
HBD 3
MW 648.75
Rotatable Bonds 10
TPSA 144.28
LogP 3.55
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 648.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea hirsuta Thymelaeaceae Plantae 69845

Showing of synonyms

  • Miyamae Y, Villareal MO, et al. (2009). Hirseins A and B, daphnane diterpenoids from Thymelaea hirsuta that inhibit melanogenesis in B16 melanoma cells. Journal of Natural Products,2009,72(5),938-941. [View] [PubMed]
Pubchem: 101477052
CPRiL: 233699
Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)C(OC(O3)O4)C3C5C(O6)C6CC(C7C245)C(=O)C=C7

Level: 1

Mol. Weight: 648.75 g/mol

Structure

SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6

Level: 0

Mol. Weight: 648.75 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 648.75 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.15
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
106.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
83.21
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.09
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.76
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-198493.08
Rat (Acute)
4.69
Rat (Chronic Oral)
3.47
Fathead Minnow
264.01
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
18320.54
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.69
Log(P)
5.59
Log S
-4.76
Log(Vapor Pressure)
-590.54
Melting Point
155.63
pKa Acid
3.38
pKa Basic
1.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7789
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7789
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7745
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7745
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7727
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7727
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7583
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7583
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7533
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7241
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7241
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7223
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7223
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7010
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7010

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