Verticillarone - Compound Card

Verticillarone

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Verticillarone

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C1C[C@H]2O[C@@]2(C)[C@@]23CC(=O)C(=C3C[C@](C(=O)C[C@H]1C(C)(C)C)(O2)C)C
InChI InChI=1S/C21H28O5/c1-11-13-9-19(5)16(24)7-12(18(2,3)4)14(22)8-17-20(6,25-17)21(13,26-19)10-15(11)23/h12,17H,7-10H2,1-6H3/t12-,17-,19-,20-,21+/m1/s1
InChIKey ZXWWGVBATVHPEG-YFRSSGQZSA-N
Formula C21H28O5
HBA 5
HBD 0
MW 360.45
Rotatable Bonds 0
TPSA 72.97
LogP 2.95
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 360.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypoestes foskalii Acanthaceae Plantae 13570

Showing of synonyms

  • Al Musayeib NM, Mothana RA, et al. (2014). Hypoestenonols A and B, new fusicoccane diterpenes from Hypoestes forskalei. Phytochemistry Letters,2014,10,23-27. [View]
Pubchem: 162960870
Nmrshiftdb2: 80014395

No compound-protein relationship available.

Structure

SMILES: C123C4C(O4)CC(=O)CCC(=O)C(O3)CC1=CC(=O)C2

Level: 0

Mol. Weight: 360.45 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
43.26
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
18.17
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.94
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-3.41
Rat (Acute)
2.68
Rat (Chronic Oral)
1.62
Fathead Minnow
3.99
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
419.23
Hydration Free Energy
-6.12
Log(D) at pH=7.4
2.22
Log(P)
2.38
Log S
-3.14
Log(Vapor Pressure)
-6.44
Melting Point
167.58
pKa Acid
4.46
pKa Basic
0.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8767
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8767
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7568
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7568
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7309
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7240
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7060
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7060
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7011
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7011

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