(+)-strigol - Compound Card

(+)-strigol

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(+)-strigol

Structure
Zoomed Structure
  • Family: Plantae - Menispermaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Strigolactone
Canonical Smiles O=C1O[C@H]2[C@@H](/C/1=C\O[C@@H]1OC(=O)C(=C1)C)CC1=C2C(C)(C)CC[C@@H]1O
InChI InChI=1S/C19H22O6/c1-9-6-14(24-17(9)21)23-8-12-10-7-11-13(20)4-5-19(2,3)15(11)16(10)25-18(12)22/h6,8,10,13-14,16,20H,4-5,7H2,1-3H3/b12-8+/t10-,13+,14-,16+/m1/s1
InChIKey VOFXXOPWCBSPAA-KCNJUGRMSA-N
Formula C19H22O6
HBA 6
HBD 1
MW 346.38
Rotatable Bonds 2
TPSA 82.06
LogP 2.14
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 346.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Menispermum dauricum Menispermaceae Plantae 49683

Showing of synonyms

  • Yasuda N, Sugimoto Y, et al. (2003). (+)-Strigol, a witchweed seed germination stimulant, from Menispermum dauricum root culture. Phytochemistry,2003,62(7),1115-1119. [View] [PubMed]
Pubchem: 5281396
Kegg Ligand: C09190
Chebi: 9290
Nmrshiftdb2: 60075240
Bindingdb: 50510028

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(O1)OC=C2C(=O)OC3C2CC(=C34)CCCC4

Level: 1

Mol. Weight: 346.38 g/mol

Structure

SMILES: C=C1C(=O)OC2C1CC(=C23)CCCC3

Level: 0

Mol. Weight: 346.38 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 346.38 g/mol

Germination stimulant

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
43.37
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.29
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
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
4.94
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
-4.04
Rat (Acute)
2.71
Rat (Chronic Oral)
2.1
Fathead Minnow
4.31
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
399.25
Hydration Free Energy
-5.84
Log(D) at pH=7.4
2.13
Log(P)
1.48
Log S
-4.34
Log(Vapor Pressure)
-6.83
Melting Point
182.04
pKa Acid
7.05
pKa Basic
5.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7906
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7906
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7583
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7583
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7477
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7477

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