Bis-(5Z-7-oxo-caryophyllene)-14-O-ether - Compound Card

Bis-(5Z-7-oxo-caryophyllene)-14-O-ether

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Bis-(5Z-7-oxo-caryophyllene)-14-O-ether

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1CC/C=C(\C(=O)CC2[C@@H]1CC2(C)C)/COC/C/1=C/CCC(=C)[C@@H]2C(CC1=O)C(C2)(C)C
InChI InChI=1S/C30H42O3/c1-19-9-7-11-21(27(31)13-25-23(19)15-29(25,3)4)17-33-18-22-12-8-10-20(2)24-16-30(5,6)26(24)14-28(22)32/h11-12,23-26H,1-2,7-10,13-18H2,3-6H3/b21-11-,22-12-/t23-,24-,25?,26?/m1/s1
InChIKey DVMLAMKRQMRWRG-JIXLKCBHSA-N
Formula C30H42O3
HBA 3
HBD 0
MW 450.66
Rotatable Bonds 4
TPSA 43.37
LogP 6.8
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 450.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria arabica Asteraceae Plantae 119185

Showing of synonyms

  • Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
Pubchem: 162890868

No compound-protein relationship available.

Structure

SMILES: C=C1CCC=C(C(=O)CC(C12)CC2)COCC(C(=O)CC(C34)CC3)=CCCC4=C

Level: 1

Mol. Weight: 450.66 g/mol

Structure

SMILES: C=C1CCC=CC(=O)CC(C12)CC2

Level: 0

Mol. Weight: 450.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.92
Plasma Protein Binding
98.3
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
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
11.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.38
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.49
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.07
Micronucleos
Safe
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
Safe
T. Pyriformis
-65.52
Rat (Acute)
2.17
Rat (Chronic Oral)
1.96
Fathead Minnow
4.76
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
479.13
Hydration Free Energy
-3.26
Log(D) at pH=7.4
5.03
Log(P)
6.22
Log S
-6.04
Log(Vapor Pressure)
-7.7
Melting Point
92.25
pKa Acid
9.2
pKa Basic
3.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9460
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9460
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7922
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7922
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7574
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7574
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7354
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7354
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7251
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7251
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7236
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7236
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7124
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7124
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7003
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7003

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