2-acetoxy-7alpha-hydroxy-14-methoxy-5E-caryophyllene - Compound Card

2-acetoxy-7alpha-hydroxy-14-methoxy-5E-caryophyllene

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2-acetoxy-7alpha-hydroxy-14-methoxy-5E-caryophyllene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C[C@]1(COC(=O)C)C[C@H]2C1C[C@@H](O)/C(=C\CCC2=C)/CO
InChI InChI=1S/C17H26O4/c1-11-5-4-6-13(9-18)16(20)7-15-14(11)8-17(15,3)10-21-12(2)19/h6,14-16,18,20H,1,4-5,7-10H2,2-3H3/b13-6-/t14-,15?,16-,17-/m1/s1
InChIKey PKCXBKBMBZLMJG-JLXWBXQLSA-N
Formula C17H26O4
HBA 4
HBD 2
MW 294.39
Rotatable Bonds 3
TPSA 66.76
LogP 2.21
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 294.18
Number of Lipinski Rule Violations 0
# 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: 163042627

No compound-protein relationship available.

Structure

SMILES: C=C1CCC=CCCC(C12)CC2

Level: 0

Mol. Weight: 294.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.35
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
46.5
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.55
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
-0.88
Rat (Acute)
3.01
Rat (Chronic Oral)
2.01
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
353.46
Hydration Free Energy
-8.48
Log(D) at pH=7.4
1.66
Log(P)
2.1
Log S
-2.88
Log(Vapor Pressure)
-6.21
Melting Point
101.91
pKa Acid
9.26
pKa Basic
5.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8973
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8973
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8619
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8619
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8210
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8210
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8152
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8152
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8151
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8151
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8004
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8004
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7943
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7943
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7799
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7799
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7605
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7605
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7283
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7283
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7197
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7197
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7192
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7192
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7191
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7191
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7162
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7162
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7161
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7161
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7158
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7158
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7130
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7130
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7120
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7120
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7092
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7092

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