Methyl-6-acetoxy-9-hydroxy-1(10)E,7Z-alpha-humulene-15-oate - Compound Card

Methyl-6-acetoxy-9-hydroxy-1(10)E,7Z-alpha-humulene-15-oate

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Methyl-6-acetoxy-9-hydroxy-1(10)E,7Z-alpha-humulene-15-oate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)/C/1=C/[C@H](OC(=O)C)C(C)(C)/C=C\C(/C(=C/CC1)/C)O
InChI InChI=1S/C18H26O5/c1-12-7-6-8-14(17(21)22-5)11-16(23-13(2)19)18(3,4)10-9-15(12)20/h7,9-11,15-16,20H,6,8H2,1-5H3/b10-9-,12-7+,14-11+/t15?,16-/m0/s1
InChIKey PBHMEHISJHZTGB-DHQLSRFDSA-N
Formula C18H26O5
HBA 5
HBD 1
MW 322.4
Rotatable Bonds 2
TPSA 72.83
LogP 2.7
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 322.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Asteriscus graveolens Asteraceae Plantae 73976

Showing of synonyms

  • El Dahmy S, Jakupovic J, et al. (1985). New humulene derivatives from Asteriscus graveolens.. Tetrahedron,1985,41(2),309-316. [View]
Pubchem: 162817338
Nmrshiftdb2: 70005340

No compound-protein relationship available.

Structure

SMILES: C1=CCCC=CCCC=CC1

Level: 0

Mol. Weight: 322.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.370
Plasma Protein Binding
43.52
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
6.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.460
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.810
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
1.830
Rat (Acute)
2.250
Rat (Chronic Oral)
1.910
Fathead Minnow
4.560
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
335.290
Hydration Free Energy
-8.830
Log(D) at pH=7.4
2.090
Log(P)
3.04
Log S
-2.88
Log(Vapor Pressure)
-5.4
Melting Point
83.82
pKa Acid
9.12
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7767
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7767
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7706
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7706
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7451
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7451
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7269
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7269
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7084
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7084
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7009
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7009

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