8-O-cinnamoylgraciline - Compound Card

8-O-cinnamoylgraciline

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8-O-cinnamoylgraciline

Structure
Zoomed Structure
  • Family: Plantae - Ranunculaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Diterpernoid Alkaloid
Canonical Smiles CCN1[C@H]2OC3[C@]45C1[C@](O)(CC4[C@@]2(C)CC3)[C@@]1(C2C5C[C@@H]([C@@H]2OC(=O)/C=C\c2ccccc2)CC1)O
InChI InChI=1S/C30H37NO5/c1-3-31-25-29(34)16-20-27(2)13-12-21(35-26(27)31)30(20,25)19-15-18-11-14-28(29,33)23(19)24(18)36-22(32)10-9-17-7-5-4-6-8-17/h4-10,18-21,23-26,33-34H,3,11-16H2,1-2H3/b10-9-/t18-,19?,20?,21?,23?,24-,25?,26-,27+,28+,29+,30+/m0/s1
InChIKey OWNAHFPYWRUSLG-OPDIYQCCSA-N
Formula C30H37NO5
HBA 6
HBD 2
MW 491.63
Rotatable Bonds 4
TPSA 79.23
LogP 3.37
Number Rings 10
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 491.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Delphinium cossonianum Ranunculaceae Plantae 984875

Showing of synonyms

  • De La Fuente G, Gavin JA, et al. (1993). Three diterpenoid alkaloids from delphinium cossonianum. Phytochemistry,1993,34(2),553-558. [View]
Pubchem: 162889851

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(C3)CCC(C2C3C456)C7C4NC8C(C5C7)CCC6O8

Level: 1

Mol. Weight: 491.63 g/mol

Structure

SMILES: C1C(C2)CCC(C2C1C345)C6C3NC7C(C4C6)CCC5O7

Level: 0

Mol. Weight: 491.63 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 491.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
77.38
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.85
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.32
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.94
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1807.68
Rat (Acute)
3.78
Rat (Chronic Oral)
2.5
Fathead Minnow
7.42
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
450.65
Hydration Free Energy
-2.81
Log(D) at pH=7.4
3.73
Log(P)
4.52
Log S
-4.54
Log(Vapor Pressure)
-9.9
Melting Point
191.72
pKa Acid
6.06
pKa Basic
6.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8345
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8345
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.8020
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.8020
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7759
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7759
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7534
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7534
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7420
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7420
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7334
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7334
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7288
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7288
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7272
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7272
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7244
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7244
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7178
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7178
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7147
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7147
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7110
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7110
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7090
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7090
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7073
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7073
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7073
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7073
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7022
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7022

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