28-nor-4alpha-carbomethoxy-11beta-hydroxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1,7-diacetate - Compound Card

28-nor-4alpha-carbomethoxy-11beta-hydroxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1,7-diacetate

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28-nor-4alpha-carbomethoxy-11beta-hydroxy-12alpha-(2-methylbutanoyloxy)-14,15-deoxyhavanensin-1,7-diacetate

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles CCC(C(=O)O[C@H]1[C@H](O)C2[C@@](C3[C@]1(C)[C@@H](CC3)c1ccoc1)(C)[C@H](O)CC1[C@]2(C)[C@@H](OC(=O)C)C[C@H]([C@@]1(C)OC(=O)C)O)C
InChI InChI=1S/C34H50O10/c1-9-17(2)30(40)43-29-27(39)28-32(6,22-11-10-21(31(22,29)5)20-12-13-41-16-20)24(37)14-23-33(28,7)26(42-18(3)35)15-25(38)34(23,8)44-19(4)36/h12-13,16-17,21-29,37-39H,9-11,14-15H2,1-8H3/t17?,21-,22?,23?,24+,25+,26-,27+,28?,29-,31-,32+,33+,34-/m0/s1
InChIKey IJJOHFFGAGRTSP-OUNGKZOHSA-N
Formula C34H50O10
HBA 10
HBD 3
MW 618.76
Rotatable Bonds 6
TPSA 152.73
LogP 4.14
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 618.34
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea floribunda Meliaceae Plantae 992802

Showing of synonyms

  • Torto B, Bentley MD, et al. (1995). Limonoids from Turraea floribunda.. Phytochemistry,1995,40(1),239-243. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1occc1C2CCC(C23)C4C(CC3)C5C(CC4)CCCC5

Level: 1

Mol. Weight: 618.76 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 618.76 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 618.76 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.27
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
7.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
88.21
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.77
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.1
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.42
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-18392.92
Rat (Acute)
5.28
Rat (Chronic Oral)
2.58
Fathead Minnow
39.9
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
255.8
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.38
Log(P)
4.26
Log S
-4.6
Log(Vapor Pressure)
-11.04
Melting Point
175.64
pKa Acid
7.35
pKa Basic
3.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8857
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8857
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7935
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7626
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7626
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7604
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7604
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7482
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7482
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7328
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7328
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7169
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7169
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7058
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7058
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7042
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7042

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