(1R*,ZR*,3E,7R*.8E,llR*,l2S*)-3.8-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside - Compound Card

(1R*,ZR*,3E,7R*.8E,llR*,l2S*)-3.8-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside

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(1R*,ZR*,3E,7R*.8E,llR*,l2S*)-3.8-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpene Glycoside
Canonical Smiles OC/C/1=C\[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2C/C=C(/[C@H](CC1)COC1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)\C)C(O)(C)C
InChI InChI=1S/C27H46O9/c1-15-5-8-19-18(26(2,3)34)9-10-27(19,4)21(30)11-16(12-28)6-7-17(15)14-35-25-24(33)23(32)22(31)20(13-29)36-25/h5,11,17-25,28-34H,6-10,12-14H2,1-4H3/b15-5+,16-11-/t17-,18-,19+,20-,21+,22-,23+,24-,25?,27+/m1/s1
InChIKey AQNPUNCGNBFMBN-PYTOJNKKSA-N
Formula C27H46O9
HBA 9
HBD 7
MW 514.66
Rotatable Bonds 6
TPSA 160.07
LogP 0.63
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 514.31
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1994). Dolabellane diterpene glucosides from Chrozophora obliqua. Phytochemistry,1994,37(2),495-500. [View] [PubMed]
Pubchem: 162817254
Nmrshiftdb2: 60051927

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(C=CC2)CCC=CCC(C23)CCC3

Level: 1

Mol. Weight: 514.66 g/mol

Structure

SMILES: C1CCC(C12)CC=CCCCC=CC2

Level: 0

Mol. Weight: 514.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 514.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.24
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
73.5
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.44
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.38
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
-313.63
Rat (Acute)
3.8
Rat (Chronic Oral)
3.22
Fathead Minnow
3.59
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
549.93
Hydration Free Energy
-3.22
Log(D) at pH=7.4
1.48
Log(P)
0.66
Log S
-2.21
Log(Vapor Pressure)
-13.67
Melting Point
179.7
pKa Acid
7.0
pKa Basic
6.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8765
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8765
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8717
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8717
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8489
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8489
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8273
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8273
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8255
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8255
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8254
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8225
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8225
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8075
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8075
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7744
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7744
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7741
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7741
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7735
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7735
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7685
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7685
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7659
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7659
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7546
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7546
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7222
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7222
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7192
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7192
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7180
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7180
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7140
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7140
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7134
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7134
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7098
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7098
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7087
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7087
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7039
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7039
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7025
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7025
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7018
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7018
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7009
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7009

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