(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol - Compound Card

(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol

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(1R*,2R*,3E,7E,11R*,12S*)-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)C[C@](CC(=O)OC/C/1=C\[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2CC/C(=C/CC1)/C)C(O)(C)C)(O)C
InChI InChI=1S/C26H42O7/c1-17-7-6-8-18(16-33-23(30)15-25(4,32)14-22(28)29)13-21(27)26(5)12-11-19(24(2,3)31)20(26)10-9-17/h7,13,19-21,27,31-32H,6,8-12,14-16H2,1-5H3,(H,28,29)/b17-7+,18-13-/t19-,20+,21+,25-,26+/m1/s1
InChIKey UQWDHHVADPTEQB-CHTQFGRBSA-N
Formula C26H42O7
HBA 6
HBD 4
MW 466.62
Rotatable Bonds 7
TPSA 124.29
LogP 3.76
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 466.29
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1995). 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry,1995,39(1),151-161. [View]
Pubchem: 162902297

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 466.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.05
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
80.0
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.04
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
Toxic
hERG Blockers
Safe
Daphnia Maga
3.93
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
Safe
T. Pyriformis
-36.13
Rat (Acute)
2.32
Rat (Chronic Oral)
2.49
Fathead Minnow
4.07
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
452.53
Hydration Free Energy
-4.26
Log(D) at pH=7.4
0.58
Log(P)
3.27
Log S
-3.35
Log(Vapor Pressure)
-9.91
Melting Point
161.26
pKa Acid
4.06
pKa Basic
7.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9308
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9308
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8286
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8286
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8191
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8191
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8111
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8111
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8108
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8108
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7943
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7911
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7911
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7855
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7855
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7800
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7800
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7795
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7795
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7642
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7642
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7624
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7624
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7599
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7599
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7555
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7555
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7525
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7525
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7491
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7491
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7446
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7446
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7394
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7394
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7333
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7333
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7326
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7326
Uncharacterized PhzA/B-like protein PA3332 Q9HYR3 Y3332_PSEAE Pseudomonas aeruginosa 4 0.7261
Uncharacterized PhzA/B-like protein PA3332 Q9HYR3 Y3332_PSEAE Pseudomonas aeruginosa 4 0.7261
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7236
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7180
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7180
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7163
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7163
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7159
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7159
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7121
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7121
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7108
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7108
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7086
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7086
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7061
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7022
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7022

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