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Neo-clerodan-3,13-dien-16,15:18,19-diolide

Family: Plantae - Sapindaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Neo-Clerodane Diterpene

Canonical Smiles	COC1C=C(C(=O)O1)CC[C@@]1(C)[C@H](C)CC[C@@]23[C@@H]1CCC=C3C(=O)OC2
InChI	InChI=1S/C21H28O5/c1-13-7-10-21-12-25-19(23)15(21)5-4-6-16(21)20(13,2)9-8-14-11-17(24-3)26-18(14)22/h5,11,13,16-17H,4,6-10,12H2,1-3H3/t13-,16-,17?,20+,21-/m1/s1
InChIKey	CWRSOQZLIYAURI-QHZMMHQPSA-N
Formula	C₂₁H₂₈O₅
HBA	5
HBD	0
MW	360.45
Rotatable Bonds	4
TPSA	61.83
LogP	3.54
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.71
Exact Mass	360.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dodonaea angustifolia	Sapindaceae	Plantae	379228

Showing of synonyms

Omosa LK, Midiwo JO, et al. (2010). neo-Clerodane diterpenoids from the leaf exudate of Dodonaea angustifolia. Phytochemistry Letters,2010,3(4),217-220. [View] [PubMed]

Pubchem: 131846663

Cas: 1309920-99-7

No compound-protein relationship available.

SMILES: O=C1OCC=C1CCC(CCC2)C3CCC=C(C234)C(=O)OC4

Level: 1

Mol. Weight: 360.45 g/mol

SMILES: C1OC(=O)C(C123)=CCCC2CCCC3

Level: 0

Mol. Weight: 360.45 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 360.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.130
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.360
Plasma Protein Binding: 54.41
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: 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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.870
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.110
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.780
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.570
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -5.840
Rat (Acute): 2.640
Rat (Chronic Oral): 1.810
Fathead Minnow: 3.940
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 426.720
Hydration Free Energy: -4.260
Log(D) at pH=7.4: 2.660
Log(P): 2.23
Log S: -5.32
Log(Vapor Pressure): -6.67
Melting Point: 151.13
pKa Acid: 8.09
pKa Basic: 6.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9444
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9444
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9267
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9267
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8734
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8734
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7811
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7811
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7551
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7551
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7518
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7518
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7322
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7322
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7231
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7231
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7198
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7198
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7167
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7167
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7143
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7143
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7142
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7142
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7067
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7067

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