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Isomassonianoside B

Family: Plantae - Pinaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Neolignan

Canonical Smiles	OCCCc1cc2[C@@H](CO)[C@@H](Oc2c(c1)O)c1ccc(c(c1)OC)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O
InChI	InChI=1S/C25H32O10/c1-12-20(29)21(30)22(31)25(33-12)34-18-6-5-14(10-19(18)32-2)23-16(11-27)15-8-13(4-3-7-26)9-17(28)24(15)35-23/h5-6,8-10,12,16,20-23,25-31H,3-4,7,11H2,1-2H3/t12-,16-,20-,21+,22+,23+,25?/m1/s1
InChIKey	PHHIEOZUONPPQY-MGSQMMTBSA-N
Formula	C₂₅H₃₂O₁₀
HBA	10
HBD	6
MW	492.52
Rotatable Bonds	8
TPSA	158.3
LogP	0.74
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.52
Exact Mass	492.2
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cedrus atlantica	Pinaceae	Plantae	123597

Showing of synonyms

Maya B, Abedini A, et al. (2017). A new δ-tocotrienolic acid derivative and other constituents from the cones of Cedrus atlantica and their in vitro antimicrobial activity. Phytochemistry Letters, 2017, 20, 252-258. [View]

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 492.52 g/mol

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 492.52 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 492.52 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 492.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 492.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.08
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.95
Plasma Protein Binding: 80.77
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: 11.93
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.91
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.93
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: -418.84
Rat (Acute): 2.6
Rat (Chronic Oral): 3.49
Fathead Minnow: 4.35
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 528.42
Hydration Free Energy: -3.08
Log(D) at pH=7.4: 1.43
Log(P): -0.11
Log S: -3.56
Log(Vapor Pressure): -11.06
Melting Point: 173.06
pKa Acid: 6.59
pKa Basic: 2.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9192
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8806
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8752
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8466
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8409
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8401
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8373
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.8314
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8290
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8209
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8186
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8159
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8129
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8097
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8013
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7989
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7791
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7776
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7710
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7675
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7663
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7634
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7591
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7568
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7559
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7532
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7506
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7502
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7447
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7318
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7293
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7278
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7263
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7222
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7213
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7199
Putative snRNP Sm-like protein	Q8ZYG5	Q8ZYG5_PYRAE	Pyrobaculum aerophilum	3	0.7175
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7160
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7152
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7147
Repressor protein	Q7X0D9	Q7X0D9_ACIAD	Acinetobacter baylyi	3	0.7127
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7125
Decapping and exoribonuclease protein	O70348	DXO_MOUSE	Mus musculus	3	0.7120
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7115
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7111
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7078
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7056
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7049
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7047
Acyl-homoserine-lactone synthase	Q4VSJ8	Q4VSJ8_BURGL	Burkholderia glumae	4	0.7041
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7038
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7019
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7014

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