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Mesozygin B

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	Oc1ccc(c(c1)O)[C@H]1CC(=C[C@@H]([C@@H]1C(=O)c1ccc(cc1O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1O)O)C
InChI	InChI=1S/C35H28O11/c1-15-8-22(19-5-2-16(36)10-24(19)39)31(34(44)21-7-4-18(38)12-26(21)41)23(9-15)32-27(42)14-30-33(35(32)45)28(43)13-29(46-30)20-6-3-17(37)11-25(20)40/h2-7,9-14,22-23,31,36-42,45H,8H2,1H3/t22-,23+,31-/m1/s1
InChIKey	CTBZWKDJYOAWCX-IKBQMQIHSA-N
Formula	C₃₅H₂₈O₁₁
HBA	11
HBD	8
MW	624.6
Rotatable Bonds	5
TPSA	209.12
LogP	5.82
Number Rings	6
Number Aromatic Rings	5
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.14
Exact Mass	624.16
Number of Lipinski Rule Violations	4

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Morus mesozygia	Moraceae	Plantae	3054370

Showing of synonyms

Fozing CD, Ali Z, et al. (2012). Phosphodiesterase I-inhibiting Diels-Alder adducts from the leaves of Morus mesozygia.. Planta medica,2012, 78(2), 154-159. [View] [PubMed]

Pubchem: 57335175

Zinc: ZINC000200729946

No compound-protein relationship available.

SMILES: c1ccccc1C2CC=CC(C2C(=O)c3ccccc3)c(c4)ccc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1C(=O)C2CCC=CC2c(c3)ccc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 624.6 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C(C3C(=O)c4ccccc4)C=CCC3c5ccccc5

Level: 3

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C=CCC(C4)c5ccccc5

Level: 3

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1C(=O)C2CCC=CC2c(c3)ccc(c34)occc4=O

Level: 2

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C=CCCC4

Level: 2

Mol. Weight: 624.6 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3C=CCC(C3)c4ccccc4

Level: 2

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1C(=O)C2C(CC=CC2)c3ccccc3

Level: 2

Mol. Weight: 624.6 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3C=CCCC3

Level: 1

Mol. Weight: 624.6 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 624.6 g/mol

SMILES: C1CC=CCC1C(=O)c2ccccc2

Level: 1

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1C2CC=CCC2

Level: 1

Mol. Weight: 624.6 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 624.6 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 624.6 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.25
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.250
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 41.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 98.34
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.100
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.600
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.440
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.270
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -70694.090
Rat (Acute): 2.510
Rat (Chronic Oral): 3.810
Fathead Minnow: 109.830
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 981.980
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.080
Log(P): 5.88
Log S: -7.21
Log(Vapor Pressure): -83.17
Melting Point: 345.43
pKa Acid: 6.39
pKa Basic: 7.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9511
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9437
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9385
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9282
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9239
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9018
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8953
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8827
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8806
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8776
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8757
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8710
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8607
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8603
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8568
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8533
Metallo-beta-lactamase type 2	P25910	BLAB_BACFG	Bacteroides fragilis	4	0.8497
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8483
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8437
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.8424
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8420
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8400
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8321
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8273
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8228
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.8102
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8091
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8082
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8045
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8017
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7966
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7952
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7941
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7936
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7925
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7921
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7900
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7899
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7853
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7841
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7802
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7792
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7785
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7782
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7780
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7765
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7727
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7687
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7673
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7663
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7663
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7642
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7636
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7622
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7608
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7564
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7557
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7552
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7534
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7534
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7510
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7505
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7485
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	4	0.7474
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7472
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7406
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7394
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7371
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7342
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7326
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7320
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7319
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7311
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7305
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7280
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7263
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7259
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7239
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7237
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7231
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7229
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7220
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.7218
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7213
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7203
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7198
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7194
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7124
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7110
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	3	0.7062
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7059
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7055
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7050
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7047
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	4	0.7034
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7019
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7018
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7017
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7008

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