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Isorhamnetin-3-O-beta-D-glucopyranoside-(2''→1''')-rhamnopyranoside

Family: Plantae - Avicenniaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@H](C([C@@H]1O)O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O
InChI	InChI=1S/C28H32O16/c1-9-18(33)21(36)23(38)27(40-9)44-26-22(37)19(34)16(8-29)42-28(26)43-25-20(35)17-13(32)6-11(30)7-15(17)41-24(25)10-3-4-12(31)14(5-10)39-2/h3-7,9,16,18-19,21-23,26-34,36-38H,8H2,1-2H3/t9-,16?,18-,19-,21+,22?,23+,26+,27?,28+/m1/s1
InChIKey	QHLKSZBFIJJREC-YCJRXWMNSA-N
Formula	C₂₈H₃₂O₁₆
HBA	16
HBD	9
MW	624.55
Rotatable Bonds	7
TPSA	258.43
LogP	-1.38
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	624.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Carissa edulis	Apocynaceae	Plantae	992661
2	Avicennia marina	Avicenniaceae	Plantae	82927

Showing of synonyms

Al-Youssef HM and Hassan WHB. (2014). Chemical constituents of Carissa edulis Vahl. Arabian Journal of Chemistry,2014,in press. [View]
Sharaf M, El-Ansari MA and Saleh NAM. (2000). New flavonoids from Avicennia marina. Fitoterapia,2000,71(3),274-277. [View] [PubMed]

Pubchem: 163018620

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 624.55 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 624.55 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 624.55 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 624.55 g/mol

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

Level: 1

Mol. Weight: 624.55 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 624.55 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 624.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 624.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.19
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 14.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 49.24
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.58
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.86
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.17
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: -23002.71
Rat (Acute): 2.29
Rat (Chronic Oral): 4.53
Fathead Minnow: 46.13
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: 365.94
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.12
Log(P): -0.38
Log S: -4.81
Log(Vapor Pressure): -16.69
Melting Point: 196.02
pKa Acid: 4.22
pKa Basic: 4.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8905
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8905
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8704
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8704
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8626
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8626
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8618
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8618
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8361
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8361
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8279
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8279
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8006
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8006
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7858
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7858
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7754
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7754
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7663
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7663
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7635
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7635
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7580
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7580
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7563
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7563
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7482
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7482
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7442
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7442
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7380
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7380
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7269
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7269
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7202
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7202
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7131
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7131
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7105
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7105
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7087
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7087
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	5	0.7067
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	5	0.7067
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7061
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7061
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7020
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7020
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7004
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7004

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