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Cyphostemmin A

Family: Plantae - Vitaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	Oc1ccc(cc1)C1=C(c2ccc(cc2)O)C(c2c(C1)cc(O)cc2O)c1cc(O)cc(c1)O
InChI	InChI=1S/C28H22O6/c29-19-5-1-15(2-6-19)24-12-18-11-23(33)14-25(34)27(18)28(17-9-21(31)13-22(32)10-17)26(24)16-3-7-20(30)8-4-16/h1-11,13-14,28-34H,12H2
InChIKey	ZUOFIYSMCLKBAS-UHFFFAOYSA-N
Formula	C₂₈H₂₂O₆
HBA	6
HBD	6
MW	454.48
Rotatable Bonds	3
TPSA	121.38
LogP	5.22
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	454.14
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cyphostemma crotalarioides	Vitaceae	Plantae	178803

Showing of synonyms

Ducrot PH, Koilmann A, et al. (1998). Cyphostemmins A-B, two new antifungal oligostilbenes from Cyphostemma crotalarioides (Vitaceae). Tetrahedron Letters,1998,39(52),9655-9658. [View]

Pubchem: 100920620

Cas: 220328-15-4

Nmrshiftdb2: 60060592

No compound-protein relationship available.

SMILES: c1ccccc1C2C(c3ccccc3)=C(c4ccccc4)Cc(c25)cccc5

Level: 3

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C(C2)=C(c3ccccc3)Cc(c24)cccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1cccc(c12)CC=C(c3ccccc3)C2c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1cccc(c12)CC(c3ccccc3)=CC2c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C(C2)=CCc(c23)cccc3

Level: 1

Mol. Weight: 454.48 g/mol

SMILES: c1cccc(c12)CC=CC2c3ccccc3

Level: 1

Mol. Weight: 454.48 g/mol

SMILES: C1C=CCc(c12)cccc2

Level: 0

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 454.48 g/mol

Antifungal

Absorption

Caco-2 (logPapp): -5.91
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.160
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.250
Plasma Protein Binding: 84.71
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.370
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.100
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.000
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -267.560
Rat (Acute): 2.170
Rat (Chronic Oral): 3.660
Fathead Minnow: 6.490
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 599.470
Hydration Free Energy: -3.600
Log(D) at pH=7.4: 2.480
Log(P): 3.93
Log S: -4.09
Log(Vapor Pressure): -10.94
Melting Point: 341.22
pKa Acid: 7.89
pKa Basic: 9.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9258
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9258
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8974
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8974
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8786
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8786
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8691
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8691
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.8684
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.8684
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8364
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8364
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8336
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8336
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8305
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8305
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8134
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8134
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.8109
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.8109
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8103
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8103
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.8017
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.8017
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7975
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7975
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7895
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7895
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7883
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7883
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7780
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7780
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7730
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7730
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7592
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7592
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7583
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7583
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7491
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7491
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7472
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7472
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7469
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7469
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7441
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7441
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7421
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7421
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7315
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7315
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7257
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7257
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7252
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7252
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7198
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7198
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7170
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7170
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7165
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7165
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	4	0.7152
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7152
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7152
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	4	0.7152
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7125
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7125
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7100
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7100
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7085
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7085
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7084
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7084
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7034
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7034
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7011
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7011
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7004
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7004
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.7000
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.7000

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