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Cyphostemmin B

Family: Plantae - Vitaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	Oc1ccc(cc1)/C=C/1\c2cc(O)cc(c2[C@H]([C@@H]1c1cc(O)cc(c1)O)c1ccc(cc1)O)O
InChI	InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9+/t26-,27+/m1/s1
InChIKey	BIQMSWPBPAKGSE-RVMRZQENSA-N
Formula	C₂₈H₂₂O₆
HBA	6
HBD	6
MW	454.48
Rotatable Bonds	3
TPSA	121.38
LogP	5.39
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: 15411553

Cas: 220328-16-5

Nmrshiftdb2: 60033715

No compound-protein relationship available.

SMILES: c1ccccc1C=C2C(c3ccccc3)C(c(c24)cccc4)c5ccccc5

Level: 3

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C=C2CC(c(c23)cccc3)c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C=C2C(Cc(c23)cccc3)c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C(C2=C)C(c(c23)cccc3)c4ccccc4

Level: 2

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C=C2CCc(c23)cccc3

Level: 1

Mol. Weight: 454.48 g/mol

SMILES: c1ccccc1C(C2=C)Cc(c23)cccc3

Level: 1

Mol. Weight: 454.48 g/mol

SMILES: c1cccc(c12)C(CC2=C)c3ccccc3

Level: 1

Mol. Weight: 454.48 g/mol

SMILES: C=C1CCc(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): -5.85
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.130
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.300
Plasma Protein Binding: 95.95
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: 6.780
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.500
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.030
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.040
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -304.590
Rat (Acute): 2.120
Rat (Chronic Oral): 3.960
Fathead Minnow: 6.470
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 595.450
Hydration Free Energy: -3.540
Log(D) at pH=7.4: 2.630
Log(P): 3.92
Log S: -3.93
Log(Vapor Pressure): -11.18
Melting Point: 305.25
pKa Acid: 8.27
pKa Basic: 9.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9093
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9093
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9055
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9055
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9016
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9016
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8500
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8500
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8435
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8435
Bromodomain-containing protein 9	Q9H8M2	BRD9_HUMAN	Homo sapiens	3	0.8257
Bromodomain-containing protein 9	Q9H8M2	BRD9_HUMAN	Homo sapiens	3	0.8257
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8189
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8189
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8147
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8147
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8098
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8098
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.8090
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.8090
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8080
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8080
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8019
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8019
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7866
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7866
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7844
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7844
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7801
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7801
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7774
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7774
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7718
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7718
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7589
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7589
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	4	0.7586
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	4	0.7586
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7465
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7465
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7465
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7465
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7460
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7460
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7420
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7420
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7344
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7344
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	4	0.7278
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	4	0.7278
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7233
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7233
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7232
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7232
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7229
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7229
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7200
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7200
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7181
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7181
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7153
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7153
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7124
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7124
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7090
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7090
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7064
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7064
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7048
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7048
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7034
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7034
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7000
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7000

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