Procyanidin tetramer - Compound Card

Procyanidin tetramer

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Procyanidin tetramer

Structure
Zoomed Structure
  • Family: Plantae - Sterculiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Polyphenol
Canonical Smiles Oc1cc(O)c2c(c1)O[C@@H]([C@H]([C@@H]2c1c(O)cc(c2c1O[C@H](c1ccc(c(c1)O)O)[C@H]([C@@H]2c1c(O)cc(c2c1O[C@H](c1ccc(c(c1)O)O)[C@H]([C@@H]2c1c(O)cc(c2c1O[C@@H]([C@H](C2)O)c1ccc(c(c1)O)O)O)O)O)O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C60H50O24/c61-23-13-34(71)42-41(14-23)81-55(20-2-6-26(63)31(68)10-20)51(78)48(42)44-36(73)17-38(75)46-50(53(80)57(83-59(44)46)22-4-8-28(65)33(70)12-22)47-39(76)18-37(74)45-49(52(79)56(84-60(45)47)21-3-7-27(64)32(69)11-21)43-35(72)16-29(66)24-15-40(77)54(82-58(24)43)19-1-5-25(62)30(67)9-19/h1-14,16-18,40,48-57,61-80H,15H2/t40-,48-,49+,50-,51-,52-,53-,54+,55+,56+,57+/m0/s1
InChIKey QFLMUASKTWGRQE-FSEIEVOYSA-N
Formula C60H50O24
HBA 24
HBD 20
MW 1155.04
Rotatable Bonds 7
TPSA 441.52
LogP 5.89
Number Rings 12
Number Aromatic Rings 8
Heavy Atom Count 84
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 1154.27
Number of Lipinski Rule Violations 4
# Species Family Kingdom NCBI Taxonomy ID
1 Sterculia setigera Sterculiaceae Plantae 66667

Showing of synonyms

  • Andima M, Coghi P, et al. (2021). Chemical constituents and biological activities of African medicinal tree Sterculia setigera Delile stem bark. South African Journal of Botany, 2021, 143, 274-281. [View]
Pubchem: 101228664

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C(CC(O4)c5ccccc5)c(c46)cccc6C(CC(O7)c8ccccc8)c(c79)cccc9C1CC(c2ccccc2)Oc(c12)cccc2

Level: 7

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C(CC(O4)c5ccccc5)c(c46)cccc6C(CCO7)c(c78)cccc8C9CC(c1ccccc1)Oc(c19)cccc1

Level: 6

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C(CC(O4)c5ccccc5)c(c46)cccc6C(CC(O7)c8ccccc8)c(c79)cccc9C1CCOc(c12)cccc2

Level: 6

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CC(O5)c6ccccc6)c7cccc(c78)C(CCO8)c9cccc(c19)CCC(O1)c1ccccc1

Level: 6

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C(CC(O6)c7ccccc7)c(c68)cccc8C9CC(c1ccccc1)Oc(c19)cccc1

Level: 6

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C(CC(O4)c5ccccc5)c(c46)cccc6C(CCO7)c(c78)cccc8C9CCOc(c19)cccc1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CC(O4)c5ccccc5)c6cccc(c67)C(CCO7)c8cccc(c89)CCC(O9)c1ccccc1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CCO5)c6cccc(c67)C(CCO7)c8cccc(c89)CCC(O9)c1ccccc1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CC(O5)c6ccccc6)c7cccc(c78)C(CCO8)c9cccc(c19)CCCO1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C(CCO6)c(c67)cccc7C8CC(c9ccccc9)Oc(c18)cccc1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C(CC(O6)c7ccccc7)c(c68)cccc8C9CCOc(c19)cccc1

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CC(O5)c6ccccc6)c7cccc(c78)CCC(O8)c9ccccc9

Level: 5

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C(CCO4)c(c45)cccc5C(CCO6)c(c67)cccc7C8CCOc(c89)cccc9

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CC(O4)c5ccccc5)c6cccc(c67)C(CCO7)c8cccc(c89)CCCO9

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CCO5)c6cccc(c67)C(CCO7)c8cccc(c89)CCCO9

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C(CCO6)c(c67)cccc7C8CCOc(c89)cccc9

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CC(O4)c5ccccc5)c6cccc(c67)CCC(O7)c8ccccc8

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CCO5)c6cccc(c67)CCC(O7)c8ccccc8

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C6CC(c7ccccc7)Oc(c68)cccc8

Level: 4

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CCO3)c(c34)cccc4C(CCO5)c(c56)cccc6C7CCOc(c78)cccc8

Level: 3

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CCO4)c5cccc(c56)CCC(O6)c7ccccc7

Level: 3

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CCO3)c(c34)cccc4C5CC(c6ccccc6)Oc(c57)cccc7

Level: 3

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C6CCOc(c67)cccc7

Level: 3

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C(CCO3)c(c34)cccc4C5CCOc(c56)cccc6

Level: 2

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5

Level: 2

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 1155.04 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 1155.04 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 1155.04 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1155.04 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
222365475.79
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
29060564528.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
67.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
9.45
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-675883065.39
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-277.19
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.05
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
-52743523681445.29
Rat (Acute)
2.12
Rat (Chronic Oral)
113128.48
Fathead Minnow
66577453267.11
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
5932183648472.22
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-3297691.62
Log(P)
-379.98
Log S
-6.06
Log(Vapor Pressure)
-195343785127.09
Melting Point
-54972.58
pKa Acid
-1423387696.5
pKa Basic
-11451074.55
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 0.8868
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8518
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8290
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8268
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8213
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8127
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8102
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8003
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7898
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7829
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7676
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7626
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7287
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7242
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7205
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7141
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7106
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7089
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7081
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7074
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7073
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7056
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7010

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