Guttiferone D - Compound Card

Guttiferone D

Select a section from the left sidebar

Guttiferone D

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=CC[C@@]12C(=O)/C(=C(\c3ccc(c(c3)O)O)/O)/C(=O)[C@](C1=O)(CC(C(=C)C)CC=C(C)C)C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)C
InChI InChI=1S/C43H58O6/c1-26(2)13-12-21-41(11)33(18-15-28(5)6)25-42(24-32(30(9)10)16-14-27(3)4)38(47)36(37(46)31-17-19-34(44)35(45)23-31)39(48)43(41,40(42)49)22-20-29(7)8/h13-15,17,19-20,23,32-33,44-46H,9,12,16,18,21-22,24-25H2,1-8,10-11H3/b37-36+/t32?,33-,41+,42-,43+/m0/s1
InChIKey MBVXGUVKDMJPQB-JYCBUDTGSA-N
Formula C43H58O6
HBA 6
HBD 3
MW 670.93
Rotatable Bonds 13
TPSA 111.9
LogP 10.48
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.51
Exact Mass 670.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 symphonia globulifera Guttiferae Plantae 156483

Showing of synonyms

  • Gustafson KR, Blunt JW, et al. (1992). The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea. Tetrahedron, 1992, 48(46), 10093-10192. [View]
Pubchem: 5469794
Nmrshiftdb2: 70001217

No compound-protein relationship available.

Structure

SMILES: C1CCC(C2=O)C(=O)C(C(=O)C12)=Cc3ccccc3

Level: 1

Mol. Weight: 670.93 g/mol

Structure

SMILES: C12C(=O)C(=C)C(=O)C(C1=O)CCC2

Level: 0

Mol. Weight: 670.93 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 670.93 g/mol

Anti-hiv

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.92
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
39.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
106.76
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
6.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.52
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.53
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-74645.05
Rat (Acute)
2.52
Rat (Chronic Oral)
3.72
Fathead Minnow
114.19
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
4176.21
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.76
Log(P)
10.71
Log S
-7.99
Log(Vapor Pressure)
-157.67
Melting Point
203.46
pKa Acid
7.14
pKa Basic
2.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9246
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8574
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8525
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8425
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8404
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8294
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8260
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8088
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.8079
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8066
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7975
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7866
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7813
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.7773
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7764
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7750
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7727
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7721
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7704
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7677
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7646
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7596
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7594
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7590
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7537
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7502
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7500
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7374
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7369
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7353
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7342
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7331
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7323
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7288
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7283
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7266
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7247
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7214
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7190
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7160
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7153
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7101
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7087
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7084
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7057
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7053
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7032

Download SDF