Hirsein B - Compound Card

Hirsein B

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Hirsein B

Structure
Zoomed Structure
  • Family: Thymelaeaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daphnane Diterpenoid
Canonical Smiles CCCCCCCCCC12O[C@H]3[C@](O2)(C(=C)C)[C@@H]([C@H](C2(O1)[C@H]3[C@@H]1O[C@@]1([C@H]([C@]1([C@H]2C=C(C1=O)C)O)O)CO)C)OC(=O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C39H50O11/c1-6-7-8-9-10-11-12-19-36-48-33-29-32-35(21-40,47-32)34(44)37(45)27(20-23(4)30(37)43)39(29,50-36)24(5)31(38(33,49-36)22(2)3)46-28(42)18-15-25-13-16-26(41)17-14-25/h13-18,20,24,27,29,31-34,40-41,44-45H,2,6-12,19,21H2,1,3-5H3/b18-15+/t24-,27-,29+,31-,32+,33-,34-,35+,36?,37-,38+,39?/m1/s1
InChIKey ISJKPVSGUKXWTP-IKHOAUTRSA-N
Formula C39H50O11
HBA 11
HBD 4
MW 694.82
Rotatable Bonds 13
TPSA 164.51
LogP 4.26
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 694.34
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea hirsuta Thymelaeaceae Plantae 69845

Showing of synonyms

  • Miyamae Y, Villareal MO, et al. (2009). Hirseins A and B, daphnane diterpenoids from Thymelaea hirsuta that inhibit melanogenesis in B16 melanoma cells. Journal of Natural Products,2009,72(5),938-941. [View] [PubMed]
Pubchem: 101477053

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2)C(OC(O3)O4)C3C5C(O6)C6CC(C7C245)C(=O)C=C7

Level: 1

Mol. Weight: 422.43 g/mol

Structure

SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6

Level: 0

Mol. Weight: 276.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-2.05
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
407.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
88.71
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
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-5.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.08
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
8.42
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-744175.5
Rat (Acute)
4.14
Rat (Chronic Oral)
3.44
Fathead Minnow
949.31
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
80052.25
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.98
Log(P)
6.34
Log S
-5.09
Log(Vapor Pressure)
-2592.77
Melting Point
178.9
pKa Acid
-0.81
pKa Basic
1.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8747
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8747
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8155
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8155
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8147
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8147
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8060
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8060
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8018
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8018
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7820
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7820
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7704
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7704
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7687
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7687
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7513
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7510
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7510
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7448
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7448
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7441
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7441
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7403
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7403
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7397
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7397
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7378
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7378
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7325
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7325
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7299
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7299
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7284
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7284
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7272
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7272
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7259
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7259
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7243
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7243
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7229
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7229
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7213
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7213
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7206
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7179
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7179
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7175
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7175
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7159
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7159
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7139
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7139
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7132
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7132
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7130
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7130
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7129
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7129
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7104
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7104
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7103
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7103
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7096
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7094
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7094
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7094
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7094
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7071
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7071
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7062
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7062
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7057
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7057
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7054
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7054
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7054
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7054
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7054
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7054
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7054
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7053
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7053
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7039
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7039
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7034
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7034
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7028
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7028
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7027
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7027
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7023
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7023
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7016
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7016
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7015
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7013
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7013
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7009
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7009
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7005
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7005
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7001
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7001

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