Swinholide I - Compound Card

Swinholide I

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Swinholide I

Family: Animalia - Theonellidae
Kingdom: Animalia
Class: Macrolide

Canonical Smiles	CO[C@H]1C[C@H](CC[C@@H]([C@@H]([C@@H]([C@@H]2OC(=O)/C=C/C(=C/C[C@H](O)C[C@H]3C=CC[C@H](O3)C[C@H](OC)[C@@H](C)[C@@H](O)C[C@@H](O)[C@H](C)[C@H](OC(=O)/C=C/C(=C\C[C@@H](C[C@@H]3O[C@H](C[C@@H]([C@H]([C@H](C[C@H]([C@@H]2C)O)O)C)OC)CC=C3)O)/C)[C@H]([C@H]([C@H](C[C@@H]([C@H]2C[C@H](OC)C[C@@H](O2)C)O)C)O)C)/C)C)O)C)O[C@H](C1)C
InChI	InChI=1S/C78H132O21/c1-44-23-28-56(79)36-58-20-18-22-61(97-58)40-71(93-16)51(8)66(82)43-68(84)53(10)78(55(12)76(89)47(4)33-69(85)72-41-64(91-14)35-49(6)95-72)99-74(87)32-26-45(2)24-29-57(80)37-59-19-17-21-60(96-59)39-70(92-15)50(7)65(81)42-67(83)52(9)77(98-73(86)31-25-44)54(11)75(88)46(3)27-30-62-38-63(90-13)34-48(5)94-62/h17-20,23-26,31-32,46-72,75-85,88-89H,21-22,27-30,33-43H2,1-16H3/b31-25+,32-26+,44-23+,45-24-/t46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59+,60-,61-,62-,63+,64+,65-,66-,67+,68+,69-,70-,71-,72+,75-,76-,77+,78-/m0/s1
InChIKey	XUQRQRKUGBIVEH-WYEHIYBJSA-N
Formula	C₇₈H₁₃₂O₂₁
HBA	21
HBD	9
MW	1405.89
Rotatable Bonds	16
TPSA	308.51
LogP	9.08
Number Rings	5
Number Aromatic Rings	0
Heavy Atom Count	99
Formal Charge	0
Fraction CSP3	0.82
Exact Mass	1404.93
Number of Lipinski Rule Violations	4

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Theonella swinhoei	Theonellidae	Animalia	37505

Showing of synonyms

Youssef DT, Mooberry SL (2006). Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the Red Sea sponge Theonella swinhoei. Journal of Natural Products,2006,69(1),154-157. [View] [PubMed]

Pubchem: 101391759

Nmrshiftdb2: 70057904

No compound-protein relationship available.

SMILES: O1CCCCC1CCCCCC(OC(=O)C=CC=CCCC2)CCCCCCCC(O3)CC=CC3CCCC=CC=CC(=O)OC(CCCCCC4CCCCO4)CCCCCCCC(O5)CC=CC25

Level: 2

Mol. Weight: 1405.89 g/mol

SMILES: O1CCCCC1CCCCCC(OC(=O)C=CC=CCCC2)CCCCCCCC(O3)CC=CC3CCCC=CC=CC(=O)OCCCCCCCCC(O4)CC=CC24

Level: 1

Mol. Weight: 1405.89 g/mol

SMILES: C12C=CCC(O2)CCCCCCCCOC(=O)C=CC=CCCCC3C=CCC(O3)CCCCCCCCOC(=O)C=CC=CCCC1

Level: 0

Mol. Weight: 1405.89 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1405.89 g/mol

Anticancer

Antifungal

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 1491624375013.270
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 194937661729004.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.730
Plasma Protein Binding: 84.46
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: 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: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 3.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 39792970075686800.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -22120924406.500
Log(P): -2575130.0
Log S: -5.67
Log(Vapor Pressure): -1310362477964903.8
Melting Point: -398168825.48
pKa Acid: -9548055130661.688
pKa Basic: -76813823140.64

No predicted protein targets found for this compound.