Swinholide A - Compound Card

Swinholide A

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Swinholide A

Family: Animalia - Theonellidae
Kingdom: Animalia
Class: Macrolide

Canonical Smiles	CO[C@H]1C[C@@H]2CC=C[C@@H](O2)C[C@@H](O)C/C=C(\C)/C=C/C(=O)O[C@H]([C@H]([C@H]([C@H](CC[C@H]2C[C@H](OC)C[C@@H](O2)C)C)O)C)[C@@H](C)[C@H](O)C[C@H](O)[C@H](C)[C@H](C[C@H]2O[C@H](C[C@H](C/C=C(/C=C/C(=O)O[C@@H]([C@H]([C@@H](C[C@@H]([C@@H]1C)O)O)C)[C@H]([C@H]([C@H](CC[C@H]1C[C@H](OC)C[C@@H](O1)C)C)O)C)\C)O)C=CC2)OC
InChI	InChI=1S/C78H132O20/c1-45-23-29-57(79)37-59-19-17-21-61(95-59)41-71(91-15)52(8)68(82)44-70(84)54(10)78(56(12)76(88)48(4)28-32-64-40-66(90-14)36-50(6)94-64)98-74(86)34-26-46(2)24-30-58(80)38-60-20-18-22-62(96-60)42-72(92-16)51(7)67(81)43-69(83)53(9)77(97-73(85)33-25-45)55(11)75(87)47(3)27-31-63-39-65(89-13)35-49(5)93-63/h17-20,23-26,33-34,47-72,75-84,87-88H,21-22,27-32,35-44H2,1-16H3/b33-25+,34-26+,45-23+,46-24+/t47-,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	RJVBVECTCMRNFG-YQVSBIDYSA-N
Formula	C₇₈H₁₃₂O₂₀
HBA	20
HBD	8
MW	1389.89
Rotatable Bonds	16
TPSA	288.28
LogP	10.11
Number Rings	5
Number Aromatic Rings	0
Heavy Atom Count	98
Formal Charge	0
Fraction CSP3	0.82
Exact Mass	1388.93
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: 6326667

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: 1389.89 g/mol

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

Level: 1

Mol. Weight: 1389.89 g/mol

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

Level: 0

Mol. Weight: 1389.89 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1389.89 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.43
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 2558882732082.200
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 334415941784773.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.830
Plasma Protein Binding: 87.11
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: 3.700
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 68264910572911040.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -37948488463.830
Log(P): -4417643.69
Log S: -6.08
Log(Vapor Pressure): -2247928491757136.0
Melting Point: -683061942.29
pKa Acid: -16379713049015.43
pKa Basic: -131774241069.62

No predicted protein targets found for this compound.